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Prices per person · incl. taxes & fees.
| 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