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Cruising the Eastern Caribbean: What to Expect

Cruising the Eastern Caribbean: What to Expect

(UPDATED AUGUST 2022) With 50+ cruises under our belts, you could say we are cruise fanatics. We love to share ideas for what to see and do or expect when cruising the Eastern Caribbean or whichever route you choose. The Eastern Caribbean typically sails to ports such as Amber Cove, Bahamas, Grand Turk, San Juan, St. Kitts, St. Maarten, and St. Thomas. 

Cruising is a year-round industry. Living in Florida, we cruise in the fall or winter months for the best prices and favorable weather. But, keep in mind that hurricane season lasts through October.


Cruise lines we like working with are Holland America, Princess, Disney, Carnival, and Celebrity. These are brands we have sailed with for years and have had good experiences and great vacations with. Once your cruise is selected and booked, it is now time to decide on what you should do while at those ports and plan your excursions.


You may want to enjoy the cruise ship and not explore the ports of call. However, if you do, we would love to offer some suggestions for what to do with your time there.


Amber Cove (Dominican Republic)

The cruise port built in the Dominican Republic is the best. You can have a great time without stepping outside of it, but it would be a shame to miss the fantastic offerings of the DR.

Amber Cove has a good amount of shopping, a couple of moderately priced restaurants with tasty food, and a massive swimming pool complex that is free of charge. You can zipline across the pool area down to the ocean, rent a colorful beach hut on the water, spend time in one of the cool hammocks strung in the shade, or pick an excursion to explore the island. 


Cultural experiences in the DR include:

  • Making paper products at a female-based business (also a giving back to the community option).
  • A hands-on visit to a working chocolate factory.
  • Learning about the coffee-making process and tasting.

If you are more interested in the beaches, you may consider Cabaret Beach, which is perfect for sunbathing and swimming. Another popular activity is sliding down the natural rock waterslides at Rio de Damajagua.

Due to the historical significance of this island, I recommend a stop at Independence Square in Puerto Plata, where you can have a gelato, step inside the gorgeous church, people watch as the locals go about their day-to-day business and shop at the street markets. I picked up some lovely artwork for my house at very affordable prices.


Bahamas (Half Moon Cay)(Castaway Cay)

Many cruise lines own space in the Bahamas. For Princess Cruises, it is on the island of Eleuthera. For Holland America, it is called Half Moon Cay.

When your ship docks at these ports, it is typically the only ship there, making for a nice beach day without crowds and opportunities to do nearly any outdoor activity you can think of.

Lunch is provided on the island at no additional charge—it typically consists of burgers, hot dogs, jerk or barbecue meats, vegetables, ice cream, and fruit. You’ll also have typical picnic-style side dishes, plus tea, water, and lemonade to drink. Alcoholic beverages are available for purchase. Some islands have an optional pay restaurant for the freshest seafood dishes in the area.


At the private island, you can book fishing charters, rent a bicycle, or take a dune buggy to explore the island on your own. You can also rent snorkeling gear, floating foam mats, stand-up paddleboards, water bikes, or kayaks to enjoy in the pristine blue waters.

There are designated swimming areas and lounge chairs for hundreds. Soaking up the sun on the white-sand beaches is free of charge. You can also rent a clamshell to enjoy the perks of being outdoors in a picturesque setting without the intense sun directly on you. Private, colorful cabanas, though pricey, are also an option. Shopping for souvenirs and local crafts is also available at the port. 


Bahamas, Continued (Princess Cays)

Disney’s Castaway Cay is one of the most fabulous cruise ports in the Caribbean. The kid’s play areas are incredible, plus you can run a 5K with other cruisers and get a coveted Disney medal.


Like the other private islands, Disney’s Castaway Cay offers lunch, shopping, fishing excursions, rentals, and such, but it is much more fun than all the rest. Perhaps because it has the Disney name, I, and many who have cruised with Disney and other cruise lines, would rank it amongst the top cruise ports in the Caribbean.

FYI: It’s even more fun to visit when it is decorated for Christmas.  


Grand Turk (Turks & Caicos)

Picture a beach with sugar-white sand, layers of turquoise waters, vibrant green plant life against the rocky white cliffs, and a weathered lighthouse that makes for perfect pictures. You just glimpsed Grand Turk, a cruise port in the Turks and Caicos Islands.


