This Winter’s 12 Greatest Caribbean Cruises

How does the sound of hopping on board a floating city and sailing down to the Caribbean sound – right smack dab in the middle of winter when you’re already growing weary of shoveling and snow blowing your driveway? 

You can give your back a rest and put your feet up on any number of Caribbean islands, courtesy of a few different luxury liners. Whether you want to pack up the family or even escape on a solo tour, you can find yourself sunning under a palm tree anytime you want. 

Let’s take a look at 12 of the best options for this upcoming winter season. 

Royal Caribbean: Allure of the Seas

When speaking of Caribbean cruises, we must start with royalty, right? The Allure of the Seas really takes the whole floating city notion to new heights. It features seven different neighborhoods, a boardwalk, a carousel, and even an ice skating rink. 

They have a nice six-night Western Caribbean cruise that starts at $675/person – with taxes and fees included. Departing from Fort Lauderdale, Florida, this could be a nice winter getaway when you’re ready to escape the cold. 

Norwegian Cruise Line: Norwegian Breakaway

As one of their larger ships, you’ll have everything at your fingertips onboard the Breakaway – from their award-winning Mandara Spa to a ropes course to an Aqua Park. Their restaurants serve everything, including Brazilian, French, and Italian cuisine. 

They, too, will sail you down to Western Caribbean hotspots like Cozumel and Costa Maya. Departing from New Orleans, Miami, Orlando, and Tampa, the options abound to hop aboard and rejuvenate your soul. 

Carnival Cruise Line: Carnival Vista

Sailing from Port Canaveral, this is one of Carnival’s luxury liners that will escort you down to the Caribbean for anywhere from six to nine days. They have lovely staterooms that are decked out in an Old Havana Style, as well as a Havana Pool & Bar that looks like its own island retreat. 

Kids will go crazy for their twin-track suspended bike course while the little ones enjoy Dr. Seuss’ Bookville®. There’s also an adults-only Serenity Retreat for a little quiet time, as well as nine onboard dining options, including a steakhouse and a BBQ joint, courtesy of Guy Fieri.

Celebrity Cruises: Celebrity Reflection

Celebrity Reflection is happy to sail you to the Southern Caribbean so you can see beautiful destinations like Antigua’s sugar plantations. Some of their staterooms are absolutely stunning, including their spa-inspired AquaClass® suites. When you add a balcony to that oceanfront view, it’s bliss – right from your bed. 

With so much luxury on board, you don’t even have to splurge on your room if you don’t want to. Three-night packages start at $289 per person, and you can take full advantage of their onsite restaurants, lounges, and spa services to indulge in every bit of decadence – even with an affordable price tag like that. 

Disney Cruise Line: Disney Fantasy

Disney usually does it right when it comes to plush accommodations, and Disney Fantasy is no exception. There are plenty of staterooms to choose from to accommodate the whole family together in one suite. The oceanview rooms are particularly splendid. 

One of their onsite restaurants, the Enchanted Garden, is inspired by Disney Princess films. So, if you have a princess in your family, she’ll absolutely love it. Their seven-night Eastern Caribbean cruise from Port Canaveral, for example, could be a wonderful Christmastime getaway, sailing to places like St. Thomas, Tortola, and the British Virgin Islands. 

MSC Cruises: MSC Seaside

MSC Seaside takes its name seriously. They’ve found a way to blend parts of the ship with the sea with certain elements like glass-floor catwalks and a seafront promenade lined with places to drink, eat, swim, sunbathe, and shop. 

Sailing from Miami, they have a four-night cruise that covers both the Caribbean and the Bahamas. Starting at $285 per person, including all taxes and fees, you don’t even have to break the bank to enjoy that glass-floor promenade. 

Princess Cruises: Sky Princess

The Sky Princess takes on a distinctive, contemporary design lined with luxury. It’s part of their new MedallionClass fleet, so you won’t find anything outdated onboard this ship. 

If you have the PTO, they have a ten-day cruise that sails out of Fort Lauderdale down to beautiful islands like Aruba, Bonaire, and Curacao. 

Holland America Line: Nieuw Statendam

Holland America is noted for its luxury and class, and the Nieuw Statendam is no exception. Just look at how they market this ship: “Her design draws inspiration from the elegant curves of musical instruments.” Don’t you just want to book right now? 

Not only will your captain be happy to sail you down to the Caribbean for a few nights, you can also visit the line’s private island for complete relaxation. Right now, they’re running a Caribbean sale, which could save you up to 40% off your fare. That’s certainly something to think about. 

Virgin Voyages: Scarlet Lady

Here comes another class act: the Scarlet Lady. This lovely lady is reserved for adults only and has all the usual fixins: world-class dining, spa services, and plenty of areas to lounge in the sun. Perhaps their most unique feature is their onboard tattoo parlor, followed by their rooftop yoga classes. 

There’s a nice East Caribbean itinerary that sails out of Miami and voyages down to island destinations like San Juan, St. Croix, and Bimini. Right now, they’re running a slick deal where you can get up to 70% off your second sailor. 

Seabourn: Seabourn Ovation

The Seabourn Ovation is an opulent option if you’re interested in small-ship cruising. With only 300 suites, you will certainly be well looked after onboard this beauty. Their Veranda Suites, in particular, will knock your socks off with full-length glass doors that lead to private verandas. 

Their offerings tend to sell out. So, if you find something you’re serious about, you won’t want to wait too long to book your trip. How does this itinerary sound: a 34-day Mediterranean cruise to the Caribbean that starts in Barcelona and ends in Barbados. Thrilling, right? 

Windstar Cruises: Wind Surf

Now, this one is fascinating. The Wind Surf is the world’s largest sailing cruise ship that only hosts up to 310 guests. Heads will turn when you pull into the various ports of call. Every detail is tended to when you’re onboard this ship, including the bowl of fresh fruit in your room upon arrival. 

They invite you to “let your soul dance” on their Caribbean getaways with over 24 itineraries, ranging from Puerto Rico to Antigua and Cartegena to Barbados. Indeed, their all-inclusive deals are quite tantalizing. 

Regent Seven Seas Cruises: Seven Seas Splendor

Even if you only ever look at the pictures, you have to check out their website to see some of their suites. We’re talking crystal chandeliers over dining room tables that open up to panoramic views, courtesy of your own private balcony. 

Their lounges, bars, and restaurants are equally decadent. With several different Caribbean itineraries, you may also find yourself gliding down the Panama Canal as you explore Central America’s glorious coastline after you’ve savored some of that cool Caribbean sun. 

Come Sail Away 

Come sail away with any of these decadent options. Whether you’re looking for family fun, adults-only fun, a floating city, or a small ship, you can have it all this winter. With multiple fine dining options and sumptuous suites, you have some lovely options here for the perfect escape. 

As you get ready to explore, check out our destination guides. We have plenty of itineraries in there to help you design the vacation of a lifetime. And you never know. Perhaps we’ll see you out there, sailing the seven seas sometime!