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View Cruise line Line / Ship Departs Nights From Inside from pp Check prices
Windstar Cruises Windstar CruisesStar Pride Oct 28, 2026 11 San Juan, Puerto Rico

from $4,290

$390 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Nov 8, 2026 14 San Juan, Puerto Rico

from $4,228

$302 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Nov 8, 2026 7 San Juan, Puerto Rico

from $2,695

$385 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Nov 15, 2026 14 San Juan, Puerto Rico

from $4,200

$300 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Nov 22, 2026 14 San Juan, Puerto Rico

from $4,536

$324 / night

Inside unavailable · least expensive available

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Silversea SilverseaSilver Shadow Dec 10, 2026 10 Miami, Florida

from $5,500

$550 / night

Inside unavailable · least expensive available

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Silversea SilverseaSilver Shadow Dec 20, 2026 14 San Juan

Call for price

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Silversea SilverseaSilver Shadow Dec 27, 2026 7 San Juan

from $7,700

$1,100 / night

Inside unavailable · least expensive available

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Silversea SilverseaSilver Spirit Dec 12, 2026 7 Bridgetown, Barbados

from $5,500

$785 / night

Inside unavailable · least expensive available

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Silversea SilverseaSilver Shadow Jan 20, 2027 10 Bridgetown, Barbados

from $8,250

$825 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesWind Surf Jan 23, 2027 14 Philipsburg, Sint Maarten

from $5,814

$415 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesWind Surf Jan 9, 2027 7 Philipsburg, Sint Maarten

from $3,675

$525 / night

Inside unavailable · least expensive available

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Silversea SilverseaSilver Shadow Feb 16, 2027 10 Bridgetown, Barbados

from $9,000

$900 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesWind Surf Feb 6, 2027 14 Philipsburg, Sint Maarten

from $6,962

$497 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesWind Surf Feb 13, 2027 14 Philipsburg, Sint Maarten

from $5,600

$400 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesWind Surf Feb 20, 2027 14 Philipsburg, Sint Maarten

from $5,404

$386 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesWind Surf Feb 27, 2027 14 Philipsburg, Sint Maarten

from $5,404

$386 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesWind Surf Mar 13, 2027 14 Philipsburg, Sint Maarten

from $4,480

$320 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesWind Surf Mar 20, 2027 7 Philipsburg, Sint Maarten

from $2,380

$340 / night

Inside unavailable · least expensive available

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Silversea SilverseaSilver Spirit Mar 11, 2028 7 Bridgetown, Barbados

from $4,700

$671 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Legend Jan 10, 2028 14 San Juan, Puerto Rico

from $4,498

$321 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Legend Jan 17, 2028 14 San Juan, Puerto Rico

from $3,808

$272 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Legend Jan 24, 2028 14 San Juan, Puerto Rico

from $3,808

$272 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Legend Jan 31, 2028 14 San Juan, Puerto Rico

from $3,808

$272 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Legend Feb 7, 2028 14 San Juan, Puerto Rico

from $4,498

$321 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Legend Feb 14, 2028 14 San Juan, Puerto Rico

from $3,808

$272 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Mar 6, 2028 21 Oranjestad, Aruba

from $5,880

$280 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Mar 13, 2028 14 San Juan, Puerto Rico

from $3,808

$272 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Mar 20, 2028 14 San Juan, Puerto Rico

from $3,808

$272 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Mar 27, 2028 23 San Juan, Puerto Rico

from $4,080

$177 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesWind Surf Dec 19, 2027 15 Philipsburg, Sint Maarten

from $4,776

$318 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Legend Dec 20, 2027 14 San Juan, Puerto Rico

from $3,808

$272 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Legend Dec 27, 2027 14 San Juan, Puerto Rico

from $3,808

$272 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesWind Surf Nov 20, 2027 15 Philipsburg, Sint Maarten

from $4,872

$324 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Nov 1, 2027 14 San Juan, Puerto Rico

from $3,808

$272 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Nov 8, 2027 14 San Juan, Puerto Rico

from $3,808

$272 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Nov 15, 2027 14 San Juan, Puerto Rico

from $3,808

$272 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Nov 22, 2027 21 San Juan, Puerto Rico

from $5,936

$282 / night

Inside unavailable · least expensive available

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Windstar Cruises Windstar CruisesStar Pride Nov 22, 2027 14 San Juan, Puerto Rico

from $3,808

$272 / night

Inside unavailable · least expensive available

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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