My First Cruise to the Eastern Caribbean

It became clear on Tuesday evening, given the scant line to debark the ship in San Juan, that my seven-night cruise to the Eastern Caribbean aboard Carnival Victory was less about the ports and more about the ship. After all, as several passengers mentioned, you barely have enough time in each of the three stops—five hours in San Juan, seven hours each in St. Thomas and St. Maarten—to get even the smallest taste of the essence of each place. Moreover, the cruise passenger congestion of these tremendously well-visited ports—at least in the area of the pier—is enough to completely alter the feel of the islands, creating a shopping mall vibe instead of something more organic. Not that we needed proof that this route was a popular itinerary, but proof came nonetheless with the sight of the same ships, Costa Magica, Mariner of the Seas, Norwegian Jewel, and others, trailing or proceeding us at each dock. (St. Thomas, in fact, has a daily winter average of at least six vessels, which can total almost 20,000 cruise passengers a day.)

The very nature of a cruise vacation—being dropped off with thousands of fellow cruisers in a “built-up” portion of a particular destination for six hours—can make you feel a bit touristy. That prospect had given me pause about taking a cruise in the first place, and to the Eastern Caribbean, one of the most congested cruise regions, in the second. With the paucity of time, it’s much easier to simply book an excursion, stay in the “duty-free” designated zone, or just as commonly, stay onboard the ship. And with everything you need—restaurants, bars, beaches, shopping—right in proximity to the vessel, why venture out?

That said, it was possible—and this was the case with my stop in St. Thomas—to sense yourself breaking the threshold of experience. And for the self-admitted palest guy in any room, I was even asked twice if I lived in St. Thomas, a fitting sign that I was fitting in.

Why Take the Cruise?

Borrowing the words of Thoreau, “I went to the woods (cruise to the Caribbean) because I wished to live deliberately, to front only the essential facts of life (a Caribbean cruise), and see if I could not learn what it (a cruise to the Caribbean) had to teach, and not, when I came to die, discover that I had not lived.”

Beyond just my first region-specific cruise, this was, in fact, my first cruise anywhere. So I selected accordingly: For a first-timer, Carnival is a safe choice: The price is reasonable, the food good to very good, and there are a lot of “fun” activities. The Eastern Caribbean is equally safe: The typical cruise stops are sufficiently built up so you won’t feel too out of place, and the lack of culture shock will be comforting for first-timers. And if you don’t like a port, the ship is usually in sight.

One of cruising’s most well-established features is the allure of destination sampling. You get to stop in three popular ports (granted for only a few hours each), with the best case scenario being a decision to make a return trip to one or several ports, and the worst case, having those places become just another notch on the travel stick. You also get to spend three sea days relaxing aboard a ship that provides solid service and the ability to indulge in as many daily feedings as you want. So while my ambitions may not have been as idealistic as Thoreau’s, I saw the cruise as a chance, not unlike any other type of travel, to acquire an experience. Because good or bad (or whatever value judgments you choose to assign), it’s the experiences that helps to shape us…no?

Nightlife, Beach, and Exploration

I’ve already griped about my failure to get a solid defining sense of each island. And yet, between the three destinations, a single picture of the Eastern Caribbean did materialize. I got to touch on Caribbean nightlife in San Juan, spend a beach day in St. Maarten at Orient Beach, and explore St. Thomas during the afternoon by way of Safari Cab.

After getting our bearings in San Juan, the first port on our itinerary, we were attracted by the lights and resonating bass noise of Senor Frogs, a tourist haunt, with an excess of seedy looking dudes staring at a smattering of women. Unnerved, we moved on to another bar, this one empty of patrons and decked out with reggae paraphernalia—Jamaica flag, marijuana leaf poster—and a Bob Marley concert DVD showing on a flat-screen TV. The barman sang along and made periodic side-trips to an adjoining room where he accompanied the music on drums. Our final stop was at Cafe Bohemio, a breezy island venue with live salsa jazz and dancing. We would have liked to feel the energy (bad vibes or good spirits, whatever) of a Friday or Saturday night, but it was not to be. The sparsely populated Tuesday evening did allow for easy navigation of Old town San Juan, and we were able to get a sense, however vague, that allowed us to picture a busy night in San Juan, streets crowded with sweating locals, drunken vacationers, and cruise ship passengers.

Only 12 hours later, we were on Orient Beach on the island of St. Maarten (the beach is actually in neighboring St. Martin), paying a cabana guy $14 for two yellow lounge chairs and two Presidentes (the beer of the Dominican Republic). In an effort to avoid hackneyed prose in describing the beach, the water was the thirst-quenching color of blue Gatorade. Technically a bay, the natural concavity of the landscape forms a semi-circle with gently rolling hills cushioning the beach on each side. Small, tree-covered islands are visible in the near distance. There’s a reason Orient Beach is considered one the world’s most beautiful, but it’s also one of the most famous thanks to its well-known nudist resort on one end.

