You’ve finally decided to take the plunge and go on your first solo trip. You’re feeling a mix of nervous, excited, and probably a bit confused. It’s perfectly natural. You’ve never taken a trip like this before, so you understandably have a lot of questions. Where will I go? Where will I stay? What do I pack?
I want your first solo trip to be an inspiring and affirming experience, one that gives you the confidence to go on future adventures. To help you get from “wanting to go somewhere” to actually taking a trip, I’ve created this guide. It will show you everything you need to know to take your first solo trip.
By the time you’re done reading this, you’ll have the knowledge and confidence to set off on your first solo adventure.
Because this is a pretty in-depth post, I’ve created a table of contents to help you navigate it. Just click on any of the links below to be taken to the relevant section. I strongly suggest that you read the guide in order to start with (you’ll get a lot more out of it that way), but the table of contents is here for when you want to refer to a specific section in the future.
Table of Contents
- Define Your Travel Motivations
- Deciding Where to Go
- Planning the Trip
Defining Your Travel Motivations
Most of us go through life without ever asking “Why?” Why do we do the things we do? Have you ever given it any serious thought?
When it comes to travel, you really should. Sure, you could just base your travels around a list of Top 100 Destinations To See Before You Die, but if you only base your travels off of what other people suggest, you’re just acting out someone else’s dream. In any arena, this is a surefire recipe for dissatisfaction.
For example, a lot of travel suggestions are based around seeing iconic landmarks and monuments. Think the Eiffel Tower, the Taj Mahal, the Burj Khalifa, etc. Seeing those is cool if you genuinely enjoy things like that, if architecture fascinates you and you can’t stop talking about it, but frankly, I couldn’t care less about things like that.
This has been one of my most powerful realizations when it comes to solo travel: you have the freedom to see and do whatever you want, so why would you base your travels on someone else’s “must-see/do” list?
This is a bold step, and people are probably going to give you some flak about it. Don’t listen to them: 99% of them have never even been to the places they’re asking about, so don’t worry about it. Base your travels around what excites you. Life’s too short for any other way.
All this is to say: you need to get clear about what motivates you to travel. It doesn’t have to be profound or complex. It just needs to be personal.
For instance, I travel to experience new cultures and improve my language skills (currently Spanish). Your reasons may be completely different. Maybe it’s to try new foods, to get out of your comfort zone, or just to relax. All perfectly valid reasons. What matters is that they’re your reasons, your motivations.
Action Step: Take 5 minutes to write one sentence describing what motivates you to travel. If you find a blank document intimidating, you can click here to access a worksheet that will take you through the process.
Deciding Where to Go
Once you’ve defined what motivates you to travel, the next step is deciding where to go. This will be much easier now that you have clear reasons for traveling, but still, the world is vast and your time and money are finite.
To help you narrow down where to go, consider (in no particular order) the following factors:
- Climate – Do you like cold weather, warm weather, temperate weather? Snowy, rainy, dry? Or maybe you don’t care.
- Landscape – Along with the above, are you looking for beaches, jungles, mountains, endless plains?
- Rural/Urban – It’s a spectrum of course, but broadly speaking are you looking for natural beauty or urban bustle? Or somewhere that has both close by?
- Available Time – Are you planning a week-long trip or a multi-year trek?
- Level of Difficulty – This is subjective, but in general it’s much easier to take a solo trip within your own country than it is to another. Or for a more extreme example, it’s more straightforward to go on a solo camping trip in a park near where you live than on an expedition up Mt. Everest.
- Broad vs. Deep – Do you want to get a broad overview of a lot of different places, constantly on the move, or do you want to go deep on a specific city?
- Level of Comfort – Are you cool with staying in hostels and eating street food, or are you looking to stay in a ritzy hotel and eat Michelin-star cuisine? Or something in between?
- Things You Like to Do – Another broad category, but in general certain destinations cater to some activities better than others. Think snowboarding vs. scuba diving or whiskey tasting vs eating exotic insects.
- Language Skills – Not the most important factor, but some countries are easier to navigate than others without a knowledge of the local language. For example, I got around very easily in Amsterdam speaking only a couple words of Dutch. Barcelona, on the other hand…¡era bueno que yo hablara español!
