Travel Packing Challenge: 6 weeks, 3 cultures, 4 climates, 1 carryon

Every time I complete a crazy trip like my solo Thanksgiving round-the-world adventure, I sleep for a week, and then when I finally wake up, I make a promise to myself that next time I’ll travel slower and try not to go to as many places on one trip.

Inevitably, after a month passes, however, I somehow forget all these promises I’ve made to myself. Even though I start with planning my next trip simply, I somehow wind up with an itinerary that crosses to the moon and back.

Confession: Some people are addicted to Girl Scout cookies and pizza. I lack complete lack self-control when it comes to national borders.

Here’s my logic: If you’ve already made the effort to fly half way around the world to go to country X, why not also go to country Y if it’s not that far away, and maybe also stop in at country Z if you have to fly past it anyway to get home?

I’m not convinced that country hopping is always a bad thing, but I do know one thing for sure: Country hopping makes for very tricky packing. Especially if you are a person, like me, committed to a carry-on only travel style.

This week I’m headed out for my first multi-country 2018 travel adventure, and as you may have guessed, I didn’t keep it simple. I’m on my way to a tango festival in Vietnam via a long weekend of hanging out at the Women’s Travel Fest in New York City.  From Vietnam I’ll go onward through South East Asia, visit friends in Cambodia and Thailand, stop for a beach week in the Maldives, and then hit up one final stop in the UAE for a fellow traveler’s birthday celebration in the desert before I head back to the US across the Atlantic.

I’m very excited about every single part of my adventure–besides the one thing I have to do to get myself out the door: Pack.

Now, some travelers will recommend that you keep it simple by always packing the same things. For me, always packing the same jeans and black shirt just never seems to work—I like to pack for the occasion.

Not only will I be traveling while working on the road for six weeks, I’ll be crisscrossing countries, climates and cultures that all require very different clothing.

New York, for example, is currently under a blizzard warning, while Bangkok is about 100 degrees every day with 100 percent humidity. A Tango festival requires me to bring specific shoes that I literally can’t wear anywhere else, and transiting home through the Middle East also means that I need to have something in my bag that is long and modest.

When your trip isn’t simple, your wardrobe isn’t simple either.

Guys might be able to get away with those zip off khaki travel pants everywhere, but if you’re a girl and you want to look decent and be appropriate for whatever culture you might have accidentally added onto your trip, you’ll need to kit yourself appropriately.

When I declared on my Instagram story this week that I would pack for six weeks, three cultures, and four climates in one carryon, so many of you said it would be impossible. I will confess it was a challenge, but here’s how I did it.

The Three Point Packing Strategy:

1.Layer, Layer, Layer

The key to any good multi-climate packing plan is layers. When it is cold you wear all the layers, when it’s bloody Asian hot, you wear as few layers as the culture deems appropriate.

A couple of tank tops, long sleeves, tights, basic skirt, and a dress that can double as a tunic go a long way in the mix and match game. Multi-weather fabrics like merino wool are also a secret weapon to keep you warm when it’s cold and cool when it’s hot (hat tip to Smartwool and Icebreaker).

Also, it helps to keep your layering strategy color coordinated. While I’m definitely not a monochromatic dresser in my day to day (orange and yellow are my favorite) I tend to stick with a color theme for the basics–most commonly blacks and grays with some pops of color. Color coordinating also means that you can get away with fewer pairs of shoes.

My bag has about 15 key pieces of clothing when it’s all packed, but I can probably make up at least 30 different outfits from its contents based on the temperature, what smells, and what I’m sick of wearing

2.Take the Goodwill pile

I’m definitely not the kind of person who buys new things to take on a trip. When it comes time to pack I’d prefer to dig to the back of my closet to see what is hiding in my Goodwill pile.

I love to pack things that I still like enough to wear for the trip, but am definitely going to be okay with getting rid of along the way. I take old tank tops instead of my new tank tops so I can fit the new tank tops I’m bound to buy in the market in Bangkok.  I take my oldest running shoes instead of the newest model because I can leave them at my last stop to make room for whatever souvenir I fancy from my adventure. And I also take the contents of my underwear drawer that really should be thrown out–it’s always nice to have extra undies and much easier to get rid of those holey ones when you’re on the road.

Disposable clothing are my key for keeping my packing light as I collect things along the way—plus you don’t have to worry as much about your things getting lost or stolen if they aren’t your absolutely favorite things.

3.Let your bag evolve as you go.

After many years of travel I’ve finally learned that I don’t actually need to purchase ahead and pack everything I need. People who live in other places usually need and want many of the same things that I want. If I need shampoo I can buy it there–why pack it? I can buy new flip flops if I lose mine, or pick up a fancy dress on the occasion that I find a hot date in my next location.

If you start somewhere cold and move on to somewhere warm, take warm layers you don’t mind leaving along the way, or organize to leave things with a friend to pick up later.

Last fall when  I packed for a beach trip to Mauritius, but decided to fly home via Paris in winter, I was worried I was going to freeze. Instead of skipping Paris,  I kitted myself out locally with a new hat from a street vendor and some jeans and a sweater. The bonus–I now have an awesome sweater and I get to say “I picked it up in Paris” when people comment on it.

You don’t have to pack to be prepared for everything—just prepare to be prepared and 99% of the time it will all work out (the other 1% will make great stories to tell someday).

So, what’s in my Mary Poppins bag?

If you really want to know, here’s everything I’m schlepping around the world for the next 6 weeks. Contents are subject to change. In fact, I’m less than 18 hours into the trip and I’ve already lost my hat!

