In April I took a long break from work to travel through the Caribbean with a group of friends. We sailed aboard Virgin Voyages’ Resilient Lady on a 12-night cruise that left from San Juan, Puerto Rico.
It took over 12 hours to get from San Francisco to San Juan, with a short layover in Denver. My partner and I arrived a few days early to explore before our friends — Roc from SF and Matt from Phoenix — flew in. We all stayed at Hotel Rumbao, which is right next to the cruise ports.
Here's a 15-second clip showing the view from Hotel Rumbao room.
I always get a little anxious about flights being delayed and missing the ship, so I try to arrive early just in case. We got in on a Saturday and didn’t set sail until Tuesday, which gave us plenty of time to wander around Old San Juan — a UNESCO World Heritage site.
Old San Juan felt full of life, color, and history. Even late at night, the streets were lively — couples walking hand-in-hand, families hanging out on benches, kids playing in plazas. It reminded me how different that energy is compared to San Francisco, where weeknights at 11pm are usually dead quiet.
Architecture of Old San Juan
The architecture here ranges from Spanish colonial, Neoclassical, Gothic, Baroque, Colonial, and more. The buildings are painted in bright blues, yellows, pinks, and greens. Narrow cobblestone streets wind through town, and many buildings date back to the 1500s. The city’s two main forts — Castillo San Felipe del Morro and Castillo San Cristóbal — are massive and nothing like I've ever seen before.
Friends arriving for the cruise
Roc and Matt got in by Sunday. We spent the day catching up, walking around, and visiting the forts. And of course, we ate a bunch of great Puerto Rican food.
Setting sail on the Resilient Lady
On Tuesday, April 1st, it was finally time to board the Resilient Lady. We got on in the afternoon and spent some time checking out the ship before departure. I’d sailed with Virgin once before — on the Valiant Lady in 2024 — so a lot of it felt familiar.
Here's a 38-second clip of us setting sail from San Juan, and how Virgin Voyages kicks off their cruises.
Itinerary
Before we go any further, let me share the itinerary for our cruise.
| Day | Port |
|---|---|
| Day 1 | San Juan, Puerto Rico |
| Day 2 | At Sea |
| Day 3 | At Sea |
| Day 4 | Cartagena, Colombia |
| Day 5 | At Sea |
| Day 6 | Oranjestad, Aruba |
| Day 7 | Willemstad, Curaçao |
| Day 8 | At Sea |
| Day 9 | Roseau, Dominica |
| Day 10 | St. John's, Antigua & Barbuda |
| Day 11 | Philipsburg, St. Maarten |
| Day 12 | San Juan, Puerto Rico |
Ship life
There was a lot to do on board: trivia nights, karaoke, themed events. The crowd was mostly young adults and older couples, with a few families — but no kids (Virgin Voyages is 18+ only).
One of the best parts of the trip was meeting new people. Someone started an LGBTQ+ group chat on WhatsApp before the cruise, which made it easy to plan meetups and hang out with other queer folks on board. We got together for trivia, karaoke, pool hangs, even some shore excursions. It really made the cruise more fun and social.
My favorite onboard restaurant was Gunbae, a Korean BBQ spot where you grill your food at the table. You're seated with other groups, and by chance, we ended up with people from our WhatsApp chat. It felt like a small-world moment.
Cartagena, Colombia
After a couple sea days, we arrived in Cartagena, Colombia, and had the whole day (until midnight) to explore.
Cruise passengers walk through Port Oasis Eco-Park to exit the port — it's basically a lush garden filled with tropical plants, birds, and even monkeys. Not a bad welcome.
Here's a short, 17-second clip showing a Yellow‑crowned Amazon (Amazona ochrocephala panamensis) parrot and a Indian Peafowl (Pavo cristatus) peacock.
From there, we took a taxi to Cartagena’s Old City — another UNESCO site — which is surrounded by a historic wall. We spent the day wandering, taking photos, and trying local food.
The timing was perfect — the Cartagena de Indias International Film Festival was happening. The streets were alive with pop-up food vendors, live music, and outdoor film screenings.
I was drawn to the rooftops. Many buildings in the Old City have terraces with views of the skyline and sea. We checked out a few rooftop bars to take it all in from above.
I basically ate only seafood while we were in Colombia — ceviche, blue crab nachos, shrimp cocktails. Zero regrets.
Aruba
I've been to Aruba before, and so for this trip, we booked a group excursion on a catamaran through Around Aruba Tours, which sailed around Aruba’s coastline, stopping at a few snorkeling spots. We saw shipwrecks, coral reefs, and a handful of fish. The captain and crew kept it lively with an open bar and music.
Curaçao
Next up was Curaçao, a Dutch Caribbean island known for its colorful buildings and beaches. We had a full day in Willemstad, the capital.
I have a friend on the island — we met there years ago and reconnected in NYC last year — but he was working, and we had to be back on board by 5pm, so we didn’t get to meet up. Still, we wandered around the city, ate Dutch croquettes, and tried local beers.
Scarlet Night + sea days
Virgin throws a themed event called Scarlet Night, where everyone wears red and the whole ship transforms into a party. It starts in the atrium and ends up around the pool deck, with dancing, music, and general chaos — in a fun way. It also happened to be Nick’s birthday, so we celebrated that too.
Here's a short clip showing Scarlet Night at the pool deck.
Antigua
We stopped next in St. John’s, Antigua, an island known for sailing and beaches. We spotted a few lizards that are only found here, which was cool.
Nick and I were walking around the port when someone from the WhatsApp group told us to check out Kon Tiki Bar, a floating bar in Dickenson Bay. It was a 10-minute taxi ride, then a short boat ride to get to it — it's literally anchored in the bay.
Kon Tiki was my favorite stop of the whole itinerary because I've never experienced a floating bar before, and the vibe was island-time chill. And if you need a bathroom? You jump in the ocean.
St. Maarten
Our last stop was St. Maarten, an island split between French and Dutch control. We were on the Dutch side, which is known for beaches and nightlife. We spent the day swimming and chatting with a woman we met on the ship and her husband.
Here's a short clip of us exploring Sint Maarten.
Back in San Juan
After 12 days, we returned to San Juan. Roc and Matt flew home that day, but Nick and I stayed a bit longer to explore more of the city.
The locals in San Juan were some of the kindest, most welcoming people I’ve ever met. Every Sunday, Condado Beach becomes a gay beach, and the nearby Tryst Hotel hosts a drag show featuring performers from RuPaul’s Drag Race. We caught some of it from the beach.
That night, some locals invited us to share drinks and dance with them as the sun went down. We danced to Sylvester, Donna Summer, and Celia Cruz on the beach. It was magic.
One of the couples we met even invited us to their home for dinner and music. We spent our final night playing piano, singing, and just hanging out with new friends.
Puerto Rico is beautiful — full of history and good energy — but it’s the people who made it one of the most memorable places I’ve ever been. I can’t wait to go back and see more of the island.