- Budget – This shouldn’t be your top concern, as most places you want to travel are almost certainly cheaper than you imagine, especially if you stay in Airbnb’s and avoid touristy areas for things like food. Still, it’s important to be aware of as you save for your trip.
- Ease of Access – This is one that I didn’t think much about when I first started solo traveling, but it’s actually very important to consider. For instance, are there flights available from your current location to your target destination? Or will you have to take a three-hour bus ride from the nearest large city? Before traveling to Reykjavik, for instance, I didn’t realize that the city was actually a 45-minute bus ride from the airport in Keflavik.
Once you’ve figured the above factors out, use them to guide your research. For instance, let’s say I wanted a place with the following criteria:
- Temperate climate
- Flat landscape
- Urban with natural beauty nearby
- 2 weeks
- Low difficulty
- Deep immersion in a specific city
- Comfort level unimportant
- Great bookstores and bars
- English spoken
- $1000 budget
- Easily accessible
I would use this info to start researching combinations of these keywords in Google. This is often enough to get some leads.
In addition, I recommend the following resources for finding places to travel:
- Wikitravel – The Wikipedia of travel info, this is the site I use when I’m researching a new destination. With entries on whole countries, regions, and specific cities, you’ll find a broad range of useful info on things like climate, language, and activities.
- Reddit – If you’re not familiar with it, Reddit is a discussion board site with pages for nearly every topic imaginable. Some of my favorite ones for travel include /r/travel, /r/SoloTravel, /r/backpacking, and /r/Shoestring. You’ll find dozens of posts along the lines of “I have X amount of money and X amount of time. Where should I go?” Make sure to search the site before asking a new question, as it’s likely been answered already.
- Quora – A question and answer site that’s great for getting travel info. The answers also tend to be a bit more detailed and media-rich than those on Reddit. Divided into different topics. I recommend starting with the Solo Travel topic.
- Nomad List – A site intended to help digital nomads and long-term travelers figure out where to base themselves, it’s great for anyone trying to figure out where to travel. It’s basically a giant list of cities that you can filter by things like cost, climate, internet speeds, and region.
- Experienced Traveler Friends/Family – If you know anyone who has travelled extensively, don’t be afraid to ask them! Someone who knows you personally can probably give you better travel recommendations than any website. And they’ll also be a great resource when it comes to planning your trip (more on this below).
Use what you learn from the above resources to start making a list of places that fit your criteria. Again, don’t worry too much about budget at this stage. You can always use it as a tiebreaker if you’re really torn between two places, but don’t let it hold back your brainstorming.
Once you’ve found the list of places, I want you to spend some time learning a little about them. This is the stage where you should get more specific in your Google searches. Here are some keyword combinations to try:
- NAME OF PLACE travel guide
- What’s it like in NAME OF PLACE
- NAME OF PLACE travel tips
- Best things about NAME OF PLACE
- Worst things about NAME OF PLACE
- NAME OF PLACE travel blog
From here, you’ll really start to learn about each place. I prefer reading what individual bloggers have to say as opposed to more mainstream travel guides, as the individual opinions tend to be less filtered.
Of course, even with individual bloggers you should take everything you read with a grain of salt. Don’t let one person’s bad experience be your only source of info. But also look for patterns – if a lot of people are saying the same things (good or bad), you should pay attention.
Once you’ve done this research, it’s time to pick a place to go. If you want, you can rank each place based on the criteria that are most important to you and pick the one with the highest score.
Honestly, though, I just pick whichever seems most exciting. If I’m not ridiculously excited about the place, why would I go there?
To make the above steps easier, I’ve created a spreadsheet that you can access here.
Planning the Trip
We’ve finally come to the moment you’ve all been waiting for: planning the trip. I know it may feel like it took a lot more work to get here than necessary, but rest assured that the time you spent thoughtfully choosing a destination will make a lot of the other planning details much easier.
This part of the guide has four sections:
- Transportation – How to get where you need to go as efficiently and affordably as possible.
- Accommodation – Finding and booking a place to stay that fits your needs and budget.
- Creating Your Itinerary – How to see and do the things you want while still leaving room for spontaneity.
- Packing – What to bring, how to pack it most efficiently, and how to avoid bringing too much.
Your first step is to decide what kind of transportation will be necessary. I know this may seem obvious, but a lot of people automatically assume that one form is cheaper or better without doing any research.
