Traveling Alone.

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A few of you have requested a post about traveling alone so I wanted to talk about that here today…

First of all, I think it’s funny whenever people tell me I am brave or adventurous for traveling by myself. I don’t feel either of those things. I’m actually not very brave at all. Brave or adventurous would be going to Asia by myself, something I’ve been thinking of doing for a long time, but also putting off as I’m sort of a scaredy cat at heart. The thing is, I’m single and self-employed with a relatively flexible schedule… and I have a ton of things that I want to do, so I just go and do them on my own rather than waiting to have someone to do the things with. I would 1,000% rather have someone to travel with (although I will be honest… there are times when I just want to get away from people… that was the case with this past trip!)

The first time I ever traveled alone was 6.5 years ago. I was 27 and in between jobs. I had severance money leftover from being laid off from the first job, so I went to Greece for two weeks. It was unbelievable and one of the best things I’ve ever done for myself. There is something so exhilarating about just picking up and going… on your own. I booked it very last minute and didn’t do a ton of research so I ended up making a lot of mistakes. I didn’t book my ferries in advance which caused for a bit of tears when I got to the ferry station and all of the ferries were sold out. I ended up just going to another port and being fine, but I was pretty overwhelmed. I got back to New York and from that trip and felt like a new human. It gave me so much confidence and made me feel like I could do anything. When I look back on life, that trip was definitely a pivotal moment for me… I learned so much about myself and really grew as a person. A few weeks later I left again, that time going to Lyon by myself – but for a friend’s wedding.

These days, I’m not quite as adventurous. Tulum is a great place to go on your own as it’s relatively safe. London is another good one because there’s no language barrier. You just have to be careful. I always stay in decently nice hotels (I’d never stay in a hostel by myself!), and I research the hell out of wherever I am headed beforehand to make a plan. Or (like this past trip), I don’t make a lot of plans. There’s something really awesome about just spending a few days by yourself on the beach with a pile of books.

I always end up making friends when I travel alone, which is kind of cool. In Greece I met two girls and a pack of Australian guys that I still keep up with via social media. The first time I was in Tulum I met some really cool girls (still Instagram pals with them), and this past time I was stuck in the rain and ended up sharing a cab with a family (the cutest mom + her two daughters). As it turned out they were avid blog readers and we had a lot to talk about. We’ve been emailing back and forth since my return which is fun.

Anyway, I’ve compiled some Do’s and Don’ts of solo travel… I hope this is helpful!


  • Research ahead of time. Trip Advisor is a great resource.. you’ll be able to tell if others traveled their solo, and if the place you are going is safe!
  • Make sure you have way to entertain yourself, especially if you are traveling internationally and won’t have Internet. I usually download a few shows or movies to my laptop to watch at night, pack at least three books, and either bring stationery or buy postcards to write notes to friends and family during solo meals. I’d say meals are really the only part where it gets awkward.
  • Make friends! I am an introvert by nature but I always find myself making friends when I travel alone… yet every time I go somewhere by myself, I end up with a new friend or two. Keep an open mind, you will find yourself meeting the most interesting people.


  • Bring nice things! Anytime I travel by myself, I leave all of my nice things at home. I do bring my nice camera but that is literally the one expensive thing I travel with.
  • Look clueless. Fake it til you make it. If you seem like you know what you are doing and act like a local, no one is going to mess with you. In London I would map out my routes ahead of time (or take a cab) so that I was never that clueless looking tourist on the street at night.
  • Wear your headphones. I’m never without mine so I hate this one, but it goes along with looking clueless and makes you a target.

For me, the best part of solo travel to me is being able to do whatever I want. I have two distinct travel modes: Do it All, and Do Nothing. When I was in London for New Years Eve, I was in Do It All mode. I was sort of with friends but mostly on my own. I made it a goal to go to as many art galleries and museums as possible and I did a really good job with it. I was pretty beat by the end of the trip and it probably would have been annoying for friends or a boyfriend. Conversely, this past trip, I didn’t want to do much of anything besides lay in my cabana and read… so I didn’t need to worry about letting anyone down by skipping the touristy things.

The other really great part is that you learn a lot about yourself. You become really comfortable with your own company, and you learn what you like and don’t like. I am a pretty easy going person by nature so often just go along with whatever the person I am with wants to do. When you’re by yourself and have to make all of the big decisions, it’s interesting to see what you decide to do!

I hope this is helpful… if you have more questions, don’t hesitate to ask – leave a comment or feel free to email me! (

Also – How to Travel Like an A-Lister!

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Leave a Comment


  1. I love this! I first traveled alone at age 18 (to Ireland) and hated when people told me I was brave for doing it (it was Ireland after all. Land of the nicest people ever and everyone spoke English). And you should go to Asia! Though when I went I was too scared to go by myself and ended up with a tour group. I was honestly very happy doing that, but maybe you’ll be braver than me!


    3.28.16 Reply
  2. Rachel:

    This is great. Thank you for sharing, Grace. Asia is a place that I’ve returned to again and again. I’ve never gone alone, but I think it would be lovely. Happy to provide any recommendations if you end up going to a city I’ve been.

    3.28.16 Reply
  3. Solo travel is my favourite. I like not being limited by anyone else’s interests or schedule plus the person whose company I enjoy the most is my own (not hate to my boyfriend).

