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The Best Caribbean Cruise Packages for Fall 2019

The Best Caribbean Cruise Packages for Fall 2019

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Sea and be seen this fall.

Roberto Machado Noa/LightRocket via Getty Images

If you’re not keen on the chillier days or the shorter hours of daylight, fear not, sailing to the tropical paradise of the Caribbean will cure any woes that ail you. When opting for a cruise vacation, you take the worry out of logistics planning and other travel headaches. Moreover, expect to capitalize on a more peaceful retreat (because the kids are back at school and the majority of people are back at work). And even better, the temperatures are plenty balmy at this time. Best of all, fall is considered a shoulder season (right before the big winter holiday break), so expect better prices and deals.

Bear in mind that these deals are also spurred on by the fact that it’s still technically hurricane season in the Caribbean—however, travel overall remains safe. Regardless, it is best to check the weather advisory and directly with cruise lines, which monitor conditions frequently and inform their guests of any issues.

Here are a few of the best Caribbean Cruise packages to take advantage of right now:

Crystal Cruises

Holiday Sojurn with Crystal Cruises.

Crystal Cruises

Crystal Cruises is offering a 12-day Holiday Sojurn aboard Crystal Serenity with a Wine Food Festival themed cruise that will allow you celebrate Thanksgiving season in epicurean style. Feast upon Michelin-level and award-winning dining options that include Umi Uma Sushi and Bar by Chef Nobu Matsuhisa, or experience a multicourse tasting menu inside the Vintage Room with exclusive varietals selected by acclaimed sommelier Eugenio Jardim. Guest mixologist Mary Barranco will also be on board to present drink forecasts and presentations to cocktail enthusiasts. The cruise begins in Fort Lauderdale, with stops that include Turks Caicos, St. Barthélemy, French West Indies, Barbados, St. Lucia, Antigua Barbuda, and the U.S. Virgin Islands. These destinations are best enjoyed with their cultural deep-dive excursions, which include everything from fishing off St. Barth to cooking classes in Martinique. On the journey back to Fort Lauderdale, guests are encouraged to take advantage of the ship’s entertainment programming, which includes the Crystal’s Magic and the Crystal on Broadway series.

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Norwegian Cruise Line#####IMG000000000#####

The Norwegian Encore sails to the Eastern Caribbean from Miami, starting on November 24, 2019.

Norwegian Cruise Line

Embark on a Caribbean vacation with Norwegian cruise line’s new ship, the Norwegian Encore. The 7-day round trip from Miami makes stops in Puerto Rico, the U.S. Virgin Islands and British Virgin Islands. Enjoy a cultural tour that includes excursions to El Morro and Blackbeard’s Castle, in San Juan and St. Thomas, respectively. Passengers can also take advantage of a wealth of innovative activities and programming that includes a racetrack on the ship’s deck, the Galaxy Pavilion (immersive virtual and augmented-reality gaming experiences), and interactive laser tag in a 10,000-square-foot-arena complete with a Lost City of Atlantis theme. Music and entertainment is also given the star-studded treatment, especially since Kelly Clarkson was recently named the godmother to the ship. Onboard, find Tony Award-winning musical Kinky Boots and U.K.-hit Choir of Man in the evenings. Lastly, when booking oceanview rooms and higher category levels, you’ll save on round-trip flights with their Free Reduced Airfares or Free Short Excursion bonus credits at each port.

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Viking Ocean Cruises#####IMG000000000#####

Day 4 port of call: St. Kitts (Basseterre), St. Kitts Nevis when sailing on the cruise line’s West Indies Explorer trip.

Viking Cruises

With trips throughout November and December onboard their Viking Sea ship, the West Indies Explorer takes you to nine different destinations in 11 days, starting in Puerto Rico and with stops in Tortola, St. Thomas, St. Kitts, St. Martin, Antigua Barbuda, Dominica, St. Lucia and Barbados. With a cultural curriculum in mind, the intimately sized cruise further enhances this with regional dining specialties and cerebral, enriching lecture series by guest Viking Resident historians. For this high-seas adventure, the focus will be on Explorers, Pirates Treasure Hunters, and Islands in History.

