How To Get Comfortable With Solo Travel – 14 Ideas To Get You Started!

I was in my mid-40s when I stumbled across this video by Tanya David and Andrea Dorfman called “How to be Alone.” It pulled at my heart so hard. I wanted to know how to be alone. I had been in relationships since I was 15 years old, with hardly a break in between. When I saw this video, I was in a relationship and yet just wanted some space for myself, but I couldn’t imagine it. It wasn’t until a few years later that I started my solo travel journey.

Now I have to calibrate before I travel with someone else. Solo travel fills my soul, but it was a journey to get there.

There were a lot of things about solo travel that scared me. Would I be lonely? Would I be embarrassed to eat by myself? Would I be afraid to do something I wanted to do if I had no one with me? The answer to all of these was yes — I felt all those things for a while. But I overcame them all, and you can too. I recommend solo travel for everyone, at least once, especially for women. We are so conditioned to take care of others our whole lives; taking a trip where you only care for yourself and do exactly what you want to do for days or weeks is liberating and empowering!

Here is what I did to get comfortable with solo travel.

Indianapolis, my first solo trip
Art in Indianapolis, IN

Book a trip just a few hours away. One of my first solo trips was to a city four times the size of my hometown, but only two hours away. I planned activities I wouldn’t feel out of place doing on my own: I went to the zoo, stopped at a couple of breweries, and went to the botanical gardens. Art museums are another great place to be alone.

Practice eating out alone. It seems crazy to me now that that was ever something I felt uncomfortable with, but it was! For a long time, I always ate at the bar. I still enjoy eating at the bar; bartenders are great company because they know when to chat and when to leave you alone, depending on your mood. I also often get a free drink or dessert, which I can’t say I mind. I eventually started getting a table for one. I have heard of other solo female travelers in some countries being asked to leave bars when dining alone, being mistaken for a prostitute. So far, no one has accused this 50-something of trying to hustle men. When the host asks, “How many?” you’ll learn to say “Just me!” with confidence.

Get familiar with public transportation. When I started traveling solo, I had some experience with the Chicago CTA (L) system, but doing it alone can be intimidating. From purchasing the correct ticket to ensuring you’re taking the right train, it’s easy to get overwhelmed. Before you go to a new city, familiarize yourself with the city’s public transit options, tickets, and routes. Download transit maps or save a screen grab to your photos, so you have them when you’re in subway tunnels and have no service. Attendants are typically working; don’t hesitate to ask questions if you’re unsure. When I was in Washington, D.C., a while back, I could NOT figure out how to exit the station. I walked around, back and forth, trying to figure it out. I finally stopped to ask someone. I felt like such a rube. It turns out that in Washington, D.C., you must use your card to leave the station and enter. I had not encountered that anywhere else. I felt like an idiot, but the attendants just chuckled, and I was on my way! Google Maps has excellent transportation instructions that will help you navigate the bus, subway, train, or other modes of transportation. Even after several years of solo travel, public transportation is still my nemesis and my biggest hurdle. It’s a me thing. I do it anyway, but man, it’s not easy for me. Want more tips on public transportation? We’ve got you!

Book an overnight stay in a hotel, even in your hometown. I have never been intimidated about staying in a hotel, but I frequently hear this from other female travelers. For some, just the unknown of sleeping alone can be intimidating. Book the stay. There are almost always things to do near your hotel. Grab a coffee or cocktail in the hotel bar. Walk around the area and explore. I avoid suburban hotels as they often don’t have much to look at besides strip malls. Find a good city center location. I love having a glass of wine while looking out of the windows at a good city view. I get my best sleep in hotels, but it can take some getting used to. A lot of people travel with familiars such as small fans, their favorite pillow, a special pillow case, stuffed animals, their partner’s t-shirt or even a favorite blanket. Take whatever will make you feel comfortable as you get used to this new adventure.

