Home » Eastern Caribbean Cruises

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	24	24	$381 pp
Apr 2026	38	49	$459 pp
May 2026	37	53	$468 pp
Jun 2026	36	42	$579 pp
Jul 2026	27	38	$548 pp
Aug 2026	37	49	$320 pp
Sep 2026	28	37	$289 pp
Oct 2026	31	46	$304 pp
Nov 2026	54	72	$256 pp
Dec 2026	59	76	$269 pp
Jan 2027	50	75	$354 pp
Feb 2027	43	60	$399 pp
Mar 2027	40	60	$514 pp
Apr 2027	39	52	$454 pp
May 2027	40	51	$484 pp
Jun 2027	30	43	$724 pp
Jul 2027	27	45	$724 pp
Aug 2027	30	41	$544 pp
Sep 2027	23	35	$424 pp
Oct 2027	29	42	$424 pp
Nov 2027	35	45	$374 pp
Dec 2027	44	58	$429 pp
Jan 2028	43	54	$429 pp
Feb 2028	23	37	$449 pp
Mar 2028	27	45	$387 pp
Apr 2028	16	22	$387 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.