Best Luxury Cruises to the Caribbean

A bright beach aerial shot with white high-rise hotels and bright blue ocean water
If you love beachy relaxation and laid-back vacation vibes, opt for a luxury cruise to the Caribbean. | Author: Luis Quintero

If you’ve daydreamed about lounging in luxury on a cruise, chances are you’ve pictured yourself in the Caribbean. With its iconic beaches, swaying palm trees, and crystal clear waters drenched in sunshine, the Caribbean is one of the most popular cruise destinations in the world. Its close proximity to several US departure ports makes the Caribbean an easy cruise destination for short and long cruises alike, and there are a wide variety of Caribbean cruises to suit all tastes. 

However, the absolute best way to cruise the Caribbean is on a luxury cruise line. What makes luxury cruises special? Not only are they all-inclusive, floating resort-style vacation packages, they also offer exclusive experiences only available to their passengers. And when visiting a cruise destination as popular as the Caribbean, having luxury options can be like experiencing the whole region again for the first time. 

Here are some of our top recommendations for the best luxury cruises in the Caribbean, when to visit and what to see, and how to make sure you get the best deal on your next luxury cruise vacation.

Why Take a Luxury Cruise to the Caribbean?

A young boy wearing a snorkeling mask holds up a starfish in shocking blue water
There are so many things to discover on a luxury cruise to the Caribbean | Author: Claude Piché

From gorgeous sun-kissed beaches caressed by turquoise waves, to vibrant rainforests sheltering ancient ruins - the Caribbean offers a little bit of everything. Architecture enthusiasts will love getting a closer look at the colonial ports, while history buffs can channel their inner Indiana Jones exploring Mayan ruins. You can relax on the beach one day, swim with pigs another, and zip line through lush rainforests the next. Refresh yourself with French Creole cuisine, rum punch, and fresh tropical fruit - all without the hassle of multiple flights or hotels. 

Still not sure if a luxury cruise is worth the upgrade? Check out this article to see what makes a luxury cruise different.

Here are a couple of our favorite reasons why your next luxury cruise should be in the Caribbean.

1. The weather

The Caribbean’s sunny, beachy reputation makes it a prime getaway destination, especially during the cold, dark winter months. While there are some weather issues to be aware of before you book your trip (which we’ll talk more about later), the weather in the Caribbean is generally sublime. Warm days and nights give it a forever-summer feel, even in the dead of winter. Rain is common, particularly in late summer and fall, but it’s fairly easy to plan your trip around serious storms.

2. Cultural and historical diversity

Despite many islands feeling like their own secluded paradise, the Caribbean has historically been quite the melting pot. Dutch, French, British, Indian, West African, and indigenous cultures have intertwined in this region for centuries. Colonial architecture is common, as is fusion-style cuisine. While it’s important to recognize that this unique cultural intermingling is the result of imperialism and exploitation, it has also led to the Caribbean’s famously welcoming and friendly attitude. Many islands celebrate their diverse heritage, and will likely invite you to join them in their joie de vivre.

3. Beaches and natural attractions

Just like the weather, the Caribbean is world famous for beaches. White sand beaches dotted by swaying palm trees are common, and some islands also boast lush rainforests and high mountain peaks. Many islands are made from ancient (or not-so-ancient) volcanoes, and they sustain massive amounts of life. Flora and fauna are abundant, from leafy flowering plants to turtles, stingrays, and tons of fish. There’s plenty to explore on a Caribbean cruise, so be sure to budget both beach days and active excursions.

Best Time to Visit

Winter is easily the best time to cruise the Caribbean. From December to April, the weather is ideal, with little rainfall and typically warm to hot days and milder nights. This makes it the perfect time for cruisers from the US, Europe, and Britain to escape the chilly winter and thaw out in the sunshine. 

As is typical with cruise destinations, ideal weather conditions mean peak season also falls during winter and early spring. This means the Caribbean is more likely to have more crowds and cruises will be more expensive during this time. However, more excursions will usually be offered, and itineraries are more stable. 

An option for cruisers seeking discount luxury cruises is to go in early summer, when rainstorms are more likely but the islands will be calmer and luxury cruise ships emptier. June to August is the beginning of hurricane season so storms, rough seas, and last-minute itinerary changes are more likely, but it may be worth it to avoid overcrowded ports and extreme prices.

Hurricane season

While you may see incredible luxury cruise deals from June to November, be aware that this is hurricane season in the Caribbean. It may not be such an issue on megaships, but rough seas can ruin small luxury cruises. Be particularly wary of cruises during September and October, as this is the height of hurricane season. If you do choose to cruise during these months, we highly recommend you invest in good cruise travel insurance - just in case. 

It’s also worth noting that many Caribbean islands were ravaged by hurricanes last year. We recommend double checking with your cruise line or shore excursion provider to make sure all your preferred activities are available before you book.

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Where to Go

When it comes to picking the perfect Caribbean itinerary, it’s important to note that Caribbean cruises typically fall into three categories: Eastern Caribbean, Western Caribbean, and Southern Caribbean. Longer cruises (lasting a week or more) can visit all three categories, but shorter cruises usually stick to just one. 

