May is my birthday month, and this year it carried some weight: I turned 40. For the last few years I have done one big travel adventure annually, usually with multiple stops, and May became this year's. I wanted to get out and see the world, and that's pretty much what happened—one trip kept turning into the next. What started as a short Memorial Day weekend cruise grew into a working week in Fort Lauderdale, and then, instead of flying home, a flight farther south to Medellín, Colombia—farther south than I had ever traveled before.
It started with a friend. Gabrielle mentioned she was taking a quick four-day cruise over Memorial Day weekend and that there were still cabins available, so my partner, Nick, and I booked a ride and met up with her on the ship. I didn't plan much past that.
🚢 Cruising — Celebrity Reflection
The sailing was three nights aboard Celebrity Reflection, out of Port Everglades in Fort Lauderdale—Friday, May 22, to Monday, May 25, with stops in Key West and Nassau, Bahamas, where we spent a day at a Royal Caribbean private beach before turning back for port. It's a short, easy itinerary, which was exactly what I wanted for a birthday weekend: pool-deck afternoons, a silent disco in the atrium with everyone wearing glowing headphones, crawfish and paella out on deck, an afternoon cocktail at the Martini Bar, and a formal night at Opus with the kind of commemorative photo the cruise lines insist you take whether you want it or not. Reuniting with Gabrielle on a moving ship, somewhere off the Florida Straits, was a fine way to start a milestone year.
🌴 Fort Lauderdale
I had actually flown into Fort Lauderdale a couple of days ahead of the sailing to be sure I made the boat, but the real stretch came after. When the ship came back to port I did not. I stayed on for a week and worked from a resort instead of rushing home—west coast hours from Florida, which worked out to about noon to eight, so the mornings and evenings were wide open. Our friend Roc flew in from San Francisco to keep Nick company while I was on the clock, which meant I could log off and find the two of them already poolside. I am unapologetic about the warmth; a typical San Francisco summer is fog and wind, and trading it for South Florida and the Caribbean—an iguana sunning on the pool's waterfall rocks, canal walks at golden hour, a slow soak in the hot tub before and after work—felt less like indulgence than like good sense.
🇨🇴 First Glance at Medellín
When the Florida week was up, going home was the obvious move and we made the other one. A last-minute flight to Medellín turned out to be short, cheap, and somehow easier than getting back to California, and I had wanted to see more of Colombia ever since a cruise stop in Cartagena a couple of years ago. So we kept going south.
Colombia handed me a real jolt of culture shock, the good kind. I speak very little Spanish—enough to get around and not be completely lost—and every time I land in Latin America I get pushed, by immersion, into learning a little more. We based ourselves in El Poblado, a tourist-friendly and LGBTQ-friendly district, at Masaya hostel, which keeps a coworking space on the second floor, so I could log on without leaving the building. Medellín made the month feel bigger immediately: brick towers climbing into green mountains, a rooftop hot tub with the whole Aburrá Valley laid out below, and neighborhoods where the best thing to do is just walk around with a camera. One night ended at La Matriarca, a mural of a smiling woman whose hair is a living vertical garden, lit up after dark.
🦁 Parque de la Conservación
On Sunday we walked from the hostel to the city zoo, Parque de la Conservación. I posed with the giant colorful wings at the entrance like a tourist (because I was one), then spent the rest of the visit wandering past crocodiles, jaguars, howler monkeys swinging through a rope playground, and an Andean cock-of-the-rock so improbably orange it looked painted on.
🌅 Outro
The rest of the month stayed in Medellín. It rained exactly once—the only day the rooftop infinity pool looked like a sheet of glass—and otherwise the city kept offering up small scenes: steak with chimichurri at an outdoor table, Birra Latina glowing at night, a ridiculous music-themed ball pit in a mall atrium, and iguanas sunning on the sidewalk like they owned the place. Outside of work, that was my May: travel, end to end, to celebrate turning 40. Looking back over the whole month, I'm surprised by how much I got to see and do—the cruise already feels like it was a lot longer ago than a few weeks.
And it's not over yet. Instead of heading home, I'm flying to San Juan, Puerto Rico, this week to celebrate Puerto Rico Pride. The adventure continues.