Caribbean Cruises May 2027

Caribbean Cruises May 2027 offer a wonderful chance to enjoy beautiful weather and vibrant island life as summer approaches. Whether you want to explore the crystal-clear waters of the Bahamas, unwind on the pristine beaches of Barbados, or experience the rich culture of Jamaica, May 2027 Caribbean Cruises have something for every traveler. With a variety of exciting itineraries and early booking deals available, May is a fantastic time to secure your dream getaway at the best price. At Hello Cruise, we make it easy to compare prices from trusted UK cruise agents, helping you find the best offers and book your perfect cruise hassle-free. Don’t miss out—book your Caribbean Cruise in May 2027 today and get ready for an unforgettable journey!
Quick Links:
May 2027 Caribbean Cruises
145 cruises
With a name derived from the Latin, valère meaning strong, our second lady ship is calling Barcelona home before setting sail on our first Virgin Voyages Mediterranean cruise, with three irresistible itineraries across Europe.
- Mega Ship
- Informal
- Adults Only
Cruise: Miami, Florida – Georgetown, Grand Cayman – Bimini Island – Miami, Florida
5 nights
A New World of CruisingDiscover A New World of Cruising on board MSC World America, MSC Cruises new World Class ship.A world where the elegant European design meets American comfort. A world that’s revolutionary yet harmonious, for a ship that meets the needs of the present and the future. A ship for guests of all ages from all around the globe.
- Mid-Size Ship
- Fun
- Family-Friendly
Cruise: Miami, Florida – Puerto Plata – San Juan (Puerto Rico) – Ocean Cay, MSC Marine Reserve – Miami, Florida – Roatán Island – Costa Maya – Cozumel – Ocean Cay, MSC Marine Reserve – Miami, Florida
14 nights
A New World of CruisingDiscover A New World of Cruising on board MSC World America, MSC Cruises new World Class ship.A world where the elegant European design meets American comfort. A world that’s revolutionary yet harmonious, for a ship that meets the needs of the present and the future. A ship for guests of all ages from all around the globe.
- Mid-Size Ship
- Fun
- Family-Friendly
Cruise: Miami, Florida – Puerto Plata – San Juan (Puerto Rico) – Ocean Cay, MSC Marine Reserve – Miami, Florida
7 nights
Building on her sisters ships’ success, MSC Grandiosa offers even more public space, along with a series of exciting innovations. Meantime, Aurea Experience guests can appreciate the pleasures of flexible dining and unlimited drinks in a dedicated restaurant.
- Mid-Size Ship
- Fun
- Family-Friendly
Cruise: Port Canaveral, Florida – Nassau – Ocean Cay, MSC Marine Reserve – Cozumel – Costa Maya – Port Canaveral, Florida
7 nights
It’s one thing to be fun, but it’s another thing to be first. Carnival Dream was at the forefront of a recent wave of amazingly innovative and fun Carnival ships. As the genesis of the Dream class, Carnival Dream set the direction for the ships that followed in her footsteps — first Carnival Magic and then Carnival Breeze.But back to Carnival Dream: the ship itself is a unique experience with the way-fun RedFrog Rum Bar® and the very cool BlueIguana Tequila Bar™. Get your appetite ready, because you’re gonna need it. Carnival Dream features two dual-level dining rooms, a gourmet steakhouse and dedicated sushi spot Bonsai Sushi™. It’s also got a full menu of our latest and greatest casual spots for a bite: BlueIguana Cantina™, Pizzeria del Capitano, Guy’s Burger Joint™ and Guy’s Pig & Anchor Smokehouse™. (That’s Guy as in Guy Fieri, by the way — so you know the food’s delish.)Carnival Dream also features the borderline-magical Alchemy Bar® and Ocean Plaza, which combines tasty treats with perhaps even tastier entertainment. Entertainment options are all up and down the ship, and so is soaking-wet fun, from the heart-racing waterslide action at Carnival WaterWorks™ to the soul-soothing Thalassotherapy pool at the Cloud 9 Spa™.Despite its name, Carnival Dream is definitely a reality. Can’t believe it? Pinch yourself… and book your dream cruise today.
