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Active: Visits San Juan, Puerto Rico 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 9, 2026	19	12	7	Montreal	San Juan, Puerto Rico	North America	from $6,560 $345 / night Inside unavailable · least expensive available	—	$6,560	$12,216	—	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Oct 20, 2026	8	4	4	Boston, USA	San Juan, Puerto Rico	North America	from $2,920 $365 / night Inside unavailable · least expensive available	—	$2,920	$5,040	$7,960	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 8, 2026	7	5	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $2,695 $385 / night Inside unavailable · least expensive available	—	$2,695	$4,060	$6,125	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 $4,928 $352 / night Inside unavailable · least expensive available	—	$4,928	$7,084	$8,400	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Dec 6, 2026	7	5	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $3,290 $470 / night Inside unavailable · least expensive available	—	$3,290	$4,095	$5,320	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 $4,900 $350 / night Inside unavailable · least expensive available	—	$4,900	$7,056	—	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 $5,432 $388 / night Inside unavailable · least expensive available	—	$5,432	$7,280	—	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 $3,745 $535 / night Inside unavailable · least expensive available	—	$3,745	$5,075	—	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 3, 2027	7	5	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $2,940 $420 / night Inside unavailable · least expensive available	—	$2,940	$4,585	$7,980	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	Apr 3, 2028	16	4	13	San Juan, Puerto Rico	Amsterdam	Caribbean	from $2,720 $170 / night Inside unavailable · least expensive available	—	$2,720	$4,000	$8,720	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	Mar 27, 2028	23	8	15	San Juan, Puerto Rico	Amsterdam	Caribbean	from $4,080 $177 / night Inside unavailable · least expensive available	—	$4,080	$6,448	$11,876	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	Nov 22, 2027	21	15	4	San Juan, Puerto Rico	Caldera, Costa Rica	Central America	from $5,936 $282 / night Inside unavailable · least expensive available	—	$5,936	$9,688	$14,700	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 29, 2027	14	11	2	San Juan, Puerto Rico	Caldera, Costa Rica	Central America	from $4,032 $288 / night Inside unavailable · least expensive available	—	$4,032	$6,496	$9,828	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 22, 2027	14	10	3	San Juan, Puerto Rico	Colon, Panama	Caribbean	from $3,808 $272 / night Inside unavailable · least expensive available	—	$3,808	$6,440	$9,800	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