Luxury cruisers planning their prime vacation of the year often ask their travel advisor to book a “bucket list” voyage to Europe, Asia or Antarctica. But 2024 travel research also shows that those same travelers are often booking a second or third getaway in the same year. Often, they’re eyeballing the Caribbean.
Top draws are that luxury lines offer a diverse Caribbean region lineup of both ships and itineraries, plus guests can sail from closer-to-home U.S. East Coast, Gulf of Mexico or Caribbean ports. That appeals to both loyal past cruisers and new-to-cruise travelers, eager to “try out” cruising as a vacation choice. So, here’s a sampling of upscale Caribbean cruise enticements now through 2027.
New Embarkation Ports
During winter 2026-2027, Regent Seven Seas Cruises will expand with two new U.S. embarkation ports for Caribbean sailings. Guests can sail from Galveston, TX, on the 746-passenger Seven Seas Splendor, or Tampa, FL, on the 700-passenger Seven Seas Mariner. That’s in addition to voyages from PortMiami on the 744-passenger Seven Seas Grandeur.
Galveston is a “go-to” cruise embarkation port for travelers desiring to drive to their cruise from the southwestern U.S. and Texas, while Tampa similarly attracts many drive-market guests from central and northern Florida, as well as Alabama, Mississippi, Georgia and other southern states. Both ports also are easily reachable via domestic air flights to/from Houston, Galveston or Tampa. That can attract luxury guests from an even larger swath of territory.
In one example, the 17-night “Tropical Sparkle and Holiday Cheer” voyage will sail round-trip from Galveston on December 11, 2026. Seven Seas Splendor will call at Montego Bay and Kingston (Port Royal), Jamaica; Punta Cana, Dominican Republic; San Juan, Puerto Rico; Tortola, B.V.I.; St. John’s, Antigua; Gustavia, St. Barthelemy; Philipsburg, St. Maarten; George Town, Grand Cayman, Cayman Islands.
During 2026-2027, the three Regent Seven Seas’ ships will also sail on other itineraries to the eastern and western Caribbean and Mexico. Among the ports of call are Castries, St. Lucia; Cartagena, Colombia; Oranjestad, Aruba; Willemstad, Curaçao; Puerto Quetzal, Guatemala; and others. Three new Caribbean voyages will also make a full Panama Canal transit.
In the recent past, Cunard Line has homeported at Port Everglades, FL, for many winter season voyages. But between October 2025 and April 2026, the 2,081-passenger Queen Elizabeth will set sail on dozens of nine- to 21-night round-trip Caribbean voyages with guests embarking/debarking at PortMiami. For those with the time for in-depth travel, we’d look at Cunard’s 21-night itinerary, spanning the eastern and western Caribbean.
On November 6, 2025, Queen Elizabeth will depart for port calls at San Juan, Puerto Rico; St. John’s, Antigua; Castries, St. Lucia; Bridgetown, Barbados; Philipsburg, St. Maarten; Road Town, Torola, B.V.I.; Grand Cayman, Cayman Islands; Montego Bay, Jamaica; Roatan, Honduras; and Costa Maya and Cozumel, Mexico. Guests will also spend six days at sea, perfect for enjoying enrichment programming, pool relaxation, spa treatments and, of course, traditional British afternoon tea.
New Ships in the Region
This coming winter season 2024-2025, several luxurious new ships will beckon luxury travelers heading to the Caribbean. In December 2024, Silversea’s new 728-passenger Silver Ray, its second ultra-luxury, Nova-class ship, will cross the Atlantic as it repositions from Europe to the Americas.
For people still in the market for a late-in-the-year holiday voyage, Superior Veranda Suites were still available at press time for Silver Ray’s December 19, 2024, sailing from Port Everglades to Cartagena, Colombia. Other categories were wait-listed. During this voyage, the ship will spend four days at sea and call at Oranjestad, Aruba; Willemstad, Curacao; and Cartagena (overnight), Colombia.
