Leaving for a holiday can be stressful enough – even if you have weeks to get ready it seems like we all are always packing up the night before. But when sorting out a trip of several weeks + (or months, as the case may be,) there are a whole host of things to consider. So often people don’t take that trip they’ve always wanted because the planning is overwhelming and feels as if you’re dismantling your life brick by brick – but it can be streamlined and seamless when planned properly.


Several months before

1-       Get your passport

If you don’t already have one, passport applications take about 2 months to process so it’s best to get one early. Additionally make sure that your passport is valid for at least 6 months past the end of your trip. Many countries have visa policies that require your passport have at least 6 months of validity left before crossing their border.

2-       Budget!

Icelandic Króna

Icelandic Króna

This is pretty much a given, but unfortunately finances dictate a significant part of planning your trip. Depending on the region you’re visiting (and the style of your travel) your daily expenses will vary. And be generous to yourself – even if you expect to be getting by on a few dollars a day, budget as if you’ll have unexpected expenses. An important part of budgeting is knowing what you want to have left over when your trip is over. Will you need to put a safety deposit on a new apartment upon your return? Hire a moving company? Consider all your possibilities.


3-      Handle your housing situation

If you’re a renter, make sure you understand your rental agreement and give your landlord proper notice of your plans. Find someone to take over your lease and make sure the contract is signed over to them so that you are not liable for the property in your absence. If you own your home, consider renting it out if you are not in the market to sell. Either way, inventory what you own and decide what you might be able to sell.

4-       Travel vaccinations

See your doctor and determine which travel vaccines you’ll need for your trip. Several types of vaccines will take 2-3 booster shots to be 100% effective, so it’s good to begin getting shots a few months prior to departure. Rabies, Tetanus, Hep A, Heb B and Typhoid are typically recommended, especially in Southeast Asia and South America, but the case varies by country (for example, some country’s immigration policies require documentation of a yellow fever vaccine to allow entry.) If you do leave this till the last minute, booster shots will be available in major cities throughout your trip. Talk to your doctor about anti-malarials as well.

5-       Decide on travel insurance

Travel insurance is a must. Not only are you protected medically as you travel, but most travel insurance policies will reimburse you (up to a certain amount) for stolen or lost property, cancelled flights or interruptions or even emergency travel back home. Most policies will run you only a few dollars a day, and it is worth every cent if you lose your camera, you break your leg hiking, get malaria, or a relative dies and you have to fly home. Here at Don’t Stay Put we use World Nomad travel insurance and we’re really happy with our policies.

6-       Research visa policies


Embassy of Myanmar in Bangkok

Depending on your nationality, you may be eligible for visa-on-entry for many countries (this means filling out a short form/paying a fee at immigration to enter a country.) For this, you often need local currency, USD or Euros to pay the fee (the neighboring country’s money is not usually accepted,) and will sometimes need passport-size photos to affix to applications. Plan ahead for both of these situations. However, there are plenty of countries that require you to get a visa before arriving, and this number grows if you aren’t a citizen of the US, Canada or EU (these policies largely go back to inter-country treaties.) Make sure you do your research before and get all the visas you can from your local embassy to avoid (potentially very expensive) headaches on the road.


7-       Begin to responsibly tie up your employment

When leaving for an extended trip, it’s so easy to begin to clock out mentally of your job entirely, but remember that you don’t want to sever ties for your (possible) return. It’s true that opportunities may arise on the road or traveling may realign your goals and pursue something else, but assume that it might not. Many companies are beginning to offer sabbatical policies for employees to take a few months off to travel with the opportunity to resume their position upon their return. If not, leave on good terms with your coworkers and continue to network in your professional community. If you need a job in your field after your travels, they’ll be more likely to refer or recommend you.

1-2 months out

1-       Research intra- and inter-country travel

KTX train in Korea

KTX train in Korea

The actual travel part of your travel can cause the most logistical headaches. Transportation can be expensive, buses can be dodgy, boats sometimes just don’t run and airlines might be unreliable, while motorbikes may increase your opportunities or hitchhiking could be super safe and widespread. Beyond that, some border crossings are complete mayhem while others just a hundred kilometers down the border are seamless. This isn’t to say that you should plan out your route precisely, but knowing what your options are will help save time, money and stress when you’re actually traveling.


