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Eastern Caribbean

Eastern Caribbean cruises focus on classic island destinations and easy sea days that pair well with larger ships. You typically visit ports such as St. Thomas, St. Maarten, and Puerto Rico, where beaches, shopping, and historical towns are close to the pier. These itineraries often include private islands, giving you a relaxed balance between onboard time and shore excursions. An Eastern Caribbean cruise is a strong choice if you enjoy sailing comfort, scenic coastlines, and a familiar introduction to cruises to the Caribbean. From large resort-style ships to luxury vessels to yachts, Caribbean cruises remain a versatile option year-round.

Eastern Caribbean Sailing Calendar

Month	Number of Itineraries	Number of Cruises	From Price
Sep 2026	18	18	$299 pp
Oct 2026	34	52	$382 pp
Nov 2026	75	96	$199 pp
Dec 2026	79	105	$359 pp
Jan 2027	76	105	$299 pp
Feb 2027	67	87	$309 pp
Mar 2027	59	86	$439 pp
Apr 2027	56	72	$354 pp
May 2027	39	56	$468 pp
Jun 2027	35	49	$667 pp
Jul 2027	33	58	$728 pp
Aug 2027	39	56	$538 pp
Sep 2027	29	43	$418 pp
Oct 2027	45	59	$420 pp
Nov 2027	65	82	$410 pp
Dec 2027	98	117	$421 pp
Jan 2028	99	120	$421 pp
Feb 2028	63	89	$442 pp
Mar 2028	65	82	$437 pp
Apr 2028	38	56	$649 pp
May 2028	7	15	$884 pp
Jun 2028	6	14	$1,184 pp
Jul 2028	6	17	$1,251 pp
Aug 2028	6	14	$841 pp
Sep 2028	6	17	$814 pp
Oct 2028	8	13	$834 pp
Nov 2028	10	11	$891 pp
Dec 2028	9	12	$3,799 pp
Jan 2029	8	12	$4,999 pp
Feb 2029	5	5	$4,299 pp
Mar 2029	2	2	$4,999 pp

Cruise Lines Sailing to Eastern 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.