On Silver Ray’s January 6, 2025, voyage from Lima (Callao), Peru, to Port Everglades, guests can choose from a broader range of available accommodations. Among the options are a sumptuous, 1,055-square-foot Owner’s Suite or 721-to-826-square-foot Master Suite. With many sea days, this voyage includes a Panama Canal transit and calls at Guayaquil, Ecuador; Panama City, Panama; Cartagena (overnight) and Oranjestad, Aruba.
Among the included Cartagena inclusions are “Bike Cartagena,” “Yoga Class and Cartagena Old City” and an “Evening Cartagena Horse Carriage Ride.” As with sister Silver Nova, the new Silver Ray was built with a unique asymmetrical design with vast expanses of glass and a different interior layout than Silversea’s other ships. Elevators aren’t in the middle of the ship but instead hug the ship’s exterior.
Launching this month is Explora Journeys’ new Explora II, its second Explora-class vessel. It has 461 ocean-facing suites, and a multitude of restaurants, bars and pools. This intimate explorer will head for the Caribbean later this year. One example? A seven-night “Journey to Yacht-filled Harbors and Scenic Sail-ins” itinerary will sail from San Juan, Puerto Rico, to Miami on November 29, 2024.
That voyage will call at Gustavia, St. Barthelemy; St. John’s, Antigua; Basseterre, St. Kitts; and Virgin Gorda, B.V.I. Explora Journeys will also offer other winter 2024-2025 Caribbean region embarkations from Bridgetown, Barbados, and Miami; many are round-trip from that South Florida port.
Another new vessel is The Ritz-Carlton Yacht Collection’s intimate, 448-passenger Ilma. Launched earlier this summer, the yacht offers suites with floor-to-ceiling windows and a private balcony. The top Owner’s Suite spans more than 1,033 square feet.
Gastronomic enthusiasts will discover five restaurants, a refreshed in-suite dining program, seven bars and a signature wine vault aboard. New dining highlights for the brand include Seta Su Ilma by Chef Fabio Trabocchi, a modern Italian fine-dining restaurant, and the Beach House, an open-air eatery featuring a Pan-Latin and Caribbean menu created in collaboration with Chef Michael Mina.
In winter 2024-2025 or winter 2025-2026, Ritz-Carlton Yacht Collection’s guests can choose a variety of itineraries. Among them are four- or five-night sailings round-trip from Port Everglades; an eight-night round-trip from Aruba; or point-to-point voyages between Aruba and Port Everglades, or, alternatively, between San Juan, Puerto Rico, and Barbados. Plus, many departures are round-trip from both San Juan and Barbados.
Upscale Oceania Cruises’ new 1,200-passenger Allura will debut in late 2025. A 14-day “Holiday Haven,” inaugural holiday voyage will sail round-trip from Miami on December 21, 2025. Guests will visit Aruba, Bonaire, Curaçao, Grenada, Barbados, St. Vincent and the Grenadines, Dominica and St. Maarten. One highlight is a late-night departure from St. John’s, Antigua on New Year’s Eve.
Guests who sail on Allura will stay in spacious suites and staterooms (even a roomy 291 square feet for a standard balcony stateroom, for instance). A new onboard Creperie will serve freshly made crepes and waffles to order in the morning and gelatos in the afternoon, plus guests seeking specialty dining might opt for Ember or Aquamar Kitchen. Atop the ship, a new social hub will provide a living room-like ambiance with sweeping seascape views. That venue will host both the ship’s library and digital center.
Many New Multigenerational Ships
On the upscale big-ship side, many new amenity-laden ships are on the horizon. Setting sail on Caribbean sailings later this year is Disney Cruise Line’s new 4,000-passenger Disney Treasure, a sister to Disney Wish. Operating multiple winter 2024-2025 departures, the ship will set sail on seven-night, eastern and western Caribbean itineraries from Port Canaveral, FL. Guests will visit such ports as Cozumel, Mexico; George Town, Grand Cayman; Falmouth, Jamaica; and Castaway Cay in the Bahamas.
