7 Tips to Ease into Traveling Alone for The First Time

7 Tips to Ease into Traveling Alone for The First Time

There’s too much of the world to see, and too much to be experienced, for you to sit around waiting for someone to tag along (can I get an amen?). Here are 7 ideas, tips, and methods that I hope help encourage you to take the leap and try solo travel for the first time!

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My first time traveling alone was when I was in college. It started the way many college students’ travel journeys start: studying abroad in one of the most beautiful old cities in Europe – Florence, Italy. 

If you’ve ever studied abroad, you know that those 6 months FLY by. You arrive in foreign territory, bright-eyed and bushy-tailed, eager to set off on a crazy adventure. 

You make friends. You learn how to not get lost wandering the streets. Before you know it, this foreign land starts to feel like the home you never knew you had.

Lil mini me studying abroad in college!  Florence, Italy (2013)

Halfway through the semester, and after a few months of traveling with my newfound friends, I realized I had only a few more empty weekends left until my adventure was over. I legitimately went into a state of panic. 

With little thought or research, and feeling a little reckless, I decided to head off on a weekend trip to Lisbon, Portugal, solo. In retrospect, it was one of the coolest and bravest things I did before turning 20 (way to go, Baby Off Duty!). 

Me on my first solo trip EVER with a few new friends I met that day  Lisbon, Portugal (2013)

I think there’s a sort of fearlessness that washes over you when you study abroad, and sometimes that sense of unabashed bravery can fade when you return home. 

And for those of us who haven’t studied abroad, it’s an even more distant, uncomfortable idea. Why travel to a foreign country where you don’t know a single person? Why go alone? Who would you spend time with? How would you handle the awkwardness of sitting in a restaurant, or a bar, by yourself? (newsflash: this last part = always awkward, no matter how many times you do it, lol).

It took me several years after studying abroad until I finally ripped the bandaid off and began challenging myself to start going places again despite the fear of traveling alone (have you seen my 5-day romp around Tasmania? THAT was a crazy solo trip!). 

What I’ve found is that there are so many ways to solo travel these days, it makes it almost impossible to not find a method that works for you. I hope the ideas I share below help encourage you to start traveling alone. There’s too much of the world to see, and too much to be experienced, for you to sit around waiting for someone to tag along (can I get an amen?).

7 Tips for Traveling Alone for The First Time

1. Start With Your Hometown

Rachel Off Duty: Woman at a Bar

Before booking a solo travel trip halfway across the world, test the waters by starting closer to home! 

Get a taste of traveling alone by exploring your hometown, taking a short road trip, or even taking yourself out for lunch or dinner. It may seem insignificant, but getting comfortable with doing things on your own is a huge factor in whether or not you’ll enjoy doing it abroad.

I personally know how awkward or bizarre it can feel sitting solo at a bar or a restaurant. I can say with complete honesty that no matter how much you do this, it never really gets ‘less awkward,’ but you will get more comfortable winging it solo. 

Some things that help me include sitting at the bar or finding a window-facing seat (both options are essentially designed for solo diners), bringing a book, or even answering emails while I’m eating alone. 

And, if a conversation with a kind stranger comes my way, I usually will embrace it unless I get creeper vibes.

RELATED: 10 Scenic Road Trips to Take in California

2. Visit a Friend or a Family Member In a New City

Rachel Off Duty: Photo of a Beach

Do you have a friend or a family member living in another part of the world? Pay them a visit and explore the city or country they live in while you’re at it. 

At the very least, you’ll get a familiar face to have dinner with and show you around town. At most, you’ll get a place to stay and a travel buddy to spend your days with!

Now, you’re probably thinking, “But Rachel, how is this solo travel if I’m not alone?”

You don’t need to be by yourself the entire time to classify a trip as “solo”. As long as you’re going to the destination alone, you’re still forcing yourself out of your comfort zone (even if a familiar face is meeting you on the other side).

It’s all about taking baby steps until you feel comfortable enough to land in a country where you don’t know anyone.

Do you have a friend or a family member living in another part of the world? Pay them a visit and explore the city or country they live in while you’re at it. 

At the very least, you’ll get a familiar face to have dinner with and show you around town. At most, you’ll get a place to stay and a travel buddy to spend your days with!

Now, you’re probably thinking, “But Rachel, how is this solo travel if I’m not alone?”

You don’t need to be by yourself the entire time to classify a trip as “solo”. As long as you’re going to the destination alone, you’re still forcing yourself out of your comfort zone (even if a familiar face is meeting you on the other side).

It’s all about taking baby steps until you feel comfortable enough to land in a country where you don’t know anyone.

3. Piggyback Off an Existing Trip

Rachel Off Duty: Woman in Australia

If you have a trip coming up with friends or family, it could be a great opportunity to spend a couple of extra days after the trip exploring a nearby place as a solo traveler. 

This way, you’ve already conquered the act of getting there (which can sometimes be the most daunting part) and had a chance to familiarize yourself with the area. 

I did this last year when I went to Australia, by hitching a quick 5-day solo trip to Tasmania onto my 2-week stay in the Gold Coast with my parents.

