I've been cruising to the Caribbean since I was five years old, starting with my first voyage: a 7-night sailing to the Eastern Caribbean onboard the Disney Magic, calling at St. Maarten, St. Thomas, and Disney's Castaway Cay.
Five years later, my family embarked on our second cruise. Once again, we sailed to the Eastern Caribbean; however, we ventured from Disney, sailing on Royal Caribbean's Freedom of the Seas. Since then I've been on 19 other cruises, most of which have been to the Caribbean.
From swimming with stingrays in Grand Cayman to exploring Water Island's Fort Segarra and zip-lining through the lush canopies of Jamaica, I've learned that each island has its own distinct flair.
Having visited 16 Caribbean islands and countries, it's easy to understand why the region is a popular tourist destination year-round. The diverse cultures, stunning beaches, welcoming hospitality, and warm climate create an irresistible allure for travelers from across the globe.
Plus, all mainstream cruise lines deploy ships to the Caribbean, including Royal Caribbean, Carnival, MSC, Virgin Voyages, Norwegian, Celebrity, Princess, Costa, and Holland America Line, making the sailings appealing to a wide array of travelers. You can also find luxury lines sailing to the Caribbean, albeit less frequently.
From someone who has sailed to the Caribbean six times in the past two years alone, here are the places I'm certain to visit again—and two I'm okay skipping.
Read more: Best Caribbean shore excursions
San Juan, Puerto Rico
I didn't see the appeal of San Juan until my recent visit on Celebrity Ascent. The first time I docked at the island, our time ashore was limited, with an all-aboard time of around 1:30pm. We booked a rushed tour of the city and had to return to the ship before we knew it! Then, I was more concerned with finding a local drug store to purchase over-the-counter cold medication than exploring San Juan during the second visit.
On my third trip to the island, I was initially taken aback, as we wouldn't arrive until later in the afternoon, eliminating the nearby beaches as an activity of interest. In fact, I wasn't too sure about getting off the ship, especially since I was on a solo cruise—I didn't want to wander the streets of an unfamiliar island alone at night!
As luck would have it, I met a group of friends traveling together, and they invited me to join them for dinner at the Cannon Club. I met them at a bar nearby for a pre-dinner drink before going to the restaurant together. Truthfully, I cannot say enough great things about that meal. From the croquettes to papas revolconas, homemade hummus, and a beautiful rooftop sunset, it was a perfect night ashore. After dinner, we walked around the streets a while longer, and I got to see just how lively San Juan is!
I'd love to return to explore the beaches, try more local cuisine, and hike El Yunque, the only tropical rainforest in the U.S. National Forest System.
Roatán, Honduras
Last February, I visited Honduras for the first time. I wasn't sure what to expect of Roatán but fell in love with the area, despite having a few short hours in port. We ventured to the lesser-explored East End to see how local islanders live. However, since most of our day was spent driving from one end of the island to the other, I didn't get to take in too many sights outside the van, except for a stop at an animal sanctuary and local lunch.
What I did see, however, I loved, and I've heard nothing but great things from other cruisers who have visited Roatán and stayed on the west side. Plus, Roatán is situated along the Roatan Barrier Reef, which is part of the Mesoamerican Barrier Reef—AKA the second largest barrier reef system in the world! In other words, the snorkeling and scuba diving in Honduras are rumored to be unmatched compared to other islands in the Caribbean.
Depending on how you choose to spend your time ashore, some destinations can be one and done. Roatán isn't one of those places. The vibrant coral reefs, dense forests, and relaxed animal sanctuaries offer a myriad of experiences to keep visitors coming back time and time again. Whether you're seeking a relaxed beach day, zip line adventure, or a tour of the local Garifuna villages, there isn't a right—or wrong—way to explore Roatán.
Read more: 10 tips for getting the best cruise shore excursion values
Costa Maya, Mexico
After visiting Cozumel a few times, seeing Costa Maya on my Western Caribbean itinerary was a welcomed change. Unlike Cozumel, Costa Maya isn't an island—it's located on the Yucatán Peninsula at the southern end of Quintana Roo. However, do not make the mistake of assuming it's closer to the more famous Mayan ruins. Tulum is roughly 2.5 hours away, while Chichén Itzá is nearly 4 hours from the port.