For example, in the U.S. driving is often cheaper than flying. It can also make for a much more adventurous trip. My friends and I took a roadtrip to D.C. this past summer, and not only was driving cheaper, it was also a great bonding experience that allowed us to see some beautiful areas of the country and visit sites not originally part of our itinerary. The fastest way to get somewhere isn’t always the best, both in terms of cost and enjoyability.
Let’s break down the forms of transportation a bit further:
Here’s how to make driving as cheap and pleasant as possible:
- Choose a Fuel Efficient Vehicle – Obviously, this isn’t something you always have control over, but to take the D.C. trip as an example, my friends and I compared the cars we had access to and went with the one with the best gas mileage. We easily saved $25-50 just by doing this small bit of research up front.
- Save Money with GasBuddy – GasBuddy is a website and mobile app that helps you find the lowest gas prices near you. I’m amazed how many times I’ve found gas 10 – 15 cents cheaper by driving a couple extra miles. Currently works in the U.S. and Canada.
- Pack as Lightweight as Possible – The less weight you’re carrying, the less fuel you’ll need. Avoid packing unnecessary items that just add weight (see the “Packing” section below for advice on packing light).
- Take Frequent Breaks – My first solo trip was in fact a road trip, and over the course of 4 days I spent at least 24 hours driving in total. When you’re driving solo, you must take frequent breaks. If you don’t, the fatigue will catch up with you, resulting in an increased chance of an accident. Not to mention that it will make your trip less enjoyable over all. I recommend taking a break at least every couple hours, if not more frequently.
- Break the Driving Up – In the same vein as the above tip, try to plan an itinerary that allows you to split the driving over a couple days. Taking my solo road trip as an example, I started just with the idea to visit New Orleans, Louisiana. When I discovered that would be a drive of ~8 hours without stopping, I decided to break the trip up with stops in Memphis, Tennessee, and Oxford, Mississippi. This not only saved me from a boring, fatiguing drive – it also led to a much more interesting trip.
And that’s all I have to say about driving.
This is a category of travel that I don’t have extensive experience with, but it’s definitely worth investigating depending on your region of travel. My own lack of experience comes from the region of the U.S. that I live in. Train service is basically non-existent, and inter-city bus service isn’t much cheaper than driving (as well as being pretty scarce in general).
Don’t rule these two forms of travel out, though. In some parts of Europe, train travel can be a great option for getting between countries (though once again it’s worth comparing, as air travel is often cheaper).
Likewise, bus service is a great option if you don’t have access to a car or want a slower pace of travel where you’re guaranteed to meet some interesting characters. When I was in Northern Ireland, I used the bus system several times to get between cities, visiting Dublin and Newcastle. The fares were cheap and the buses were quite comfortable.
Because my experience with train travel is limited, here are some posts I suggest for further reading:
- The Beginner’s Guide to Train Travel in Europe (The Blonde Abroad)
- Are Eurail Passes a Giant Scam or Do They Save Money? (Nomadic Matt)
If you’re making any kind of international or cross-country trip, you’ll probably end up flying. And there’s no getting around it: flying is often expensive. But it’s not always as expensive as you might imagine.
In Europe, for example, flights between countries are often quite cheap, particularly with the presence of budget carriers like easyJet and Ryanair. I’ve flown between European countries for as little as $40, and it’s not unheard of to find flights for as little as $10 one-way.
Even in cases where the flights are relatively expensive, proper planning and the right tools can help you score flights for much lower than you’d otherwise pay.
Here’s how to get the best deals on flights:
- Use flight search engines – Instead of searching dozens of individual sites for flights, use a search engine to collect them all in one place. My favorite is Momondo since it’s by far the most comprehensive and easiest to use, but other options include Kayak, Hipmunk, and Google Flights. The basic premise of all these sites is that you enter your departure and arrival destinations, the date(s) you want to leave, and some other optional info like price, and the search engine scours booking websites to find you the best deal. The first place I go when looking to book a flight.
- Be flexible on dates – One thing you’ll quickly discover when you start to browse flight search engines is that prices vary wildly from day to day. For reasons that are complex, the price difference between two days can be hundreds of dollars for the same flight. Because of this, it’s handy to be flexible when booking your flight. Even if it means getting somewhere a couple days earlier than you’d planned, the savings are often worth it.