Familiarize yourself with parking options in cities if you aren’t from one. You’ll likely need to find parking when staying at hotels in larger cities. If you aren’t comfortable with public garages or parking lots, pay the extra for valet. I hate paying extra, so I use apps like SpotHero to find the closest, cheapest parking. Make sure you check the rules for the lot you are in. One time in Atlanta, I had my car booted because I didn’t leave my ticket on the dash and took it with me. Every lot or garage has rules and time limits, and costs are often confusing. There is often fine print on the $9.99 lots. SpotHero allows you to pay in advance through the app, which I love. Street parking is available in most places, but follow the meter rules (usually time limits) and learn how to parallel park. So often I hear that people don’t park in urban areas because they can’t parallel park! When parking in public garages I also look for a spot closest to the exit in a well lit area. I also carry a small flashlight with me that I can use as a defensive weapon and take other safety measures.

Book a solo road trip. Once you’ve conquered a few of your fears in your home state, book a road trip further away. Little things like stopping for gas, stopping at travel plazas (my preferred restroom choice), or grabbing a bite on the road will help hone your spidey senses. If you ever feel uncomfortable, turn around and leave. Don’t ever question your gut. Whenever I stop, I take a minute to gauge the crowd. Are there families around? Other women? I’m not paranoid, but I am very aware of my surroundings. I feel more comfortable in urban areas than in rural areas, and when I’m driving, I keep a close eye on my fuel levels. I do not want to stop in an area where I’m not comfortable, and I never want to run out of gas. My longest solo road trip was a 10-day trip from my home state of Indiana through Tennessee and North Carolina. I went far south and drove up the coast. I visited the Outer Banks, where I had camped as a child, and also took my kids when they were growing up. This was a very cathartic trip for me in the first fall of COVID-19. It was a lot of drive time, listening to podcasts, camping on an island for the first time, and visiting the wild ponies on Shackleford Banks. My father even drove out and joined me for a couple of days in the place we had visited frequently as a family when I was a kid. It’s always good to have an emergency road kit, and Julianne has an excellent one you can find in our post What’s in my emergency road kit.”

When you really start to feel brave, venture out from the comfort of hotels … maybe. From Airbnbs, to hostels there are a variety of places you can stay, you can even stay at Convents! When I first started traveling I used Airbnb quite a bit. Most of my stays were shared-space stays, which is not everyone’s comfort level. My first shared-space stay was in midtown Atlanta for $45. The woman rented out every inch of her apartment (both bedrooms and the couch). After taking myself to dinner, I walked in to find a young man sitting on the floor in the living room in his underwear, eating pizza. I just said hello and went to my room. It amused me, and I did not feel unsafe, but it opened my eyes to the reality of shared spaces. I did two more shared-space stays in Austin with similar experiences. When using Airbnb, or any booking platform, make sure you read the descriptions and all the information provided. What is the cancellation policy? If you have to change your plans, how flexible is it? What additional fees do they have? If you will be working remotely, how reliable is their wifi? Will you be getting a key or will there be a keypad you can use to enter? Consider what is most important to you and read the reviews to ensure it’s a good stay for you. A great option for those of you who are a little more social is hostels. Many major cities in the US have hostels, and there are everywhere in Europe. You can find incredible deals and choose between mixed dorms, same-sex dorms or even private rooms! My favorite way to find a place to stay is using You will find everything: hotels, hostels, apartments for rent, and even some really unique stays. Their loyalty program is really great too!

Flying solo—now you’re cooking! I love to fly. I love airports. Once you’re ready to book your first flight, consider what is important. Do you prefer the window, aisle or the dreaded middle? Do you like to chat or want to be alone with your thoughts? I am an alone-with-my-thoughts window person. I travel with a large scarf that I can use as a travel blanket, head covering, or for its intended use. I once flew home from a business trip sick as all get out and used it to cover my whole head to help protect the people around me. (Seems funny now, I could have just worn a mask!) It also makes an effective pillow or eye covering when I’m trying to sleep. I use headphones to listen to my podcast, audiobook or music, and this also alerts my seatmate; I’m not DTC (down to chat). I like to board late if I’m not worried about overhead bin space and early if I am. I want to get off the plane as soon as possible, so I prefer to sit closer to the front. One of the perks of traveling solo is if you pick your seat, if it’s not a full flight you might get the row to yourself, it happens!

