The hardest part of travelling alone for me is finding a dinner companion. It just gets awkward for me to eat dinner by myself when I am out. I have done it a lot, but still prefer someone else to talk to.

One of the best things is putting oneself out to meet people. Not forcing oneself, but just engaging in conversation whenever one can. And take every opportunity to do so, whether in a store or saying hello to s a stranger on the street, or asking someone for a recommendation for a place to get lunch or even what they think of something in a gallery.

If you can, staying at hostels or a bed and breakfast where you eat breakfast at a communal table is a great way to travel.

In the days when I wasn’t spliced to the wife & no kids, I travelled across Europe by train, all anyone needs to know is I pretended to be James Bond & kept an eye on any white haired male russian passengers…lots of fun.

I’ll assume you are asking about vacation travel where you are touring alone as well as getting there.

I have only done day trips completely alone for pleasure travel. I like it. If I get lost driving there is no fight to be had for costing the trip a few minutes more. When I get to where I am going I can do exactly what I want. I have been to Disney alone, small towns, big cities, museums, historical sights, boat rides, mountains, beaches, all over the US.

I have travelled alone for business and to visit family or friends quite often. Travelled all modes possible. Plane, train, automobile. Sometimes taking a day trip on my own to see a sight while there, even though I am visiting people. Sometimes stay with them, sometimes I am in a hotel alone. As a woman I like hotels that feel safe to me. Safe neighborhood, inside room entrance.

I travel to and from college by myself quite a bit these days, and it’s fine. I always thought it would be so terrifying, but it’s really not. I was pretty sheltered before college. It makes me feel good to do things independently and see that I am capable of doing so.

I worry sometimes because I am a very small woman and the cities through which I travel are large population centers, but nothing scary has ever happened. My worst experience was nearly getting stranded in an unfamiliar city far from either home or college. I was told my bus was cancelled. That turned into a good experience when a good Samaritan/fellow passenger sought me out to let me know our bus was actually running and would depart soon.

Man, I am the king of traveling alone. Internationally, with a demanding chronic disease and no medical SNAFUs. It’s something I’m proud of. It’s a nice feeling to be completely on my own, no one looking out for me but myself, and come out of it alright.

I guess some factors that affect the quality of your experience are whether you are traveling within your own country or abroad, and whether you are on vacation or an extended visit. Going on a brief vacation within your own country should not be a problem, but traveling abroad and/or traveling for an extended time can be challenging, logistically speaking and in other ways. On my last trip abroad, the biggest challenge I faced was not in terms of logistics but in terms of emotions. I experienced the most profound loneliness I’ve ever known, because I was not taking courses or working in a regular environment, and had few ways to meet people to socialize beyond everyday greetings. I ended up spending time with some bad people (not criminals, just… not people I should have become friends with) because I was so lonely for human contact and touch. The next time I travel abroad alone, I am going to be more proactive and commit to some Meetup groups and local clubs.

I agree with @zenvelo that one of the best parts of traveling alone is the opportunity to meet people. Talking with others who grew up in a different world will be a chance to expand your knowledge of humans, grow your personality and reflect on what your values are.

If you are nervous about traveling by yourself, maybe one way to lessen your fear would be to do a thorough investigation of the place you will be visiting from a distance. Buy a guide book (they still write those, right?) or read reviews on the Internet, written by visitors and locals. Figure out what kind of stuff you would like to do once you get there. Get yourself excited about your trip.

You should definitely familiarize yourself with the neighborhood once you arrive. Figure out the transportation, what sorts of restaurants and stores you will need to visit, and how long things stay open (you don’t generally want to walk around a commercial district after all the stores and restaurants are closed, for instance). And on that latter point, do be careful if you are a woman or queer or gender non conforming in some way. You need to watch out for yourself, and you can’t count on the cops coming to your rescue.

Good luck and have fun!

I travel a lot for work (alone) and so I’ve long since adapted to eating alone in restaurants and have little fear of being on my own in a different city/state/country.. but recently I took a side trip (a vacation) to Tokyo alone and I really loved it.

First, I have to clarify that I’m a bit of an introvert and a geek – and Tokyo is a place where I’ve lived in the past—so it was completely wonderful to have the freedom to eat where I wanted to eat (my favorite burger joint MOS Burger, my favorite comfort food, Royal Host) and not be judged by any companions that we weren’t eating every meal kaiseki ryori or uber-traditional Japanese meals.

The main benefit of traveling on your own is that YOU are the master of your schedule and what you see, eat & do. Want to eat lunch at 3pm? Go for it – no one else will complain. Want to have just an amazing pastry you found as your dinner? Yes.You.Can.

Here are my tips:
1. Study up on advance – know where the “safe” parts and good neighborhoods are wherever you want to go and carefully research hotels & venues so you aren’t wandering off someplace you shouldn’t be. Once you have a sense of the place (and/or enough of the language to ask for help) – you’ll be able to at least feel safer. For example, when I was in Cape Town, South Africa alone I knew where was safe and not safe for me to go off on my own. I knew which beaches/towns/restaurant areas to be more mindful of being mugged. My inn keepers were able to give the best info (in Cape Town) on what would be safe or not.

2. Bring something to read/entertain you while you dine out alone. Or, get accommodations where you can eat in-room or prepare your own meals a bit. Personally, I LOVE shopping in groceries around the world / new places I travel..it gives you a really neat perspective on the people/culture.

3. Plan out your agenda leaving space for rest/reflection. Pick a few places you want to see..but leave yourself free time to rest / wander the streets on your own. Part of what I loved so very much in Tokyo was my room. I splurged and used hotel points to stay (for essentially free) at the Ritz-Carlton Tokyo. It was so opulent, comfy and posh I never wanted to leave the room (except I did to go shopping, go back to my favorite parts of town & eat at my favorite places).

I have always loved it. You can go where you want, stay as long as you want and not worry about the feelings of anyone else. You have to use your head, don’t walk alone in strange areas at night, unless you are in Singapore, it is safe there. I don’t mind eating alone, I like watching the other people or else read a book on your smart phone. It is so freeing. Go and have a wonderful time, then come back and tell us all about it.