Though I was disappointed I'd have to hold off on exploring Mayan ruins, I was particularly excited to venture into Mahahaul. Instead of being filled with basic all-inclusive packages at massive beach clubs and resorts, the quaint town is home to boutique hotels, restaurants, and shops. The fishing village is a short ride from the cruise port, and it's easy to hail a cab for around $4 per person, per way.
During my visit, I spent the day at Jamie's at The Blue Reef. For just $57, I enjoyed all-inclusive food and drink. Plus, the service was top-notch since it wasn't a large establishment. At times, it almost felt as though we had private butlers, which isn't usually the case on cruise ships with thousands of passengers. The food was freshly prepared, too! I could have eaten more of the guacamole than I care to admit.
While I could easily spend another day in Mahahaul focusing on eating at other local restaurants, Costa Maya boasts numerous other activities that interest me, such as the Bacalar Lagoon and Chacchoben Mayan Ruins. It's impossible to see everything that makes the port unique in a single trip!
Willemstad, Curaçao
In May 2022, I set sail on an 8-night cruise to the Southern Caribbean aboard Royal Caribbean's Allure of the Seas. The combination of an Oasis Class ship and new ports of call was enticing, as I had yet to cross Aruba and Curaçao off my bucket list. However, despite Willemstad's colorful buildings and friendly residents, it's an island I'm okay not returning to.
We booked an island tour to the Curaçao Museum, Hato Caves, and Curaçao Liqueur Distillery. While I wasn't a fan of the excursion (nothing's less thrilling than sitting on a hot tour bus), after seeing the country's highlights, I would prefer to explore other destinations more!
While that's not to say one should avoid visiting Curaçao, it was more of a one-and-done-type place for me. The Queen Emma Bridge, which rests atop a set of pontoons, was a unique site, and Handelskade was just as beautiful as pictures make it out to be, though living 3.5 hours from Charleston, I'm accustomed to colorful buildings.
If I were to return, the visit would be far more beach-centered, and I prefer destinations where I have different activities to fall back on, especially if other ports on the itinerary are just as beachy (i.e., Aruba).
Labadee, Haiti
Royal Caribbean is the only cruise line offering regular sailings to Haiti, though they've been suspended through at least September due to civil unrest. However, when visits restart, I won't be scouring the internet for the next available sailing.
Labadee may be a favorite for those who prefer a laid-back private destination, but it simply doesn't compare to Perfect Day at CocoCay. From CocoCay's adult-only Hideaway Beach to the upscale Coco Beach Club, delicious snacks at the Snack Shack, adrenaline-pumping water park, and more, it's hard not to find an activity of interest at Royal Caribbean's island in The Bahamas.
Labadee, however, lacks the same thrills. While there's no denying the beaches are beautiful, nothing makes Haiti stand out compared to other ports in the Caribbean, other than the fact that Royal Caribbean's drink packages work ashore. After visiting Labadee twice, I avoid itineraries that list it as a stop. My time—and money—is better spent exploring new places, rather than sitting on the same beach or riding the same zip-line.
Honorable mention: Nassau
Though Nassau isn't geographically in the Caribbean, it's a port I truly have no desire to visit again. Excursions tend to be pricer than those in the Western Caribbean. Day passes to resorts can cost well over $100 per person and may not include unlimited food and beverages. If you want to visit the infamous Atlantis Resort, be prepared to shell out at least $200 per person for access to their waterpark facilities.
Not only that, but it's extremely busy, as it's one of the most popular ports of call in The Bahamas for 3- and 4-night cruises. In December 2023, the port set a new single-day record with 29,316 cruise ship passengers in port.
While I appreciate the effort put into revitalizing the cruise area, it's not enough to convince me to book a cruise to Nassau. When sailing to The Bahamas, I prefer visiting cruise line private islands, such as Half Moon Cay, where I'm at the very least guaranteed a cheap beach day with complimentary food.
Read more: What is free on Half Moon Cay?
Elizabeth Wright
Elizabeth graduated from New York University's Arthur L. Carter Journalism Institute with her M.A. in Journalism in May 2023. Growing up, she had the privilege of traveling frequently with her family and fell in love with cruising after sailing on the Oasis of the Seas her freshman year of high school. She wanted to pursue a career that highlighted her passion for travel and strengths as a writer.