Rent a car. What could possibly be scary about renting a car? Well, lots of things. Here are things I did NOT know about renting cars when I first started traveling. Insurance: Holy #$%l, the first time I rented a car I paid them to insure it. Talk to your car insurance agent before you rent a car. When I was with State Farm they would add on rental car insurance for specific trips I was taking. My current car insurance provider doesn’t offer that service so now I use a Chase Sapphire Preferred card, which offers rental car coverage protection and gives me points when I travel! The person with the credit card must be the one who rents the car, signs all the paperwork and is the primary driver. I have a series of protocols I use when renting a car. Start by walking around the car and taking photos. If possible, walk it with a rep of the rental car company. Make them note any dent or scratch on the car. If you have an issue talk to a desk agent. They are so used to terrible customers, be kind. They will work hard to make sure you are taken care of.

Speak up if you don’t like the car they want to give you. You don’t have to take the first one you are offered. Check the car for refuse or signs it has not been cleaned. If it is dirty or smells off ask for another. I tend to rent domestically from Enterprise. They are easy to book with, have a great cancellation policy, and I rarely have issues with them. I have a rewards program with them and occasionally get free upgrades. You can often upgrade when you pick up your car for an extra $10 or so a day, which can be totally worth it if it’s just a day or two.

Find good solo activities. Any activity can be a solo activity, but I started with ones that interested me and that I felt comfortable doing. Museums are great. Generally, they’re quiet spaces anyway. I love both art and history and going to museums when I travel tells me a lot about the place I’m in. When I was in New Mexico I learned so much about Native Americans and South Americans’ immigration to the United States through the art and history museums there. I pop in my earbuds, put on some nice chill tunes, and walk to my heart’s content. Zoos, botanical gardens and outdoor sculpture parks are also high on my list. Live music, plays, philharmonic performances, ballet … most cities have beautiful theaters to enjoy!

If you get to a city and aren’t sure what to explore, look to see if they have free walking tours. This is a great way to get a feel for the city, orient yourself and meet other travelers. Most cities also have paid tours that align with your interests — boat tours, architecture tours, and haunted tours! Airbnb Adventures is also a great way to get to know the local landscape, meet residents and see hot spots.

Find your people. I am an introvert and like being on my own, but I still want to connect with other travelers on occasion who share some common goals or experiences. There are a lot of travel groups on social media that cater to solo travelers, even down to your demographic. I’m in several groups for solo female travelers over 50. I had been looking for packing tips, and the video I found was done by a 20-something who packed 16 bikinis and 100 tampons. No joke. That is not relevant information to me. Connecting with older travelers helps me dial in my specific needs and meet other travelers I can sometimes meet up with when I’m in their area!

Join a meet-up group. There are so many meetup groups. Just throw in a Google search for where you want to go or join a travel group on social media and ask who is in the area you will be in. I’ve even gone on dates while traveling, using dating apps. Just because you are traveling, solo doesn’t mean you might not want company! Speaking of company, be smart if you want to hook up on the road. Don’t drink too much; be careful about who you hook up with. I think getting a photo of someone’s ID and face and sending it to a friend back home is smart. If someone takes offense to that, that’s not someone who cares enough about my safety, and I don’t want to hook up with them. Also, use condoms; STDs are not a souvenir you want to bring home.

Playing in the sea in Madeira

Have fun. Clearly, the whole point of solo travel is to have fun, learn more about yourself, test your limits and enjoy the absolute freedom that comes from doing what YOU want to do, literally every minute of a day, for as long as you choose. Women especially don’t get that kind of luxurious freedom often, and it can be overwhelming when you first try it. But once you get used to it, you will wonder why you wanted to wait for others to travel with you.

Don’t let fear hold you back. Maybe traveling solo isn’t for you right now, but don’t let fear hold you back if it is. Book the trip, prepare and go. If you aren’t quite ready, find a good travel group. There are many options for solo travelers! In the meantime, check out our post on staying safe when traveling solo; being prepared is the first step!

I’ve never felt more “ME” than when I travel solo. I’ve learned what I like, what my pace is, where I like to eat and how much I like to sleep, all without someone else’s influence. I have friends I enjoy traveling with, and I still do, but solo trips will always be my favorite way to travel!

The freedom and self-exploration that occurs when traveling solo is something I can’t imagine giving up.

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