- Book at the right time – Booking at the right time can make a huge difference in the price of your ticket. Aside from the obvious advice of not to book the day before the flight leaves (unless you’re really flexible on dates), when is the best time to book? It depends. According to a study by CheapAir, the best time to by a U.S. domestic plane ticket is 54 days before the flight (on average). For international flights, it varies heavily with the region you’re visiting. For instance, CheapAir found that the best time to buy a flight from the U.S. to Latin America is 75 days in advance. A flight from the U.S. to the Caribbean, on the other hand, is at it’s lowest price 320 days before departure. For more info, check out CheapAir’s full post on when to book international flights.
- Use airline miles/points – I haven’t experimented with this (yet), but taking advantage of airline reward programs is how a lot of travel bloggers manage to save a ton on airfare. To learn more about how to use these programs, I recommend Extra Pack of Peanuts and /r/churning.
- Pack only carry-on luggage – I never check baggage if I can avoid it. Even if it’s free (rare), it adds to the list of crap I have to keep up with, and there’s always the chance of it getting lost. Get the right travel backpack and you’ll have no need for a bulky suitcase that’s just making your travel more expensive and difficult.
Follow the above advice, and you’ll be on your way to flying more cheaply and easily than most travelers out there.
Other Forms of Transportation
I can’t help but mention a few other forms of transportation that may be a great option in certain situations. I don’t have much experience traveling by any of these means, but I’ve read lots of blog posts from people who have. All of these make for a unique and memorable experience.
Here are four “alternative” modes of transportation to consider:
- Cycling – Think your bike is only good for getting around town or tearing up the trails on weekends? Think again! There’s a whole subculture of bike travel known as bicycle touring, with people biking across countries or even whole continents. To top it all off, cycling is cheap and great exercise!
- Walking/Trekking – The most ancient form of transportation, walking allows you to take in the scenery like no other method of transportation. From trekking to Machu Picchu to walking across America, make your next trip foot-powered for a whole different kind of adventure.
- Animal-Powered – Whether it’s riding horses across Iceland or gliding through the Jordanian desert atop a camel, this is another ancient form of transportation that could be perfect if you like animals or already know/want to learn how to ride.
- Boat/Ferry – When I was living in Belfast, Northern Ireland, I learned that the ferry was a very popular way of getting between Belfast and England. While water transportation has become less popular with the advent of air travel, it’s still something you might consider in certain cases. Indeed, there are people who build whole adventures around traveling by boat.
Now that you’ve finished this section, you should have a better idea of how to find the best possible transportation for your trip at the best possible price. With getting there taken care of, let’s move on and cover where to stay when you arrive.
Accommodation is one of the biggest costs when traveling. Luckily, it’s also an area that’s pretty easy to “hack,” provided, you know about a few important resources (more on those in a moment).
My biggest piece of advice when it comes to accommodation is this: decide how crucial it is to your trip. If you’re not planning to be in your accommodation much, you don’t need to stay anywhere fancy. But if the whole point of your trip is doing nothing and vegging out, then naturally you’ll want to spend more for a more luxurious places (and consequently spend less in other areas).
Affordable travel is really all about tradeoffs. A lot of people have this idea that if they’re taking a “vacation,” they have to splurge on everything. But why do that as an end in itself? If you don’t care about staying in a fancy hotel, don’t.
When it comes to the details of finding accommodation, here are the options I recommend you consider:
Airbnb is the first place I look when trying to find accommodation. If you’re not familiar with it, it’s a website that allows individuals (and property management companies) to rent out rooms, apartments, or even whole houses.
Part of the emerging “sharing economy”, Airbnb allows you to find rooms much cheaper than hotels in almost all cases. Certainly in the U.S. and Europe, it’s frequently the best deal you can find.
And if you’re concerned about safety, don’t be. Sure, there are Airbnb horror stories out there, but that’s not different than hotels. All the hosts on Airbnb are well-vetted by the platform and by the reviews others have left. So as long as the place has positive reviews, there’s no need to worry.
If you want to save $35 off your first trip on Airbnb, sign-up using this link. It doesn’t cost you anything extra, and it helps support this site.
