Two years ago when I began planning my first trip to Costa Rica

I went a little crazy.

I spent countless hours reading every page on Lonely Planet’s website.

I contacted hundreds of property owners for vacation rentals.

I booked my flight and accommodations months in advance.

I did everything I could to predict and control my experience.

But in reality, I couldn’t.

Did I mention I used to be a control freak?

One of the most amazing things about travel is that you simply cannot anticipate how you will feel when you arrive, what adventures and misadventures might transpire, nor the people and places that will steal your heart.

Since then I have taken trips with no guidebook, no plans, and no preparation.

For me, that route was stressful.

I found myself planning the trip while I was on the trip.

Reading guidebooks and doing online research in my hostel was hardly how I wanted to spend my last day in Seville before booking a last minute ferry to Morocco.

Arriving with no plan late at night at the border in Nicaragua was less than ideal.

I have learned that I enjoy my time best when I have created a general itinerary with transportation connections, scouted accommodations, and researched tours before departing.

I like to be well researched but also need flexibility to feel free to stay longer if I like the place and to get the heck out if I’m hating it.

Decide Where to Go

The first step in planning for travel is (obviously) determining where it is you want to go. In this immense world filled with beauty and diversity this step can often be the hardest.

I have usually chosen my destination based on my gut. Where is your heart longing to go? Remove all rational for a moment and consider a place that gives you wanderlust.

Now return to practicality. Can you budget the flight expense and the cost of living in that part of the world? Do you have enough time to truly wander and explore it? I am a firm believer that you are capable of doing anything you really want. Decide that with practical considerations in mind, this is still where you want to venture. Remember that if you want to travel again you will. There is no reason why you can’t see every single part of the world your heart longs to know.

Once I’ve chosen an area of the world I usually make a list of the top places in that region I’m dying to wander. This is particularly helpful if you do not have unlimited time to travel.

For instance when I had only one month to spend in Europe I chose Barcelona as the top place I wanted to see. I designed my trip around visiting that location and added in Lisbon, Lagos, and several destinations in Morocco.

For first time backpackers in North America, I highly recommend Central America. It’s an inexpensive flight and is close to home in case you run out of money. There is an excellent tourist infrastructure with awesome hostels and a strong backpacker culture.

If you don’t speak Spanish, most people speak at least a little bit of English and in tourist/expat towns you may not need to use Spanish at all. However, Spanish is a very easy language to learn and I do highly recommend learning some phrases and practicing as much as you can. The depth and ease of my travel experiences increased exponentially when I learned to speak the local language.

Culturally Latin America is more similar to North American culture than many other parts of the world. In my opinion it is a great introduction to extended travel.

Plan Your Route

When planning my route there are several questions I consistently ask myself.

What kind of experience do I want?

This factor will differ greatly for everyone.

I have taken trips where I wanted to simply relax and spend weeks or even months in one destination. I have also hopped from one town to the next every few days trying to get a flavor of the country as a whole and see as much as possible in a short period of time.

Neither is better than the other. They are different styles of travel that will offer different experiences.

My most recent backpacking trip in Costa Rica I decided that I wanted to spend time on beaches exclusively. I literally did not visit one site in Costa Rica that was not oceanside. I’m almost embarrassed to admit it. Does it make me sound like an ignorant traveler?

Yes there is more to Costa Rica than beaches. It has amazing parks with volcanoes, animals, and gorgeous vegetation. It has lovely indigenous people living in hillside towns. But I’m happiest near the ocean where I can lay in the sun and swim in the sea at least once a day.

Remember, this is your trip and you can design it any way that you want. Do what makes you happy!

How much time can I allow?

How much time I have to travel significantly affects my itinerary. I’ve typically planned backpacking stints of a month or two broken up by several months of relaxation in Puerto Viejo.

The truth is, backpacking can be really exhausting and it’s nice at times to have a home base. Historically two months has been my limit.

My upcoming trip to Southeast Asia will be my first time traveling with absolutely no time constraints. I also will need to work while I’m abroad to continue to fund the trip.

I’ve tried to cram a lot of places in a short period of time in the past. This trip I am hoping to really go slowly and find beach towns in different countries to call home.

How much money can I budget?

The places you go to and the speed of your travel will in part be determined by your budget. The least expensive forms of travel often take the longest and the longer you spend in each destination the less money you’ll need on a daily basis.

Cooking your own food, finding free activities, and enjoying accommodation discounts are much easier the longer you spend in a destination. My last trip to Puerto Viejo I purchased 100% organic groceries, lived in a cute apartment across the street from the beach, took yoga classes daily, used a bicycle daily, and occasionally took taxis and went to restaurants. I spend $700 per month. Compare that to backpacking in Costa Rica where I slept in hostels, took chicken buses, ate lower quality food, and occasionally took yoga classes, and spent $1200 per month.

What is the weather pattern?

If you are traveling during the low season or in countries with different climate zones, the weather may predict your itinerary.

