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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	Nov 8, 2026	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $5,488 $392 / night Inside unavailable · least expensive available	—	$5,488	$6,888	$8,036	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 $2,380 $340 / night Inside unavailable · least expensive available	—	$2,380	$3,500	$4,970	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 $4,340 $310 / night Inside unavailable · least expensive available	—	$4,340	$6,608	$7,980	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 15, 2026	7	7	0	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $2,800 $400 / night Inside unavailable · least expensive available	—	$2,800	$4,340	$4,865	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 22, 2026	7	5	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $1,987 $283 / night Inside unavailable · least expensive available	—	$1,987	$3,191	$5,040	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 29, 2026	7	7	0	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $4,025 $575 / night Inside unavailable · least expensive available	—	$4,025	$5,425	$5,915	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 $5,712 $408 / night Inside unavailable · least expensive available	—	$5,712	$7,532	$8,960	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 $3,955 $565 / night Inside unavailable · least expensive available	—	$3,955	$5,320	$5,845	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 $4,844 $346 / night Inside unavailable · least expensive available	—	$4,844	$6,776	$9,156	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Dec 13, 2026	7	7	0	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $3,150 $450 / night Inside unavailable · least expensive available	—	$3,150	$4,270	$5,740	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 $7,980 $570 / night Inside unavailable · least expensive available	—	—	$7,980	—	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 $6,776 $484 / night Inside unavailable · least expensive available	—	$6,776	$8,540	—	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Dec 20, 2026	7	5	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $3,185 $455 / night Inside unavailable · least expensive available	—	$3,185	$4,480	$5,670	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 $4,795 $685 / night Inside unavailable · least expensive available	—	$4,795	$5,495	—	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 $6,944 $496 / night Inside unavailable · least expensive available	—	$6,944	$9,548	$16,464	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	$4,620	$7,840	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 $4,865 $695 / night Inside unavailable · least expensive available	—	$4,865	$6,685	$11,760	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Jan 3, 2028	7	7	1	Colon, Panama	Caldera, Costa Rica	Panama Canal	from $2,520 $360 / night Inside unavailable · least expensive available	—	$2,520	$4,480	$6,580	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Jan 10, 2028	7	7	1	Caldera, Costa Rica	Colon, Panama	Central America	from $2,660 $380 / night Inside unavailable · least expensive available	—	$2,660	$4,690	$6,790	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Jan 17, 2028	7	7	1	Colon, Panama	Caldera, Costa Rica	Central America	from $2,520 $360 / night Inside unavailable · least expensive available	—	$2,520	$4,410	$6,510	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Oct 22, 2027	17	10	4	Boston, USA	San Juan, Puerto Rico	Caribbean	from $4,304 $253 / night Inside unavailable · least expensive available	—	$4,304	$7,644	$11,416	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Feb 14, 2028	7	7	1	Colon, Panama	Caldera, Costa Rica	Panama Canal	from $2,765 $395 / night Inside unavailable · least expensive available	—	$2,765	$4,445	$6,545	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Feb 28, 2028	14	11	2	Fuerte Amador, Panama City	San Juan, Puerto Rico	Caribbean	from $3,892 $278 / night Inside unavailable · least expensive available	—	$3,892	$7,280	$10,612	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Mar 6, 2028	21	14	3	Oranjestad, Aruba	San Juan, Puerto Rico	Caribbean	from $5,992 $285 / night Inside unavailable · least expensive available	—	$5,992	$10,108	$15,148	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	$9,380	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Dec 6, 2027	7	7	1	Colon, Panama	Caldera, Costa Rica	Panama Canal	from $2,730 $390 / night Inside unavailable · least expensive available	—	$2,730	$4,200	$6,300	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Dec 27, 2027	7	7	1	Caldera, Costa Rica	Colon, Panama	Central America	from $2,905 $415 / night Inside unavailable · least expensive available	—	$2,905	$4,550	$6,650	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	$7,112	$10,444	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	$6,720	$10,080	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	$6,860	$10,220	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 $5,992 $285 / night Inside unavailable · least expensive available	—	$5,992	$10,248	$15,288	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 $4,088 $292 / night Inside unavailable · least expensive available	—	$4,088	$6,832	$10,192	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Nov 1, 2027	7	7	0	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $2,380 $340 / night Inside unavailable · least expensive available	—	$2,380	$4,795	$6,860	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	$6,888	$10,248	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Oct 22, 2027	10	6	4	Boston, USA	San Juan, Puerto Rico	Caribbean	from $4,000 $400 / night Inside unavailable · least expensive available	—	$4,000	$6,350	$9,350	Check prices
Windstar Cruises	Windstar CruisesStar Pride	1988	4	Feb 28, 2028	7	5	1	Fuerte Amador, Panama City	Oranjestad, Aruba	Central America	from $2,415 $345 / night Inside unavailable · least expensive available	—	$2,415	$3,850	$5,915	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

Lowest fares with no residency, age, or service requirement — verify eligibility at booking. How our pricing works