Caribbean Cruise with Seabourn: Eleven Days in Paradise

Andrew Keenan-Bolger
The Keenan-Blogger - December 22, 2019

A few months ago, I was approached with the opportunity to go on an 11-day cruise in the Caribbean. I’ve always liked cruising, but heading out for nearly two weeks during the holiday season would take some serious finagling. My husband was slammed with work covering the Democratic presidential primary, and I knew leaving him alone with the dog would be a burden. Plus, pilot season was ramping up, which meant possibly missing out on auditions. At first, it seemed impossible, but when I was grabbing lunch with my Aunt Paddy (easily the chicest person in the Bolger lineage), I mentioned the trip in passing. “Which cruise line would it be?” The second I said “Seabourn,” her eyes lit up. “Oh, you have to go! Find a dog sitter! Bribe your husband! Send your agent flowers! Whatever it takes! I promise you it will be worth it.” I did some internet sleuthing and found out pretty quickly that there were two kinds of cruisers — Seabourn people, and everyone else. The reviews all gushed about the ultra-luxury experience and claimed that the Seabourn fleet of ships are the absolute best in the world. 

Okay, so now I was enticed, but I needed someone to bring along. Enter Maggie. Maggie is my sister and I feel so lucky that she also happens one of my best friends — not necessarily true of all people with siblings. Most of the travel she’s done is work-related, and I suddenly remembered her once saying that if she could pick a dream vacation, it would be on a cruise ship. I figured that if I could get her to be my travel companion, then I would do whatever it would take to clear my schedule and board the Seabourn Sojourn

Luckily, Maggie was available, and on December 10th we boarded the ship in Miami and set sail on their 11-day “Gem of the Antilles” cruise. The second we stepped aboard, the first word uttered was “whoa.” Our room was huge by cruise-ship standards, and boasted a beautiful veranda with a view of the Miami coastline. The common areas were opulent and spacious, and all this early excitement was before we tasted our first bite of food. Seabourn has famously partnered with celebrity chef Thomas Keller, and the result is a world-class dining experience with four different restaurant options for every meal. 

After two luxurious days at sea being pampered with poolside drinks and entertainment, we docked at our first port city, Santo Domingo in the Dominican Republic. Maggie and I gave ourselves a little self-guided walking tour of the “Zona Colonial,” the old historic part of town, complete with 500-year-old cathedrals and cobblestone streets.

Our next stop was a complete change of scene. After dropping anchor, we tendered out to Isla Catalina, a private island with one of the most beautiful beaches I have ever seen. The sand was white and dotted with palm trees, and the water was warm and brimming with tropical fish. As if we weren’t already feeling extravagant while sipping piña coladas from hollowed-out pineapples, we looked to the turquoise water and found a gang of Seabourn staff pushing a surfboard out into the waves. On top of the surf board was… no, that can’t be. Is that...caviar? Yep! That’s right. We quickly learned that as tradition, the Seabourn crew delighted in presenting their “Caviar in the Surf” — a chance for their guests to soak in the ocean while sipping champagne and loading on up crackers topped with caviar.

While the destinations themselves were impressive, the ship itself hosted a number of enticing activities. We were quickly recruited to a group trivia team (which we actually won!). We were treated to wonderful onboard entertainment, and every day at 4 PM we had the option of attending High Tea. This was one of our favorite experiences. Turns out nibbling on sandwiches and petits fours while gazing at panoramic views of the ocean is never a terrible way to spend an afternoon.

Another treat unique to the Seabourn fleet is the option to order champagne and caviar to your room, free of charge, around the clock! Few things feel more decadent than enjoying a sunset on your balcony while munching on fancy fish eggs and bubbles.

Forte-de-France, Martinique was the next stop on our itinerary and after some research, I found a nearby beach, famous for its exotic residents. Immediately, we began noticing that most of the inhabitants on the beach were not traditional sunbathers, but rather spine-y iguanas. We legitimately spent an hour laughing as one by one, the iguanas would come down from a nearby tree and eat fruit and bread left by some of the locals. At one point we found ourselves surrounded by, no joke, twenty iguanas. While the city itself was fun to walk around, it was hard to compare architecture with “Iguana TV.”

One place that I had never been and was really excited to visit was the small island of Terre-de-Haut, a part of the archipelago of Guadeloupe. Pulling into the marina, I could immediately tell this place was special. The tiny buildings were brightly painted and the vegetation lush and flowering. The culture is undeniably French with chic beach huts selling fancy soaps and ice cream. After a bit of a hike, passing a gang of wandering goats, we found Plage de Pompierre, a nearly empty beach paradise teaming with chickens. If our iguana adventure the previous day was entertaining, this animal encounter was decidedly more adorable — a seemingly endless stream of chickens strolled past us as we relaxed on our beach towels. With a tip from one of our servers, we headed next door to the small outdoor restaurant and were treated to some of the freshest fish I’ve had in ages. While it was hard to pick a favorite stop on our itinerary, I think I would choose Terre-de-Haut. It just felt the most other worldly with its French-speaking locals and lush rolling hills. It’s a place I hope to return to, either with Seabourn or on my own.