Winter:

  • Boots, Jacket, Dress and shoes for speaking event, jeans,  and long sleeves (I’ll keep the long sleeves and jeans and leave the rest with a friend in NY to pick up later).
  • Winter Hat (already lost), yoga pants to wear as long underwear
  • Overside Scarf – doubles as beach and shoulder covering for Asia & Middle East
  • Merino Wool cardigan- doubles to wear over long dress for Middle East & for aircon in Asia

Tango Festival:

  • 3 Dresses for Tango that can double as sundresses for wandering around Asia
  • One pair of shoes I won’t be able to throw away of wear anywhere else (note: if you have big feet, don’t skimp on shoe packing when traveling to Asia)

Asia (Cambodia, Thailand, Vietnam):

  • Jean skirt, 3 tank tops, sandals, flip flops + all my sundresses from tango + oversized scarf
  • Lightweight goodwill-ready orange pants

Beach (Maldives):

  • Bathing Suit, Hat, Sunglasses.
  • Will use oversize scarf, jean skirt and tango dresses for cover up
  • (I would normally bring my hammock on a beach trip but had to leave it at home to make room for blizzard jacket and tango shoes)

Middle East:

  • One ankle length dress.
  • Yoga pants/leggings under sundresses with scarf to be modest

Other Clothes:

  • yoga pants & short, sports bra, running shoes – these can be used for exercise, comfy clothes for cold plane rides, and also as PJs

Other Stuff:

  • minimal toiletries (get what you need where you are)
  • emergency food rations(almonds & almond butter for plane rides and #hangry moments)
  • book  and journal
  • headphones, computer, folded up flip chart paper and sharpies, work papers that I will dispose of as I go.
  • phone (doubles as camera for this trip since I’m traveling to all places I’ve been to before)

What will be in the Mary Poppins bag by the end of the trip? Follow along, or wait and see!

25 Years of Wandering Lessons

This week marked a big milestone. Travel and I hit our big 25 year-silver anniversary of being inseparable.

I know you’re wondering how is it biologically possible that Stephanie has been traveling for 25 years since she’s barely even that old?  Let’s just say that travel keeps you young.

Maybe it’s odd to you that I celebrate my travel anniversary every year. Perhaps it’s because I don’t really have another anniversary taking up calendar real-estate. More likely it is because travel has changed me and shaped me so much over the years, and I’m a pretty big fan of reflecting and growing.

Throughout the years, I’ve celebrated this day by writing about all kinds of memories and lessons like the addictive sound of my first passport stamp, how my sense of travel fashion has improved, and how I eventually realized that traveling more than half of my life didn’t help me find myself.

The truth of the matter is that travel and I have learned a lot together. And really, wouldn’t all those misadventures have been a waste if I hadn’t learned anything?

To celebrate all that she’s taught me, I decided to write down 25 wandering lessons I’ve learned–one for every year that we’ve been together.  And yes, we are aware that some of these lessons contradict other lessons in the list- but hey, that’s travel, isn’t it?

1. When in doubt buy a plane ticket

Start with the basics. If you’re thinking about going somewhere, the answer should always be yes, unless you already know that it’s no. There are plenty of trips I regret not taking, but none that I wished I hadn’t gone on.

2.The confirm button never disappoints

Just buy the damn ticket already or make the hotel reservation. There are so many options when traveling and there is never ever a perfect decision. The best decision is the one that you have already made. Seriously, you won’t regret it, press buy now. (And repeat this to yourself every time you spend days researching plane tickets even after 25 years of travel)

3.You can’t do everything

The world is full, full, full of stuff to see and do. Even if you never travel you’ll never do everything in your own home town. How could you possible to see everything in the places that you visit? Slow your roll, decide what’s important to you (not what’s important to a guide book writer) and let go of everything else.

4. There aren’t wrong choices about where you should go

Everywhere is a new adventure, and since you can’t see everything (see above), you really can’t go wrong seeing whatever it is you like exactly where you’re at. Don’t listen to unsolicited advice about where you should go. There really are no wrong choices. And if you really don’t like a place, guess what– you can leave.

5. The world is not nearly as scary as CNN and FOX news would have you believe

You’re mom wasn’t lying: Things on television are not as they are in real life. Most of the places that you fear based on what you’ve seen in the news are 99.9% occupied by regular old people worrying about their families, cooking dinner, washing the dishes, and picking their kids up from school. (You should still probably stay away from places with active wars though unless you’re being paid to go there as military or a humanitarian. War zones aren’t great travel destinations.)

6. Don’t get stressed over dimes and dollars

Money stresses me out, but on the road, you can’t be stressed over small change, because you’ll literally be stressed all the time. If you get overcharged by a dollar and can’t get the rockbottom price you want at the market don’t sweat it. You’re joy is worth a lot more. Be thrifty, but not cheap. If some small expense is going to make your travel experience remarkably better, get over your budget and just do it. It’s a cost of living.

7. A bathing suit is never (and will never be) appropriate airplane attire

No one wants to sit next to you in your bikini top, plus airplanes are cold. Keep your clothes on. (Note: This lesson was not learned by experience. It was learned by over-exposure to backpackers in bathing suits at 30,000 feet).

8. Travel styles change over time- and that’s perfectly okay

If you travel as long as I have your tastes are going to grow up on the road. You might eventually feel like a sell out because you now prefer to stay at the fancy beach resort instead of the 4$ hostel dorm that you always loved in your youth. Own the season you’re in and whatever experience you like. And don’t forget to be nice to yourself.