In another effort to dig below the surface of a tourist place, I utilized the Safari cab public transport system in St. Thomas, a service that for $4 per person can get you about anywhere on the island. Or as one driver responded to a couple’s “how much?”, “It’s $8 for you. Your wife rides free.” The number of robust, 180-degree turns and the remarkably high percentage of dented vehicles (called “island cars”) formed solid sensory experiences. And if your senses are aroused in a place, as they were for me in St. Thomas, you’ll form a bond with that place.

Make Sure Your Watch Is Set on “Ship’s Time” and Not Actual Time

In retrospect, I’m actually glad that I almost missed the ship in St. Thomas.

It had taken about 25 minutes to travel by safari cab from Havensight (cruise dock) to Red Hook. I casually felt that the same could be expected on my return trip, so I delayed leaving until about 10 minutes to five; the ship required passengers to return no later than 5:30 p.m.

In the tropics, the concept of typical rush hour traffic failed to register. The congestion left me with a slight feeling of unease, but my confidence wasn’t yet shaken. The problem was that the rolling hilliness of the area, combined with the snail’s pace of our forward movement, made any approximation of distance to the pier impossible. I was winding down a hill, not having any idea of where I was on the island. What was initially a seedpod of fright had by 5:20 p.m. germinated into full-blown hysteria. Had I missed the ship’s departure—bloop—there goes the rest of the cruise, as St. Thomas was the last stop before Sunday’s arrival in Miami. I would have to fly back to Miami at my own expense, missing the final two days at sea. To say I was horrified at the prospect would be considerably insulting to my actual level of fear.

When we suddenly rounded a bend five minutes later, the pier materialized—with its line of ships visible in the hazy distance—Carnival Victory clearly emitting plumes of smoke from its funnel. Panic set in, and I decided to run for it, thinking I could move faster and in a more direct fashion (straight down hill rather than winding) than the plodding cab. I jumped turnstiles, fled through dense greenery, and hyper-ventilated through the puddled streets of neighborhoods, all the while catching snap-shots of the knowing smiles of locals, who had likely witnessed many times before the comic spectacle of an out-of-breath moron sprinting down the hill toward the pier, with the fear of the Infinite on his face.

When I finally arrived at the ship, my cell phone reading 5:30, I was overjoyed. Once back onboard, I looked at the ship’s digital clock, which read 4:30. Ships’ time was an hour earlier than island time. Woops.

Take Public Transport and Get Lost (Not Too Lost, See Above)

Now I know that this is a well-established idea about travel, but I can’t stress its importance—for me at least—enough. During one semester in college, I spent three and a half months in London. For the first month or so, I felt like a hipster dufus in a land of squares. It wasn’t until I began regularly using the tube and bus system on a daily basis, going wherever intuition took me, that I started to blend into the British landscape, acquiring the filmy residue that was so clearly part of that place.

The night before we arrived in St. Thomas, I received note that my Water Island bike excursion there had been cancelled due to lack of participation. This turned out to be a benefit, as I had the chance to jump on a Safari cab, and wind around the hilly eastern part of the island on my way to Red Hook. On the way there and back, I was joined by school children in pink Ralph Lauren polos braiding each other’s hair, people heading to work and home, and locals heading to do some shopping at the Cost-U-Less, the island’s utilitarian superstore. Two schoolgirls conversed about classmates and teased each other while the Captain and Tennille (Love Will Keep us Together) played softly in the background; the cab driver flirted lazily with the female passengers, with a smile exposing his gold-fronted mouth jewelry ; and Islanders in track suits talked business of some sort on their cell phones. Just this hour or so of riding was enough to give me the sense that I was actually part of the scenery of St. Thomas.

Talking to the Locals Is Essential

Our editor at Cruise Critic was once a somewhat genuine local, living in St. Thomas for a year in 2000, so I had the benefit of her help in planning my itinerary. She recommended a charming Italian restaurant for lunch, Virgilio’s, where I was served minestrone soup so fresh that it finished cooking in its sauce pan as the waiter brought it out to me.

After lunch, I did a little Charlotte Amalie exploration of my own, aping fellow cruisers in search of duty-free liquor and jewelry deals. The most memorable thing certainly wasn’t the shopping venues that quickly began bleeding into one another in monotonous repetition, but the fact that one block over, the edifice was clearly crumbling. I mistakenly assumed that the look of poverty was the result of a recent hurricane, and I even asked the cashier at the Blackbeard’s Ale store if this was the case. She looked a little confused, but then responded, “It just takes a while to rebuild.” The last hurricane to affect St. Thomas was Marilyn, in 1995.

