How I plan my backpacking trips

Having spent 4 months in Asia this year, the number one question I get about my travels is: “How do you plan such a long trip?” For those curious, I thought it would be interesting to share how I do this.

To sum up my method: I do plenty of research before the trip, but I don’t book most things until I get there. I’ve found that booking things on the fly opens up adventure and allows for taking advice from backpackers along the way. I also don’t feel guilty for changing plans and losing out on money for things already committed to.

I’ll never forget when I saw a flyer for a remote hostel in Kenya and hopped on a bus that very day; to when some friends told me about a mushroom farm in Guatemala, and I hiked up a mountain to meet a group of young farmers…experiences I probably wouldn’t have if I was tied down by existing reservations. At the same time, I’ve slept on a park bench in Greece and knocked door-to-door for a bed late at night in Costa Rica…over years of travel, I’ve certainly learned the importance of having structure and knowing where you’ll spend the night.

From long-term travel to short-term trips (~1 week), I’ve developed a method that has worked well in balancing spontaneity and peace of mind. So with that, let’s get to it!

Village in Kilifi, Kenya, 2019

Before the trip…

As I mentioned, I do quite a lot of research before a trip. That’s my type A personality coming in. šŸ˜‰ For long-term travel, I’ll research each country as I go, starting ~2 weeks before entering the next country:

What to research:

  • Draft a list of cities and do a “vibe check”: After picking a country, I start off broadly creating a list of any city that might be interesting, mostly through travel blogs. Blogs are my favorite way to devour content (surprise, surprise šŸ˜‰ ). Once I have my list of cities, I try to get a better sense of the vibe in each city to narrow things down. For this, I like to supplement my research with travel forums, Facebook groups, Google images, and Youtube. Ultimately, the goal of this first step is to create my own opinion about a place.
    • This might sound obvious, but just because a place is highly recommended, it doesn’t mean you need to do it. I actually experience reverse psychology, where if a lot of blogs recommend a place, I don’t want to go there. šŸ˜› I often find myself going into the depths of the internet to find what’s right for me, but it’s well worth soul-searching to craft your ideal trip. For instance, when I researched India, every resource recommended the Golden Triangle…I realized I didn’t want to spend time in these crowded cities; so I instead decided to volunteer at a hostel in the Himalayas.
  • Map out the country: Once I have my “short list” of places, I like to map things out on Google My Maps. I’m a very visual person, and understanding where places are in relation to each other is helpful to figure out ordering.
  • Research transportation: Once I have a sense of geography, I like to look up how to actually get from point A to B. This is an important step as I’ll often scratch cities if getting to them sounds miserable. My favorite source is Rome2Rio, where you can input any two cities and it will spit out all your options. If there’s no info online (especially for countries without good infrastructure), Facebook groups are good for getting feedback.
  • Create a general outline: Finally, with all this info, my last step is creating a general outline of the country – not booking anything yet, but just creating a high-level roadmap. Most of the time, I don’t stick with the plan exactly, but it’s helpful to generally know where I’m going.

So we’re done with the research phase! But as I mentioned, most things are booked on the trip itself. Here are a few crucial things to book before a trip.

What to book before the trip:

  • International flights (in and out): Personally, I don’t like having an outbound flight because I like to have flexibility in leaving a country, but after too many incidents of being rejected by Immigration for not having an outbound ticket and scrambling to book a flight on my phone, I now make sure to have this covered.
  • Hostel for night #1: The only accommodation to book beforehand šŸ™‚ – everything else can be booked as you go. More on this below.
  • Visa / COVID tests / health insurance – Important especially during COVID travel, as tourist visas may not be issued on arrival. Make sure you know what paperwork to bring to immigration to fulfill their requirements.

Other helpful things to know before the trip:

  • Recent events: I think it’s important to stay in tune with current events before visiting a country in case you need to take precautions. In 2019, I booked a trip to Sri Lanka, but after the Easter bombings, I canceled the trip 2 weeks before my flight….what a blessing to finally make it this year. šŸ™‚
  • FOR WOMEN – how to dress: This one is very important, especially after experiencing harassment during my gap year – when in doubt, dress conservatively and try to blend in!
  • Phrases in local languages – Nothing crazy here. At a minimum, I like to know “hello” and “thank you” to show respect.

On the trip

Finally, we made it to the trip! Here are all the things I like to book on the trip itself to have flexibility and incorporate advice I get along the way.

What to book on the trip:

  • Hostels: Besides night #1, I like to book my hostels day-by-day. Even in high season, I’ve found that there is usually more supply than demand. It’s easy to extend day-by-day in most places, so I can have flexibility on when to leave a place (#commitmentissues). Worst case, if the hostel you’re staying in is full, you can just pop by one down the street. Hostelworld and Agoda are my go to’s.
  • Activities & tours: I usually find things to do once I get to the actual city by talking to hostel staff, locals, and other backpackers. Nothing beats word of mouth. šŸ™‚ My preference is to join tours through my hostel with other backpackers.
  • Transportation: Booking transportation is easily done in person or online when you get there – trains, buses, motorbike rentals, and even domestic flights – I’ve never had any issues booking these last minute.
  • Other places not on your radar: Almost all my memories of getting “off the beaten path” have been from talking to people on the ground. And hopefully with this method, you’ll have plenty of flexibility to pivot plans if you hear about a cool place.

I hope this was insightful. Let me know if you do anything different or want to share your own tips too. I love hearing from you. šŸ™‚

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