- Large Ship
Cruise: Galveston, Texas – Roatán Island – Belize City – Cozumel – Galveston, Texas
7 nights
Mardi Gras: Fun-Fueled Vacation Innovation Powered by LNGWhen we launched our first ship, 1972’s TSS Mardi Gras, we made cruising a lot less stuffy, a bit less fancy, the kind of fun everybody could enjoy. Nobody expected this ship to change the cruise world, but… here we are! So here’s a brand-new ship with a familiar name. With this Mardi Gras™ we aren’t just paying homage to our first ship — in cruising circles this name suggests innovation, signals the start of something big. Oh, and this Mardi Gras still shouts “fun!” at the top of its lungs. This ship introduces Zones — six themed areas packed with brand-new experiences for eating, drinking and spectacularly getting down to fun. There’s BOLT™, the first-ever rollercoaster at sea, Emeril’s Bistro 1396™ from yes-that-Emeril, Family Feud™ Live for everybody… plus incredible new bars like The Brass Magnolia and Fortune Teller. Everybody can enjoy Mardi Gras, sailing now. Come on down!
- Mid-Size Ship
- Lively
- Family-Friendly
Cruise: Port Canaveral, Florida – Celebration Key – Cozumel – Roatán Island – Port Canaveral, Florida
7 nights
Building on her sisters ships’ success, MSC Grandiosa offers even more public space, along with a series of exciting innovations. Meantime, Aurea Experience guests can appreciate the pleasures of flexible dining and unlimited drinks in a dedicated restaurant.
- Mid-Size Ship
- Fun
- Family-Friendly
Cruise: Port Canaveral, Florida – Nassau – Ocean Cay, MSC Marine Reserve – Cozumel – Costa Maya – Port Canaveral, Florida – Nassau – Ocean Cay, MSC Marine Reserve – Puerto Plata – Port Canaveral, Florida
14 nights
From summer 2026 the newly Amplified Harmony of the Seas® is geared up for maxed-out with an unbelievable lineup of upgrades on an Oasis Class showstopper. Crush every craving with mouthwatering bites at over 20 venues, including bold flavours at the brand-new Samba Grill Brazilian Steakhouse. Turn up after dark with all new nightlife at Playmakers Sports Bar & Arcade and with an expanded new casino — the largest in fleet. Conquer daredevil-worthy feats together on The Perfect Storm waterslides, then soar over the Boardwalk on a high-flying zipline ride. And with tropical sips from The Lime and Coconut®, you can make it your chillest day yet on the revamped pool deck. Experience the newly Amplified Harmony of the Seas® — sailing a mini-season from Barcelona May 2026 and full-time from Port Canaveral in August.
- Large Ship
- Fun-filled
- Family-Friendly
Cruise: Port Canaveral, Florida – Coco Cay – Charlotte Amalie – Philipsburg – Port Canaveral, Florida
7 nights
From Summer 2026, go even bolder in Europe on the newly Amplified Liberty of the Seas® after a makeover for the ages, bringing all-new adventures to a fleet favourite ship. Dial thrills all the way up, conquering a new Royal Escape Room and twisting, turning dares on The Perfect Storm waterslides — including the first boomerang slide at sea. Charge up your chill with private new casitas complete with attendant service and cocktails from The Lime and Coconut® at the totally-revamped pool deck. Fill up on fresh faves at 15 crave- worthy restaurants like the new El Loco Fresh® and Izumi Teppanyaki. And hit a bolder jackpot at the expanded casino, loaded with even more slots and table games. Take your holiday to the next level on the newly Amplified Liberty of the Seas®, sailing from Southampton summer 2026.
- Large Ship
- Fun-filled
- Family-Friendly
Cruise: Galveston, Texas – Costa Maya – Cozumel – Galveston, Texas
5 nights
This is more than a holiday upgrade. It’s the best family holiday in the world. Introducing the new Icon of the Seas℠, a first-of-its-kind Royal Caribbean® adventure where you’ll have the time of your life, multiple times a day. It’s thrills you never dared to imagine and next-level chill you never dreamed possible. Let your adrenaline surge at the largest waterpark at sea or conquer an all-out test of courage dangling high above the ocean. Pick from seven unique pools to satisfy any mood, this is an all-you-can-swim buffet. Fuel bolder bonding with tons to do for everyone in your crew at Surfside℠, the ultimate stay-all-day family neighbourhood right onboard. And discover dishes to delight every appetite with 40 ways to dine and drink. This is the Icon of the Seas.
- Mid-Size Ship
- Fun-filled
- Family-Friendly
Cruise: Miami, Florida – Costa Maya – Roatán Island – Cozumel – Miami, Florida
7 nights
Explore deck-defying discoveries, world-class dining and the best cruise entertainment onboard Allure of the Seas® – the most awarded ship in the world.This Oasis Class favourite brings adventure to soaring new heights. Discover next-level thrills on every deck of Allure of the Seas®, from white-knuckle zip line rides ten decks up to totally splashworthy spaces for kids, like the interactive H20 Zone℠ Water Park. Get down after dark with more bars than any ship out there and savour a world of possibilities right onboard. Recognised for its dazzling onboard entertainment, thrilling attractions and wanderlust-fuelled itineraries, this ship has already been named Best Large Cruise Ship, Best for Entertainment and Best Individual Ship – and it’s just getting started.
- Mid-Size Ship
- Fun-filled
- Family-Friendly
Cruise: Fort Lauderdale, Florida – Willemstad – Oranjestad – Coco Cay – Fort Lauderdale, Florida
8 nights
Top-rated coasts. Bow-to-stern boasts. The best of both worlds combine for an all-in-one adventure on the Amplified Freedom of the Seas®. Wherever you choose to wander, you’ll find plenty of unparalleled thrills onboard in between adventures ashore. Like adrenaline-pumping slides and rides here on deck. A new pool scene designed to upgrade your time in the sun. And fresh, authentic flavours that will satisfy any craving.
- Mid-Size Ship
- Fun-filled
- Family-Friendly
Cruise: Miami, Florida – Falmouth – Labadee – Miami, Florida
5 nights
Whether you choose to wander the tropical shores of the Eastern, Western or Southern Caribbean, adventure is always guaranteed on Grandeur of the Seas®.Grandeur of the Seas is the ultimate Caribbean adventure. It’s the perfect blend of unique experiences onboard and unbelievable shores, like the lush islands of the Southern Caribbean, the crystal-clear waters of St Maarten, and Mexico’s aquamarine sinkholes that make Grandeur of the Seas one of the best intimate cruise ships for families and couples.
- Mega Ship
- Fun-filled
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Charlotte Amalie – Saint Croix Island – Philipsburg – Castries – Bridgetown – San Juan (Puerto Rico)
7 nights
An immersive experience truly connecting you to the sea awaits you onboard MSC Seascape.MSC Seascape ship pays tribute to the beauty of the ocean with a whole host of innovative design features to enable guests to enjoy new horizons at sea, through her impressive outdoor spaces designed for relaxation, dining and entertainment.Covered pools, panoramic lifts and the breath-taking glass skywalk Bridge of Sighs, make MSC Seascape iconic and unique for sensational points of view on the ocean.Beyond that, the new immersive high-tech entertainment with innovative technology provides guests with endless options.
- Mid-Size Ship
- Fun
- Family-Friendly
Cruise: Galveston, Texas – Costa Maya – Roatán Island – Cozumel – Galveston, Texas
7 nights
We think you should have a great time at sea. Carnival Liberty feels the same way! This is one ship that’s ready to put its fun where your vacation is, with plenty of ways to enjoy your time away.All day long, Carnival Liberty can be found serving up signature burgers designed by Guy Fieri, right there at Guy’s Burger Joint™ — and look! — just over there is SkyBox™ Sports Bar: a double-header of a sports bar that brings together live sports on TV and lively sports-gaming competition… oh, not to mention great drinks! Enjoy BlueIguana Cantina™ tacos and burritos on Lido deck — made fresh, and fast, while you wait — plus two great bars: one rum-slinging, one tequila-wielding, both dueling for your heart. That’s right: just a quick stroll from RedFrog Rum Bar® you’ll find BlueIguana Tequila Bar™.On the entertainment side of things, Carnival Liberty features two of our best, live on stage. First there’s Playlist Productions™, where pros sing and dance their hearts out, performing high-energy themed revues of tunes you know, backed by amazing visual effects. Then there’s Punchliner™ Comedy Club where you’ll find some real pros who know how to wedge a little laughter into anyone’s evening. Kids have three unique youth spaces where they can hang out with others their age and enjoy supervised activities, games and more.You might call Carnival Liberty a vacation spot that’s just full of great vacation spots… and we’d agree!
- Mega Ship
Cruise: New Orleans, Louisiana – Roatán Island – Belize City – Cozumel – New Orleans, Louisiana
7 nights
The second stunning ship in the Prima Class, Norwegian Viva® is designed for you to live life to the fullest. Stretch out, way out, in some of our most spacious accommodations. Stay connected to the ocean along the 360° Ocean Boulevard or by enjoying a dip in the Infinity pool. And with high staff-to-guest levels, you’ll always feel prioritized and pampered. From our three-story race track and immersive virtual-reality games to the luxurious Mandara Spa® and mesmerising three-story theatre that transforms into a Vegas-style nightclub, get ready to live it up on Norwegian Viva from sunrise to long after the sun has set.
- Mega Ship
- Relaxed
- Family-Friendly
Cruise: Miami, Florida – Roatán Island – Harvest Caye – Cozumel – Great Stirrup Cay – Miami, Florida
7 nights
Set sail on Celebrity Silhouette® and discover amazing enhancements at every turn. You’ll relax in transformed staterooms that are so gorgeous, you may never want to leave your room. Gather for a toast at the newly reimagined Passport Bar or the new Craft Social Bar, a cool and casual spot. Shop in exciting new boutiques featuring the hottest designers. And, The Spa on Silhouette is taking rejuvenation to new heights with new spa treatment rooms, new flooring throughout, and much more. Your next vacation aboard Celebrity Silhouette is bound to be even more stunning now than ever before. Discover how the world’s best premium cruise line becomes more incredible than ever.Celebrity Silhouette is sailing with Starlink – the world’s most advanced broadband satellite internet – to bring you high-speed connectivity for a better onboard experience.
- Mega Ship
- Contemporary
- Premium
Cruise: Cape Liberty, Bayonne, New Jersey – Cruising by the Statue of Liberty – Kings Wharf – Kings Wharf – Kings Wharf – Cape Liberty, Bayonne, New Jersey
7 nights
CARNIVAL CELEBRATION: GREAT FUN TOGETHER, ALL POWERED BY LNGYou know, it’s hard work making effortlessly-fun vacations. That’s why we’re looking forward to kicking back with you on the new Carnival Celebration as we toast to the last 50 years. So please bring that unique Carnival spirit… and know that this ship’s bringing the fun. Just like sister ship Mardi Gras®, Carnival Celebration has six Zones — themed areas that bring together incredible experiences and flavor. New flavors you haven’t experienced yet — nobody has! — are heating up at Latitudes™, The Golden Jubilee™ and Emeril’s Bistro 1397™. (Mmm, new Emeril.) Carnival Celebration also marks the return of innovations like BOLT® — our onboard rollercoaster, Bonsai Teppanyaki™, RedFrog® Tiki Bar, Family Feud™ Live, Havana Bar™, Seuss at Sea™, and Playlist Productions™. Perhaps best of all, all the fun you’ll have on Carnival Celebration is powered by clean LNG fuel!
- Mid-Size Ship
- Lively
- Family-Friendly
Cruise: Miami, Florida – Saint Thomas – San Juan (Puerto Rico) – Celebration Key – Miami, Florida
7 nights
The new Star of the Seas is now welcoming the first lucky guests to step on board — launching the world’s best family vacation from Port Canaveral, Florida. This is Orlando’s biggest adventure, the vacation of a lifetime for everyone in your crew — and nothing comes close. From record-breaking thrills and Caribbean chill to mouthwatering bites and sensational wows, there’s a forever-favorite family moment waiting around every corner. And the party goes nonstop both onboard and on shore with each sailing stopping at the unrivaled, unmatched, and undeniably awesome Perfect Day at CocoCay. This incredible ship marks a bold new day for family vacations, and nothing will ever be the same.
- Mid-Size Ship
- Fun-filled
- Family-Friendly
Cruise: Port Canaveral, Florida – Charlotte Amalie – Samaná – Labadee – Port Canaveral, Florida
7 nights
Welcome to a place where you can experience all the things you’ve been missing for so long. Only now, those things are even better than you’ve imagined. This is a place where the possibilities are as endless as the views. where you can disconnect entirely while you reconnect with each other-and the world. This place is Celebrity Beyond℠.The Third ship in our revolutionary Edge® Series takes our innovative outward-facing design further than ever, creating an even closer connection between you, the sea, and every exciting place on the horizon. Unwind in expanded open-air spaces. Savor fine dining that rivals anything you’d find on land. And discover even more ways to relax and renew.Celebrity Beyond is sailing with Starlink – the world’s most advanced broadband satellite internet – to bring you high-speed connectivity for a better onboard experience.
- Mega Ship
- Contemporary
- Premium
Cruise: Miami, Florida – Grand Turk Island – Puerto Plata – Nassau – Miami, Florida
6 nights