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Active: Visits Gustavia, Saint Barthelemy Star Pride Clear all

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Cruise line	Line / Ship	Built	Stars	Departs	Nights	Ports	Sea days	From	To	Destination	Inside from pp	Inside	Oceanview	Balcony	Suite	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Oct 28, 2026	11	10	1	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $4,290 $390 / night Inside unavailable · least expensive available	—	$4,290	$7,040	$10,285	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 8, 2026	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $4,228 $302 / night Inside unavailable · least expensive available	—	$4,228	$6,160	$8,232	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 15, 2026	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $4,200 $300 / night Inside unavailable · least expensive available	—	$4,200	$6,412	$8,624	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 22, 2026	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $4,536 $324 / night Inside unavailable · least expensive available	—	$4,536	$7,168	$9,240	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 29, 2026	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $6,004 $428 / night Inside unavailable · least expensive available	—	$6,004	$8,132	$9,812	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Dec 6, 2026	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $5,220 $372 / night Inside unavailable · least expensive available	—	$5,220	$7,432	$8,804	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Dec 13, 2026	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $4,492 $320 / night Inside unavailable · least expensive available	—	$4,492	$7,264	$9,252	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Dec 20, 2026	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $5,612 $400 / night Inside unavailable · least expensive available	—	$5,612	$7,376	$12,892	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Dec 27, 2026	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $6,704 $478 / night Inside unavailable · least expensive available	—	$6,704	$7,824	$11,940	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Dec 27, 2026	7	7	0	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $3,780 $540 / night Inside unavailable · least expensive available	—	$3,780	$4,480	$6,090	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Jan 3, 2027	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $9,744 $696 / night Inside unavailable · least expensive available	—	—	$9,744	—	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Jan 10, 2027	7	7	0	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $5,215 $745 / night Inside unavailable · least expensive available	—	$5,215	$7,385	$11,340	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Oct 11, 2027	21	13	7	Montreal	San Juan, Puerto Rico	Caribbean	from $6,624 $315 / night Inside unavailable · least expensive available	—	$6,624	$10,300	$15,408	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Feb 21, 2028	21	17	3	Caldera, Costa Rica	San Juan, Puerto Rico	Central America	from $7,099 $338 / night Inside unavailable · least expensive available	—	$7,099	$11,523	$16,507	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Feb 28, 2028	14	11	2	Fuerte Amador, Panama City	San Juan, Puerto Rico	Panama Canal	from $4,620 $330 / night Inside unavailable · least expensive available	—	$4,620	$7,896	$11,228	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Mar 6, 2028	21	14	3	Oranjestad, Aruba	San Juan, Puerto Rico	Caribbean	from $5,880 $280 / night Inside unavailable · least expensive available	—	$5,880	$9,940	$14,952	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Mar 13, 2028	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $3,808 $272 / night Inside unavailable · least expensive available	—	$3,808	$5,684	$9,016	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Mar 20, 2028	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $3,808 $272 / night Inside unavailable · least expensive available	—	$3,808	$6,048	$9,352	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 1, 2027	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $3,808 $272 / night Inside unavailable · least expensive available	—	$3,808	$6,552	$9,856	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 8, 2027	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $3,808 $272 / night Inside unavailable · least expensive available	—	$3,808	$6,356	$9,660	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 15, 2027	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $3,808 $272 / night Inside unavailable · least expensive available	—	$3,808	$6,384	$9,716	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Mar 6, 2028	14	11	3	Oranjestad, Aruba	San Juan, Puerto Rico	Caribbean	from $4,830 $345 / night Inside unavailable · least expensive available	—	$4,830	$7,854	$11,214	Check prices

Prices are indicative, sourced from third-party data feeds, and not guaranteed — they may differ from the cruise line's current fare. Always confirm the final price directly with the cruise line or a travel agent before booking. How our pricing works