With the Viking Inclusive Value program, the luxury liner includes one complimentary shore excursion in every port of call, focusing on culture, arts and panoramic guided tours. Or book your own adventure, from salsa dancing in Puerto Rico to Champagne Reef Snorkeling in Dominica. They’re also offering a promotion for air travel from $299 per person from select major airports (including New York’s JFK).

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Disney Cruise Line#####IMG000000000#####

Eastern Caribbean Cruise with Disney begins November 10 in New York and ends in San Juan.

Disney Cruise

If you’ve always been curious about sailing with Disney, now is definitely the time to do it. Expect a more peaceful ship, especially with the little ones back-at-school. For its Eastern Caribbean Cruise from New York ending in San Juan, the Disney Magic ship sets sail from the U.S. on November 10. For five nights, you visit three destinations, with three days at sea. Onboard, catch their lively versions of Broadway shows such as The Lion King and Aladdin. Also unique to the cruise is the Rotational Dining where you and your personal wait staff will rotate to each of their three themed restaurants on the ship, from fine French fare at Beauty and the Beast’s Lumière to American contemporary dishes inside Rapunzel’s Royal Table. Or opt for La Dolce Vita at Palo, an adults-exclusive restaurant offering Northern Italian cuisine. Everyday, expect plenty of entertainment and partying, which includes Sail-a-Wave and pirate-themed parties. Before you know it, you’ll be on the sandy shores of Antigua in the West Indies. Disembarkation occurs on the following day in San Juan.

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Oceania Cruises#####IMG000000000#####

Oceania Cruises is offering a ten-day voyage on the Riviera with ports of call that include Puerto Rico, Antingua, St. Lucia, and St. Barthélemy. The trip departs November 15, 2019.

Oceania Cruises

Oceana cruise line’s Sun Serenade 10-day voyage ensures plenty of rest and relaxation. Currently they have an OLife Choice offer, which includes roundtrip airfare, free internet and one of the three options of your choice: 6 shore excursions, a free beverage package or $600 in shipboard credits. Ports of call include the Dominican Republic, Puerto Rico, St. Maarten, Antigua, St. Lucia, and St. Barth—before returning to Miami. While ashore, partake in snorkeling through majestic coral reefs in St. Maarten, or when in St. Barth go on a semi-submarine expedition. Meanwhile, life aboard the Riveria is nothing short of luxurious. Enjoy refined elegance on their OceaniaNEXT suites, furnished exclusively with Ralph Lauren home accents. Also of note is their tantalizing roster of international cuisine. Thanks to executive culinary director Jacques Pépin, you can enjoy everything from Tuscan fare and Paris bistro comfort cuisine to contemporary interpretations of Asian dishes at Red Ginger. And of course, such meals aren’t complete without fine wines: Make sure you visit La Reserve by Wine Spectator, where they can host you for a memorable multicourse Dom Pérignon-themed dinner.

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Windstar Cruises#####IMG000000000#####

Star Pride is an all-suite, star-class ship that sails to the Caribbean. Their November 6 trip sails from San Juan to Bridgetown.

Windstar Cruises

If you’re seeking a boutique-sized luxury liner, Windstar is your best bet, with only 212 guests and 106 suites (all outside with ocean views) on board their Star Pride. Travel with them on the appropriately named Winter Antilles Escape, which departs November 6, 2019—with sale prices on oceanview and balcony suites. It’s seven days of nonstop ports of call, including Puerto Rico, St. Barth, Montserrat, Dominica, St. Lucia, Grenada and Barbados. When not soaking up the breathtaking beaches, heritage sites and concierge collection-based excursions, retreat to the comfort of your ship for gourmet meals, welcome cocktails and onboard entertainment.

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