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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 | Outside | 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 15, 2026 | 7 | 7 | 0 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,095 $585 / night Inside unavailable · least expensive available |
— | $4,095 | $5,005 | $6,265 | |
| 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 CruisesWind Surf | 1989 | 4 | Dec 19, 2026 | 14 | 12 | 0 | Philipsburg, Sint Maarten | Philipsburg, Sint Maarten | Caribbean |
from $4,340 $310 / night Inside unavailable · least expensive available |
— | $4,340 | — | $5,684 | |
| Windstar Cruises | Windstar CruisesWind Surf | 1989 | 4 | Dec 19, 2026 | 7 | 7 | 0 | Philipsburg, Sint Maarten | Philipsburg, Sint Maarten | Caribbean |
from $2,730 $390 / night Inside unavailable · least expensive available |
— | $2,730 | — | $3,570 | |
| Windstar Cruises | Windstar CruisesWind Surf | 1989 | 4 | Dec 26, 2026 | 7 | 7 | 0 | Philipsburg, Sint Maarten | Philipsburg, Sint Maarten | Caribbean |
from $2,695 $385 / night Inside unavailable · least expensive available |
— | $2,695 | — | $3,535 | |
| 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 $7,112 $508 / night Inside unavailable · least expensive available |
— | $7,112 | $8,232 | $11,536 | |
| 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 CruisesWind Surf | 1989 | 4 | Jan 2, 2027 | 14 | 12 | 0 | Philipsburg, Sint Maarten | Philipsburg, Sint Maarten | Caribbean |
from $4,088 $292 / night Inside unavailable · least expensive available |
— | $4,088 | — | $5,152 | |
| Windstar Cruises | Windstar CruisesWind Surf | 1989 | 4 | Jan 30, 2027 | 14 | 12 | 0 | Philipsburg, Sint Maarten | Philipsburg, Sint Maarten | Caribbean |
from $5,842 $417 / night Inside unavailable · least expensive available |
— | $5,842 | — | $7,186 | |
| Windstar Cruises | Windstar CruisesWind Surf | 1989 | 4 | Jan 16, 2027 | 7 | 7 | 0 | Philipsburg, Sint Maarten | Philipsburg, Sint Maarten | Caribbean |
from $3,395 $485 / night Inside unavailable · least expensive available |
— | $3,395 | — | $4,235 | |
| 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 CruisesWind Surf | 1989 | 4 | Feb 20, 2027 | 14 | 12 | 0 | Philipsburg, Sint Maarten | Philipsburg, Sint Maarten | Caribbean |
from $6,178 $441 / night Inside unavailable · least expensive available |
— | $6,178 | — | $7,522 | |
| Windstar Cruises | Windstar CruisesWind Surf | 1989 | 4 | Feb 27, 2027 | 14 | 12 | 0 | Philipsburg, Sint Maarten | Philipsburg, Sint Maarten | Caribbean |
from $5,842 $417 / night Inside unavailable · least expensive available |
— | $5,842 | — | $7,186 | |
| Windstar Cruises | Windstar CruisesWind Surf | 1989 | 4 | Feb 27, 2027 | 7 | 7 | 0 | Philipsburg, Sint Maarten | Philipsburg, Sint Maarten | Caribbean |
from $3,220 $460 / night Inside unavailable · least expensive available |
— | $3,220 | — | $4,060 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Jan 3, 2028 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,256 $304 / night Inside unavailable · least expensive available |
— | $4,256 | $5,740 | $9,044 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Jan 10, 2028 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,256 $304 / night Inside unavailable · least expensive available |
— | $4,256 | $5,740 | $9,044 | |
| 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 Pride | 1988 | 4 | Oct 11, 2027 | 21 | 13 | 7 | Montreal | San Juan, Puerto Rico | Caribbean |
from $8,736 $416 / night Inside unavailable · least expensive available |
— | $8,736 | $11,788 | $17,096 | |
| Windstar Cruises | Windstar CruisesStar Legend | 1991 | 4 | Feb 7, 2028 | 14 | 11 | 2 | San Juan, Puerto Rico | San Juan, Puerto Rico | Caribbean |
from $4,424 $316 / night Inside unavailable · least expensive available |
— | $4,424 | $5,880 | $9,212 | |
| 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 | Feb 21, 2028 | 21 | 17 | 3 | Caldera, Costa Rica | San Juan, Puerto Rico | Central America |
from $7,099 $338 / night Inside unavailable · least expensive available |
— | $7,099 | $11,523 | $16,507 | |
| Windstar Cruises | Windstar CruisesStar Pride | 1988 | 4 | Feb 28, 2028 | 14 | 11 | 2 | Fuerte Amador, Panama City | San Juan, Puerto Rico | Panama Canal |
from $4,620 $330 / night Inside unavailable · least expensive available |
— | $4,620 | $7,896 | $11,228 | |
| 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 CruisesWind Surf | 1989 | 4 | Dec 12, 2027 | 15 | 12 | 0 | Philipsburg, Sint Maarten | Philipsburg, Sint Maarten | Caribbean |
from $5,074 $338 / night Inside unavailable · least expensive available |
— | $5,074 | — | $6,514 | |
| 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 CruisesWind Surf | 1989 | 4 | Nov 20, 2027 | 15 | 13 | 0 | Philipsburg, Sint Maarten | Philipsburg, Sint Maarten | Caribbean |
from $5,358 $357 / night Inside unavailable · least expensive available |
— | $5,358 | — | $6,798 | |
| 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 CruisesWind Surf | 1989 | 4 | Dec 19, 2027 | 8 | 8 | 0 | Philipsburg, Sint Maarten | Philipsburg, Sint Maarten | Caribbean |
from $3,240 $405 / night Inside unavailable · least expensive available |
— | $3,240 | — | $4,200 | |
| 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 6, 2028 | 7 | 7 | 1 | Oranjestad, Aruba | San Juan, Puerto Rico | Caribbean |
from $2,800 $400 / night Inside unavailable · least expensive available |
— | $2,800 | $4,935 | $7,035 |
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