Roomorama is similar to Airbnb, but it’s aimed more at long-term rentals (think at least 1 month). Because it’s marketed toward a vacation crowd, the properties also tend to be a bit more luxurious (and consequently a little pricier). I haven’t used the site myself, but it comes highly recommended as an alternative to Airbnb, so I think it’s worth including. Plus, it never hurts to comparison shop when booking accommodation, especially if it’s for a longer period of time.
If you’re picturing a dingy room with a row of stained mattresses and a high chance of being murdered, you need to recalibrate your image of hostels. Far from being gross and unsafe, they’re usually lovely places to stay. Sure, they’re often much more basic than a hotel, requiring you to provide your own toiletries and towels, but they’re great for the price. On top of that, they’re a great way to meet new people from all over the world. Highly recommended for young people traveling internationally, although older travelers shouldn’t rule them out either.
There are several different hostel booking sites out there, but Hostelworld is my favorite for both ease of use and number of reviews.
If you really want to save on accommodation, you can try your hand at Couchsurfing. You sign up for the site, fill out your profile, pay a small fee, and ideally get a couple people to write you references. You can then post a request to stay in basically anywhere in the world. After conversing with your potential host and verifying that you can trust each other, you arrange to stay.
I should be clear: this isn’t freeloading. Couchsurfing is a tight community, and it’s understood that even though you’re not paying any money to stay you’ll bring your host a gift and help them with things around their house. In return, the host often acts as a guide to their city, showing it to you through the eyes of a local.
I have yet to experiment with Couchsurfing, but it’s also on my list of accommodation ideas to try. I’ve heard such positive things about it from friends and other travel bloggers that I have to include it.
If you don’t have money to trade for accommodation, other kinds of trades are possible. No, I don’t mean that kind of trade, get your mind out of the gutter. 😉 What I mean is trading your labor in exchange for food and a place to stay. Workaway allows you to do just that. You spend a few hours a day helping your host with anything from farm chores to hostel management and in exchange you get food and a place to stay.
There is a small fee for joining the site, but it seems like a no-brainer in exchange for all the travel opportunities the site affords. I haven’t used it yet, but I have a couple friends who have with great success. Another place on the radar, no doubt.
This won’t be for everyone, but if you don’t mind “roughing it” a little bit, camping can make your accommodation practically free. All it requires is a good tent, a sleeping bag, and of course some s’mores!
If you’re trying to find a campsite near your destination (and you’re in America) I recommend USACampgrounds.info. Or just Google “campsites near LOCATION”. Besides being cheap, it’s a great way to connect with nature.
I’ve slept in my car in campsites a couple times, and while it’s not the most luxurious experience ever, it’s a great way to save money on accommodation. Curl up in the back or just lean your seat back. I strongly recommend bringing a pillow and a blanket if you’re going to do this. And don’t sleep in your car at a public rest stop or gas station. Much too dangerous.
And of course, renting an RV or camp trailer is another option that fall in this category, allowing you to combine accommodation and transportation.
This is another option that’s especially great for couples. Basically, people arrange for you to watch their house while they’re on vacation or otherwise traveling. This often includes caring for pets and making sure pipes don’t freeze, but it’s really a no-brainer in exchange for free rent and utilities. In some cases, you can even get paid.
Because I don’t have any experience with it, I’ll refer you to Nomadic Matt’s post on How to Be A House Sitter.
I hope you now realize that the options for accommodation are both broader and more affordable than you’d imagined. With accommodation and flights now settled, let’s move on to one of the most exciting parts of travel-planning: creating your itinerary.
Creating Your Itinerary
When it comes to creating your itinerary, there are two main philosophies:
- Plan a very detailed itinerary minute-by-minute.
- Show up with nothing more than your luggage and a place to stay, then figure it out from there.
I’ve done both of the above kinds of trips, and nowadays I like to do something in the middle. I plan a general itinerary with places I might want to go each day, noting especially activities or events that are only open during certain hours/days.
Once I get there, I follow that itinerary in general but also stay open to cool things I might see or hear about while in town. If you’re staying in an Airbnb, make sure to ask your host what they suggest. Same goes for hostels. Locals will tell you about things you could never find otherwise, and by staying a hostel or Airbnb you’re already going to get a greater taste of the local character than you would in a chain hotel.
Need more guidance than that?
Here’s how to make an itinerary in six easy steps:
- Keep it simple. Most of the itinerary templates out there are way to complicated for me. I just use a document with a heading for each day. Here’s an example from a recent trip.
