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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
Mar 2026	23	23	$488 pp
Apr 2026	33	39	$469 pp
May 2026	28	39	$488 pp
Jun 2026	21	26	$588 pp
Jul 2026	19	27	$611 pp
Aug 2026	30	39	$370 pp
Sep 2026	23	29	$348 pp
Oct 2026	27	39	$294 pp
Nov 2026	36	45	$349 pp
Dec 2026	44	57	$269 pp
Jan 2027	33	49	$334 pp
Feb 2027	30	40	$398 pp
Mar 2027	20	32	$514 pp
Apr 2027	28	35	$454 pp
May 2027	26	31	$484 pp
Jun 2027	19	26	$724 pp
Jul 2027	22	33	$724 pp
Aug 2027	20	30	$544 pp
Sep 2027	16	22	$424 pp
Oct 2027	25	32	$424 pp
Nov 2027	24	32	$384 pp
Dec 2027	32	41	$429 pp
Jan 2028	30	36	$429 pp
Feb 2028	21	32	$479 pp
Mar 2028	23	32	$437 pp
Apr 2028	7	11	$694 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.