With so many destinations to choose from in the Caribbean, it’s easy to see why these itineraries are so popular with cruisers. From mountainous regions to the sandy beaches, there is a little bit of something for everyone.
Since I was a toddler, I have been cruising around the Caribbean. Even growing up in the Midwest, my parents would take me and my sister on a yearly Royal Caribbean cruise, typically over spring break or summer vacation.
I’ve been able to visit nearly all of the Caribbean destinations reachable by cruise ship. With the exception of a few islands - such as Aruba, Bonaire, and Curaçao - and a few countries, like Colombia, I’ve enjoyed exploring this region of the world over the last two decades.
Overall, I’ve been to 25 Caribbean destinations by cruise ship. Therefore, it’s pretty rare when I sail on a cruise that visits a new port of call. Anytime I can visit a new destination in the Caribbean, I am giddy like a little kid.
Last year I was able to visit two new countries while cruising: Honduras and the Dominican Republic. I also visited Turks and Caicos for the first time - and I loved the experience. However, at this point, I’ve done almost all of the touristy excursions throughout the Caribbean that you can possibly do.
I’ve held a stingray in Grand Cayman, zip-lined in Costa Rica, swam with the dolphins in Mexico, snorkeled with sea turtles in Barbados, and lounged on all of the picturesque beaches. Finally, I’ve been lucky enough to transit through the Panama Canal by cruise ship, which was a once-in-a-lifetime experience.
Read more: How to choose the right Caribbean cruise sailing
Of course, there is always a new experience to be had regardless of how many times you’ve visited the Caribbean! There are some destinations that I can’t wait to return to while others are fine as one-and-done.
Here are the four Caribbean destinations I would visit again in a heartbeat, along with three ports that I would skip.
St. Maarten
One of my all-time favorite ports in the Caribbean is Philipsburg, St. Maarten. The island is actually owned by both the Netherlands and France, with the northern part of the island being French and the Southern part being Dutch. As such, St. Maarten has a unique blend of varying cultures and so much to offer.
I’ve been to St. Maarten multiple times and one of my all-time favorite activities is visiting Maho Beach. Being married to a pilot, my husband absolutely geeks out over this iconic beach where the runway approach is right over the beach. The planes land so close to the beach it almost seems like you can touch them!
Is Maho Beach the nicest beach in St. Maarten? Not necessarily, but it’s certainly one of the most memorable and unique beaches you’ll find in the Caribbean. For me and my family personally, this is such a fun place to visit while cruising.
Moreover, there is so much to do in St. Maarten, including relaxing on the island’s many pristine beaches, shopping on Front Street, and hiking to Mount Concordia. The island feels quaint, clean, and easy to navigate.
Whenever I am looking to book a Caribbean cruise, I look to find an itinerary with a port stop in St. Maarten. It’s one of those places that I find myself always excited to visit again after countless good experiences ashore.
Dominica
Nicknamed "The Nature Island," Dominica is one of the prettiest Caribbean ports I’ve ever visited. Although I’ve only been to Roseau once, I’ve been wanting to return ever since. The island has such a diverse, mountainous landscape with hot springs, beaches, and tropical rainforests.
While cruising on Jewel of the Seas a few years ago, my husband and I took an excursion through Royal Caribbean to Morne Bruce, Trafalgar Falls, and the Emerald Pool. We marveled at the Trafalgar Falls before swimming in the freshwater Emerald pools, surrounded by more cascading falls.
We were able to see so much of the island, but I wished we had more time to explore! Dominica was lusciously green with beautifully blue ocean water. I also appreciated that we were the only ship docked, as Dominica can only accommodate one cruise ship each day. It didn’t feel like the island was overtaken by cruisers!
Roseau is a more rare cruise port for Royal Caribbean. You’ll either need to fly to San Juan, Puerto Rico, or book a longer itinerary from Florida that visits the Southern Caribbean. However, I highly recommend booking an itinerary with a stop in Dominica if you can.
St. Thomas
I’ve been able to visit St. Thomas multiple times over the years and it continues to be one of my favorite Caribbean destinations.
The first time I visited St. Thomas was in middle school on a family reunion cruise. We booked a sailboat tour and sailed around the island - my mom still makes the sailor’s homemade guacamole recipe to this day! I remember thinking it was one of the bluest ocean waters I had ever seen.
Typically, I like to head over to the famous Magens Bay for a lovely beach day. Magens Bay has soft sand and crystal-clear ocean water for swimming. Because the bay is shaped like a horseshoe, you don’t have to worry about rough seas. There are plenty of other beautiful beaches on the island too.
St. Thomas also has great shopping and quaint villages! During my last visit to St. Thomas, my dad purchased a stunning emerald ring for me as a special keepsake. I wear it every day with fond memories of St. Thomas! The island has so much to do, including visiting Blackbeard’s Castle or the Skyride to Paradise Point.
Overall, I’ve had only positive experiences during my time in St. Thomas. Look to book either Southern or Eastern Caribbean sailings with Royal Caribbean if you want to visit St. Thomas on your future cruise.
Perfect Day at CocoCay
Perhaps unsurprising, I truly love visiting Royal Caribbean’s private island in the Bahamas: Perfect Day at CocoCay. If I am being honest about which destinations in the Caribbean that I look forward to returning to, Perfect Day at CocoCay is at the top of my list.