As many luxury cruise lines tend to offer small ships exclusively, luxury Caribbean cruises can look a bit different from their mainstream counterparts. Luxury lines like Crystal Cruises, Regent Seven Seas, and Viking Cruises still visit many of the most popular ports in each area. Meanwhile small ship cruise lines Ponant, SeaDream Yacht Club, and Star Clippers offer even more immersive and secluded itineraries. 

Here are some of the best ports to visit during your luxury Caribbean cruise, plus some hidden gems you may have missed out on.

Most Popular Eastern Caribbean Ports

The Eastern Caribbean is ideal for cruisers seeking beachy relaxation and plenty of aquatic adventures. Islands are close together, so it’s common for Eastern Caribbean cruises to be port-heavy, with fewer sea days. Shore excursions usually focus on more strenuous activity, like hiking or biking, or more individual pursuits like shopping. 

Here are some of our favorite cruise ports in the Eastern Caribbean.

Nassau, Bahamas

An aerial shot of five cruise ships at port in shocking blue waters
Nassau is one of the Caribbean's most popular ports | Author: Fernando Jorge

Although technically the Bahamas aren’t in the Caribbean Sea, Nassau tops the charts as one of the most popular destinations for Eastern Caribbean cruises. The capital of the Bahamas, the port of Nassau is close to the city’s downtown, making it easily accessible for cruisers. Beautiful white sand beaches slope gently into brilliant blue water, making this cruise destination ideal for beach days. Other great excursion options include golf and snorkeling.

St. Maarten / St. Martin

People on a white sand beach take pictures of a low-flying airplane coming in for a landing in St. Maarten
Even a beach day in St. Maarten can be thrilling when planes land at the airport | Author: Ramon Kagie

It may surprise you to find out that St. Maarten and St. Martin are very distinct from each other, and each offers something different. St. Maarten has Dutch roots, while St. Martin is French. St. Maarten welcomes larger cruise ships; St. Martin invites small vessels. Both sides of the island have great beaches, and St. Martin’s Baie Orientale is notoriously “clothing optional.” This is a great destination for catamaran excursions, beaches, and shopping.

St. Barts (St. Barthélemy)

Two tables with chairs on a beach beneath a dark cabana canopy with a palm tree
St. Barts offers plenty of alfresco dining options | Author: Shanna Camilleri

An ideal Eastern Caribbean luxury cruise destination, St. Barts boasts plenty of prime beaches and charming architecture. But the real draw of this island is the shopping. Haute couture may seem unlikely with iguanas roaming the isle, but St. Barts’ French roots grow deep, and boutique shopping is excellent. Dining options are also superb - try Restaurant Le Gaiac for an al fresco meal.

Most Popular Western Caribbean Ports

Western Caribbean cruises tend to focus more on culture, history, architecture, art, and food. With plenty of ports in Mexico and Central America, these itineraries are infused with active shore excursions and exploratory spirit. Head inland to explore Mayan ruins, zip line through the rainforest in Belize, or swim with stingrays in Grand Cayman. 

Here are some of the Western Caribbean’s most popular cruise ports.

Cozumel, Mexico

Shocking blue ocean waters lie just beyond white stone cliffs with a thatch umbrella
Cozumel offers stunning beach experiences, including swimming with dolphins | Author: Jakob Owens

One of the Western Caribbean’s most famous hotspots, Cozumel combines stunning beaches with ancient history, shopping, and wildlife. This small island boasts a diverse array of activities from swimming with dolphins to exploring the Mayan ruins of San Gervasio. Take a cab to San Miguel in the island’s interior for prime shopping, or hop on a ferry to nearby Playa del Carmen to explore Mayan site Tulum.

Grand Cayman Island

An aerial shot of two people floating in bright blue water with white sand beach on the left side of the image
Let your troubles float away with a luxury cruise to Grand Cayman Island | Author: Marc Babin

Another well-known and well-loved port, Grand Cayman Island wows cruisers with its close encounters with sea life. Go snorkeling with Stingrays in Stingray City, a shallow sandbar where the sea creatures come to catch a meal. Or visit the island’s turtle farm to learn more about sea turtles. Beyond animals, Grand Cayman also offers excellent shopping and nightlife, though it can get very busy during the high season.

Montego Bay, Jamaica

Lush palm trees and dense vegetation extend past a white sand beach and a whitewashed building
Avoid the crowds by setting forth on an exclusive excursion in Jamaica | Author: Lakeisha Bennett

Jamaica’s second-largest city and unofficial capital of tourism, Montego Bay delivers excellent shopping, beaches, and unparalleled golf courses. Luxury beaches are abundant, so plan for a tan. Nature lovers will also delight in the island’s many natural attractions, including the picturesque Dunn’s River Falls. While Jamaica can get crowded during peak season, exclusive luxury excursions are available.

