November 6th, 2017

6 Things I’ve Learned in 6 Months of Travel

I left New York on April 29; this month in Chiang Mai is my seventh on the road. I’m not quite halfway through—currently planning to head back sometime in June probably—but it seems like a good moment to pause and take stock.

I was feeling a bit melancholy in September, thinking about how I don’t feel [Read More]

October 6th, 2017

When You Date While Traveling, Don’t Expect a Hollywood Ending

Yesterday I seriously considered hurling my phone out my 25th floor window. Only two things stopped me: one, the fact that I’ve replaced three phones in the last six months (not from throwing them, I swear) and two, a legitimate worry that I might injure person or property.

Apparently a memo went out yesterday to all the men I’ve [Read More]

October 4th, 2017

Embarking on a Year of Travel, Part Two

I’m not quite halfway through my year on We Roam—this month is number six. But this month marks a huge shift in my experience, enough so to qualify as a second chapter.

I’m in Seoul for the month of October, which is a half day’s journey and a world away from Belgrade. After Seoul, [Read More]

September 5th, 2017

The Difference Between Vacationing and Living

Whenever I go on vacation, I find myself wondering if I should live there. I definitely contemplated it when I went to Anguilla last winter. Why return to snowy New York?, I thought. Anguilla has everything I need.

Traveling with We Roam has allowed me to test this idea. While a month isn’t long enough to experience [Read More]

September 1st, 2017

Catching Flights AND Feelings

“Catch flights, not feelings” has become a rallying cry. And when I started this trip, I thought maybe it could be mine. I left a string of romantic disappointments behind in New York, and I hoped a year with We Roam would be a much-needed break from the pressure of dating in my 30s. 

But four months [Read More]

August 25th, 2017

When Epic Becomes Your New Normal

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Two weekends ago, I was walking the city walls of Dubrovnik. Last Friday, I was talking to my [Read More]

August 16th, 2017

I Drove 119 km for a First Date

When I wrote about bailing on my island hop last week, I mentioned that it freed me up to accept an invitation to visit the little town of Tisno—here’s the story I hinted at.

Shortly after I arrived in Barcelona back in May, right after I’d started traveling, a guy messaged me on OKCupid. We’ll call [Read More]

August 11th, 2017

4 Things I Learned from Bailing on My Croatian Island Hop

Last Saturday, I boarded a catamaran to visit the island of Vis, the first stop on what was supposed to be a 10-day vacation, hopping to Hvar, Korcula, and Dubrovnik. The very next day, I returned home to Split, tired and sweaty and annoyed.

I haven’t made a secret of the fact that Croatia is not [Read More]

July 20th, 2017

3 Problems with Constant Travel

I’m nearly to the end of my third month with We Roam, a quarter of the way through the time I’ve signed up for. My challenges so far haven’t exactly been the ones you’d imagine. In the midst of a busy month, I’ve been mulling over a few unexpected hazards of constantly circling the globe.

[Read More]

June 14th, 2017

Traveling with Steamer-Trunk-Sized Emotional Baggage

People always say you can’t run away from your problems, but I’ve done a pretty damn good job of it over the years. When life gets messy, travel. When life turns catastrophic, move. I took Cher’s mantra in Mermaids (a classic) to heart: “Death is dwelling on the past or staying in one place too [Read More]