9. Your experience is more important than your instagram feed

If you spend all your time caring what other people think about your trip, you’re creating an image for others rather than an experience for yourself. Take pictures to capture the memories that you’re making, and for the love of God, put your phone into your pocket every now and then and use your eyes to look at the view instead of your screen.

10. When in doubt stay

If you are feeling overwhelmed, can’t decide where to go next, and are failing at implementing lessons 1 & 2 for inexplicable reasons, walk yourself to the reception desk of your hotel or hostel and book yourself in for another night. There is usually a reason for indecisiveness–channel your inner wise friend, and chill the F out. Then make your decision after you eat food and take a nap.

11. You never need to carry any more than you can lift into an overhead bin

You never need a giant suitcase. Unless you’re going somewhere long term, traveling for an occasion that requires lots of special equipment, or hauling multiple children along, you can get by- and even look good- with a modest amount of clothing. Mastering packing may take years of practice, but you should start practicing today. And even if you can lift your case into the overhead bin by yourself, it’s definitely appropriate to let the kind gentlemen from the aisle seat lift if up there for you.

12. Always take one thing out of your suitcase before you leave for the airport

Even when you become a zen master of packing, you’ll still overpack. To keep this at minimum, always take one item out of your suitcase right before you leave for the airport. There is always one thing that you won’t need or could at least live without. The worst case is that you really do need it- and that’s what shops are markets are for. See if you can make underpacking your new goal.

13. Not all clothes can be dried safely with a hotel hairdryer

Packing masters eventually also become masters of doing piecemeal laundry in hotel sinks and bathtubs. While learning this art it is important to note that some clothing will actually melt when you attempt to dry them with a hairdryer. Due to the laws of the universe the clothes that you melt will inevitably be your favorite shirt, socks and underwear. You will eventually learn to batch your washing in locations where you have ample time to air dry.

14. Solo-traveler honeymoons should be a thing

Don’t put off going to your dream destination because you’re waiting for the perfect person to take you there. Take yourself to Bora Bora. I felt awkward the first time I holidayed solo on honeymoon island, and now it’s one of my favorite things. Tahiti- check. Maldives- check. Mauritius- check. If everyone owned up to their awkward and just did this, you’d all help increase the odds of meeting other amazing people in these romantic places. (commercial interruption for couples: If you are actually planning a honeymoon, have you checked out The Honeymoon Hack?)

15. There is always another way off the island

If you happen to miss your flight out of the Seychelles, or just decide that you really want to stay another day in Maui, there is almost always an alternative option to your plans. This may cost money (consider indecision as a travel tax–see #2) but it’s always cheaper to figure out how to stay than it is to go all the way home and then pay for another trip to come back. (note: leaving the Seychelles by boat is not a viable option thanks to actual pirates. It is recommended to enjoy another day on the beach while waiting for tomorrow’s flight.)

16. Bad things will happen and prove your resilience

Bad things–some even worse than being stranded on an island–will eventually happen. These will suck. Some of them will suck at the moment, some will suck bad enough to ruin your trip, and some of them may suck so bad that you may consider going home and never traveling again. But when you eventually recover and find your wings again, you will recognize you are a resilient badass.

17. Excuses are always readily available

The world is full of reasons to not travel, or to not travel now. Fear (see #5) is a big one of these, and so is missing out on other parts of life that the people in your community will be experiencing while you are away. The problem with excuses is that they have no expiration. Excuses will keep showing up as long as you pay attention to them. Ignoring them is the only way out the door. (Note: this truth applies to both life and travel.)

18. There is always a way to make your dream trip happen

International travel doesn’t have to be a once in a lifetime opportunity. Creativity and ingenuity can really take you a long way to dreaming bigger than you have before, and figuring out a way to pay for experiences that are larger than your budget. Learning this for myself took lots of trial and error. Lucky for you, if you really want a dream trip and aren’t sure how to do that, I taught a whole course on it. Seriously, you can go anywhere.

19. You’ll never get what you don’t ask for

I hate asking strangers for things, but after 25 years I’ve gotten a lot better. You know what– sometimes people actually want to help you with upgrades, information, cups of tea and rooms with views. While asking has no guarantee, not asking has a 100% rate of failure.

20. There are always trains going the opposite way

I’m always in a hurry, and I jump onto the wrong train all of the time. Even though I get very frustrated with myself every time I do this, I’ve also learned that this isn’t the end of the world. Nine times out of ten you can get off at the next stop and get on a train that will take you back the opposite way. Going backwards sucks, but most travel mistakes are reversible like this. In the 1 out of 10 situation where you can’t simply turn around to reverse course see #15. Or who knows, maybe the destination you’re going to wind up at will be the place you’re supposed to be (see #4).

21. Contribute where you visit

I’ve come to dislike the phrase “give-back” when you travel. A wise traveler should be acting in a way that isn’t taking anything away from a place. Figure out how you can let a place transform you for the better when you visit, and be cognizant of the effects of your interactions. It’s way more important to travel well than to “do good”.  An ethical traveler often does more good than many well-intentioned volunteers.

22. Your own culture is just as weird as every other culture you encounter

After you visit a lot of different place, you will eventually realize that all cultures are super weird and your own traditions seem as strange to an outsider as theirs do to you. Stretching your culture perspective will eventually help you become more open minded and grant you the ability to see your own life from an outsiders perspective.