If you definitely want sunny beach days, be sure that you are traveling during the dry season. If you can’t stand the cold, don’t go to the desert in the middle of winter.

I chose to begin my trip to Southeast Asia in the North of Vietnam because the weather is beginning to turn cold. I’m a baby in cold climates. It’s currently monsoon season in Thailand, which means that by the time I travel through Vietnam, Cambodia, and Laos, peak season will just be beginning.

When are festivals and holidays happening?

Attending festivals across the world can be an amazing way to experience local culture. I partied London for the famous Nottinghill Carnival, witnessed a Caribbean maypole celebration on Little Corn Island, and booked a last minute flight to the US last summer to attend a Fourth of July blockparty.

Keep in mind that festivals and holidays can also detract from your experience and make travel very difficult. In Morocco during Ramadan most local restaurants were closed during the day, which made tasting street food a challenge. I made the mistake of heading to Cartagena on New Year’s Day and spent hours finding a place to sleep. Puerto Viejo is positively dreadful during Easter week, a lesson a learned most recently.

In my experience national festivals are lovely to visit but holidays can be a total headache. Chiang Mai’s Lantern Festival looks incredible and I may rush through Vietnam, Cambodia, and Laos to make it there in time. I will be overseas during Christmas and New Years again this year and plan to stay put wherever I am at least a week before Christmas and at least a week after New Years.

What countries are cheapest to fly in and out of?

What dictates where my trip begins and ends is usually flight cost. I research on kayak.com which countries are least expensive to fly in and out of from my home country.

In Central America San Jose, Cancun, and Panama City are usually the least expensive locations to fly to and from the US. Bangkok appears to be pretty consistently the cheapest flight destination in Southeast Asia. In Europe London is far cheaper to fly to than other places, so it’s worth it to just fly there and book an inexpensive Easy Jet flight onward.

Find Accommodation

I’ve found guidebooks to generally be unhelpful on this front. Reviews and photos are key, so I do most of my research on Trip Advisor, Hostel World, and Hostel Bookers. Typically I scout out the places I like but wait to book until a couple of days ahead of time.

If you’re looking for a free place to stay, Couch Surfing might change your life.

VRBO and AirBnB are good options for housing rentals, but I’ve found that they are way more expensive than homes rented locally. Especially in developing countries. You can usually find much better and cheaper housing rentals (if you’re staying somewhere long term) by first showing up, connecting with some expats and finding the homes that are being rented at local rates. You can also join groups on Facebook created specifically for the local community.

Create an Itinerary

Remember my crazy anal budgeting spreadsheet that I use when I travel? Well guess what? The geeky fun never stops! I also make a super obsessive spreadsheet when planning my trip.

Hey, I like to be organized people.

Here’s a sample of what I include:

Ok sorry, I realize that is impossible to read because it’s so tiny.

I include a column for the location, the date range I plan to span in the area, how to get there (in serious detail), how much time it takes to get there, how much it costs when I get there, where I plan to stay when I am there, and the highlights of the area I want to see.

Still with me?

To download your own spreadsheet and get a much closer look, click here.

You can either select file > download, then choose to download it as an excel file or you can select file > make a copy to have your own version in google docs that you can edit as you please.

Travel Planning Tips

These are some basic insights I’ve gained after planning many trips. Take all of them with a grain of sea salt.

Get your visa organized before you leave to avoid some serious stress.

I’m in the process of doing this now with Vietnam. I have this strong desire to just wing it, but don’t worry I’m taking the responsible route… just very last minute. I’m printing out my travel photos for onward travel between borders, filling out my forms, and getting my ducks in a row before I arrive. Airport security and customs officers can be scary!

Book a one way ticket if you feel so bold.

I always fly on a one way ticket to give myself as much flexibility as possible. If I time it right I end up paying the same as a round trip ticket for both legs. If you decide to fly one way make sure to investigate if the entry country or airline requires proof of onward travel. In the past I’ve purchased inexpensive bus tickets and have made fake flight itineraries for myself and others. I know, I know, I’m a criminal. Please don’t judge me.

Prebook your airport transportation the day you arrive.

I get really overwhelmed when I first get off of an airplane. Flying terrifies me and I never sleep on the plane so I’m a frazzled wreck at the taxi line. People can see this and it makes me vulnerable for those who want to take advantage of me.

By arranging transportation ahead you can avoid some of the stress. Booking a shuttle through your hotel or hostel, though expensive, is usually a good call unless you speak the language or have been to the country before.

Prebook your first two nights only.

If you haven’t realized this already, I do not like booking anything ahead. To feel secure I usually research different hostels and add them to my spreadsheet, but only book the first two days of my trip so I have the option to stay for more or less time if I want.

This pattern has gotten me into trouble during the high season in Europe. We’re talking sleeping on a loveseat in the hostel lobby. If you will be traveling during a time when everything is booked, ahem August in Ibiza anyone, obviously book ahead.

What steps do you take when planning long-term trips abroad? Do you plan your trips totally differently from the way that I do? Share what works for you in the comments!