We then headed to Red Hook, a place typically viewed as the jumping off point to get to St. John, the more tropical sister island reachable by a 20-minute ferry ride. When I arrived at the eastern part of the island after the 25-minute cab ride, I started to feel a distance from the pier. Dropped off in the middle of a series of strip malls flanking the street, it felt slightly reminiscent of New Jersey, except the road was two lanes, instead of six. And despite the fact that Red Hook lacked any sense of the exotic, it had a comfortable vibe.

I chatted with the bartender at Duffy’s Love Shack, a bar oddly planted in the parking lot of a strip mall. It wasn’t necessarily a locals’ hang; but despite its tackiness—wall kitsch and drinks called “booty call” and “shark tank” (64 ounces)—the faded feel and non-tourist prices ($1.50 for a Red Stripe) were welcoming. He was an Alaskan who’d been residing in St. Thomas for five years. We talked about the love-hate relationship that some of the locals have with cruise passengers. On one hand, he quoted the figure that each cruise ship pumps approximately one million dollars of revenue into the local economy; but conversely, he mentioned the sense of intrusion, the crowds, tourists walking with their heads down, meager tips, and a general attitude of entitlement. Not sure I entirely agree, but we didn’t get into it.

He mentioned what he would do given eight hours in St. Thomas—rent a jeep and hit a few local beaches, have sushi in Frenchtown at Benny Iguanas; finish by bar hopping. For communion with nature, St. John and its eco-hippie-vibe would be another prime choice. He shared the bizarre saga of ending up in St. Thomas there from Alaska (it’s a long story, some girl was involved though). When we finished talking, we cordially exchanged a handshake and a “pound” (something dudes do, fist to fist). I came out of the meeting with some new insights on what I would do given the opportunity to visit for a second time—the most notable being a side-trip to St. John.

My trip to St. Maarten/St. Martin was also well-informed by local commentary. I was heading to Orient Beach, a place known for its nudist resort and crystalline waters. The cab ride over was basically an advertisement for Dawn Beach, because, says the cab driver, we would have a much nicer time with a more relaxed, less disgusting (nudity in a place where the nude beach is one of the top attractions, being repellent to her), cheaper experience. It at least got me thinking about the island’s other possibilities—ferry to Anguilla, diving at Proselyte Reef, Haitian art in Marigot. After we arrived at Orient Beach I spoke to the cabana guy who sold us our chairs, and he echoed the cab driver’s sentiments about the nudity being disgusting. He was repulsed by the fact that given “their” own nude area, naturalists would venture into the more restrained section of the beach. Though it only lasted for ten minutes or so, our little debate helped to give a touch of context to St. Martin.

Sea Days—Not All the Time Is Spent Onshore

In addition to St. Maarten, St. Thomas, and San Juan, the ship served as a port in itself. The three land-based ports were sandwiched in between one sea day at the front end and two at the back. These days were spent searching for the most strategic deck spot to allow for optimal burning, eating Carnival’s phenomenonally delicious pizza, attending horrible (and that’s being generous, “What’s the deal with airline peanuts?” “You guys heard about that Lewinsky thing?”) standup comedians at the “R-rated” comedy show, eating at the daily International buffets (bowl of guacamole on my stomach on Lido Deck), losing and winning money at the blackjack table, consuming two or three meals per sitting in the dining rooms, and listening to the jazz trio in Victory’s Ionian Room. In short, the ship was a glutton’s paradise.

In Memoriam, the Eastern Caribbean, and Cruise vs. Land

Something that arose as a clear difference between a land-based vacation and a cruise vacation was the relationships formed on a cruise between service staff and guests. Eating in the same restaurant for dinner four nights out of seven, chatting with your faithful Indian room steward every day, having a pre-dinner cocktail brought to you by the same bartender, tends to establish friendly interaction, whether you’re an affable person or not. Case in point: as a touching tribute to family bonds, our room steward Leslie shared with us that he used his four hours in San Juan to call his wife and family in Mumbai. He told us about his two kids, and he and his wife’s dream of opening up a fashion boutique in Mumbai. Then, in a tribute to deification, he told me I was the representation of knowledge and he much respected me as his “master.” I was made a little uncomfortable by this, but it certainly was a testament to the bond we formed.

Ultimately, there are so many places to travel to in the rest of the world that it seems somewhat unlikely that I’ll be back in St. Thomas, St. Maarten, or San Juan in the near future (unless someone else is paying). At the same time, that’s not to say that to these places don’t have a lot to offer. In St. Thomas especially, it only took a few hours of riding around to experience a distinctive personality (exactly what that personality was is hard to define). You just need more time to explore, to blend in with the island scenery.

Where did you take your first cruise and what lessons did you learn? Do you have any tips for experiencing ports of call like a local? Share your experiences, thoughts, and advice by submitting a comment below!