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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
Jun 2026 4 5 $745 pp
Jul 2026 10 11 $679 pp
Aug 2026 17 23 $399 pp
Sep 2026 21 23 $486 pp
Oct 2026 42 45 $539 pp
Nov 2026 96 107 $499 pp
Dec 2026 117 130 $578 pp
Jan 2027 109 131 $471 pp
Feb 2027 92 103 $477 pp
Mar 2027 79 89 $619 pp
Apr 2027 25 28 $209 pp
May 2027 6 12 $819 pp
Jun 2027 9 14 $745 pp
Jul 2027 8 16 $795 pp
Aug 2027 9 15 $649 pp
Sep 2027 10 16 $629 pp
Oct 2027 20 28 $629 pp
Nov 2027 74 81 $209 pp
Dec 2027 83 94 $554 pp
Jan 2028 77 95 $410 pp
Feb 2028 60 71 $574 pp
Mar 2028 55 60 $645 pp
Apr 2028 20 24 $645 pp
May 2028 8 17 $748 pp
Jun 2028 7 15 $878 pp
Jul 2028 9 18 $888 pp
Aug 2028 10 18 $699 pp
Sep 2028 10 18 $629 pp
Oct 2028 9 17 $658 pp
Nov 2028 8 10 $718 pp
Dec 2028 4 7 $3,624 pp
Jan 2029 3 5 $16,998 pp
Feb 2029 3 5 $15,498 pp
Mar 2029 1 2 $14,498 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
3 Itineraries • 3 Cruises
from $2,539
Signature Collection
Carnival Cruises cruises to Caribbean
Carnival Cruises
Contemporary Cruise Line
Very Large Ships • Up to 5,200 guests
8 Itineraries • 17 Cruises
from $847
Signature Collection
Celebrity Cruises cruises to Caribbean
Celebrity Cruises
Premium Cruise Line
Large Ships • Up to 3,200 guests
2 Itineraries • 2 Cruises
from $868
Signature Collection
Costa Cruises cruises to Caribbean
Costa Cruises
Contemporary Cruise Line
Very Large Ships • Up to 6,500 guests
22 Itineraries • 22 Cruises
from $906
Crystal Cruises cruises to Caribbean
Crystal Cruises
Luxury Cruise Line
Small Ships • Up to 740 guests
22 Itineraries • 22 Cruises
from $3,090
Signature Collection
Cunard Line cruises to Caribbean
Cunard Line
Upper Premium
Mid-Size to Large • Up to 3,000 guests
30 Itineraries • 35 Cruises
from $610
Signature Collection
Explora Journeys cruises to Caribbean
Explora Journeys
Luxury Cruise Line
Small Ships • Up to 920 guests
8 Itineraries • 8 Cruises
from $4,880
Signature Collection
Holland America Line cruises to Caribbean
Holland America Line
Premium Cruise Line
Mid-Size to Large • Up to 2,600 guests
62 Itineraries • 81 Cruises
from $608
Signature Collection
Margaritaville at Sea cruises to Caribbean
Margaritaville at Sea
Contemporary Cruise Line
Mid-Size to Large • Up to 2,400 guests
3 Itineraries • 4 Cruises
from $399
MSC Cruises cruises to Caribbean
MSC Cruises
Contemporary Cruise Line
Very Large Ships • Up to 6,700 guests
76 Itineraries • 306 Cruises
from $209
Norwegian Cruise Line cruises to Caribbean
Norwegian Cruise Line
Contemporary Cruise Line
Large Ships • Up to 4,000 guests
33 Itineraries • 82 Cruises
from $779
Signature Collection
Oceania Cruises cruises to Caribbean
Oceania Cruises
Luxury, Adults Only
Small - Mid-Size • 700 - 1,250 guests
10 Itineraries • 10 Cruises
from $5,449
Signature Collection
Ponant Cruises cruises to Caribbean
Ponant Cruises
Upper Premium
Very Small to Small • 32 - 264 guests
2 Itineraries • 2 Cruises
from $4,460
Signature Collection
Princess Cruises cruises to Caribbean
Princess Cruises
Premium Cruise Line
Mid-Size to Large • up to 4,300 guests
256 Itineraries • 418 Cruises
from $471
Signature Collection
Royal Caribbean Cruises cruises to Caribbean
Royal Caribbean Cruises
Contemporary Cruise Line
Very Large Ships • Up to 6,700 guests
1 Itineraries • 1 Cruises
from $1,228
Signature Collection
Seabourn Cruises cruises to Caribbean
Seabourn Cruises
Luxury & Expedition Cruises
Small Ships • 264 – 600 guests
24 Itineraries • 77 Cruises
from $3,219
Signature Collection
SeaDream Yacht Club cruises to Caribbean
SeaDream Yacht Club
Luxury / Yacht Cruises
Very Small Ships • Up to 112 guests
21 Itineraries • 26 Cruises
from $3,959
Signature Collection
Silversea Cruises cruises to Caribbean
Silversea Cruises
Luxury & Expedition Cruises
Small & Mid-Size • 100 – 728 guests
22 Itineraries • 22 Cruises
from $2,730
Signature Collection
Viking Oceans cruises to Caribbean
Viking Oceans
Upper Premium, Adults Only
Small Ships • Up to 998 guests
2 Itineraries • 6 Cruises
from $4,999
Signature Collection
Virgin Voyages cruises to Caribbean
Virgin Voyages
Contemporary, Adults Only
Large Ships • Up to 2,700 guests
76 Itineraries • 143 Cruises
from $410
Signature Collection
Windstar Cruises cruises to Caribbean
Windstar Cruises
Castual Luxury
Very Small to Small • 148 – 342 guests
43 Itineraries • 66 Cruises
from $1,826
Signature Collection

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