Starting in November 2025, another new sister ship, Disney Destiny, will offer an inaugural season of four- and five-night Bahamas and western Caribbean cruises from Port Everglades. Unique is that this will be Disney’s first “Heroes or Villains” themed ship. Look for interior decor, design and activities that reflect Disney stories, characters and theme park attractions.
For example, a first-of-its-kind dining experience will be inspired by the music of “The Lion King” and the Edna a La Mode Sweets confectionary will feature theming from “The Incredibles.” In addition, a new Sanctum will be the line’s first lounge inspired by sorcerers and artifacts from Marvel Studios’ “Doctor Strange.” Sales for Disney Destiny open on September 12, 2024.
In November 2025, Celebrity Cruises’ 3,248-passenger Celebrity Xcel, the line’s fifth Edge-class ship, will debut in the Caribbean. Sailing an inaugural winter season from Port Everglades, FL, the ship will operate alternating seven-night itineraries. One will include destinations in the Bahamas, Mexico and the Cayman Islands. The other will take guests to Puerto Plata, the Dominican Republic; St. Thomas, B.V.I.; and St. Maarten.
Setting sail in 2025, Princess Cruises’ 4,300-passenger Star Princess will be 20 percent larger than any of the line’s existing ships. Highlights will include the Dome, an entertainment venue inspired by the terraces of Santorini and a next-level Piazza featuring a glass sphere. In addition, the ship has expanded accommodations options including the new Reserve and Signature Collections. Star Princess will sail in Europe and then depart in October 2025 for a transatlantic sailing to Port Everglades, its winter 2025-2026 home port.
Separately, in August 2025, Royal Caribbean International will launch its second, 7,600-passenger Icon-class vessel, Star of the Seas, sailing from Port Canaveral to the Caribbean and the cruise line’s popular private-island experience, Perfect Day at CocoCay, in the Bahamas.
Inaugural Calls, Unique Experiences
Luxury travelers who sail with ultra-luxury Seabourn to the Caribbean between November 2025 and March 2026 can choose from multiple, seven- to 20-day itineraries calling at 23 island destinations. The 600-passenger Seabourn Ovation and 458-passenger Seabourn Sojourn will operate 27 departures. In the Caribbean, guests will enjoy such signature experiences as “Caviar in the Surf” and the “Marina Event.”
Seabourn’s ultra-luxury voyages will depart from Barbados, St. Maarten, Miami, and a new embarkation port, San Juan, Puerto Rico. In addition, one inaugural port call is Little Bay, Montserrat, dubbed the “Pompei of the Caribbean,” known for its natural beauty and volcanic landscapes. During time ashore on this mountainous island, Seabourn’s guests can opt to tour the Soufriere Hills Volcano observatory or the exclusion zone encompassing the island’s southern area. Besides coastal touring, guests might also “soak up some rays” on a black sand beach.
One highlight is that several Seabourn Ovation voyages will visit the “ABC islands” of Aruba, Bonaire and Curacao in the Southern Caribbean. In addition, Seabourn will also offer an exclusive beach experience at Prickly Pear Cays, Anguilla. Guests will spend a day on a pristine uninhabited isle to enjoy gorgeous beaches, and a gourmet barbecue lunch. Three reefs and clear waters provide an optimum environment for swimming, snorkeling and water play.
During its 2025-2026 winter season sailing, upscale Azamara Cruises will offer several inaugural port calls. They include Scarborough, capital of Tobago; Santa Marta, Colombia; and St. Pierre, Martinique. Azamara’s new sailings through the Caribbean also include a 79-night “Grand Voyage” round-trip from Miami that circumnavigates South America.
For port collectors and those who love exploring ashore, the line—which already has a strong destination focus—has now built some new itineraries that further maximize port time. For example, back-to-back Caribbean sailings will create a 14-day journey where guests will spend every day ashore exploring different destinations and spend no days at sea. That’s quite unusual for a two-week journey.
Look for a Caribbean inaugural call at Ocho Rios, Jamaica, when Virgin Voyages’ new Brilliant Lady debuts in the Caribbean from October 2025 through April 2026. With design by Toronto-based illustrator Janice Sung, the ship’s “look” and “feel” is inspired by both Renaissance-era paintings as well as traditional Japanese and Chinese art, fashion and beauty. Voyage sales will open to the public on September 12, 2024.