- Consult the right resources. I find places and activities by looking on Trip Advisor (better for some places than others, it just depends), Wikitravel (invaluable but not always complete), Wikipedia, Google, and even YouTube. Searching something along the lines of “things to do in X PLACE” will often pull up guides written by local publications or other bloggers who’ve been to the place. “Local’s guide to X PLACE” is also a useful search.
- Search for things that interest you. For me, this is things like live music, bars, arts/culture/museums, bookstores, and outdoor activities. Again, the procedure is a simple as searching terms like “live music in X CITY” or “best bookstores in X PLACE.” If you’re really feeling stuck, search “what to do in X PLACE” or “best things to do in X PLACE.”
- Record your search results. As I’m doing all the above research, I make note of it in a Google Doc. I don’t worry about organization, though sometimes I group things by broad categories such as “Food” or “Events.”
- Build a tentative schedule. Once I have the above list, I start to organize it around the days of my trip. I don’t worry about specific times unless an activity truly is time sensitive. For instance, when I was in Portland, ME, I learned that the Portland Museum of Art was free to the public on Friday evenings. Consequently, it made sense to build my Friday schedule around that.
- Don’t be a slave to your itinerary. I suggest that you view your itinerary merely as a jumping off point for your trip. Don’t follow it because you feel like you “have to.” Some of my best travel days have been spent just walking around a city and taking in all its crazy sights. Remember: the map is not the territory.
Want an example? Here’s the exact itinerary I created for a recent trip to Portland, Maine. Feel free to use it for planning your trips (to get a copy you can edit, make a copy by going to to File > Make a copy…).
What to pack is a massive, contentious topic, but it really doesn’t have to be. Regardless of the specifics, all you really need to know when packing is this: pack half as much as you think you should. This piece of wisdom pops up again and again in travel guides, and it’s the most solid I’ve find.
If you need more information, though, here are some of my packing tips:
- Get a good travel backpack. There are some impressively slick and durable suitcase on the market today, but for solo travel I strongly suggest a backpack. For short weekend trips I just use the same backpack I used in school. No need to make things complicated, after all. For longer trips, I recommend picking up a Tortuga backpack. These backpacks are made to hold everything you could need to bring while still fitting in the overhead luggage compartments of, well, every plane I’ve ever traveled on. Using a bag you can carry on saves you time, money, and the risk of your bag being lost.
- Don’t pack toiletries. If you’re flying, there’s no need to pack toiletries. I despise having to put things in little bags and am always worried they’ll slow me down, so I don’t bother. Just buy the toiletries you need when you get to your destination.
- Do pack food. Regardless of whether you’re driving, flying, or sitting astride a camel, packing your own food is going to save you a lot of money. Seriously, have you seen how much airports charge for the simplest of snacks? I always pack my own food to eat before a flight, since besides the money saved there’s also the chance of the food onboard being sketchy, overpriced, or both.
- Consult a good packing list. I know I said that you don’t need a packing list, but having one to refer to is reassuring, especially for your first trip. I like the ones from Expert Vagabond, James Clear, and The Blonde Abroad.
- Learn how to pack a carry on. How do I pack a suit jacket? Won’t my laptop get crushed? Where do I stash my condoms? I’ve found Tortuga’s Definitive Carry On Packing List to be very helpful in answering all these questions and more. It’s written with their backpack in mind, but the advice applies to any kind of carry-on packing.
- Remember that you can live without most things. You need much less to travel than you think. Anything that you forget is easy enough to buy, barter for, or just do without.
That’s all I have to say about packing. Like all skills, it takes practice, and over time you’ll get a better sense of what items you should and shouldn’t bring. Approach packing with a mindset of experimentation and you’ll be fine.
Whew! If you made it all the way through, thanks. I hope that you now feel prepared to embark on your first solo trip.
Solo travel has been one of the most inspiring, confidence-boosting experiences of my life, and I want you to experience those same benefits. Now that you have this guide, you should be that much closer to taking the trip.
Remember that all of the above is useless without action. If you’re feeling overwhelmed, remember that perfect is the enemy of good. No trip will go perfectly, so don’t worry about it. Instead, just get started.
If you need more help, don’t hesitate to contact me.
See you on the road!