How to Plan a Long-Term Trip

woman standing on bridge touching her pink hat__long term tripIf we’re stereotyping, American travel tends to have the same “go, go, go” mentality that the rest of our lives do. We like to cram things in to try to get the most out of the few PTO days we’ve been able to string together. Micro trips can certainly work, but if that’s all you normally do, you may feel lost trying to plan a long-term trip.

Long-term trips are a marathon, not a sprint, and they require a total shift from the typical short-term trip planning mentality. Here, we’re walking you through how to plan a long-term trip with a series of questions. A choose-your-own-adventure, if you will.

Step 1: What are your goals? What’s your travel style?

Whether you’re backpacking through South America for the next six months or spending three weeks in Paris trying to have a writing breakthrough in cafés, decide now what you want to get out of this trip. Maybe you need a long break after leaving a stressful job, maybe you want to gain a sense of independence, or maybe you want to meet a bunch of new people. These goals will help you guide you through planning your trip and help you decide things like location and duration—if you don’t already have that figured out.

You should write your goals down and use them to lead you as you plan the rest of the trip. It’s tempting to want to do everything when you’re traveling, but defining your priorities will help you cull the trip to only the things that will be best for you. For example, if your goal is to rest, getting on a train to a new city every three days probably isn’t the right route for you this time.

These goals will also help you determine your travel style. Are you a backpacker staying in hostels? An adventurer hoping to hike, ski, scuba dive, etc.? A more luxurious traveler who wants a nice hotel at every stop? Your travel style will also help you plan your route, activities, and priorities. 

Step 2: Where are you going, and for how long?

Using those goals as a guide, start to map out where you want to go over the course of your travels. Unlike on a short trip, you don’t have to plan out every moment in order to maximize your time. You may even have time to research more options once you’re there. It’s a good idea to have a loose schedule of which cities you want to visit on which days, including hotel options and an idea of transportation. We recommend booking your hotels and transportation ahead of time. You’ll still have the flexibility of your days without the stress of finding somewhere to stay last minute or frantically searching for train tickets in an internet café.

Step 3: What’s your budget?

Budgeting for travel is much more important for a long-term trip than a short one, and that alone is a good reason to plan your trip out ahead of time. Your budget might also determine some of your goals and locations. It’s much cheaper to spend a few weeks in Southeast Asia or South America than it is in Europe. But if you’re set on Europe, more popular tourist countries like Spain are typically cheaper than Nordic countries or Switzerland. Do your research on the average price of hotels, meals, and things such as museum and train tickets before you get there. This can help you determine how much you will need to spend per day and how much wiggle room you’ll have.

While on the trip, track your spending diligently, and keep your trip priorities at the front of your mind. If it’s most important for you to go to museums or to buy a ski pass in the Alps, don’t blow your money on gourmet food.

Step 4: Have you thought about the details and documents? What about insurance?

Depending on the countries you visit, there are different visa and tourism requirements. You absolutely need to research these before you get there (Travisa is a good resource for this), unless you’d like to be shipped directly back to where you came from. Many countries will require evidence of an outbound ticket when you arrive—they want to make sure that you aren’t planning to stay in the country. This means you’ll have to think at least one step ahead throughout your trip. Always carry a photocopy of all important documents with you, and have them saved somewhere online or on your phone.

Check in on the status of your passport before you leave as well. Many countries will turn you away if your passport is due to expire in 60 days or less, or if you have less than two pages remaining. Also, if you’re planning to drive while abroad, you may need an International Driving Permit.

Consider travel insurance and/or additional health insurance if you’re traveling for more than a week. Many long-term travelers recommend World Nomads for travel insurance but be sure to research your options. (There are some travel insurance sources that we don’t recommend.) Plan visits to your doctor and dentist before you go to get any necessary vaccinations and make sure everything’s in order.

Step 5: Are you packed?

When packing for a long-term trip, minimalist packing is the first priority. Depending on your travel style and how often you plan to switch locations, you might want to invest in a backpack. Roller bags are notoriously difficult to deal with in Europe, with cobblestone streets, winding staircases, and few elevators. Whatever bag you choose, stuff it with light layers.

It’s also a good idea to bring packing cubes, or something else you can use to segment your bag easily. You can use these to separate dirty laundry, swim gear, cold wear accessories, or other categories to stay organized throughout your trip.

Before you pack, be sure to check the bag weight limits for all the airlines you plan to fly. While U.S. airlines don’t typically weigh your carry on, some international airlines (especially budget airlines) definitely will.

Step 6: Book Your Hotels Through

When planning a long-term trip, you’re going to need at least one, two, maybe 12 hotels to stay in along the way. That’s where we come in. We make it easy to search for hotels all around the world, and we’re the only site that lets you compare rates against exclusive loyalty member rates to save you money. No matter if you’re booking a room for five nights or 20 nights, simply visit, enter your destination, filter by amenities, hotel brand, price, or loyalty program, and you’ll be well on your way to booking your hotel at the best rate available. With Roomkey, there are no tricks. Just travel.