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Luxury Caribbean Cruises: All You Need to Know

Irene S. Levine

Last updated
Mar 6, 2020

Read time
7 min read

The Caribbean consistently ranks among the most appealing cruise destinations for singles, couples and families alike. This isn't surprising given the region's near-idyllic mix of temperate weather, white sandy beaches, pristine blue waters and picturesque ports.

With a choice of eastern, southern and western itineraries, Caribbean cruisers can sample diverse island and coastal locations, each with a unique personality in terms of culture, history and terrain.

Luxury Caribbean cruises offer distinct advantages over mainstream ones. They allow passengers to visit smaller, off-the-beaten-track ports like Bequia, St. Vincent & the Grenadines; take advantage of water sports (such as swimming, snorkeling, paddle boarding and scuba diving) at more secluded beaches; experience a wide variety of bespoke, small-group, culinary and cultural excursions on shore; and enjoy personalized service and first-class dining and amenities onboard the ship.

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Why Choose a Luxury Caribbean Cruise?

The most luxurious Caribbean cruises tend to be aboard smaller ships carrying fewer passengers, enabling them to navigate more intimate, unspoiled and less crowded ports. Even the logistics of getting ashore tends to be easier and more efficient: On smaller ships, passengers can disembark more quickly without long waits or queues and when these ships need to anchor, they are able to position themselves closer to the shore and centers of towns.

In fact, luxury Caribbean cruises avoid many of the most congested ports. Once ashore, passengers are less likely to find themselves among hoards of fellow tourists from their ship and  others. The numbers of passengers on each shore excursion also tend to be lower on luxury lines. All these factors combine to create onshore experiences that feel more authentic and immersive, creating the most luxurious Caribbean cruise experience.

In general, luxury vessels forgo glitz in favor of a more sophisticated ambiance and decor. They are heavier on enrichment and port lectures as opposed to elaborate entertainment. Staterooms and suites (usually with balconies) are more spacious; they're stocked with upscale toiletries, fresh fruit and water in the room daily, and complimentary minibars.

Staff to passenger ratios are higher with more personalized service throughout the ship; many luxury lines provide butlers and concierges to address every need and whim of their passengers. Onboard service is akin to what one might expect from a five-star resort.

Culinary offerings also differentiate luxury Caribbean cruises. Dining options are more upscale with greater emphasis on fresh, local ingredients; more creative menus, often tied to ports; a la minute (made-to-order) preparation; and more pampered table service. Twenty-four-hour room service, top-shelf wines and spirits, and specialty coffees are often provided at no extra cost.

Passengers on these ships tend to be older and more affluent, although luxury lines sailing the Caribbean are increasingly booking families and multigenerational families -- especially during the summer, and over Christmas, Easter and Presidents' Day holidays.

Although luxury comes at a cost, pricing on luxury cruises is "mostly inclusive" -- often covering ground transportation between airports and ports, most shore excursions, Internet access, prepaid gratuities and sometimes even airfare. To compare costs, it pays to read the fine print to determine exactly what is included and what is not on any specific cruise.

Most Luxurious Caribbean Luxury Cruise Lines

Travelers looking for a luxury Caribbean cruise will find a wide choice of departure ports, itineraries, and price points within the luxury and ultra-premium categories.

Within the luxury category, Crystal Cruises, Regent Seven Seas Cruises, Seabourn, Sea Cloud Cruises, SeaDream Yacht Club, and Silversea Cruises all offer Caribbean voyages of varying durations throughout the winter months. These lines offer an all-inclusive philosophy, including things like beverages, gratuities and even shore excursions (in the case of Regent) in the cost of the cruise.

In the ultra-premium category, Oceania Cruises, Windstar Cruises, and Viking all offer Caribbean cruises. Most itineraries are 7 to 14 nights in duration but some can be as lengthy as 26. These lines may not be all-inclusive, but they offer a step up from the big mainstream ships – and Viking comes pretty close to emulating a full luxury experience.

Many luxury Caribbean cruises depart from Miami and Fort Lauderdale, but some start at Caribbean ports like Barbados, St. Maarten, and San Juan. Departing right from the Caribbean allows passengers more time onboard exploring the region -- as opposed to getting there -- but airfares to and from these island ports can be expensive.

