Planning your first solo trip 101

Planning your first solo trip can be an anxiety-ridden experience. It seems like all the Instagram travelers know EXACTLY what they’re doing. Like, what’s the secret? Where do I go? How do I find cheap flights? Do I stay at hotels or hostels? What do I do while I’m there? How long should I stay in each place?


I promise you, I have been there. Here are some tips for the absolute beginner and feel free to ask any questions in the comments section below!

First, you have to decide where to go.

Where do YOU want to go? Most Americans find Western Europe and South East Asia to be ideal first round backpacking destinations. I skipped straight to Africa because I like something a little different, but it’s completely up to you. Don’t even ask the fucking question okay - YES, you will be safe. Only consult the website for information on visas, NOT on safety. Seriously, they post the most sensationalist safety warnings. I’m pretty sure they said Australia was a serious threat last year.

Only threats Australia makes are ones to break your heart with all the sexy beasts born down under!

Only threats Australia makes are ones to break your heart with all the sexy beasts born down under!

Second, you have to get your flights over there. Check out  this post on my favorite travel sites for cheap tickets.

Now, I assume you are traveling to numerous countries and that you have an idea of what these countries are. The question now becomes, what cities should I visit and how long should I stay? This can be the tricky part and requires some solid research on your end. You can consult Lonely Planet, but take it as a starting point. If the book has been published any more than a year ago, it’s probably somewhat outdated. Your best bet is Google and your own intuition. I personally cannot stomach more than two days relaxing by a beach, so I would only pass through an island briefly. I also don’t have much interest in going to most museums so I skip that shit too. But if there’s a bike riding tour of the city or bungee jumping or fantastic breweries in the area or gorgeous hiking, I spend more time there. So find what interest YOU. Sometimes it helps to literally make a list of what you would do every day. By doing this, you ensure that your day is packed  exactly how you want it to be. You don’t have to stick to this list, obviously. You want to be malleable. But it does allow you to see on paper how much you can fit in a few days. Here's an example of one I made a few years ago:

I also recommend that you not go to a city or town just because people say you “can’t miss it.” Go where YOU want to go, it’s okay if you don’t do everything. The important thing is that you do what you want to do. Don’t waste your travel time fulfilling someone else’s travel dreams.

Don’t forget to plan some down time, as well. I’m a big fan of speed traveling, so as a rule I seldom spend more than 3 or 4 days in any city (I bend this rule for certain events, like the Full Moon Party in Thailand where most accommodation requires a minimum of 4 or 5 nights stay). That said, sometimes the “go go go” of it all really overwhelms me and I need to recharge, so I’ll plan an empty day where I can sit in a cafe and people watch or sleep in until noon. But this is just MY style, you gotta do you. 

Next, you have to find accommodation for these cities. Check out my post on hostels vs. hotels here. For hostels, I use and for hotels, Typically, I search hostels first. If a town doesn’t seem to have any hostels or they aren’t appealing to me, I go to AirBnB. If AirBnB doesn’t suit my taste, I head over to Trip Advisor. I also almost always stay in a hotel towards the end of my trip because I really appreciate the downtime to reflect on my journey. But again, that’s just my travel style.

Okay, now you have to figure out how you are going to get from one city to another. This again, requires research and planning on your part. Thankfully, by 2015, someone in the world has done a similar route and written about it online, so it’s not too tough. Google, guys. Google. "How to get from Bangkok to Phuket" or "How to get from Iguazu to Mendoza" will supply you with plenty of options.

Check flights, buses, trains and ferries from one city to another. Sometimes your timing might be tight so you need to throw down an additional $50 to fly instead of taking a 17 hour bus. Sometimes there is an overnight train which can save you a night’s accommodation. Explore all options, and if possible, try to take a train, bus, and domestic flight at some point during your trip, just for the experience.

Also note - If you are going somewhere less developed, there probably won’t be a website for you to buy these tickets in advance. The rest of the world just doesn’t work like that. Sometimes you just show up when you get there. Sometimes you have to buy in person a day in advance. This is one reason why I really like hostels - employees have dealt with all of this before and know exactly the best and cheapest route to get you where you want to go. They also can introduce you to someone who is going on your same route, and then you make a new friend! Like my mate Ben from Belize, whom I took a bus with from Tel Aviv to Jerusalem back in 2012!

Excuse my shit posture - I had just schlepped up Masada

Excuse my shit posture - I had just schlepped up Masada

Don’t forget to check to see if you need a visa for the countries you are visiting. You can find this at Some visas you have to apply for in advance, while some you can get on arrival. Some countries don’t require any kind of visa for Americans, depending on length of stay. You’ll also need to double check the amount of time you are allowed to spend in the country. It may be 30 days, it may be 60, sometimes more. But you’ll definitely need to make sure you are out of the country by the end of that time frame or you’ll run into problems. Also, be clear on whether your visa is single, double or multiple entry. For example: when you get a visa to China from the US, it is the same price whether you get a single, double or multiple entry. Even if you don’t think you’re ever going to go back to China, just get the multiple entry. It’s good for ten years and saves you from ever having to return to the WHAT THE FUCK IS THAT HORRIBLE EMBASSY ON 12TH AVENUE FUCK ME.

I’m sure your next question is, well what and how much do I pack? Don’t worry, I’ll get into that in a future post!

These tips are for people who like to plan a bit more intensely. If you are a fly by the seat of your  pants kind of person, and you have infinite time and just want to go with the flow, then fantastic. Sometimes I enjoy traveling like that too. If you have a set time, like 4 or 5 weeks, you probably do need to tighten it up a bit in order to see and experience as much as possible. I hope this was a good starting place. Remember, you can’t plan everything. Confusion and a bit of a kerfuffle is normal when traveling, and adds to your experience. Have your outline, but adjust according to your taste.