Most Popular Southern Caribbean Ports

The Southern Caribbean is generally less crowded than the Eastern or Western Caribbean, as it’s further afield from common US departure ports like Port Miami or Fort Lauderdale. For this reason, many luxury cruise lines focus on immersive experiences in these culturally diverse and naturally beautiful islands. 

Here are our top picks for the most popular cruise ports in the Southern Caribbean.

St. Kitts, St. Kitts and Nevis

Green letters above a yellow arched entryway in a building beneath bright blue sky
Head to St. Kitts on a luxury cruise for excellent snorkeling and aquatic activities | Author: Phil Hauser

The island of St. Kitts makes up one half of the country St. Kitts and Nevis. Its towering, verdant mountains make for great hiking and ziplining excursions, and its wildlife-filled waters are great for snorkeling and diving. Take a walking tour through historic Basseterre or a railroad tour of the island. You could also rent a catamaran to nearby Nevis and spend a day on the water, or simply lounge on a beach.

Antigua, Antigua and Barbuda

A hill at sunset dipping into calm waters with palm fronds in the foreground
Antigua is a gorgeous port of call with many charms | Author: Mark Jordan

Pink and white sand beaches give this island a whimsical feel. Shore excursions range from shopping to helicopter tours and diving. Plus, Antigua’s colonial past lends it a colorful and charming city center, perfect for a walking tour or a night out on the town.

St. Lucia

Beautiful blue waters with a small boat in the foreground with a dramatic triangular green mountain in the background
The iconic landscape of St. Lucia makes it an unforgettable cruise destination | Author: Claudio Trigueros

One of the wilder islands in terms of natural attractions, St. Lucia is home to reefs, rainforests, and even volcanoes. It’s a favorite getaway among the well-heeled, and has earned its reputation as one of the Caribbean’s most stunning locales. Whether you stay on the beach, venture inland for a hiking or adventure excursion, or sample fresh-caught fish from the reefs, St. Lucia is an unforgettable cruise destination.

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Most Underrated Caribbean Cruise Destinations

Since the Caribbean is one of the most popular and well-trod cruise regions in the world, it’s likely you’ve heard of these hidden gems. They may not exactly be secrets, but these cruise destinations certainly offer a little something extra that it’s worth discovering for yourself.

Virgin Gorda, British Virgin Islands

A white sand beach with blue waters, green palm trees and bushes, and large white and gray boulders
Virgin Gorda's brilliant white sand beaches lend its landscape an atmosphere of untouched beauty | Author: Freddie01

Dwarfed in many ways by neighboring Tortola, Virgin Gorda is nevertheless a stunner in its own right. With yacht clubs, wintering movie stars and billionaires, and incredible natural geologic formations, Virgin Gorda is 8.5 square miles of pristine Caribbean paradise. It’s only the third-largest of the British Virgin Islands, and its small size means few cruise lines can access it. Because of that intimacy and exclusivity, it’s a favorite port of call for luxury lines like Windstar and SeaDream Yacht Club.

Cartagena, Colombia

A partially obscured photo of a street with cars, bright blue and orange buildings, and lush palm trees
Stroll the streets of Cartagena to see beautiful colonial architecture and sample the local cuisine | Author: Luis Vidal

Colombia’s picturesque 16th-century port city is a charming entrypoint into the South American continent. While larger cruise lines like Princess Cruises and Royal Caribbean do venture there, Cartagena is best experienced aboard the Seabourn cruise line. Opt for an immersive itinerary aboard Seabourn Sojourn to sidestep the frequent complaint from megaship cruisers that there wasn’t enough time to explore.

Bequia Island, The Grenadines

A wind-worn tree overlooking nothing but blue sky
Take an afternoon hike to feel on top of the world in Bequia Island | Author: Ernie Stephens

If you’re looking for pure relaxation and luxury, visit Bequia Island in the Grenadines. This tiny island measures just 7 square miles, and is particularly popular among the yachting and sailing crowd. Choose a sailing on Royal Clipper by Star Clippers, Windstar’s Star Legend, or Silversea’s Silver Shadow. This island is still something of a secret among luxury cruisers, but it comes highly rated by those who value slowing down for an afternoon and taking it all in.

How to Find the Best Deal on Luxury Caribbean Cruises

No matter what your luxury cruise vacation to the Caribbean has in store, it’s always best to get it at a great deal. That’s why we’ve put together some amazing free tools and resources to help you save up to 70% off your perfect cruise! Simply follow these steps to get the best deal on your Caribbean cruise.

1. Use our cruise search

Find your ideal Caribbean sailing easily with our ultra-refined cruise search. Filter results by cruise port, dates, cruise line, cruise ship, price, and more.

2. Set free price alerts on your perfect cruise

Never miss a great deal again by activating a free price alert on your preferred sailing. We’ll automatically notify you via email if prices change so you can book at the right time.

3. See 80% accurate price predictions

One of our best features - and one you won’t find anywhere else - is our price prediction. We analyze data on every sailing over the last 5 years to offer clear recommendations on whether you should book now or wait for fares to drop. 

Did you know? You can save hundreds of dollars when you combine all three of these services.

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