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Prices per person · incl. taxes & fees.
| View | Cruise line | Line / Ship | Built | Stars | Departs | Nights | Ports | Sea days | From | To | Destination | Inside from pp | Inside | Oceanview | Balcony | Suite |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Oct 19, 2026 | 70 | 39 | 28 | Istanbul | Caldera, Costa Rica | Mediterranean |
from $35,650 $509 / night Inside unavailable · least expensive available |
— | — | $35,650 | — | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Nov 8, 2026 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $6,032 $430 / night Inside unavailable · least expensive available |
— | $6,032 | $7,376 | $10,036 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Nov 8, 2026 | 7 | 5 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $2,695 $385 / night Inside unavailable · least expensive available |
— | $2,695 | $4,060 | $6,125 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Nov 15, 2026 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $5,528 $394 / night Inside unavailable · least expensive available |
— | $5,528 | $7,348 | $10,036 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Nov 22, 2026 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $5,360 $382 / night Inside unavailable · least expensive available |
— | $5,360 | $8,076 | $10,456 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Nov 29, 2026 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,872 $348 / night Inside unavailable · least expensive available |
— | $4,872 | $6,496 | $8,876 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Nov 27, 2026 | 7 | 7 | 1 | Bridgetown, Barbados | Bridgetown, Barbados | Caribbean |
from $2,380 $340 / night Inside unavailable · least expensive available |
— | $2,380 | $3,535 | $5,635 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Nov 27, 2026 | 15 | 10 | 3 | Bridgetown, Barbados | Oranjestad, Aruba | Caribbean |
from $4,952 $330 / night Inside unavailable · least expensive available |
— | $4,952 | $6,880 | $12,748 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Dec 6, 2026 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $6,172 $440 / night Inside unavailable · least expensive available |
— | $6,172 | $7,432 | $8,804 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Dec 6, 2026 | 7 | 5 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $2,905 $415 / night Inside unavailable · least expensive available |
— | $2,905 | $3,395 | $4,305 | |
| 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 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Dec 20, 2026 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $5,612 $400 / night Inside unavailable · least expensive available |
— | $5,612 | $7,376 | $12,892 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Dec 27, 2026 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $6,704 $478 / night Inside unavailable · least expensive available |
— | $6,704 | $7,824 | $11,940 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Dec 4, 2026 | 8 | 8 | 2 | Bridgetown, Barbados | Oranjestad, Aruba | Caribbean |
from $2,680 $335 / night Inside unavailable · least expensive available |
— | $2,680 | $4,240 | $6,600 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Dec 4, 2026 | 16 | 12 | 4 | Bridgetown, Barbados | Fuerte Amador, Panama City | Panama Canal |
from $5,997 $374 / night Inside unavailable · least expensive available |
— | $5,997 | $8,173 | $11,277 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Jan 3, 2027 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $10,316 $736 / night Inside unavailable · least expensive available |
— | — | $10,316 | — | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Jan 3, 2027 | 7 | 5 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $3,745 $535 / night Inside unavailable · least expensive available |
— | $3,745 | $4,445 | $7,980 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Feb 16, 2027 | 14 | 12 | 3 | Fuerte Amador, Panama City | Bridgetown, Barbados | Panama Canal |
from $7,904 $564 / night Inside unavailable · least expensive available |
— | $7,904 | — | — | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Jan 17, 2028 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,498 $321 / night Inside unavailable · least expensive available |
— | $4,498 | $6,878 | $10,210 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Jan 24, 2028 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,498 $321 / night Inside unavailable · least expensive available |
— | $4,498 | $6,906 | $10,266 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Jan 31, 2028 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,498 $321 / night Inside unavailable · least expensive available |
— | $4,498 | $6,682 | $10,042 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Feb 14, 2028 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,498 $321 / night Inside unavailable · least expensive available |
— | $4,498 | $6,878 | $10,210 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Mar 6, 2028 | 21 | 14 | 3 | Oranjestad, Aruba | San Juan, Puerto Rico | Caribbean |
from $7,093 $337 / night Inside unavailable · least expensive available |
— | $7,093 | $11,349 | $16,361 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Mar 13, 2028 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,498 $321 / night Inside unavailable · least expensive available |
— | $4,498 | $7,046 | $10,378 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Mar 20, 2028 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,498 $321 / night Inside unavailable · least expensive available |
— | $4,498 | $7,018 | $10,322 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Mar 27, 2028 | 23 | 8 | 15 | San Juan, Puerto Rico | Amsterdam | Caribbean |
from $4,648 $202 / night Inside unavailable · least expensive available |
— | $4,648 | $6,960 | $10,020 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Dec 20, 2027 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,492 $320 / night Inside unavailable · least expensive available |
— | $4,492 | $6,872 | $10,232 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Dec 27, 2027 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,495 $321 / night Inside unavailable · least expensive available |
— | $4,495 | $6,903 | $10,235 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Nov 1, 2027 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,492 $320 / night Inside unavailable · least expensive available |
— | $4,492 | $7,124 | $10,428 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Nov 8, 2027 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,492 $320 / night Inside unavailable · least expensive available |
— | $4,492 | $6,900 | $10,204 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Nov 15, 2027 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,492 $320 / night Inside unavailable · least expensive available |
— | $4,492 | $7,012 | $10,344 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Nov 22, 2027 | 21 | 15 | 4 | San Juan, Puerto Rico | Caldera, Costa Rica | Central America |
from $6,779 $322 / night Inside unavailable · least expensive available |
— | $6,779 | $10,503 | $15,515 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Feb 22, 2027 | 8 | 8 | 2 | Oranjestad, Aruba | Bridgetown, Barbados | Caribbean |
from $6,600 $825 / night Inside unavailable · least expensive available |
— | $6,600 | $7,640 | — | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Nov 12, 2026 | 22 | 11 | 12 | Malaga | Bridgetown, Barbados | Northern Europe |
from $5,767 $262 / night Inside unavailable · least expensive available |
— | $5,767 | $7,127 | $10,487 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Nov 22, 2027 | 14 | 10 | 3 | San Juan, Puerto Rico | Colon, Panama | Caribbean |
from $4,547 $324 / night Inside unavailable · least expensive available |
— | $4,547 | $7,123 | $10,483 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Mar 6, 2028 | 14 | 11 | 3 | Oranjestad, Aruba | San Juan, Puerto Rico | Caribbean |
from $4,830 $345 / night Inside unavailable · least expensive available |
— | $4,830 | $7,854 | $11,214 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Mar 27, 2028 | 7 | 5 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $2,380 $340 / night Inside unavailable · least expensive available |
— | $2,380 | $3,990 | $6,055 |
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