One thing that can’t be understated is the sense of community aboard the ship. With most cruises, you’re one of a thousand (or a few thousand in many cases), but on Seabourn, it felt so much more intimate with only 400 guests. When you’d meet someone, you felt like it was actually worth investing in conversation because you were almost guaranteed to be sunbathing alongside them the next day, or sharing a fruity drink with them at one of the many bars the day after. One thing that I really valued was that Seabourn scheduled an LGBT meetup one evening for both guests and staff. Maggie and I are both gay and jumped at the opportunity to meet the other LGBT people on the ship. It’s an unspoken truth that when you’re a queer person traveling, you often seek out other people like you. It’s not a clique-y thing, but an acknowledgment of shared experience. And especially in certain countries where being LGBT isn’t always accepted, it’s often a matter of security. None of the places we visited were unwelcoming to gay people, but I still loved that Seabourn fostered this opportunity to connect us with other people from our community. We even hit it off so well with a couple from San Francisco that we made dinner reservations with them for the following evening. Also a nice touch: Seabourn somehow arranging a giant rainbow for us on the final day of the trip ;-)

On our last three stops, Seabourn organized excursions for us at each port city, and after a week of being lazy and eating and drinking ourselves silly, they were quite welcome. First up was Antigua for a day of ziplining through the rainforest. Maggie has never been ziplining, and when choosing excursions, this was at the top of her list. Antigua Canopy Tours did not disappoint! It was exhilarating to soar hundreds of feet above the treetops and it was awfully beautiful seeing your feet dangle over the giant forested canyon below.

In Sint Maarten we booked something called a Rhino Wave Rider, which upon closer examination, seemed to be something akin to a jet ski. Of everything we did, this was probably our favorite onshore activity, zipping across the waves of Simpson Bay up to the top of the island to Happy Bay, a cinematic beach with azure waters and the occasional nude sunbather. If soaring hundreds of feet above a rainforest was thrilling, zooming 40 miles an hour along the coastline was borderline terrifying (in the best way, of course). By the end, we were almost hoarse from laughing. Turns out I’m just as terrible a driver on the water as I am on the road! It was also a great way to see the island (when, of course, we weren’t being splashed in the face by a wave).

Our final port city was Cruz Bay, St. John, the smallest of the U.S. Virgin Islands. After a taxi ride followed by a golf-cart trip, we rolled up to a wide stretch of powdery sand called Honeymoon Beach. The beach was gorgeous enough to just lay in the perfect 79-degree sun and stare at the teal water, but we were tipped off that it also had some of the best snorkeling in the Caribbean. The second we placed our face masks in the water, we were dazzled. It’s been a long time since I’ve seen a thriving coral colony and Honeymoon Beach had just that. The fish were electric blue and yellow and they played in the fluorescent seaweed and brain coral. We were also told by a local guide the best area to spot sea turtles. I’m taking this opportunity to apologize in writing to Maggie, because “spot sea turtles,” we did. In fact, I was so captivated that I took off and ended up swimming alongside a very sweet turtle for nearly twenty minutes. I was amazed how gentle and unafraid it was of people. My hard shelled friend swam right next to me the entire time, only pausing briefly to take sips of air from the surface. Finally, when I poked my head above water, I heard for the first time my sister calling my name. It seems I had seriously underestimated how far I’d swam, making it almost halfway back to the cruise ship! But honestly, for an encounter with a rare and beautiful creature like this, it was worth it.

In our final few hours, we said goodbye to the friends we’d made, both guests and crew members. Shout out to our awesome trivia team, our sweet and attentive housekeeper Melissa, and one staff member in particular, Theresa, the hotel director, who went above and beyond to make our trip extraordinary. Theresa introduced herself on the first day while Maggie and I were playing Connect Four in the card room, and on the second day, invited us to dine with her in the restaurant. On our final day at sea she arranged a visit for us to the bridge to see the control room and meet the first officers. It was fascinating to see a behind-the-scenes look at just how much goes into keeping the ship cruising and comfortable.

When most vacations end, I’m often sad to return home, but saying goodbye to Seabourn was especially hard. I had never been with a group of people more proud to call themselves “Seabourn-folk” and by the end of the trip, I finally understood what all the fuss is about. Whenever we’d meet a fellow passenger, they were always so excited to find out this was our first time cruising with Seabourn (for most it, was their seventh or eighth time). They couldn’t wait for us to experience their secret to ultra-luxury travel and kept insisting that “once you sail with Seabourn, you are ruined for life.” Well, I can say confidently that “ruined” has never felt so good. Looking back on our trip, it’s hard to pinpoint just what makes Seabourn so special to so many people, but with the taste of lingonberry pancakes from the Colonnade still lingering on my tongue, I’ll give it a shot: It’s not just the five-star food or the fancy lodgings. Not just the dream itinerary or the adventurous excursions. I think it has more to do with the people. The effortless culture of care and the willingness of the crew to not only serve, but to engage with you in meaningful ways that puts Seabourn at the top of the heap.