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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 29, 2026	14	11	2	San Juan, Puerto Rico	San Juan, Puerto Rico	Caribbean	from $6,188 $442 / night Inside unavailable · least expensive available	—	$6,188	$8,344	$9,464	Check prices
Silversea	SilverseaSilver Spirit	2009	5	Dec 12, 2026	7	7	0	Bridgetown, Barbados	Bridgetown, Barbados	Caribbean	from $5,500 $785 / night Inside unavailable · least expensive available	—	—	—	$5,500	Check prices
Silversea	SilverseaSilver Spirit	2009	5	Dec 27, 2026	8	7	1	Bridgetown, Barbados	Bridgetown, Barbados	Caribbean	from $6,700 $837 / night Inside unavailable · least expensive available	—	—	—	$6,700	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	$7,448	—	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 $5,348 $382 / night Inside unavailable · least expensive available	—	$5,348	$7,728	—	Check prices
Silversea	SilverseaSilver Spirit	2009	5	Jan 4, 2027	11	9	2	Bridgetown, Barbados	Bridgetown, Barbados	Caribbean	from $8,300 $754 / night Inside unavailable · least expensive available	—	—	—	$8,300	Check prices
Silversea	SilverseaSilver Ray	2024	5	Jan 5, 2027	11	7	4	Miami, Florida	Miami, Florida	Central America	from $11,170 $1,015 / night Inside unavailable · least expensive available	—	—	—	$11,170	Check prices
Silversea	SilverseaSilver Ray	2024	5	Jan 27, 2027	11	7	4	Miami, Florida	Miami, Florida	Caribbean	from $11,370 $1,033 / night Inside unavailable · least expensive available	—	—	—	$11,370	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	—	Check prices
Emerald Yacht Cruises	Emerald Yacht CruisesEmerald Azzurra	2021	4	Jan 16, 2027	14	11	0	Marigot, Saint Martin	Bridgetown, Barbados	Caribbean	from $24,780 $1,770 / night Inside unavailable · least expensive available	—	$24,780	—	$31,360	Check prices
Emerald Yacht Cruises	Emerald Yacht CruisesEmerald Sakara	2023	4	Jan 9, 2027	7	8	0	San Juan, Puerto Rico	St. Thomas (US Virgin Islands)	Caribbean	from $5,318 $759 / night Inside unavailable · least expensive available	—	—	—	$5,318	Check prices
Silversea	SilverseaSilver Ray	2024	5	Feb 26, 2027	12	11	2	Bridgetown, Barbados	Miami, Florida	Caribbean	from $10,900 $908 / night Inside unavailable · least expensive available	—	—	—	$10,900	Check prices
Silversea	SilverseaSilver Ray	2024	5	Feb 7, 2027	12	11	2	Miami, Florida	Bridgetown, Barbados	Central America	from $10,600 $883 / night Inside unavailable · least expensive available	—	—	—	$10,600	Check prices
Emerald Yacht Cruises	Emerald Yacht CruisesEmerald Azzurra	2021	4	Feb 13, 2027	14	11	0	Marigot, Saint Martin	Bridgetown, Barbados	Caribbean	from $25,380 $1,812 / night Inside unavailable · least expensive available	—	$25,380	—	$31,960	Check prices
Emerald Yacht Cruises	Emerald Yacht CruisesEmerald Azzurra	2021	4	Mar 13, 2027	14	11	0	Marigot, Saint Martin	Bridgetown, Barbados	Caribbean	from $32,560 $2,325 / night Inside unavailable · least expensive available	—	—	—	$32,560	Check prices
Emerald Yacht Cruises	Emerald Yacht CruisesEmerald Sakara	2023	4	Mar 13, 2027	7	8	0	St. Thomas (US Virgin Islands)	San Juan, Puerto Rico	Caribbean	from $12,290 $1,755 / night Inside unavailable · least expensive available	—	$12,290	—	$15,580	Check prices
Silversea	SilverseaSilver Nova	2023	5	Dec 18, 2027	11	6	5	Miami, Florida	Miami, Florida	Caribbean	from $9,400 $854 / night Inside unavailable · least expensive available	—	—	—	$9,400	Check prices
Emerald Yacht Cruises	Emerald Yacht CruisesEmerald Sakara	2023	4	Dec 18, 2027	9	9	0	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $5,545 $616 / night Inside unavailable · least expensive available	—	$5,545	—	$7,795	Check prices
Emerald Yacht Cruises	Emerald Yacht CruisesEmerald Sakara	2023	4	Dec 27, 2027	9	9	0	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $6,045 $671 / night Inside unavailable · least expensive available	—	$6,045	—	$8,295	Check prices
Emerald Yacht Cruises	Emerald Yacht CruisesEmerald Sakara	2023	4	Feb 12, 2028	14	11	0	Marigot, Saint Martin	Bridgetown, Barbados	Caribbean	from $26,680 $1,905 / night Inside unavailable · least expensive available	—	$26,680	—	$33,680	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Nov 20, 2027	15	13	0	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $4,872 $324 / night Inside unavailable · least expensive available	—	$4,872	—	$6,312	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Nov 20, 2027	8	8	0	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $3,080 $385 / night Inside unavailable · least expensive available	—	$3,080	—	$4,040	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