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Traveling Solo? Here Is the Best Advice You Can Get

Annie Gabillet

Whether you find yourself traveling alone for work or fun, solo adventures provide perspective. With fewer distractions, you can observe the world around you, as well as your own inner thoughts. If done well, a trip alone will leave you with a deeper understanding of yourself and — ironically — others.

All these benefits don’t mean you won’t get lonely or bored while traveling alone. Or that you won’t be tempted to take out your phone and spend your time keeping up with what’s going on back home. So to help make the most of a solo trip, we tapped into some of the most successful women we know, who also happen to travel a ton. Each of these women who are going places shared their best piece of advice for solo travelers. Armed with these tips, we’re adding alone time on the road to our travel bucket list. 

Tips for Solo Travel 

Start Your Day Earlier

Often nights at bars and pubs are not appealing alone, so instead start your day earlier. Whenever I go to a new city alone, the first thing I do is look up the nearest morning marketplace, like farmer, antique, or flea markets. It’s a great place to start your day outside of the touristy path where you can experience cultural tastes and meet locals.

— Sara Cullen, founder of  GEMRead our full interview with Sara.

Image Courtesy of Unsplash // John Towner

Observe Your Surroundings

I get some of my best product and content ideas while travelling. Just seeing needs and patterns and trends.

— Sara Panton, CEO and co-founder of VitruviRead our full interview with Sara.

Make Eye Contact

Don’t be afraid to sit in a cafe with a book and make eye contact with friendly looking strangers. I have met some incredible friends through the years by just being open. I believe that the energy you put out is palpable to other people. If you are putting out nervous, anxious, tired, closed off energy, you won’t attract anyone to you. If on the other hand you have excitement and light in your eyes, you won’t fail to make connections!

— Tegan Bukowski, founder of WellSetRead our full interview with Tegen.

Read in Public

Reading at a bar or restaurant at night is a great way to spend some time and to avoid spending time on a phone.

— Claire Fauquier, principal at Highland CapitalRead our full interview with Claire.

“Reading at a bar or restaurant at night is a great way to avoid spending time on a phone.”

Talk to a Local Before You Leave

Make sure you connect with a local before you get to your destination. The “lost in translation” journey starts as soon as you land at the airport.

— Bouchra Ezzahraoui, founder of AUrate jewelryRead our full interview with Bouchra.

Do Your Research Ahead of Time

It helps maximize your time in each location. And ask for recommendations. I have lists upon lists of everything from best restaurant to best shops to off-the-beaten path sites that I dole out to anyone that asks.

— Cate Luzio, founder of LuminaryRead our full interview with Cate.

Image Courtesy of Unsplah // L A L A

Don’t Compromise

Traveling solo is such a special experience. You’re in a unique position where you can be completely true to yourself because you’re alone. No compromises — you can do what you want, whenever you want, in this completely new environment. I think that’s the perfect formula for self exploration and growth.

— Carly Stein, founder of Beekeeper’s NaturalsRead our full interview with Carly.


Bring a journal. Traveling gets you out of your comfort zone so take advantage of this by allowing new thoughts and observations enter your psyche.

— Claire Wasserman, the founder of Ladies Get PaidRead our full interview with Claire.

Image Courtesy of Unsplash // Toa Heftiba

Send Yourself a Postcard

The last time I took a short trip on my own I brought a postcard and wrote to myself.  I wanted to remember the details and found it was a way to harbor the calm solitude of the trip that I could re-visit when the trip was over.

— Chelsea Nicholson, CEO of CeremonyRead our full interview with Chelsea.

Try Coffee Shops, Instead of Bars

For meeting people, recharging, and getting a good sense for the local vibe, I always research cool coffee shops in advance. I’ve never been any good at making friends in bars.

— Nicole Johnson, investor at Forerunner VenturesRead our full interview with Nicole.

Get Some Exercise

Instead of taking cabs, walk or jog to places in new neighborhoods, after ensuring they’re well-lit and not dodgy of course. I find it’s the coolest way to explore a city when traveling. I’m often the crazy foreigner jogging around Tsim Tsa Tsui in Hong Kong or Piccadilly in London.

— Shrankhla Holecek, founder of Uma OilsRead our full interview with Shrankhla.

Talk to People

Don’t let yourself fall into the loneliness that is fed by isolation. Be outgoing. Talk up the people on the bus, plane, or barstool next to you. Keep your itinerary full, and be open to the magic of even the most casual connection with fellow travelers or locals along the way.

— Molly Hayward, founder of CoraRead our full interview with Molly.

Make Friends

Make friends! That’s the best part of traveling solo. Sit at the bar with a book or magazine. Put your phone away and start a conversation with someone.

— Allison Moss, founder of  type:A DeodorantRead our full interview with Allison.

Find the Local Food

Go to open air food markets in every city you go to. You will meet the most interesting people there and really experience the culture.

— Kat Schneider, founder of RitualRead our full interview with Kat.

Image Courtesy of Unsplash // Pietro Rampazzo

 Don’t Use Your Phone at Meal Times

“This used to terrify me, and now it is one of my favorite things to do, even when I’m not traveling. A solo date is the best. It’s important to treat ourselves and enjoy some time alone.”

— Kingsley Delacato, a Reiki masterRead our full interview with Kingsley.


Enjoy the opportunity to write your own itinerary and sleep in! Do something spontaneous. Make friends along the way.

— Alison Ryu, Managing Director and General Partner at CircleUp Growth PartnersRead our full interview with Alison.

If you could take these tips with you anywhere in the world for a solo trip, where would you go?