5 best luxury Caribbean cruises for next winter’s getaway

Imagine: You’re lounging poolside in a tranquil port, your novel the only distraction from an azure sky melting into a turquoise sea. No jostling passengers or behemoth ships docked on either side, casting shadows, blocking breezes and blaring music.

Later, a white-gloved butler welcomes you back after a small-group excursion — perhaps lunch at an exclusive resort — with complimentary Champagne and caviar. More than likely, you’re staying in a suite or oversized cabin, your plush bed dressed in silken sheets and fluffy down pillows.

Welcome to luxury cruising in the Caribbean, where personalized pampering and indulgence go hand-in-(white)-glove with exploring less-visited islands and serene harbors away from tourist crowds — and where access to fancy hotels, private clubs and championship golf courses proves easy-peasy. Upscale ships retreat to the tropics to escape from winter’s chill, and you will want to book early for the best prices and suite availability.

To inspire your next getaway, we’ve chosen the five best luxury Caribbean cruises for the 2024-2025 winter season.

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SeaDream Yacht Club


Would you like to yacht your way through the Caribbean? Then consider SeaDream Yacht Club‘s 112-passenger SeaDream I and twin SeaDream II cruise ships.

On these teeny posh ships, the passenger-to-crew ratio is one-to-one, and outdoor space abounds. Scoring deck chairs, a romantic alfresco dining table for two or a massage in the Thai-inspired SeaDream Spa is a snap.

Fares include superb, sophisticated cuisine (plus delicious raw, vegan and organic dishes), fine wines, gratuities and watersport activities like paddleboarding, jet-skiing and even a fun slide whooshing you from the yacht to the sea.

A seven-night Leeward Islands Discovery on SeaDream I, round-trip Philipsburg, Sint Maarten, sounds particularly alluring (although every SeaDream cruise sounds, well, dreamy). In most cases, you’ll anchor, rather than dock, at these beyond-beautiful islands, with primarily private yachts for company.

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Sail into halcyon ports, like Norman Island in the British Virgin Islands, for stunner hikes and superb snorkeling and scuba diving. The ship’s early morning anchor off Spanish Town in Virgin Gorda is designed so that you may experience “The Baths” before the hordes of big-ship cruisers arrive. Wait until you see this natural wonder of maze-like boulders and caverns leading to a powdery white-sand beach and crystalline waters.

Savor St. Barths’ French vibe, where chichi boutiques and Paris-meets-the-tropics restaurants thrive. Scuba dive, swim with dolphins, hike and bike with ship officers or play golf at a posh resort.

Related: The best luxury cruise lines for elegance and exclusivity

A major SeaDream perk is the signature Champagne and Caviar Splash (perhaps on Antigua’s Prickly Pear Island), with officers serving caviar from a surfboard in shallow water. Smiling servers roll up their pants, wade in and ensure glasses of bubbly are filled to the top.

SeaDream I departs on this seven-night cruise, sailing round-trip from St. Maarten, on February 1, 2025. Fares start from $3,999 per person.

Silversea Cruises

Silver Moon, Patmos, Greece. LUCIA GRIGGI/SILVERSEA

Pretty much every moment feels pinch-me on board Silversea Cruises‘ 596-passenger Silver Moon. Revel in a spacious suite with a smiling butler primed for pampering. Sustainable Ars Italica Oscietra caviar is served anytime, anywhere, at no extra charge; such sensational roe normally costs a bundle.

On a 10-night cruise, you can visit all eight restaurants on board and spend the last evening dining in-suite, with your butler serving dinner course-by-course. Culinary highlights include Caribbean-inspired dishes at S.A.L.T. Kitchen, hand-fashioned pastas at La Terrazza and Kaiseki’s exquisite Japanese plates.

Post-dinner, belly-up to Silver Note’s bar; the velvety-voiced jazz singer always amazes. Alcohol and most eateries are complimentary, and the no-tipping culture makes onboard life more enjoyable.

Around the ship, you can learn to prepare Caribbean cuisine in a hands-on cooking class, dance to the Panorama Lounge’s live band, break a sweat in the Fitness Centre or seek Lady Luck at the casino. Or succumb to treatments at Zagara Beauty Spa; the wide array includes massages, body wraps and acupuncture. With so much happening on board, you might forget to leave the ship.

Related: 5 best Silversea Cruises destinations

Please don’t; the Caribbean ports are perfect, and the shore excursions are complimentary. On this round-trip Fort Lauderdale cruise, you can explore several idyllic isles, each one prettier than the next.

In über-glam St. Barths, wave credit cards in posh boutiques, snorkel in coral reefs teeming with bright-hued fish or join a romantic catamaran sail at sunset. In Antigua, book a Segway beach tour or zip-line through a rainforest. On St. Kitts, sink into a waiting chaise on Cockleshell Bay and splash in the ever-inviting Caribbean Sea. Silver Moon also offers tee times at the Royal St. Kitts Golf Club — one of the Caribbean’s most scenic — and a lazy day at the exclusive Carambola Beach Club.

Silver Moon departs on this 10-night Caribbean cruise, sailing round-trip from Fort Lauderdale, on January 6, 2025. Fares start from $5,900 per person.