23. Plans are sometimes good, but uncertainty can be awesome too

No one lives their regular days with a minute by minute operating plan, and the best travel doesn’t need to be conducted with this type of rigorous activity schedule either. The more comfortable you become with uncertainty, the more open you will become to adventure. You might miss something on the “best sites to see before you die list” but you’ll nearly be guaranteed to have an experience that isn’t in any book.

24. No one tells you that will get tired of traveling

Living in a perpetual state of motion is awesome. It’s also tiring AF. There should be a chapter in every “How to Become a Digital Nomad Course” that is entitled “What the hell do I do when I get really exhausted from traveling?” One day you will wake up and the thing that you’ll desire is to eat your dinner off of your own plates and not to have to decide where you are going to maybe live next. This is absolutely normal. It does not mean that you don’t want to be a traveler anymore. You may just need a year long nap, or maybe a small home base to anchor yourself between trips and cook dinner every once in awhile.

25. The best travel stories will never be all about you

We are each just a small part of the big picture of what is happening across the globe. Your very best stories will be about how this world welcomes you, the beauty you find in unexpected people and places, and the misadventures you encounter when that same world spins you in circles and spits you out and you still find the meaning in it. Learn these lessons and let these interactions become your narrative. Make sure you speak them loudly and broadly so everyone hears them and recognizes that our incredible world is still a good place.

There are so many more lessons that travel has taught me, and I’m pretty sure she’ll keep teaching me more as we continue our journey. Learning like travel is never complete.

Happy Wanderings Friends. Here’s to 25 more years.

Flying Solo on Honeymoon Island: Lessons Learned in Traveling Alone

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I mostly travel alone. Sometimes it is by choice, and sometimes it is simply because I’m not one to let my perpetually single status stop me from doing anything I dream of doing.

To be honest, most times I travel solo, I don’t even notice. I’m pretty awesome company (I think), and there are always people to talk to on the road. Plus with modern capabilities to connect from the remotest places, I’m never further than a Facetime away from my mother when I get tired of talking to myself. She always likes to see what I’m seeing.

Yet, even as independent as I can be, there are times that I choose to not go somewhere because I’m solo. And it isn’t just about safety. There are lots of reasons that cause the unaccompanied to press pause on their travel plans.

For years I’d wanted to travel to the French Polynesian island of Bora Bora and sleep in an overwater bungalow with tropical fish below me. But I put it off, and I put it off. Pushing pause on my dream time and time again.

You see, the entire tourism structure of Bora Bora is designed to cater to couples—destination weddings, honeymooners, and 25th anniversary celebrators. The airlines might as well sell tickets by the pair. Part of me was waiting for +1 to present to Air Tahiti to validate my worthiness to see this Polynesian paradise.

It wasn’t until recently that I said, F*%& it. My +1 is apparently lost in the Bermuda Triangle or undertaking a very extended journey across the Sahara. And so I went to Bora Bora by myself. Honeymoon island, party of one.

In all of my alone time watching the fish swim in the crystal clear lagoon from the perch of my over-the-water bungalow dock I spent some time reflecting on what really stops many of us from solo travel—and why we should do it anyway.

If you’re struggling with any of these reasons of why you shouldn’t travel alone, here’s some real reasons you should ignore them.

Reason not to go #1: It isn’t a solo-traveler kind of place.
Like Bora Bora, many of the most beautiful destinations in the world have been turned into “honeymoon hot-spots” and “romantic getaways”. Some places are tagged “family destinations”. Other places just have reputations for being more difficult to see solo. Most of this is a marketing ploy. At honeymoon resorts, tables are for two–but who cares. You have just as much right to take up space in your dream destination as any one else- and you don’t have to share the bread basket.

Lesson: If you want to go somewhere solo do your own research and don’t let the reputation of the place stop you from going. There are single people everywhere in the world (therefore there is no destination that isn’t solo-appropriate with a little bit of creativity). There are also ways that you can connect up with other solo travelers if you feel more confident being part of a group.

Reason not to go #2: Other people question why you’d go there alone

When I checked into the Intercontinental in Bora Bora, the woman working at reception asked me three times where my husband was. Her disbelief that I was in Bora Bora by myself was palpable. “Just one? Are you sure? No husband?”
I replied with a question- “Do you not have many guests with single bookings?”
“Well, we’ve had one other this week—a man,” she said. “Maybe you should meet.”
(sidenote: I wasn’t aware that the IHG hotel group was now offering matchmaking as part of its benefits for elite members.)

Lesson: When it comes to travel (and, well, a lot of other things) the lesson that I’ve learned is that it really doesn’t matter what other people think about where you want to go and if you want to be there by yourself. Sure, you may have to explain your situation, but why not make it fun and be true to what you want? Most of the travelers I talked to were intrigued about why I was there alone. I used this opportunity to talk to them about a new travel guide I’m writing (stay tuned) and handed out more business cards in Bora Bora than I do at a typical networking event.

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The wedding chapel at the Intercontinental in Bora Bora (convenient for when that elite matchmaking works out)

Reason not to go #3: You won’t be safe
Most people assume that safety is the primary concern of solo travelers—and solo female travelers in particular. However, as I’ve talked to more and more female travelers I’ve learned that safety isn’t often their biggest fear—they are much more afraid of being lonely and not having anyone to share their trip with. While safety isn’t always at the top of the list for what holds people back—or at the top of your worries in a pretty peaceful place like Bora Bora staying safe on the road is still important.

Lesson: The thing I’ve learned from years of solo globetrotting and my own run-ins with danger, is that staying safe on the road is very much like staying safe at home. Know where you’re going, be intentional when you’re wandering around alone in the dark, stick to areas with people, make local connections and ask if there are places that you should stay away from.

