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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 Pride | 1988 | 4 | Oct 28, 2026 | 11 | 10 | 1 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,290 $390 / night Inside unavailable · least expensive available |
— | $4,290 | $7,040 | $10,285 | |
| 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 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 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 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 Pride | 1988 | 4 | Dec 27, 2026 | 7 | 7 | 0 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $3,780 $540 / night Inside unavailable · least expensive available |
— | $3,780 | $4,480 | $6,090 | |
| 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 10, 2027 | 7 | 7 | 0 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $3,815 $545 / night Inside unavailable · least expensive available |
— | $3,815 | $6,685 | $8,540 | |
| 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 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 |
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