2-       Look into new credit cards

Even if you’re totally happy with your credit card now, but before you travel check and see what your bank’s policies are. Are there international fees when using your credit card? Will you be charged $5 each time you make a cash withdrawal overseas? What happens if you lose your card in Jakarta, or it keeps getting declined throughout France? Can you call a customer service representative to pay your bill in case you can’t access wifi? It might be pragmatic to choose another card to use while traveling.

Chase Sapphire Preferred Credit Card is a good credit card, charging no international fees when used and offering excellent customer service worldwide at any time. And to eliminate those awful ATM fees, check out debit cards from either Charles Schwab or Capitol One.

3-       Go to the doctor and dentist!

This is a must-must-must. We can all get quite lazy about visiting the doctor and dentist in our day-to-day lives… we’re busy, appointments get dropped, whatever. But you’re even less likely to see out a teeth cleaning in Brazil. You’ll probably already visit your doctor to sort out travel vaccinations (or you should be,) but insist on getting a full physical check-up just to be on the conservative side. And start flossing!

1 month before

1-       Suspend your phone plan, car insurance, subscriptions

This can be the most exciting part of planning your trip, when the entire process becomes tangible, like turning off certain switches of your life. Any charges you’d have to pay during your trip that can be suspended should be. A lot of phone companies are beginning to offer several month suspensions during contracts, so that can help you avoid paying contract cancellation fees. Magazine subscriptions, cable and internet… anything that won’t be used while you’re away should be suspended or cancelled. Having financial ties at home slowly draining from your travel account can be one of the most stressful things on the road.

2-       Get your phone unlocked

Even if you’re only spending a week or two in a country, getting a SIM card is easier than ever, and super cheap. Phone companies in the US are a bit skittish about unlocking your smartphone, especially if you got it from them as a contractual deal, but tons of services are out there that will unlock your phone for a small fee. This essentially means that it is no longer explicitly tied to your carrier. Then when you’re traveling, you just pop in a $1 SIM card, load it up with a bit of credit, and you have a phone number for [wherever.] There are pretty reasonable 3G plans for SIM card users, too, often just a couple of dollars a week.

3-       Make necessary accommodation plans

Treehouse bungalow in Koh Rong, Cambodia

Treehouse bungalow in Koh Rong, Cambodia

Are you traveling during high season? Are hostels and guesthouses available or is it an area that you might need to arrange homestays or hotels? Will you be camping? Is there a treehouse overlooking the ocean you’re dying to stay in? Are you looking to Couchsurf? It’s best to take a look into what options you’ll have for accommodation, even if you don’t book quite yet. It’s totally great if you’re the type who prefers to rely on the whole turn-up-and-sort-it-out-then model, but have some back-up plans in mind.



4-       Choose your luggage

Your backpack will basically become an extension of your body, and if you don’t get something comfortable and with the specs that you want, you’ll regret it fully.  You’ll want something durable and appropriate in size for your trip (always scale down… it’ll prevent you from overpacking,) that is sized for your body and needs.

5-       Packing list

Obviously what you decide to bring with you is a big part of trip planning, but it’s where people really seem to stress out and overdo it altogether. The best rule to follow is to assemble what you want to pack… and then cut the pile in half. You will absolutely not need as much as you think you will – and especially if you are living out of a backpack, you’ll appreciate having downsized.

6-       Automate your bills

So you’ve already canceled the pertinent subscriptions and services, but there are bound to be some bills that you need to continue paying – implement a plan to tackle those before you travel. This could mean scheduling payments for student loans or car payments or automating your credit card bill payments to avoid accidental late fees (it’s easier than anything to totally forget the date when you’re on the road.) But it’s also a good idea to designate a power of attorney over your finances at home or give someone you trust access to your bank account in case of emergency.

7-       Stock up on over-the-counter medicines that you are used to

There is nothing worse then when you’re traveling and poof… you get sick. Not much else brings your holidays to a screeching halt more than an upset stomach or head congestion. But what can extrapolate matters more is when you drag your tired, grumpy self into the local pharmacy and have absolutely no idea what will make you feel better. Ginseng taro root paste? Something something something-cycline? You’ll be really glad you stowed those antacids and decongestants when the time inevitably comes that you’ll need them.

And don’t stress out! Planning a trip can honestly be one of the most rewarding parts of the entire journey. Be flexible and know that your schedule may change 100% from the day you begin planning until the plane ride home. It’s all part of the adventure.