And guess what?

Those 5-days traveling alone were the highlight of my trip!

RELATED: How to See Byron Bay in One Day

4. Extend a Work Trip and Travel Solo for The First Time

Rachel Off Duty: Woman at the Airport

Do you have a 9-to-5 that involves some travel?

In my case, I sometimes go to Utah for work meetings, once a year. Every single time I go, I try to extend my trip by even just one or two days, so that I can go off and travel alone.

I have fallen in love with Utah, and would have never known just how beautiful this state was if it wasn’t for these work trips and taking the plunge to travel solo for the first time.

When you start planning for your next work trip and are looking up flights, take a look at whether flights will cost the same if you come home a few days later (since your company is likely paying for your flights on work-related trips, this is important!). 

If you have evidence to support how flying home on a Sunday will cost your company no more than it would if you flew home on a Thursday, they likely won’t say no! 

But of course, you’ll almost definitely need to cover the costs of accommodation on the extra days yourself – which is, honestly, a small hit to your wallet, considering the fact that your transportation costs would be covered.

Sites I use to compare flight costs for my solo adventures:

  • Skyscanner: Find the cheapest flight deals across multiple airlines
  • Momondo: Find flight deals by destination, or, if you aren’t sure where you want to go, you can use the search engine’s ‘Anywhere’ option to show you different destinations you can visit on your budget
  • Kayak: Popular tool for comparing prices on flights, accommodations, and more
  • Google Flights: Another flight finder that I like to use to compare routes. If you input your origin and leave the destination field blank, Google Flights pulls up a map that shows you different destinations and the estimated costs of round-trip airfare, which I love.

Tip: Before I book anything, I typically look at what the cheapest flights are using the above resources and then go directly to that airline’s website to compare prices and see if there are any special deals going on that these third-party sites didn’t list. Also, this is a good way to make sure you know exactly what you’re paying for (some discount flight costs don’t include things like checked luggage, seat selection, or meals).

RELATED: 5 websites I use to book cheap flights

5. Fill Your Days With Tours, Group Activities, or Bar Crawls

Does the thought of long stretches of traveling solo for the first time sound a little intimidating? 

Some people crave this kind of adventure, but for many, being alone and unfamiliar with where you are and what to do can be daunting, and is one of the biggest reasons why people avoid traveling alone. 

Instead of going it solo the entire time, fill your itinerary with day tours, group activities, and bar crawls. These kinds of activities take the guesswork out of navigating a new city, provide a sense of belonging, and serve as the perfect way to meet other solo travelers and make new friends along the way.

Resources for Tour & Activity Searching:

6. Try Out the Hostel Life to Meet Other Solo Travelers

Rachel Off Duty: Woman Reading a Book

Hostels are a polarizing subject. 

In college, I loved hostels because they are a dirt-cheap option for lodging, and they are set up to help you mingle with fellow solo travelers. 

Now that I am a little older, I like to pay a little more for private accommodations because I’m a fan of having my own bathroom and my own space. That said, hostels can be a fantastic opportunity to meet other adventure-seekers, compare itineraries, and maybe even find new experiences that you otherwise would have never heard of. 

At most hostels, you have the option of bunking in 4, 8, or even 12-person rooms that are either co-ed or same-sex. If you’re like me and prefer your own space, some hostels do have the option to book a private room with a private or a shared bathroom. 

Plan to spend as much time as possible hanging out in the common areas of the hostel and chatting it up with other people traveling alone!

Hostel booking sites to use:

7. Sign Up for a Group Trip

Rachel Off Duty: Group Trip

Some people love group trips and swear by them, others are unsure, and question what it’s like to be in a foreign place lumped together with a group of strangers. 

After trying out a group trip for myself, let me tell you: it was incredible and it’s one of my top tips for traveling alone for the first time. Signing up for a group trip has SO many benefits when you want to go somewhere but none of your friends are able to tag along.

 You get a guaranteed support system, you likely have a pretty cool itinerary already figured out for you, and you’d be surprised how quickly friendships can form when you’re halfway across the world dancing to songs sung in a different language while sipping on cocktails you can’t pronounce the names of.

It’s the best way to ease into traveling solo.

Here are some group trip companies to kickstart your research:

RELATED: Everything you need to know for your first Contiki tour

Have you traveled solo before, or are you thinking of giving it a shot for the first time? Tell me where you’ve been, or where you want to go, in the comments section below!

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Rachel Off Duty: 7 Simple Ways to Ease into Solo Travel If It's Your First Time
Rachel Off Duty: 7 Simple Ways to Ease into Solo Travel If It's Your First Time

Hey there! I’m Rachel, a travel writer and a full-time advertising / marketing expert. In 2019, I traveled more than 25 times while working 9 to 5, and since then I’ve committed myself to living a more adventurous life, even if it means bringing my laptop along for the ride.

Are you hungry to travel more, but overwhelmed with how to juggle work and play? You’ve come to the right place!

Recent Adventures:
Let's Go Places!

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