If you can afford to travel, you’re luckier than an enormous chunk of the world’s population. Be grateful that you were born in a country that’s safe and stable. Be grateful you have a passport that allows you to easily travel. Be grateful that you have your health. Be grateful you were able to get a job; that you had the ability to save up enough money to travel. Yes, you worked goddamn hard to get to this point, but you’re still unbelievably privileged. Never forget it.
If you can afford to travel, you’re luckier than an enormous chunk of the world’s population. Be grateful that you were born in a country that’s safe and stable. Be grateful you have a passport that allows you to easily travel. Be grateful that you have your health. Be grateful you were able to get a job; that you had the ability to save up enough money to travel. Yes, you worked goddamn hard to get to this point, but you’re still unbelievably privileged. Never forget it.
I travel a lot for work, from Florida to Vegas to Ecuador, and I’m usually on a bus, train, boat or airplane! I visit trade shows, I speak at conferences, and I visit clients. The key to success when you are constantly traveling is organization. I have a written day planner where I can see my week at a glance, which helps me prepare my flights and schedule, as well as not overlap or miss any details. 

“You’ll likely need to wash your clothes at some point, and carrying around a big bottle of Downy or Tide isn’t even enjoyable when you’re not toting your belongings on your back. My suggestion? Bring a ziplock baggie of powder detergent, and extra gallon size ziplock baggies (these come in handy in more ways than you can imagine). If you find yourself sans-washing machine, you can make your own by stuffing water/laundry/soap into the bag and giving it a little (okay, a lot of) shake. Rinse in water and voila: clean clothes. Easy peezy, fresh and breezy!”
It’s very important to have copies of such documents, should you lose them and then require emergency assistance. To cover all eventualities, scan the documents and email them to yourself, then save the email somewhere where it is easily accessible. I would also recommend taking photos of them on your phone and saving them to your favorites. It is also a good idea to make some photocopies of these documents. Keep a paper copy for yourself in your important documents folder and leave copies with your next of kin. That way, if you need help and can’t get hold of your copies for any reason, they can act on your behalf quickly with all the necessary information.
I travel a lot for work, from Florida to Vegas to Ecuador, and I’m usually on a bus, train, boat or airplane! I visit trade shows, I speak at conferences, and I visit clients. The key to success when you are constantly traveling is organization. I have a written day planner where I can see my week at a glance, which helps me prepare my flights and schedule, as well as not overlap or miss any details.
Sure, you should have a rough plan for your trip, but don’t book everything in advance or you’ll likely feel too restricted and end up regretting it. Book a one-way ticket and your first few nights of accommodation — you’ll figure the rest out along the way. It’s not as intimidating as it sounds. If you’re in a tourist destination there’ll always be someone who’s willing to take your money by giving you a place to stay.

So many people email me for advice on their itineraries and I nearly always go back to them recommending that they visit half the number of places. You’ll enjoy your trip more if you work in rest days, and you’ll get a better taste for a place if you spend more time in it. Don’t plan a trip that has you jumping from capital city to capital city every few days. And take account of travel time! Don’t be like two nights in Bangok, two nights in Phuket, two nights in Koh Phi Phi, when it’ll take a day to travel between them all, leaving you with one day to actually see those places. Oh, and you’ll likely be jetlagged, too, so you’ll want to take that into account too.
Your best bet for flexibility in these areas comes if you book your stay during the shoulder season when the owner might simply be pleased to fill an otherwise-open weekend or midweek-to-midweek slot. The additional savings in that case might be on your flights to and from your destination, because you won't be paying exorbitant weekend fares to get there and back.
Whether it’s that steamy romance novel, thrilling sci-fi, or a dog-eared travel guide, download it before your trip.  Even if at home you’re a paper-til-I-die sort, save the space and weight for your holiday.  And don’t count on wi-fi to jump back into the story from your perfectly positioned beach chair.  Make sure it’s on a water-resistent covered device (check out Otterbox for some serious protection for your cherished e-reader, phone or tablet).
“I’m a firm believer that everything you need for a trip — whether it be three days or three weeks — should be able to be packed in a carry-on. This is simple once you master the art of layering your clothes. Choose a color combination for your attire and pack only pieces that match this so that you can mix, match and layer to create different looks (instead of packing completely separate outfits).”
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