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Caribbean Cruises

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Caribbean Cruises

Caribbean cruises introduce you to one of the world’s most popular cruising regions, offering a wide range of itineraries, ship styles, and travel lengths. You can choose from quick escapes or longer voyages that visit multiple island groups on a single sailing. A Caribbean cruise is known for warm weather, turquoise waters, and easygoing days balanced with cultural stops and beach-focused ports. Cruises to the Caribbean appeal to first-time cruisers because of their simplicity, while repeat travelers value the ability to explore different islands on each trip. From large resort-style ships to luxury vessels to yachts, Caribbean cruises remain a versatile option year-round.

Caribbean Cruises Sailing Calendar

Month Number of Itineraries Number of Cruises From Price
Mar 2026 63 65 $521 pp
Apr 2026 20 23 $518 pp
May 2026 21 27 $349 pp
Jun 2026 11 14 $689 pp
Jul 2026 13 18 $647 pp
Aug 2026 12 16 $564 pp
Sep 2026 12 15 $413 pp
Oct 2026 40 44 $509 pp
Nov 2026 86 96 $520 pp
Dec 2026 101 117 $664 pp
Jan 2027 83 97 $564 pp
Feb 2027 58 67 $470 pp
Mar 2027 45 53 $664 pp
Apr 2027 14 14 $269 pp
May 2027 2 3 $789 pp
Jun 2027 6 6 $749 pp
Jul 2027 4 6 $808 pp
Aug 2027 9 11 $729 pp
Sep 2027 9 10 $629 pp
Oct 2027 8 9 $629 pp
Nov 2027 37 41 $219 pp
Dec 2027 41 48 $724 pp
Jan 2028 33 41 $649 pp
Feb 2028 23 28 $859 pp
Mar 2028 28 32 $829 pp
Apr 2028 6 6 $859 pp

Cruise Lines Sailing to Caribbean

The cruise lines sail to this destination, spanning a variety of cruise line categories and ship sizes. For each cruise line, you’ll find the number of unique itineraries and sailing dates available.  Signature Preferred Partners may offer added value, exclusive perks, or additional savings.

Signature Collection

Cruise Lines with the SC icon are part of the Signature Collection and often include added value, exclusive perks or additional savings. 

Azamara Cruises cruises to Caribbean
Azamara Cruises
Upper Premium
Small Ships • Up to 700 guests
12 Itineraries • 12 Cruises
from $1,549
Signature Collection
Carnival Cruises cruises to Caribbean
Carnival Cruises
Contemporary Cruise Line
Very Large Ships • Up to 5,200 guests
9 Itineraries • 23 Cruises
from $794
Signature Collection
Celebrity Cruises cruises to Caribbean
Celebrity Cruises
Premium Cruise Line
Large Ships • Up to 3,200 guests
1 Itineraries • 1 Cruises
from $728
Signature Collection
Costa Cruises cruises to Caribbean
Costa Cruises
Contemporary Cruise Line
Very Large Ships • Up to 6,500 guests
39 Itineraries • 44 Cruises
from $521
Crystal Cruises cruises to Caribbean
Crystal Cruises
Luxury Cruise Line
Small Ships • Up to 740 guests
14 Itineraries • 14 Cruises
from $3,000
Signature Collection
Cunard Line cruises to Caribbean
Cunard Line
Upper Premium
Mid-Size to Large • Up to 3,000 guests
11 Itineraries • 14 Cruises
from $830
Signature Collection
Emerald Cruises cruises to Caribbean
Emerald Cruises
Rivers & Yacht Cruises
Very Small Ships • 84 to 180 gurests
1 Itineraries • 1 Cruises
from $5,810
Explora Journeys cruises to Caribbean
Explora Journeys
Luxury Cruise Line
Small Ships • Up to 920 guests
20 Itineraries • 20 Cruises
from $4,025
Signature Collection
Holland America Line cruises to Caribbean
Holland America Line
Premium Cruise Line
Mid-Size to Large • Up to 2,600 guests
66 Itineraries • 76 Cruises
from $546
Signature Collection
Margaritaville at Sea cruises to Caribbean
Margaritaville at Sea
Contemporary Cruise Line
Mid-Size to Large • Up to 2,400 guests
1 Itineraries • 2 Cruises
from $649
MSC Cruises cruises to Caribbean
MSC Cruises
Contemporary Cruise Line
Very Large Ships • Up to 6,700 guests
96 Itineraries • 167 Cruises
from $219
Norwegian Cruise Line cruises to Caribbean
Norwegian Cruise Line
Contemporary Cruise Line
Large Ships • Up to 4,000 guests
48 Itineraries • 140 Cruises
from $759
Signature Collection
Oceania Cruises cruises to Caribbean
Oceania Cruises
Luxury, Adults Only
Small - Mid-Size • 700 - 1,250 guests
19 Itineraries • 19 Cruises
from $3,649
Signature Collection
Ponant Cruises cruises to Caribbean
Ponant Cruises
Upper Premium
Very Small to Small • 32 - 264 guests
1 Itineraries • 1 Cruises
from $4,350
Signature Collection
Princess Cruises cruises to Caribbean
Princess Cruises
Premium Cruise Line
Mid-Size to Large • up to 4,300 guests
101 Itineraries • 143 Cruises
from $413
Signature Collection
Royal Caribbean Cruises cruises to Caribbean
Royal Caribbean Cruises
Contemporary Cruise Line
Very Large Ships • Up to 6,700 guests
2 Itineraries • 2 Cruises
from $349
Signature Collection
Scenic Cruises cruises to Caribbean
Scenic Cruises
Rivers & Yacht Cruises
Very Small Ships • 68 - 169 guests
1 Itineraries • 1 Cruises
from $8,285
Sea Cloud Cruises cruises to Caribbean
Sea Cloud Cruises
Specialty / Adventure
Small Sailing Ships • 64 – 136 guests
3 Itineraries • 3 Cruises
from $6,490
Signature Collection
Seabourn Cruises cruises to Caribbean
Seabourn Cruises
Luxury & Expedition Cruises
Small Ships • 264 – 600 guests
20 Itineraries • 20 Cruises
from $3,974
Signature Collection
SeaDream Yacht Club cruises to Caribbean
SeaDream Yacht Club
Luxury / Yacht Cruises
Very Small Ships • Up to 112 guests
1 Itineraries • 1 Cruises
from $4,299
Signature Collection
Silversea Cruises cruises to Caribbean
Silversea Cruises
Luxury & Expedition Cruises
Small & Mid-Size • 100 – 728 guests
42 Itineraries • 43 Cruises
from $2,880
Signature Collection
Viking Oceans cruises to Caribbean
Viking Oceans
Upper Premium, Adults Only
Small Ships • Up to 998 guests
2 Itineraries • 8 Cruises
from $5,099
Signature Collection
Virgin Voyages cruises to Caribbean
Virgin Voyages
Contemporary, Adults Only
Large Ships • Up to 2,700 guests
42 Itineraries • 82 Cruises
from $520
Signature Collection
Windstar Cruises cruises to Caribbean
Windstar Cruises
Castual Luxury
Very Small to Small • 148 – 342 guests
30 Itineraries • 70 Cruises
from $2,166
Signature Collection

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