Wintergarden Suite on Seabourn Ovation. ERIC LAIGNEL/SEABOURN

The 600-passenger Seabourn Ovation shows superbly on a Caribbean cruise. The casually elegant (think country club-ish) Seabourn ship offers guests multiple opportunities to lounge outside, admiring the region’s impeccable scenery. Don’t be surprised when servers quickly learn your name and favorite cocktail.

Want to splurge? Book a day in the Retreat, a VIP enclave with 15 private cabanas circling a central whirlpool and shaded by a flower-shaped canopy. Here, melt into a massage in the Spa Treatment Cabana or schmooze with fellow passengers at the private bar.

Even if you don’t visit the Retreat, you’ll love that this all-suite ship includes so many amenities, including primo caviar service, gratuities, wine and spirits and fine dining. (Don’t miss Solis, the new signature Mediterranean restaurant launching in 2024; the buzz is it will be a knockout.)

Balance fine dining with working out at the expansive, well-equipped fitness center. Find your Zen at wellness-driven programs designed in partnership with integrative medicine pioneer and icon Dr. Andrew Weil.

Related: 5 secrets to getting a luxury cruise for less

The 14-night Exotic Caribbean in Depth itinerary provides ample time to revel in the ship’s amenities and pleasures ashore. This cruise, sailing round-trip from Barbados, visits St. Lucia, Antigua, Barbuda, Guadeloupe, British Virgin Islands and Nevis. At Sopers Hole (Frenchmans Cay), BVI, rub shoulders with the yachting crowd at cafes, restaurants and bars. Relish time in Bequia (the Grenadines’ largest isle) in Admiralty Bay, another yachter hot spot.

Seabourn’s Caviar in the Surf is paradisiacal perfection. It stars a lavish beach barbecue luncheon on a stunning white-sand beach, with uniformed crew members serving Champagne and caviar at a surfboard bar.

Seabourn Ovation departs on this 14-night cruise, sailing round-trip from Barbados, on January 18, 2025. Fares start from $6,999 per person.

The Ritz-Carlton Yacht Collection


The Ritz-Carlton Yacht Collection‘s two all-suite ships totally vibe superyacht. The second — and newest — ship, 448-passenger Ilma (which debuts in 2024), will cosset you in luxury and indulgence, with a nearly one-to-one passenger-to-crew ratio.

Expect abundant outdoor space for lounging, dining alfresco or enjoying watersports like kayaking and paddleboarding from the yacht’s marina. On Ilma, even the smallest 294-square-foot suite provides a generous-sized private veranda, with features like an espresso machine and a double-vanity bath with an oversized shower.

Count on many inclusions, such as five restaurants, 24-hour in-suite dining, a personal concierge, alcohol and gratuities. A signature Ritz-Carlton spa, gym and humidor also beckon. Good to know that the ship hosts RitzKids programs year-round (three a day for ages 4 to 12) with enhanced activities during the summer and holidays — rare on a small luxury ship.

Related: I love luxury hotels, and The Ritz-Carlton Yacht was made for people like me

The seven-night round-trip Bridgetown, Barbados cruise includes visits to Soufrière, St. Lucia, a small town with tropical colonial architecture and natural attractions such as rainforests and a “drive-in” volcano. For another St. Lucia outing, bathe in mineral-rich mud in Sulphur Springs Park before savoring lunch at the ritzy Ladeira Resort.

In Grenada, go snorkeling among bright-hued tropical fish, and in Martinique, join a 4×4 island tour, which includes swimming in a cooling river and strolling black sand beaches.

Ilma departs on this seven-night cruise, sailing round-trip from Barbados, on March 14, 2025. Fares start from $5,800 per person.

Regent Seven Seas Cruises


All Regent Seven Seas Cruises ships ooze luxury and opulence. The all-inclusive line really is — think valet laundry service, unlimited shore excursions, seven superb dining venues and airfare among inclusions.

Regent’s newest vessel, 746-passenger Seven Seas Grandeur, ups the line’s incredibly high bar. Like its siblings, this extravagant ship drips in exquisite marble and crystal. Its multi-million-dollar 1,600-piece art collection features the first Fabergé egg to reside permanently at sea.

Your jaw will drop at the sleek redesign of some of Seven Seas Grandeur’s suites and public venues. All-suite accommodations begin at 300 square feet and run up to the 4,443-square-foot Regent Suite. The latter touts a spa with a steam room and Jacuzzi, two original Picasso lithographs, handblown Lalique art vases, butler service and a private car and guide in each port.

Entertainment overhauls include new high-energy shows, like tango-driven Pasión. The Serene Spa & Wellness emphasizes mindful living, with reflexology and meditation among offerings.

The 10-night Champagne Colored Sands itinerary is round-trip Miami, offering easy access to the Caribbean from home airports. At Puerto Plata in the Dominican Republic, you can luxuriate for hours at beachfront resort Emotions by Hodelpa Playa Dorada, snorkel in a reef aquarium or dare to swim and snorkel with sharks. On St. Barth’s, transfer to the exquisite Hotel Manapany, where celebs and other famous faces frequent; this outing includes an organic two-course lunch showcasing hotel-grown ingredients.

Seven Seas Grandeur departs on this 10-night cruise, sailing round-trip from Miami, on February 13, 2025. Fares start from $7,499 per person.

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