I’m not alone in this either, as Royal Caribbean has stated that CocoCay is the cruise line’s highest-rated destination! First, visiting CocoCay is not only extremely convenient, but also so relaxing.
The private island feels all-inclusive with so many beaches, pools, and restaurants included in the cost of your Royal Caribbean cruise. As a Diamond Plus loyalty member, I love that I can use my free drink vouchers while ashore. Anyone with a drink package can also take advantage of their purchase at CocoCay as well, which is a huge perk!
The island has a little bit of something for everyone, including Thrill Waterpark, the adults-only Hideaway Beach, the exclusive Coco Beach Club, Oasis Lagoon swim-up bar, a floating tiki bar, and multiple beaches with loungers.
Overall, Perfect Day at CocoCay really feels like a beach getaway. There is no denying you are on vacation when you’re docked here. I love being able to truly unwind and not have to worry about how I am going to spend my day.
Royal Caribbean sails to Perfect Day at CocoCay on nearly every Caribbean itinerary. Currently, the cruise line has 144 itineraries with stops scheduled in CocoCay. If you’re hoping to visit this private destination, there’s a good chance your itinerary already includes a stop!
Honorable Mention: Key West
While not necessarily in the Caribbean, one of my all-time favorite cruise destinations is Key West, Florida. Known as the southernmost city in the continental United States, Key West is a lovely destination while cruising.
The port of Key West is right in the city center, so you hardly have to venture far if you’re looking for shops and restaurants. The city is so charming with pastel-colored buildings, wandering chickens, and live music coming from the many beach bars.
Key West is laid-back and easy to walk around. I love visiting all of the shops and bars around the port. My sister and I recently visited Key West during our cruise on Celebrity Silhouette and walked to the Southernmost Point Buoy and enjoyed leisurely strolling the side streets. I would never turn down a port stop in Key West.
Skip: Jamaica
Perhaps my least favorite destination in the Caribbean, Jamaica is one port of call that I would be fine skipping for the foreseeable future. In fact, I am surprised cruise ships continue sailing to Jamaica. Royal Caribbean cruise ships typically dock in Falmouth, Jamaica, although I’ve also visited Ocho Rios, Jamaica by cruise ship.
First, the area outside of the port and touristy area is very rough. The last time I visited Jamaica, I remember thinking that I’d be fine if I never visited the island again. Generally speaking, the area outside of the cruise port feels unsafe once you leave the secure area. It’s not uncommon to be offered drugs for purchase, sometimes by pushy sellers. Unless I book an excursion, I typically stay on the ship when docked in Jamaica.
Read more: Caribbean tourist traps to avoid on a cruise
Even on an excursion, you can expect to spend nearly two hours driving to and from the cruise port. Many cruisers find their excursions run behind schedule or deviate from the planned agenda, although this hasn’t been my experience. If you’re visiting Dunn’s River Falls, which is one of the main tourist attractions for cruisers, you can expect to find a massive tourist trap upon arrival.
Overall, I am glad that Jamaica is crossed off my bucket list of countries that I’ve visited, but it’s certainly not a destination that I need to visit again.
Skip: Nassau
Located in the Bahamas, Nassau is one of the most common cruise ports for Caribbean sailings. It seems like every cruise I book these days has a port stop in Nassau! However, it’s one port that I would be fine never visiting again.
To start, the cruise port is always jam-packed with cruise ships, as the port can accommodate up to six ships in a single day. Nassau can even accommodate up to three Oasis Class ships! This leads to a very crowded port with tens of thousands of cruisers taking over the city. Last year, Nassau set a record for having almost 30,000 cruise passengers visiting the port in a single day!
Also, the excursions in Nassau are super expensive. If you want to visit Atlantis, be prepared to fork out hundreds of dollars per person for a few hours at the resort. Those choosing to visit a resort for the day will likely spend $100 per person. I’m always shocked by the inflated excursion costs in Nassau!
Unless you book an excursion or take a taxi to Paradise Island, Nassau itself feels disingenuous. If you wander too far outside of the port area, you can find yourself in tough areas very quickly. I’ve never run into an unsafe situation while visiting Nassau, but it’s not a port that I look forward to visiting.
Even after visiting Nassau close to 12 times, the port has never left me very impressed. I consider Nassau one of those port days where I stay on the ship and take advantage of everyone being ashore. Staying onboard during a port day allows you to enjoy a quiet ship and all of the amenities to yourself.
Skip: Belize
One port in the Caribbean that I don’t need to visit again anytime soon is Belize. Royal Caribbean’s ships dock in Belize City, which certainly isn’t the safest destination in the Caribbean. Unless you decide to visit the Mayan Ruins or tube down the caves, Belize doesn’t have much else to offer.
The port area for Belize is very lackluster, not to mention you need to tender to and from the ship to get ashore. I first visited Belize back in elementary school during a cruise on Enchantment of the Seas. We walked around the port area and decided there wasn’t much to see before tendering back to the ship.
Although I’ve visited Belize by cruise ship, I also traveled to the country for a mission trip back in high school. After seeing so much of the country in a very different light, I haven’t had much desire to return for vacation.
Overall, Belize isn’t a destination that I feel the need to visit again on a cruise ship. I find the tender ride to and from the ship to be the most exciting part of visiting this destination. Again, I am happy to cross this off my list of countries visited, but Belize City leaves little to be desired for me.
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