I always opt for situations that make me feel safe—even when they cost a few dollars extra. When I booked my ticket to Tahiti, the only flight available arrived late at night, so I booked the hotel’s shared shuttle. Normally I’d hop outside and hail a taxi to save a few bucks, but for my own security, an extra 10$ ensured that I’d be with other people and not looking for an ATM in the dark and negotiating with a taxi driver in bad French at midnight. (Note – doing things that aren’t safe alone when you’re at home are also not safe to do when you’re traveling–make a friend to do things that require a safety buddy)

Reason not to go #4: You’ll be lonely
Being alone does not always equal being lonely. By the time I left Bora Bora and Tahiti, I’d made a dozen new and very interesting friends: My over-the-water bungalow neighbor who had patented an inflatable tent and was celebrating his 25th anniversary, an American sailor who’d just finished a 31 day crossing of the Pacific Ocean from Mexico in his 26 foot sailboat, two Belgian grandfathers on a dive trip who wanted to buy me beer and talk about pre-election U.S. politics, and a dozen honeymooning and anniversary-ing couples who were really thrilled to have an unusual person to talk to after a week on an island with only their significant other.

Lesson: Being lonely and being alone are not the same thing (It’s worth repeating). The world is full of amazing people and amazing stories and people worth talking to. You don’t have to be that chatty person on the airplane who talks for the whole flight to make friends (please, don’t be him/her)—just be friendly. Just do you.

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Reason not to go #5: You’ve never traveled alone before

Maybe you aren’t single, maybe you just wonder what having a solo adventure would be like, or you want to go somewhere that your partner doesn’t want to go–but you’ve never traveled alone before and aren’t sure if you’ll like it. Well, one thing is for certain, you’ll never know unless you try it. When I was preparing to take my first solo backpacking trip around Indonesia I confess I was a little nervous (even though I was already living alone in Thailand) so I faced my fear and took myself on a practice weekend trip to a Thai island all by myself–and I was totally fine!

Lesson: Think about what makes you afraid of traveling solo and figure out a way to practice so you can reassure yourself you’ll be okay on the road. Worried about being alone? Get in your car by yourself and go on a weekend road trip. Worried about flying alone? Practice with some domestic flights by yourself.

I’m guessing you’re stronger, braver, and more prepared than you believe. I definitely learned that I was.

Happy Solo Travels!

 

Bora Bora or Bust: Why aren’t you getting on the plane?

BOB - 3For several years I’ve been helping people learn how to travel for nearly free using points and miles. There’s something amazing about encouraging people to dream about a place they’ve never visited—one that would most likely never be accessible to them if they had to save the money to get there—and then show a few practical tools to make this a reality.

As I challenge people to learn to travel hack by working towards a goal of a dream destination, I’ve always shared my own dream of sleeping in an over-the-water bungalow in Bora Bora–falling asleep to the sound of the surf, waking up to the fish under my feet, and morning coffee with my toes in the brilliant blue water.

The funny thing was, however, after years of teaching people how to hack their way to Bora Bora, I’d still never actually been there myself.

I had the points, I’d done all the research. If there ever was anyone qualified to hack their way to Bora Bora, I was she. What was I waiting for?

In October I flew to New Zealand. As my plane crossed the Pacific on it’s 17 hour journey I watched as we flew directly over Tahiti and the rest of French Polynesia on the inflight entertainment system flight tracker. Then it struck me. Was this the closest I was ever going to get to Bora Bora? A mile above it in the sky?

The wheels in my brain started turning. What was keeping me from going there if it wasn’t time or money? Why wasn’t I getting on the plane bound for Bora Bora? Was I subconsciously waiting for a significant moment. For my perfect traveling companion. For all the stars in the southern cross to align?

As I watched the sun rise at 37,000 feet, it literally dawned on me that I was waiting for no real reason. I was just putting it off because later felt easier than now. And then I thought some more. What other things was I putting off in my life like Bora Bora with no reason whatsoever?

Why is it that we put off our dreams and desires while waiting for the perfect time or circumstance to magically present itself? Aren’t we old enough to know that the magical present is the actual PRESENT? I made a pledge to myself to make it happen. And since I had to fly over Bora Bora again to get home from New Zealand —I decided that I would just do it now.

And as I typed the draft of this post from the deck of my over-the-water bungalow of my dreams, I can ensure you that NOW was the exact right time.

Whether you’re putting off a dream trip, calling your long lost family, waiting to pick up your pen to write your best-seller (points finger at self),  the lesson is this: The perfect time is now. If you’re waiting for a sign, this is it. 

I guess next time I teach this lesson I’ll be using my own photos and telling my own Bora Bora stories—and perhaps I’ll have to find another travel dream to share!

What are you waiting for?

Wonder how I actually hacked my way to Bora Bora? I knew you’d ask. Keep reading the bonus section below if you want to know how to plan this kind of trip.

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How’d I get there?

Here’s how my travel to Bora Bora worked, how I booked it, and what it cost. The route I took was a little bit different than the one I’ve laid out in my lesson plans, since I traveled via New Zealand rather than direct to Tahiti from my home base of Portland, OR. (Don’t worry, you can easily do this as a return trip originating in the US with flights on Hawaiian, AirFrance or AirTahiti Nui.)

