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Prices per person · incl. taxes & fees.
Charting 165 priced sailings; 9 matching sailings had no fare
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| View | Sailing | Departs | Route | Inside from pp | Price drop | ||||||||||||||
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| Costa Rica & Panama Canal - Colon to Puerto Caldera Wind Star · Windstar Cruises | Jan 31, 20278 nights | from |
from $4,650 $581 / night Inside unavailable · least expensive available ↓ 5% |
↓ 5% Oceanview | |||||||||||||||
| Barcelona to Bridgetown Wind Star · Windstar Cruises | Oct 31, 202624 nights | from |
Call for price |
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| San Juan to San Juan Star Pride · Windstar Cruises | Oct 28, 202611 nights | from |
from $5,118 $465 / night Inside unavailable · least expensive available |
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| Lisbon to Colón Wind Star · Windstar Cruises | Nov 10, 202614 nights | from |
from $3,596 $256 / night Inside unavailable · least expensive available |
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| Lisbon to Bridgetown Wind Star · Windstar Cruises | Nov 10, 202625 nights | from |
Call for price |
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| Colombian & Southern Caribbean Coastlines - Bridgetown to Colón Wind Star · Windstar Cruises | Nov 24, 202611 nights | from |
from $4,761 $432 / night Inside unavailable · least expensive available |
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| Bridgetown to Puerto Caldera Wind Star · Windstar Cruises | Nov 24, 202618 nights | from |
from $8,591 $477 / night Inside unavailable · least expensive available |
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| San Juan to San Juan Star Pride · Windstar Cruises | Nov 8, 202614 nights | from |
Call for price |
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| San Juan to San Juan Star Pride · Windstar Cruises | Nov 8, 20267 nights | from |
from $3,181 $454 / night Inside unavailable · least expensive available |
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| San Juan to San Juan Star Pride · Windstar Cruises | Nov 15, 202614 nights | from |
Call for price |
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| San Juan to San Juan Star Pride · Windstar Cruises | Nov 15, 20267 nights | from |
Call for price |
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| San Juan to San Juan Star Pride · Windstar Cruises | Nov 22, 202614 nights | from |
from $7,164 $511 / night Inside unavailable · least expensive available |
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| San Juan to San Juan Star Pride · Windstar Cruises | Nov 22, 20267 nights | from |
from $2,866 $409 / night Inside unavailable · least expensive available |
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| San Juan to San Juan Star Pride · Windstar Cruises | Nov 29, 202614 nights | from |
from $7,234 $516 / night Inside unavailable · least expensive available |
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| San Juan to San Juan Star Pride · Windstar Cruises | Nov 29, 20267 nights | from |
from $3,528 $504 / night Inside unavailable · least expensive available |
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| Jewels of The Windward Islands - Bridgetown to Bridgetown Star Legend · Windstar Cruises | Nov 27, 20267 nights | from |
from $2,699 $385 / night Inside unavailable · least expensive available |
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| Captivating Caribbean - Bridgetown to Oranjestad Star Legend · Windstar Cruises | Nov 27, 202615 nights | from |
from $5,459 $363 / night Inside unavailable · least expensive available |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Dec 19, 202614 nights | from |
from $7,680 $548 / night Inside unavailable · least expensive available |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Dec 26, 202614 nights | from |
from $6,770 $483 / night Inside unavailable · least expensive available |
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| Beach Fun & Sun: A Remote Caribbean Getaway - Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Dec 19, 20267 nights | from |
from $3,638 $519 / night Inside unavailable · least expensive available |
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| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Dec 26, 20267 nights | from |
from $4,392 $627 / night Inside unavailable · least expensive available |
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| Colón to Puerto Caldera Wind Star · Windstar Cruises | Dec 5, 20267 nights | from |
from $4,185 $597 / night Inside unavailable · least expensive available |
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| Colón to Puerto Caldera Wind Star · Windstar Cruises | Dec 19, 20267 nights | from |
from $4,010 $572 / night Inside unavailable · least expensive available |
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| Costa Rica & Panama Canal -Puerto Caldera to Colón Wind Star · Windstar Cruises | Dec 26, 20267 nights | from |
Call for price |
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| Costa Rica & Panama Canal -Puerto Caldera to Colón Wind Star · Windstar Cruises | Dec 12, 20267 nights | from |