Accommodating 2,700 or so guests, the ship will operate from the company’s LEED-gold Terminal V in Miami. During its first Caribbean season, travelers will discover a collection of extended Caribbean getaways with options between seven and 12 nights. Besides the first-time port calls at Ocho Rios, Brilliant Lady will take “sailors” to the ABC islands (Aruba, Bonaire and Curaçao) in the Southern Caribbean, along with Cartagena, Colombia. The new ship will also call at past guest favorites, including the Turks & Caicos, Antigua and Grand Cayman in the Cayman Islands.
Brilliant Lady will also sail through the Panama Canal, operating a 16-night “Panama Canal” crossing on March 21, 2026, from Miami to Los Angeles. Along the route, the ship will call at ports in Costa Rica, Antigua, Colombia and Panama, before heading into the Pacific Ocean.
Separately, multiple departures of Viking’s 11-day “Classic Panama Canal Passage” itinerary in 2025 will take guests to six countries with five included guided tours. The 930-passenger Viking Mars, launched in 2022, will sail between Florida’s Port Everglades and Fuerte Amador (Panama City), Panama, on February 7, February 17, October 23, November 2, December 10 and December 20, 2025.
Within the western Caribbean, the Viking ship will call at Cozumel, Mexico; Belize City, Belize; Roatan, Honduras; San Jose (Puerto Limon), Costa Rica; and Colon, Panama. It will also give guests a day of scenic sailing within the Panama Canal, which connects the Pacific and Atlantic Oceans, crossing the narrowest stretch of the Isthmus of Panama. Transiting this 48-mile-long canal takes eight to 10 hours and Viking Mars will pass through Gatun Lake and the Culebra Cut, an artificial valley that runs through the Continental Divide. The crossing also involves transit through a series of locks that lift and lower ships some 85 feet.
For Outdoor Adventure
For guests seeking eco-adventure, Swan Hellenic’s “Land of the Maya: Belize, Guatemala & Honduras” itinerary operates round-trip from Belize City. Departing April 30, 2025, the line’s 158-passenger Vega, a luxurious expedition ship, will sail to such ports as Guanaja Island and Roatan Island, Honduras; Santo Tomas de Castillo in Guatemala; Placencia and Half Moon Caye in Belize.
Not to be confused with Half Moon Cay, Holland America Line’s private island-style experience in the Bahamas, the crescent Half Moon Caye at Belize’s Lighthouse Reef is Central America’s first marine reserve. Home to an old-growth littoral forest, the island is best known for its colorful bird life—4,000 red-footed boobies.
In addition, on January 6, 2025, Ponant’s 184-passenger Le Bellot will set sail on “Panama and Costa Rica by Sea: The Natural Wonders of Central America.” Encompassing destinations in both the Caribbean and the Pacific, this Smithsonian Journeys voyage is expected to draw passionate outdoor enthusiasts and aspiring marine scientists.
Sailing between Colon, Panama, and Puntarenas, Costa Rica, guests will peruse mangrove forests and white sand beaches, and learn about nature conservation efforts. One guest highlight will be an exclusive tour of the Smithsonian Tropical Research Institute’s Punta Culebra Nature Center. Another is sailing with Hugh Neighbour, a former diplomat and U.S. Navy officer; he’s an onboard Smithsonian expert tapped to offer guests insight on history, culture, and current affairs.
Guests will also spend time with local Indigenous communities on the Caribbean’s San Blas Islands and in the World Heritage Site of Darien National Park and Playa Muerto, a small coastal village inhabited by the Emberas Amerindian people. Not able to go in early 2025? The good news is that Ponant and Smithsonian Journeys also offer this popular itinerary on many other departures in 2026.
New in Boutique Luxury
SeaDream Yacht Club’s two recently refurbished yachts, each with 100 or so guests and a 1-to-1 crew-to-guest ratio, will offer 28 new “Best of the Best” Caribbean voyages between January and April 2027. SeaDream is introducing these winter-season, seven-day itineraries earlier for sale than is usually the case.
