A Working Vacation and Chance to Decompress in Key West

by Jen May

I arrived in Key West at 12:15 a.m. after a four-hour shuttle ride from the airport. The driver went around the block a few times looking for the alley leading to the driveway of my rental.

I’d found and dismissed several housing options after communicating with owners who later revealed — via a Google search — to have a mugshot and record. I admit that I could have viewed the full charges and seen if it was something serious, but since that involved a fee, I decided on a “no rap sheet” policy for my initial rental.

I’m writing this after several months in Key West, and while I’m on the next leg of my travel, so my “very dangerous” (I hear this whenever I travel alone because I’m a woman) decision to find housing on Craigslist worked out for me. I ended up staying at the lovely little bungalow for three weeks, and had some nice times with the three roommates and a feisty dog. At $250 per week it was more than I wanted to spend on rent, so I moved to another Craigslist find (listing: “women only, this isn’t a f*ckpad”) at $750 a month that was farther outside of the picturesque Old Town, but included a bike.

When I first arrived in the Keys, I didn’t have much in mind for what I wanted to do. I had given myself two months to decompress after working at an office job in San Francisco that I despised. I knew the job would end after the midterm elections, giving me about nine months left at the office. So I got a $600/month room in a beautiful house in Oakland (Craigslist, again), and saved up for whatever I decided on next. To stay sane, I budgeted for one solo trip a month, where I’d rent a car and go to the mountains / camping / to natural springs / tn the desert, and so on.

I knew I’d need a major chunk of time off, not only to recoup after the soul-sucking job (I’d been there at four months by that point), but to figure out how to, well, not be in an office again.

I chose Key West because the ticket to Miami was cheap, I’d never been, and I wanted to stay in the US. Plus, there’s something special about border towns/end of the line type places. As a real estate agent who’d been in Key West for 30 years told me: “This place attracts the exceptional and those running from something” before telling me a funny story about a visit from the FBI looking for a criminal renting one of his houses.

I typically read the want ads while traveling to get a sense of a place. On the second day, I saw a call for first mate of a sailing charter. I have minimal sailing experience: just tending bar on a catamaran tourist boat for 7 months after college, almost 10 years prior.

I told this to the captain when he answered, and that I was only in town for two months. “That’s great!” he answered. “That’s a lifetime! Besides you’ll come back to visit and call me to get back on the water.” This is probably true.

The interview took place in the car while driving to get more towels for the new guests arriving that afternoon. The captain had three small boats (around 45 feet) that were rented by the night on AirBnB, and taken out for sunset sails and snorkeling trips, as well as overnight camping trips to nearby keys; those trips were what I’d go on with the captain. The pay was minimal: $12/hr for cleaning, $100 per overnight trip, and tips.

I was elated — sailing is fantastic! Of course, sailing is only a small part of being on a boat, and an even smaller portion when working on a boat for other people. This isn’t a complaint so much as clarification for how overly romanticized this sort of gig can be. Getting rocked to sleep under the stars and swimming with turtles is countered with pumping out toilets and swabbing decks.

During my second week, the manager quit and the captain began calling me several times every day to come in at the last minute. When I’d started it was agreed that I’d work a maximum of four days per week, so I said “no,” which is when it really began to feel like I was on vacation. I was going to do what I want (and wouldn’t yield to demanding men!).

I think this audience will sympathize with the need to feel productive, accumulate skills, and yes, make a bit of money, even during a time explicitly set aside for rest and relaxation. If the point of vacation is to get a new perspective, and through doing so feel refreshed and inspired, this experience was about as good as I could hope for.

This story is part of our Travel Month series.

Jen May has removed herself from the workforce for the time being. This is her first post for The Billfold.

Photo: Gabe Popa

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