I Quit My Job To Take A Yearlong Honeymoon—& Here's What Happened

On May 24, 2014, my fiancé, Andy, and I got married in New York City. Seven days later, we hopped on a plane with two carry-on suitcases and two one-way tickets to Paris. We had just pressed pause on our careers, sublet our apartment, moved all of our things into storage. The only plan was to have no plans at all — and we ended up traveling for 394 days through 25 countries, stopping in nearly 100 destinations. Over the next few weeks, come along on this crazy journey to learn more about how we did it — packing, plotting, budgeting — and see some of the tens of thousands of photos we took along the way.

Originally, we hadn’t planned on stopping in Italy, since both of us had visited the country before. (Outside of Paris, our goal was to hit places that at least one of us hadn’t been to.) But a few weeks into our journey, we got a note from some friends saying that they were headed to Sicily for a five-day sailing excursion through the Aeolian Islands. The couple they had planned on going with had canceled last-minute, and they needed another duo to share the catamaran. The trip was all planned. We just needed to show up. Were we interested? Um, yes. Yes is the only answer to that question.

At this point, we had already booked our travel from Paris to Amsterdam, thinking we’d continue north through Europe. For a quick second, Sicily sounded like a bit of a detour until we realized that it was a short three-hour flight on a budget airline. You know, like flying from New York to Miami, except you pass through a few countries. Oh, Europeans…

We flew into Palermo, where we met Jason and Madison and immediately set out on our most important duty — stocking the boat. We’d be sleeping, showering, and living on the boat for the next week and periodically hopping off to explore the islands. After a successful sprint through the local Sicilian supermarket, we compared purchases. Wine, cheese, meat, espresso — check! We arrived at the port and met the boat owner and his wife. After a quick tour of the boat, an instructional on how to use the bathrooms (wait, the faucet head is also the shower?), the owner surveyed our purchases. “Did you buy toilet paper and water?” he asked. No, but we did have six blocks of cheese and five bottles of rosé…

It was already evening by the time we ironed out the paperwork and laid a map over the dining table, contemplating our route. We were just waiting for our captain, who the boat's owner described as “a beautiful man.” What? Shortly thereafter, our captain, Roland, arrived and we all agreed to set out that night. Our first stop was the island of Filicudi, 10 hours away. The plan was to sail through the night, taking turns to stay up with Roland, and arrive by morning.