For those who want only a taste of the Caribbean as part of a larger voyage, Panama Canal and World Cruise itineraries often include one or more Caribbean ports of call and are readily offered by luxury cruise lines in the Caribbean.

While mainstream lines cruise the Caribbean year-round, sailings on smaller, luxury sailings tend to be seasonal -- generally between November and May. During the remainder of the year (which coincides with hurricane season in the Caribbean), these smaller ships tend to sail the Mediterranean and Alaska.

Given that luxury Caribbean cruises are less frequent and the passenger capacity more limited, it's prudent to book these cruises as far in advance as possible.

Mainstream Luxury in the Caribbean

If you're traveling in a family group with children or simply prefer larger, more mainstream ships because they offer more of everything -- entertainment, swimming pools, activities, shops, gaming, restaurants and bars, teen clubs and organized children's programs -- you don't necessarily need to give up all luxury touches.

Almost every major cruise line -- including Carnival, Royal Caribbean, Disney Cruise Line, Celebrity Cruises, Holland America Line, Princess Cruises, MSC and Norwegian Cruise Line -- offers Caribbean cruises, and all feature some type of suite accommodation, often with VIP privileges, such as priority check-in and exclusive dining options. However, you will be sharing the ship with thousands of fellow cruisers, fighting for lounge chair space on the pool deck, hunting for the best seats at shows and exploring larger, well-known ports with throngs of passengers from multiple mega-ships.

However, exclusive suite complexes (such as those offered by Norwegian Cruise Line and MSC Cruises) may offer the best of both worlds. Called The Haven (on Norwegian Cruise Line) and MSC Yacht Club, these enclaves often appeal to couples or multigenerational families who want to sail the Caribbean in more refined, luxurious quarters without sacrificing "big ship" amenities and entertainment for children and adults.

Book a suite in these areas, and you'll have access to intimate dining venues and lounges; private swimming pools and sundecks; butler and concierge services; priority boarding, embarkation and disembarkation; priority reservations at shows and specialty restaurants throughout the ship; and other perks.

Luxury Experiences in Port

Caribbean cruises tend to be port-intensive, so opportunities for one-of-a-kind experiences, offered both by cruise lines and independent operators, are endless. When it comes to choosing luxury cruise ship shore excursions in the Caribbean, depending on your budget, interests and sense of adventure, the sky's the limit. A few examples:

Passengers can take a helicopter ride over Grand Cayman Island to view the clear waters below, said to house 325 shipwrecks, or board an Atlantis submarine to explore the waters 80 to 100 feet below sea level.

Adventurous passengers can take an off-road safari in a custom-built jeep to see rare plant life on St. John's; zip around on a Segway on their way to the beach in Cozumel; or see the flora and fauna of St. Kitts on a quad bike. The more laid back can soak up the sun while enjoying Champagne and lobster on a catamaran cruise.

Because the costs of excursions can add up quickly, especially for large families, sailing on a luxury line may offer another advantage: included tours. For example, Regent Seven Seas offers free shore excursions at every port (cultural, culinary, ecotourism, water adventures and more) along with options for truly bespoke one-off adventures at additional cost. Viking includes at least one complimentary shore excursion, and many offer complimentary shuttle service into port. Several luxury Caribbean cruise lines offer private beach parties, with deluxe BBQs and complimentary use of water toys.

Of course, luxury lines also offer opportunities for passengers to design and customize their own tours with private vehicles and English-speaking guides. Look for shore tour concierges onboard, or tour options listed as "private." (Crystal, for example, offers customized private adventures, your own car and driver as part of private services, or a group tour itinerary offered via a private guide and transport with private options.)

Alternatively, some cruisers simply opt to explore ports on their own. On St. Barths, a chic getaway for the rich and famous, visitors can take a short taxi ride to one of the island's 22 white-sand beaches or dine at upscale French restaurants and small cafes fit for foodies in the main town of Gustavia. On St. Martin or Martinique, luxury cruise travelers can shop on their own for high-end French goods, like clothing, accessories or perfume, in the local boutiques.

Luxury Caribbean cruises are an amazing way to escape the weather and the everyday. Just be sure to book early: these once-in-a-lifetime journeys sell out faster than their mainstream counterparts.

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