from $3,520 $502 / night Inside unavailable · least expensive available |
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| San Juan to San Juan Star Pride · Windstar Cruises | Dec 6, 202614 nights | from |
from $5,904 $421 / night Inside unavailable · least expensive available ↓ 21% |
↓ 21% Oceanview | |||||||||||||||
| San Juan to San Juan Star Pride · Windstar Cruises | Dec 6, 20267 nights | from |
from $3,076 $439 / night Inside unavailable · least expensive available |
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| San Juan to San Juan Star Pride · Windstar Cruises | Dec 13, 202614 nights | from |
from $6,604 $471 / night Inside unavailable · least expensive available |
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| San Juan to San Juan Star Pride · Windstar Cruises | Dec 13, 20267 nights | from |
from $2,863 $409 / night Inside unavailable · least expensive available |
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| San Juan to San Juan Star Pride · Windstar Cruises | Dec 20, 202614 nights | from |
Call for price |
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| San Juan to San Juan Star Pride · Windstar Cruises | Dec 27, 202614 nights | from |
from $8,424 $601 / night Inside unavailable · least expensive available |
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| San Juan to San Juan Star Pride · Windstar Cruises | Dec 20, 20267 nights | from |
from $3,671 $524 / night Inside unavailable · least expensive available |
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| San Juan to San Juan Star Pride · Windstar Cruises | Dec 27, 20267 nights | from |
from $5,278 $754 / night Inside unavailable · least expensive available |
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| Windward Ways & Tobago Cays - Bridgetown to Oranjestad Star Legend · Windstar Cruises | Dec 4, 20268 nights | from |
from $3,060 $382 / night Inside unavailable · least expensive available ↓ 8% |
↓ 8% Balcony | |||||||||||||||
| Emeralds Of The Southern Caribbean - Bridgetown to Balboa Star Legend · Windstar Cruises | Dec 4, 202616 nights | from |
from $5,742 $358 / night Inside unavailable · least expensive available |
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| Panama Canal, Cartagena, San Blas Islands Star Legend · Windstar Cruises | Dec 12, 20268 nights | from |
from $3,246 $405 / night Inside unavailable · least expensive available |
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| Naturally Costa Rica - Balboa to Puerto Caldera Star Legend · Windstar Cruises | Dec 20, 20268 nights | from |
from $2,942 $367 / night Inside unavailable · least expensive available ↓ 10% |
↓ 10% Suite | |||||||||||||||
| Oranjestad to Puerto Caldera Star Legend · Windstar Cruises | Dec 12, 202616 nights | from |
from $6,188 $386 / night Inside unavailable · least expensive available |
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| Puerto Caldera to Colón Star Legend · Windstar Cruises | Dec 28, 20268 nights | from |
from $3,438 $429 / night Inside unavailable · least expensive available |
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| Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Jan 30, 20277 nights | from |
from $3,428 $489 / night Inside unavailable · least expensive available |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Jan 2, 202714 nights | from |
from $5,440 $388 / night Inside unavailable · least expensive available |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Jan 9, 202714 nights | from |
from $6,210 $443 / night Inside unavailable · least expensive available |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Jan 16, 202714 nights | from |
from $8,170 $583 / night Inside unavailable · least expensive available |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Jan 23, 202714 nights | from |
from $8,100 $578 / night Inside unavailable · least expensive available |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Jan 30, 202714 nights | from |
from $6,350 $453 / night Inside unavailable · least expensive available ↓ 16% |
↓ 16% Suite | |||||||||||||||
| Philipsburg, St.Marteen to Philipsburg, St.Marteen Wind Surf · Windstar Cruises | Jan 2, 20277 nights | from |
from $2,728 $389 / night Inside unavailable · least expensive available ↓ 21% |
↓ 21% Oceanview | |||||||||||||||
| Beach Fun & Sun: A Remote Caribbean Getaway - Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Jan 16, 20277 nights | from |
from $3,428 $489 / night Inside unavailable · least expensive available |
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| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Jan 9, 20277 nights | from |
from $2,922 $417 / night Inside unavailable · least expensive available |
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| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten Wind Surf · Windstar Cruises | Jan 23, 20277 nights | from |
from $4,672 $667 / night Inside unavailable · least expensive available |
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| Colón to Puerto Caldera Wind Star · Windstar Cruises | Jan 2, 20277 nights | from |
from $3,205 $457 / 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
Lowest fares with no residency, age, or service requirement — verify eligibility at booking. How our pricing works