Notable for guests is that all the Caribbean voyages will offer at least one overnight stay per cruise, mostly at St. Barthelemy. Guests will also visit the U.S. and British Virgin Islands, Anguilla, Guadeloupe, St. Vincent and the Grenadines, St. Lucia and Barbados and elsewhere. Most voyages will operate round-trip from San Juan, Puerto Rico, or St. Thomas, U.S.V.I., with a handful of departures exploring the more southerly isles of Guadeloupe, Grenadines, St. Lucia and Barbados. Select voyages will also embark guests in St. Martin and Barbados.
For customers who are interested in sustainability, SeaDream’s new yachting itineraries have been optimized for slower speeds and lower fuel consumption. That’s estimated to reduce emissions by an estimated 15 percent from 2025 to 2027.
In late 2025, Sea Cloud Cruises’ flagship, the 64-passenger Sea Cloud will undergo an extensive drydock renovation. Prior to that, during the 2025 season, guests on all three of the line’s vessels can expect special shipboard and shoreside events in celebration of the flagship’s 95-year history. The historic windjammer was originally built by Marjorie Merriweather Post and her then husband E.F. Hutton.
Other lines also utilize that historic, four-masted sailing vessel for select guest offerings. For instance, Lindblad Expeditions-National Geographic will offer a “Sailing the Caribbean aboard Sea Cloud” itinerary in January and February 2025. On the January 19, 2025, departure, Susan Seubert, a National Geographic photography expert, will sail with guests.
Boutique luxury Windstar Cruises will celebrate its 40-year anniversary across its fleet from October 2024 through October 2025. While more details will be unveiled soon, guests including those on Caribbean sailings can expect complimentary Ruby Anniversary cocktails served at a special “40 Years of Windstar” trivia event on board the small-ship line’s ships.
In addition, trivia winners will be entered into a random drawing to be conducted in December 2025 to win a cruise for two aboard the new 224-passenger Star Seeker inaugural cruise. In addition, limited edition Seabags, a 40th anniversary series crafted from recycled Wind Surf sails, will be sold in the ships’ shops.
Accessible Exploring
Broadening Caribbean options for guests who may not have thought they could explore is Holland America Line. Earlier this year, the line introduced 13 new Caribbean “accessible tours”—spanning 12 ports in 11 countries. Offering Caribbean voyages from its Port Everglades home port, Holland America confirms to Luxury Travel Advisor that those will be offered again in next year, as well.
These accessible tours are designed to avoid steps and stairs. Tour vehicles have wheelchair ramps or lifts. Along the touring routes, the line also has identified accessible bathrooms that can accommodate wide wheelchairs. Here’s one example. On Holland America’s four-hour “Easy Harrison’s Cave” accessible excursion in Barbados, guests will board an accessible van for a scenic drive to the cave.
From the visitor center, they’ll take a special elevator down to the ground level of the cave entrance. They can visit small handicraft shops and the botanic gardens, and also view Indigenous artifacts. The tour’s highlight is boarding an accessible tram for a 45-minute journey beneath the earth’s surface to view gorgeous calcite and limestone formations.
Return to the Caribbean
While much is new in the Caribbean, sometimes it’s the return of a tried-and-true favorite that makes waves. That will be the case in 2026, when Crystal’s 606-passenger Crystal Symphony will return to the U.S. for the first time since 2019. After sailing an Alaska season as well as Canada and U.S. East Coast voyages, the ultra-luxury ship will end the year with Caribbean holiday sailings in November and December 2026; the embarkation port for those late-in-the-year sailings won’t be known until the voyages open for sale in a few months.
But when it comes to Caribbean cruises, experienced luxury travelers also have new embarkation points, new itineraries, inaugural ports of call, unusual journeys, new accessible tours, and special events and activities. For those who may be new to cruise, the Caribbean offers a close-to-home opportunity to try out cruising. Then once they sail, they’re often hooked and start planning another cruise vacation in Europe, Asia, the Americas or even the polar regions.
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