All 73 sailings from Philipsburg, Sint Maarten
Ordered soonest first. Prices per person, including taxes and fees. Want to filter by price, date, or ship?
Open these cruises in search →| View | Sailing | Departs | Nights | Ship | From |
|---|---|---|---|---|---|
| 7-Day Yachtsman's Caribbean | Dec 5, 2026 | 7 | Seabourn Ovation |
from $3,879 $554 / night |
|
| 14-Day Yachtsman's Caribbean in Depth | Dec 5, 2026 | 14 | Seabourn Ovation |
from $6,749 $482 / night |
|
| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Dec 19, 2026 | 14 | Wind Surf |
from $5,320 $380 / night |
|
| Beach Fun & Sun: A Remote Caribbean Getaway - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Dec 19, 2026 | 7 | Wind Surf |
from $3,255 $465 / night |
|
| 7-Day Yachtsman's Caribbean | Dec 26, 2026 | 7 | Seabourn Ovation |
from $4,979 $711 / night |
|
| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 2, 2027 | 14 | Wind Surf |
from $5,880 $420 / night |
|
| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 9, 2027 | 7 | Wind Surf |
from $3,465 $495 / night |
|
| 14-Day Caribbean Gems in Depth | Jan 16, 2027 | 14 | Seabourn Ovation |
from $8,779 $627 / night |
|
| 7-Day Yachtsman's Caribbean | Jan 16, 2027 | 7 | Seabourn Ovation |
from $4,809 $687 / night |
|
| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 16, 2027 | 14 | Wind Surf |
from $7,084 $506 / night |
|
| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 23, 2027 | 7 | Wind Surf |
from $5,005 $715 / night |
|
| 7-Day Yachtsman's Caribbean | Jan 30, 2027 | 7 | Seabourn Ovation |
from $4,044 $577 / night |
|
| Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 30, 2027 | 7 | Wind Surf |
from $3,535 $505 / night |
|
| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 30, 2027 | 14 | Wind Surf |
from $6,160 $440 / night |
|
| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 6, 2027 | 14 | Wind Surf |
from $6,692 $478 / night |
|
| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 13, 2027 | 14 | Wind Surf |
from $6,188 $442 / night |
|
| Philipsburg, St.Marteen to Philipsburg, St.Marteen | Feb 13, 2027 | 7 | Wind Surf |
from $3,710 $530 / night |
|
| 14-Day Caribbean Gems in Depth | Feb 20, 2027 | 14 | Seabourn Ovation |
from $8,439 $602 / night |
|
| 7-Day Yachtsman's Caribbean | Feb 20, 2027 | 7 | Seabourn Ovation |
from $4,724 $674 / night |
|
| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 20, 2027 | 14 | Wind Surf |
from $5,852 $418 / night |
|
| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 20, 2027 | 7 | Wind Surf |
from $3,430 $490 / night |
|
| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 27, 2027 | 14 | Wind Surf |
from $5,208 $372 / night |
|
| Beach Fun & Sun: A Remote Caribbean Getaway - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 27, 2027 | 7 | Wind Surf |
from $3,465 $495 / night |
|
| 14-Day Caribbean Gems in Depth | Mar 6, 2027 | 14 | Seabourn Ovation |
from $7,712 $550 / night |
|
| 7-Day Yachtsman's Caribbean | Mar 6, 2027 | 7 | Seabourn Ovation |
from $4,214 $602 / night |
|
| Philipsburg, St.Marteen to Philipsburg, St.Marteen | Mar 13, 2027 | 7 | Wind Surf |
from $3,710 $530 / night |
|
| 7-Day Yachtsman's Caribbean | Mar 20, 2027 | 7 | Seabourn Ovation |
from $5,064 $723 / night |
|
| 19-Day Yachtsman's Caribbean & Atlantic Passage | Mar 20, 2027 | 19 | Seabourn Ovation |
from $10,698 $563 / night |
|
| Ocean Crossings - Philipsburg, St. Maarten to Lisbon | Mar 27, 2027 | 15 | Wind Surf |
from $2,775 $185 / night |
|
| Star Collector: Caribbean Explorations | Nov 20, 2027 | 15 | Wind Surf |
from $4,564 $304 / night |
|
| Beach Fun & Sun: A Remote Caribbean Getaway | Nov 20, 2027 | 8 | Wind Surf |
from $3,080 $385 / night |
|
| Classic Caribbean | Nov 28, 2027 | 7 | Wind Surf |
from $2,415 $345 / night |
|
| 7-Day Yachtsman's Caribbean | Dec 4, 2027 | 7 | Seabourn Ovation |
from $3,869 $552 / night |
|
| Star Collector: Caribbean Explorations | Dec 12, 2027 | 15 | Wind Surf |
from $4,496 $299 / night |
|
| Star Collector: Caribbean Explorations | Dec 19, 2027 | 15 | Wind Surf |
from $4,692 $312 / night |
|
| Beach Fun & Sun: A Remote Caribbean Getaway | Dec 19, 2027 | 8 | Wind Surf |
from $2,960 $370 / night |
|
| 11-Day Yachtsman's Holiday in Aruba, Bonaire & Curacao | Dec 28, 2027 | 11 | Seabourn Ovation |
from $5,529 $502 / night |
|
| Star Collector: Caribbean Explorations | Jan 3, 2028 | 13 | Wind Surf |
from $4,065 $312 / night |
|
| Star Collector: Caribbean Explorations | Jan 9, 2028 | 14 | Wind Surf |
from $4,197 $299 / night |
|
| Caribbean Island Hopping: Sint Maarten to Barbados | Jan 12, 2028 | 10 | Emerald Sakara |
from $8,012 $801 / night |
|
| Star Collector: Caribbean Explorations | Jan 16, 2028 | 14 | Wind Surf |
from $4,197 $299 / night |
|
| 7-Day Yachtsman's Caribbean | Jan 22, 2028 | 7 | Seabourn Ovation |
from $4,379 $625 / night |
|
| Star Collector: Caribbean Explorations | Jan 23, 2028 | 14 | Wind Surf |
from $4,197 $299 / night |
|
| 14-Day Caribbean Yacht Harbors in Depth | Feb 5, 2028 | 14 | Seabourn Ovation |
from $7,929 $566 / night |
|
| 7-Day Yachtsman's Caribbean | Feb 5, 2028 | 7 | Seabourn Ovation |
from $4,379 $625 / night |
|
| Star Collector: Caribbean Explorations | Feb 6, 2028 | 14 | Wind Surf |
from $4,340 $310 / night |
|
| Classic Caribbean | Feb 6, 2028 | 7 | Wind Surf |
from $2,485 $355 / night |
|
| Star Collector: Caribbean Explorations | Feb 13, 2028 | 14 | Wind Surf |
from $4,564 $326 / night |
|
| Beach Fun & Sun: A Remote Caribbean Getaway | Feb 13, 2028 | 7 | Wind Surf |
from $2,380 $340 / night |
|
| 14-Day Caribbean Yacht Harbors in Depth | Feb 19, 2028 | 14 | Seabourn Ovation |
from $7,759 $554 / night |
|
| 7-Day Yachtsman's Caribbean | Feb 19, 2028 | 7 | Seabourn Ovation |
from $4,549 $649 / night |
|
| Classic Caribbean | Feb 20, 2028 | 7 | Wind Surf |
from $2,590 $370 / night |
|
| