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!
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May 2027 Caribbean Cruises
64 cruises
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
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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
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
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
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
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
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
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
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 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
A refined style, precious materials and attention to detail make MSC Opera a cruise ship that really is something to sing about! She is built along more classic lines than her sisters in the Musica and Fantasia classes, making for a special atmosphere on board while enabling you to visit those destinations that are inaccessible to larger vessels.
- Mega Ship
- Fun
- Family-Friendly
Cruise: La Romana – Catalina Island – Virgin Gorda – Philipsburg – Fort-de-France – Saint John's – La Romana
7 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 – Roatán Island – Costa Maya – Cozumel – Ocean Cay, MSC Marine Reserve – Miami, Florida – Puerto Plata – San Juan (Puerto Rico) – Ocean Cay, MSC Marine Reserve – Miami, Florida
14 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 – Puerto Plata – Port Canaveral, Florida
7 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 – Roatán Island – Costa Maya – Cozumel – Ocean Cay, MSC Marine Reserve – Miami, 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 – Key West, Florida – Celebration Key – Nassau – 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 – San Juan (Puerto Rico) – Saint Thomas – Port Canaveral, Florida
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 – Montego Bay – Grand Cayman – Cozumel – New Orleans, Louisiana
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
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
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 – Amber Cove – Half Moon Cay – Nassau – Celebration Key – Miami, Florida
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
A refined style, precious materials and attention to detail make MSC Opera a cruise ship that really is something to sing about! She is built along more classic lines than her sisters in the Musica and Fantasia classes, making for a special atmosphere on board while enabling you to visit those destinations that are inaccessible to larger vessels.
- Mega Ship
- Fun
- Family-Friendly
Cruise: La Romana – Catalina Island – Bridgetown – Fort-de-France – Pointe-à-Pitre – Road Town, Tortola – La Romana
7 nights
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