PDX-LAX-SYD-AKL: 72,500 AA miles (or $11,000)

My first ticket was from Portland (PDX) to Auckland, New Zealand (AKL) on American Airlines with a stop in Los Angeles (LAX) and an intentional one day layover in Sydney, Australia (SYD). This ticket was First Class and cost a total of 72,500 American Airlines points with a dollar value of $11,000! As this ticket was on American and Qantas flights, I was able to search for and book the ticket online at aa.com. I booked this flight 10 months in advance as a one way award. (This ticket was purchased prior to American’s devaluation in early 2016- the current ticket cost for this same route one way is 90,000 AA Miles on a First Class saver award). Most of my miles on AA are earned from AA domestic flights and from my Citi AAdvantage credit card.

While the first half of my trip was booked very far in advance, all of the remaining flights were booked at the very last minute since I didn’t decide to fly home via Bora Bora until I was already in New Zealand.

AKL-PPT: 30,000 Miles (or $1,400)

Starting in New Zealand, I booked a flight from Auckland (AKL) to Papaetee, Tahiti (PPT) on Air Tahiti Nui using American Airlines Miles. The cost was 30,000 miles for a one way business class ticket at a cash value of $1,400 (or 15,000 for economy class). Booking this ticket required making a call to AA reservations as the tickets are not searchable online. It’s the only airline I’ve ever flown that gives you flowers for your hair and serves pre-flight mai-tai’s. (Also, I think I was also the only person on the flight traveling alone)

PPT-BOB-PPT: $220 each way in Travel Credits

Air Tahiti (not to be confused with Air Tahiti Nui) has a monopoly of the French Polynesian skies and is the only way to get to Bora Bora once you’ve made it as far as Tahiti. I flew PPT to BOB and came back to Tahiti via Moorea—another island that connected to Papaetee by ferry. The only way to hack this leg is with lots of points on a credit card with a “travel eraser” or cash back travel credits like my Chase Sapphire Reserve. The cost of the flight is about $220 each way and doesn’t fluctuate much. I booked the flight directly through airtahiti.com to receive travel credits on my credit card. The most important thing to know about this flight is that you want a seat on the left side on the way out and right side on the way back. Catching a view of Bora Bora from the sky is worth the cost of the flight alone.

* Note: if you make it this far, and are hoping to use points to stay at hotels in Tahiti and Bora Bora, you’ll want to stock up on Starwood, Hilton or IHG points. These are the chains that operate properties around French Polynesia. I used points from my IHG and SPG Amex Credit cards to cover my hotel nights.

 PPT-HNL-KON: 27,500 Hawaiian Miles (or $950)

To get from Tahiti back across the Pacific to the US, there are very limited choices of Airlines: Air Tahiti Nui, Air France, and Hawaiian Airlines–and not all of these airlines fly to the island every day. Since I had a stash of Hawaiian airlines miles that I’d never used after signing up for a Hawaiian airlines credit card, I decided to take the once a week Hawaiian flight to Honolulu (HNL) and then connect onward to Kona (KON) for no additional cost. An economy class ticket for the 5 hour overnight flight was 27,500 (at a cash value of $950) and bookable online at Hawaiian Airlines. The same flight was also bookable online via AA.com using American Advantage points, but cost more at 37,500 points.

KOA-PHX-PDX :$220 (or 20,000 miles)

Since I had to fly through Hawaii anyway, I took the opportunity to explore the big island for a few days before heading the rest of the way home via American Airlines. There were dozens of flights to choose at all times of day from on an assortment of airlines for about $220 or 20,000 miles on American. I went with a paid AA flight so the redemption value was low. Buying the ticket allowed me to earn qualifying miles and a paid flight allowed me to request a complimentary upgrade with my status..

All together, I saved more than $14,010 on flights by using points and miles!  But more importantly than getting something of high value for a fraction of the cost. I finally got to see Bora Bora for myself!

Roots and Regrets: Travel Lessons from Italy

255770_10200641354510145_265673010_nMy first trip to Italy was in 1993. I was a young and hip backpacker, too cool for the universe—as most teenagers are—and especially too cool for my family. Or so I thought.

Now that I’m much older and a little wiser I’ve come to realize that this whole time my family is awesome.

My family has deep Italian roots. My father is Italian. His parents were Italian. My great grandparents were Italians straight off the boat. (See above, those were the immigration papers of my Grandmother’s mother).

I don’t know enough stories about that boat and why the patriarchs and matriarchs of my “Italian-American” family came to the “new” world of their time. Perhaps they were “explorers” rather than “settlers”. Maybe this is where my genes of adventure come from. If I am cool now, it is only because it is hereditary.

There is one story that I do remember well about my learning my family history. Sadly, it is both my own story and a story of regret.

In 1993 when I took my very first trip to Europe, my Italian grandparents were alive. They religiously hand wrote me letters nearly every week during the duration of my first study abroad semester in London. I’ll never forget my Grammy’s perfect cursive penmanship or the way she and Pappy always tucked 20$ bills into their tri-folded drugstore notepad letters.

As the end of my time in the U.K. neared, I prepared for my first backpacking trip through Italy–Rome, Florence, Pisa, and Venice were on the list. I was excited, and in advance of the trip received one of Grammy and Pappy’s letters with a 20$ travel bonus! This time, however, the letter wasn’t the ordinary update with the regular news of their local Italian choir and spaghetti dinner club they hosted. In preparation for my first trip to Italy, they had carefully created a list of the names and telephone numbers of all of my relatives in the cities I would be visiting so I could connect with my roots. It was a treasure map.