    3.28.16 Reply
  4. Thank you for this post! I traveled to the UK last year on my own, and everyone constantly asked why my boyfriend didn’t come along. Pretty simple … it was something I wanted to do by myself. Sure there were times when I wished I could share things with him, but that’s what Facebook and Skype are for!

    That Twenty Something

    3.28.16 Reply
    • Annie:

      Grace, you are bright, beautiful and very talented! The fact some dude hasn’t scooped you up makes me think your grandmother is right. They’re all mentally ill in NY! You have been such a light for me each day. I know she is looking out for you and will find you your match very soon. I can feel it. We’re all rooting for you. You deserve every happiness after all the happiness you bring others.

      3.28.16 Reply
  5. Great ideas. I had the idea to travel alone from my past trip… I don’t know if I could do it! But I want to!

    3.28.16 Reply
  6. kelly owens:

    thank you for this! I always think about planning a solo vacation but am too nervous!

    3.28.16 Reply
  7. terri martin:

    I still think you’re brave. I could never plan a trip alone. But maybe I’ll try. We’ll see.

    3.28.16 Reply
  8. Kara:

    yes! love this! i love traveling alone and take a lot of flack from my friends… but it really is the best.

    3.28.16 Reply
  9. mary:

    dying to take a trip alone.. you’ve inspired me!

    3.28.16 Reply
  10. Agree that staying in hostels alone can be sketchy but I once stayed in Lisbon in a private room in a nicer/boutique like hostel and it was fine. That way, I could still meet people my age but have the privacy and security necessary. Still cheaper than a hotel too.

    3.29.16 Reply
  11. Gigi:

    Thanks… I will be single soon and need encouragement to co tinue to do and go to the places I have dreamt about.

    3.29.16 Reply
  12. I love this post and reading about all your experiences and insights. Still working on planning a solo trip for myself, but I’m going to try to make it happen before the end of this year!

    3.29.16 Reply
  13. Sharon:

    Hi Grace, I’m a bit older than you and have found solo travel both a break from the world and frustrating at the same time. I used to be quite the social butterfly in my 20s and 30s – but now in my 40s I find it more difficult to make friends whether traveling solo or even here in NYC (for a big city it can be quite lonely at times – most of my friends live out of the city). I appreciate your tips – I also bring my iPad and an adapter to transfer photos when I have down time, that way my card doesn’t get full (when i went to Iceland this happened and I had trouble transferring photos. Needless to say I lost some). So always be sure to have a backup card. I also like going someplace to have a drink before going to dinner by myself – it provides an opportunity to meet others. Always ask at your hotel what is recommended for solo travelers in your age range.


    3.29.16 Reply
  14. Such great tips! I frequently travel alone for business, and I try to always tack on an extra day since my flights are already paid for. I LOVE it!! I find it so freeing, and you definitely learn so much about yourself.

    Kris | Love. Loft. Life.

    3.31.16 Reply
  15. So brave of you to travel to Greece on your own. I am Greek and I suppose it can be hard for someone who doesn’t speak the language. I’ve travel by myself for work, for interviews and for fun. I’ve met incredible people I wouldn’t have met otherwise and these trips were some of the best I’ve ever been to. Such an inspiring post!

    4.3.16 Reply
  16. Love this post! I’m at an age where my travel needs/interests don’t always match up with my friends (who are dealing with spouses and kids and all of that), so solo travel is kind of important if I want to see and do all of the things I’m curious about.

    You comment about Do It All mode made me remember the first time I really made a trip by myself. I tacked it on to the end of a business trip and decided to spend a few days site seeing. I was so excited to be able to plan my own itinerary and not be slowed down by others. By the end of day two I was in bed with ice packs and Advil — happy but very sore 🙂 Still, there is something satisfying about doing things exactly your own way.

    4.3.16 Reply
  17. That photo! Makes me want to go to the beach immediately.


    4.5.16 Reply
  18. Sonya:

    Solo travel is the best! I have done quite a bit solo travel in the US and last year I took my first solo international trip, to Iceland! It was amazing and now its my preferred way to travel. I’m headed to Poland, Latvia, and Lithuania next month by myself, to Budapest, Bratislava, Vienna, and Prague in the fall with a friend, and I’ve already booked my 2017 winter getaway to Panama and Colombia – solo! I love being able to do what I want, when I want. But I also love the sense of freedom and strength I get from traveling alone. I am also single and 35 and I do not want to spend my life waiting for a partner or friends to travel with, I need to seize the opportunity when it is available and just GO! My motto is explore.

    You should totally go to Asia alone! I am pondering it as well but since I’ve got three trips on the horizon, I should hold off on planning another until I’ve at least come back from one.

    4.8.16 Reply
  19. Jake:

    What are some good sites to see in London? I am interested in seeing the touristy stuff, but I also really want to see the little places locals frequent, places with character.

    I am also thinking about hitting Germany and France while I am out there.

    Suggestions are very much welcome.

    4.16.16 Reply
    • graceatwood:

      My trips to London have been very short but I love all the museums! The Tate Modern is one of my favorites and I love the Serpentine Gallery. And you have to have a drink at the Chiltern Firehouse.

      For a more comprehensive guide, my friend Merritt lived there for a few months – check out her post here:

      4.16.16 Reply
  20. headed solo to Greece in 3/weeks — thanks for the inspired read and great tips!

    4.16.16 Reply