At only seven square miles, this cruise port is a great place to soak up the surroundings or just lay around the pool at Jimmy Buffet’s Margaritaville, the largest in the Caribbean. Lounge chairs and pool access are free, and a DJ spins awesome dance tunes for everyone to enjoy. You can have a meal there, sip a tropical beverage from the swim-up bar, or mellow out with a good book and warm sun.


Grand Turk excursions include visiting the old salt ponds, the Bermudian buildings in Cockburn Town, or Gibbs Cay Stingray encounter. One of the newest tours is a dune buggy experience, which sounds fun for this island. You may even see the wild horses and donkeys roaming the streets (and beaches) on your way to the lighthouse at the island’s northernmost tip. Scuba, snorkeling, kayaking, and fishing are other popular excursions.


San Juan (Puerto Rico)

I’ve been visiting the cruise port of San Juan for over fifteen years, and the improvements made to the streets, signs, and buildings are much appreciated. San Juan is a beautiful place to get out on foot and explore the city on your own. Find a local cafe and enjoy a delicious tapas meal and cool mojito. Rosa de Triano is one of my faves.


A great way to taste the local delicacies is to take the Flavors of Old San Juan Food Tour, which is also sprinkled with history about the beautiful town.

Or, visit the historic fort, now part of the National Parks system. It is nothing less than amazing! Be sure to bring your National Park Passport to get stamped. Glass-bottom kayaking, horseback riding, and snorkeling are also popular outdoor offerings.


St. Kitts (Lesser Antilles)

St. Kitts (and its neighbor, Nevis Island) are two of the Crown Jewels of the Caribbean Sea. The contrast of the lush green mountains against the blue sky and waters is magnificent. Here, you can explore a historical fortress, the museum of Alexander Hamilton (yes, THAT Hamilton), and see impressive sugarcane fields.

St. Kitt’s colonial buildings are unbridled to those of its Caribbean neighbors, making this a unique island to explore. 

St. Maarten (Kingdom of the Netherlands)

St. Maarten and St. Martin, properties belonging to different countries, make up the unique dual-country cruise port that offers imposing beauty and a laid-back vibe that makes it a cruiser’s favorite, myself included. The Dutch influence of St. Maarten is depicted in the cruise port of Phillipsburg with colonial architecture and world-class beaches.


Orient Beach is one of the world’s most beloved beaches. You won’t want to miss sticking your toes in the sand, and it’s great for people-watching, too. Please note that the invisible line separating Orient Beach between countries is important. The French side is optional clothing, which won’t be shocking for Europeans, but possibly many American travelers.

On the other side of the island, Marigot on St. Martin, a French territory, has excellent designer shopping, fantastic cafes, and bistros. I honestly love both sides, but St. Maarten gets the most tourists.


St. Thomas (USVI)

If I had to guess which Caribbean cruise port is voted #1 year after year, I would say St. Thomas in the US Virgin Islands is it. St. Thomas is known for its pirate history, upscale shopping, high-end jewelry stores, and banana daiquiris. You have to take an excursion or taxi from your port to the world-famous Mountain Top to enjoy a banana daiquiri, but it is so worth it. Mountain Top’s views and photo-ops are magnificent, too. 


If a beach visit is your passion in St. Thomas, consider an excursion or ride to Magen’s Bay, rated one of the best beaches in the world by most magazines, such as National Geographic.

St. Thomas is the perfect place to book a sailing or snorkeling adventure or enjoy a catamaran experience. Scuba diving is a primo option since there are amazing coral reefs and shipwrecks around the island.


I’ve been to the island so often that I like to just walk into town, browse the shops, have a tasty lunch at the Greenhouse Restaurant & Bar, and check out the open-air markets with beautiful jewelry. Larimar is a stone you can find abundantly in the USVI and makes an excellent purchase for you or your loved one.


You also have the option to take an excursion to St. John or St. Croix, the other two islands in the USVI chain. I haven’t been to St. Croix, but I love exploring St. John, an island not nearly as modernized as St. Thomas.

The boat ride there will take you past enormous waterfront mansions and add an extra thrill to your day in port. St. John’s white-sand beaches and warm waters beckon you to visit and keep calling my name again to come back.


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