Unfortunately, the thing about teenagers and treasure maps, was that I wasn’t smart enough to know the value of this letter at the time. It was just a piece of the same old drug-store notepad paper from my grandparents with the names of people I didn’t know on it. I put the 20$ in my wallet, tucked the address list into my Let’s Go guide, and hit the road!

As a teenager I thought of my relatives as the people who I saw at family reunions and funerals. They were the ones who brought funny Italian dishes like cold pizza with no cheese they called tomato pie, and pinched my cheeks, and always asked me if I remembered their names. (And of course I didn’t.)

One day in Florence, where some of the relatives on the list lived, I pulled out the piece of paper from my guidebook, admired Grammy’s perfect cursive, and picked up a hostel payphone. And then I got scared and put the receiver down. I didn’t know who these people were. Maybe they were somehow related to my ‘old’ grandparents, but I didn’t know them, I didn’t know what to say to them, AND they didn’t speak English. Game over.

I never made that call. I put the list back in my book and never looked at it again. I had assumed that I was living my once in a lifetime chance to visit Italy and I didn’t want to waste it with cheek pinching strangers who might serve me funny food and not be able to talk to me in 18 year old English. I had no inkling that I’d spend the next 20+ years traveling.

I’ve been back to Italy at least ten times since, and I’ve thought about this moment dozens of times. I’d give anything to be able to pick up the phone, dial into the past, and get to know the family on that list. I’d call them all and mumble in my best incoherent Duo-Lingo Italian.

Sadly, I lost that paper, and within a few years after that trip I also lost both of my grandparents who were my connections to these living stories. For some reason, however, I’ve never lost that memory of putting down the receiver and making that choice not to call.

Sure, it was just a phone call in the past that I didn’t make, but moments like these also go by another name. We call them regret, and regret strangely has a way of sticking around—even longer than estranged relatives and cold cheese-less pizza.

Perhaps regret sticks and stings because it so badly doesn’t want us to forget the lesson it teaches. She stays with us to remind us to run the other way from our fears and failures. Not to condemn, but to condition us for the better and to prepare us for the future. To make us stronger and more willing to pick up the phone the next time we get the chance.

I’m headed back to Italy next week, making my own mission to chase my roots into the village where my great grandparents came from. I’m not sure what I’ll discover, but I know one thing that won’t be hanging out there: Regret.

You may never get a rewrite of that moment from your past, but you do get to write the end of your story.

###

 

 

The Paradox of Settling

settledown - 1“When are you going to settle down?” As a wander of more than 20 years, this is the question I’ve learned to field at least once a week. Friends, family, people I date, random acquaintances, and readers of the internet inquire about my ability to “settle” all of the time.

“Settle down?” It’s a simple question, and most often  curious and well-meaning. Yet, on most occasions whenever these words enter my ears this question triggers my inner world into a mild state of panic.

Part of my brain screams “YES!”. Part of my brain screams “NO!”. It’s paralyzing.

What does settling down even mean for goodness sake? As a traveler who has built much of her existence on the premise of not being long-term geographically committed to one place, this question instantaneously triggers my self doubt to the very core.

For a long time I thought this inner struggle was a sign I must be broken, but eventually I realized that this is a trick question.

You see, there is no right answer to the “When will you settle down?” question, because, my friend, there’s a paradox in the very concept of settling.

In the strange universe of the English language, the word “settle” has multiple and very different—perhaps even contradictory–meanings.

Settle: verb

1) To stop, let something rest, to build a place to dwell
2) To accept or agree to something less than the best, less than satisfactory, or below what you want or deserve

When I hear, “When will you settle down,” my panicked brain translates these mystery words into a variety of other things like:

Why can’t you to commit to anything?” or “When are you going to stop chasing your dreams and start doing stuff like regular people?” or “Will you ever grow up?”

After 20 years of breaking out in a sweat trying to make sense of this question I’ve finally learned a couple important things:

1. The Question is Actually Not About ME

If you’re a traveler, most people actually don’t care, beyond a mild curiosity, where you go or how long you stay there. The asker is usually just wondering “Are you going to stick around for awhile?” This usually isn’t a question that comes from a place of judgment, rather people want to know where they fit into your life.

When you don’t see the people you love very often, “when will you settle” is often an indirect way of stating “I really hope you’re going to be around more.”

2. The Real Question is for All of Us

While wanderers commonly gets asked this question most often, the real question is a little different, and it applies to all of us:

Can you be settled without settling?

Maybe the question for you is, “Can you be in a fixed location without taking less then you deserve”, or perhaps, “Can you be at a place of contentment and stillness without being in a fixed location?”

I’ve lived a very non-traditional life for most of the last 20+ years. Although it seems to some on the outside that I’ve been wandering aimlessly, I have been very “settled” into a global community and cause. I have been at home in my purpose-driven wandering. I have been settled without settling for years.

Three years ago I chose to move to a place where I could build a more sustainable geographically-based home and community. While I’ve unpacked and settled into Portland for now, I’m less about “settling down” and more about extraordinary living from a fixed address. It’s less settling and more striving for the new things that I want–making decisions for important things that are bigger than me—community, home, relationships, roots, etc.

A permanent address or our drive to be location interdependent doesn’t determine a settled or un-settled life.

Perhaps you’ve lived in the same home for 20 years, yet have given up on your dreams to be a painter or a writer or a supreme court justice (I hear there’s a job vacancy). If where you live makes you happy, great, but perhaps it’s time to choose to change something if life circumstances have driven you to settle for something less than what you were born to be.

We only have one chance in this life after all.

Stop settling. Start living your dreams.

