Join Caribbean cruise and stay adventures in 2027, with flights and hotels included to help you unwind on stunning beaches and explore colourful islands.
Starting Port
34
11
5
1
Stopover
Arrival port
31
11
4
1
87 cruises
Sun Sea & Magic With Orlando Stay


Cruise with Flight, Hotel
From / To Port Canaveral
MSC Grandiosa
Full board
Tips
20 Jan 2027
11 nights
No Alternative Dates
Best Price Guarantee
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Magic Of Orlando with Sunsets of The Bahamas & Caribbean


Cruise with Flight, Hotel
From / To Port Canaveral
MSC Grandiosa
Full board
Tips
5 May 2027
11 nights
No Alternative Dates
Tropical Caribbean Experience With Miami Escape


Cruise with Flight, Hotel
From / To Miami
MSC World America
Full board
Tips
27 Jan 2027
11 nights
No Alternative Dates
St. Maarten, Tortola, San Juan with Magic City Stay


Cruise with Flight, Hotel
From / To Miami
Brilliant Lady
Adults Only
Full board
5 Mar 2027
14 nights
Luxury Caribbean & San Juan Sunsets with Miami Stay


Cruise with Flight, Hotel
From / To Fort Lauderdale
Enchanted Princess
4 Apr 2027
13 nights
No Alternative Dates
St. Isles and Sun Soaked Seas with Magic City Stay


Cruise with Flight, Hotel
From / To Miami
Brilliant Lady
Adults Only
Full board
22 Jan 2027
14 nights
Western Caribbean Discovery & New Orleans Stay


Cruise with Flight, Hotel
From / To New Orleans
Mariner of the Seas
20 Jan 2027
11 nights
No Alternative Dates
Indulge in the Caribbean with Miami Chic


Cruise with Flight, Hotel
From / To Fort Lauderdale
Celebrity Ascent
9 Nov 2027
14 nights
No Alternative Dates
Luxury Eastern and Southern Caribbean with Miami Stay


Cruise with Flight, Hotel
From / To Fort Lauderdale
Celebrity Eclipse
26 Feb 2027
15 nights
Luxury Southern Caribbean & St Lucia with Barbados Stay


Cruise with Flight, Hotel
From / To Barbados
Emerald Princess
30 Nov 2027
11 nights
No Alternative Dates
Caribbean Cruise and Stay 2027 holidays bring together two dream experiences — sailing across crystal-clear seas and relaxing at stunning island resorts. From palm-fringed beaches to lively Caribbean ports, enjoy sunshine-filled days, diverse cultures, and endless adventure on this ultimate island escape.
Looking for more inspiration? Discover all Caribbean Cruises and uncover sun-soaked itineraries from all major cruise lines and ports worldwide.
Insider Tip: Late November to April offers the best weather for Caribbean cruising — calm seas, dry days, and fewer crowds on the islands make it the ideal time to travel.
Did you know: Caribbean Cruises attract over 12 million travellers annually, accounting for more than 30% of the global cruise market, making it the most popular region for holidaymakers year after year.
Speak with our Cruise1st specialists today to reserve your 2027 Caribbean Cruise and Stay experience and take advantage of early-booking upgrades and exclusive value packages.
Caribbean Cruise and Stay 2027