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Active: Visits Soper's Hole, Tortola, British Wind Surf Clear all

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Cruise line	Line / Ship	Built	Stars	Departs	Nights	Ports	From	To	Destination	Inside from pp	Inside	Oceanview	Balcony	Suite	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Jan 23, 2027	14	12	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $5,814 $415 / night Inside unavailable · least expensive available	—	$5,814	—	$6,850	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Jan 16, 2027	7	7	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $3,395 $485 / night Inside unavailable · least expensive available	—	$3,395	—	$4,235	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Feb 6, 2027	14	12	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $6,962 $497 / night Inside unavailable · least expensive available	—	$6,962	—	$8,306	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Feb 13, 2027	14	12	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $5,740 $410 / night Inside unavailable · least expensive available	—	$5,740	—	$7,084	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Feb 20, 2027	14	12	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $5,404 $386 / night Inside unavailable · least expensive available	—	$5,404	—	$6,748	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Feb 27, 2027	14	12	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $5,404 $386 / night Inside unavailable · least expensive available	—	$5,404	—	$6,748	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Mar 6, 2027	14	12	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $5,628 $402 / night Inside unavailable · least expensive available	—	$5,628	—	$6,692	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Mar 13, 2027	14	12	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $4,760 $340 / night Inside unavailable · least expensive available	—	$4,760	—	$9,044	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Mar 13, 2027	7	7	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $3,395 $485 / night Inside unavailable · least expensive available	—	$3,395	—	$4,060	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Feb 13, 2028	14	12	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $3,836 $274 / night Inside unavailable · least expensive available	—	$3,836	—	$5,180	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Feb 20, 2028	14	12	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $3,864 $276 / night Inside unavailable · least expensive available	—	$3,864	—	$5,208	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Dec 19, 2027	15	12	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $4,776 $318 / night Inside unavailable · least expensive available	—	$4,776	—	$6,216	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Nov 20, 2027	15	13	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	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $3,080 $385 / night Inside unavailable · least expensive available	—	$3,080	—	$4,040	Check prices
Windstar Cruises	Windstar CruisesWind Surf	1989	4	Feb 13, 2028	7	7	Philipsburg, Sint Maarten	Philipsburg, Sint Maarten	Caribbean	from $2,380 $340 / night Inside unavailable · least expensive available	—	$2,380	—	$3,220	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