5 Lessons from a Half a Life of Travel

TRAVEL LESSONS - 1 (1)It’s official. I’ve now been traveling over half of my life. And I don’t regret it for one minute.

Now that I’m twice as wise as I was when I got my first passport stamp on 01/26/93, I thought I’d share a few of the hundreds of lessons I’ve learned from 23 years on the road. Be warned, these aren’t the normal things people tell you on travel blogs.

1. Travel Will Not Help You Find Yourself

You can read Eat, Pray, Love as many times you want, and wish upon a star that getting on airplane to a distant land is going to unravel all your emotional baggage, solve your life problem, and reveal who you truly are inside, but this is fiction. YOU are not lost, and you will not find yourself by traveling.

In 23 years of travel, I didn’t find myself at all. I became myself. Travel, like any other life journey, will press you and shape you, make you uncomfortable, and open your eyes to new things that will change the way you think about the world and perhaps even your place in it.

Of course, you will definitely get actually lost at some point, but even then you won’t find yourself. Hopefully you’ll find where you were meant to be, or enjoy the discovery you didn’t mean to have.
2. There is No Such Thing as “Location Independent”

In the past few years the concept of being “location independent” is the trendy new terminology in the travel scene. This is a fancy way to say quit your office job and apartment, and “live and work on the road.” As a way of life, there is merit in modern day long-term wandering, but as a self proclaimed title, this is nonsense.

None of us are ever independent—especially as travelers. We are always interdependent on whatever place we find ourselves in and on whichever people we find ourselves among. You are always somewhere even if you don’t have a fixed address or a permanent cell phone number. (I mean, you do need an address after all to register for your points and miles earning credit cards to fund all this travel).

Call yourself whatever you want right now and #hashtag the hell out of it until it stops trending, but remember you can’t go everywhere without being anywhere. And after a half life of traveling, you may very well wish you had nourished some roots along the way.

3. The More You Learn, the Less You Know

Travel teaches you a lot, but it isn’t like school. The lessons you learn on the road are not cumulative. They are actually kind of reverse cumulative (if that’s a thing).

For example, you plan a trip to Italy and read all the books in preparation to learn as much as you can about the history, language, people, and culture. Even if you learn a lot in advance, when you get there  you realize that you know very little. Then you stay for a few months or even a few years, and you realize that even though your knowledge has increased exponentially, you truly understand that you aren’t an expert on Italy at all.

The more you you’ve been exposed to, the greater your understanding becomes that you know very little. After nearly a quarter century and the memory erasing effects of chronic jetlag, I’m pretty sure I now know nothing. Thank God for Google.

4. The World, Like You, is in a Constant State of Change

It’s a fact, I look absolutely nothing today like I did in my first passport picture in 1992. I have changed not only in how I look, but also in how I act and think, and how I see the world.

Guess what, the world has also changed a lot in in the past couple decades.

Since I first started traveling, I’ve been to Thailand more than 100 times. (In addition to being obsessed with Thai food, I also have lived and worked there for extended periods of time). You know what? The Thailand of 2016 looks very little like the Thailand of 1997. The country is never the same twice. There is always something new to be discovered. And I’ll keep going back every chance I get.

I’ve traveled to a number of countries with my friend Chris who has been to every UN recognized country in the world (that’s 193 of them if you’re wondering), and even he has barely scratched the surface of the globe (he also knows very little-see point 3).

My friend Lisa has a pet peeve about people who talk about “doing” countries. I like to say, “Oh, we did Colombia for Christmas,” because the thought of “doing” a country, and checking an entire nation and people group off your bucket list makes her crazy.

No matter how you personally feel about this terminology, countries aren’t something that you “Do”. They are art, life, and culture in motion. You can only experience a place in its present moment. Some countries you may go back to experience again, the others will keep right on changing after you’ve graced them with your presence and departed. They aren’t waiting for you to return to continue their progress.

Keep count of your countries, continent, and passport stamps however you like (and enjoy counting—it’s fun). But remember that you’ll never be done. The world is on constant refill. There will always be more to experience.

5. You CAN Start Any Time You Want

The pictures in my series of expired passports prove it. I’m not the young backpacker I was in 1993. I know less, I care more, and I like to shower when I travel (even on an airplane sometimes). Sometimes I have the fleeting thought—“Maybe you’re too old for this, maybe you should finally settle down.” And then I snap back into reality and remember this truth: There are NO age limits to travel. In fact, I’m pretty sure I’m still just getting started.

 When I climbed Kilimanjaro, I distinctly remember my guide telling the story of a 80+ year old woman he led to the summit a year before. Maybe he was telling that story to encourage us up the mountain on our 6th day of trekking in hail, but nevertheless, I hope in another 23 years, I’ll be that grandma training for Everest.

Traveling doesn’t care if you’re young or old. Families are traveling long term, empty nesters are spending their retirement on the road, heck, even elderly ladies have traded in knitting for mountain climbing.

The world is more accessible now than ever before. You don’t need any special skills to get on an airplane. The cost of international travel is no longer prohibitive. In fact, the airlines and credit card companies have made it easier than ever in history to fly for nearly free.

If you want to travel—be it a single getaway to a destination you’ve been dreaming about or selling all you have and trading in your 9-5 for a life of living and working on the road—it is possible.

What are you waiting for? Get out there: Find yourself, be location independent, master the world, and do as many countries as possible.

Or maybe just enjoy the journey, love the people you meet, and try to learn as much as you can along the way. You and the world will be much better because of it.

Onward.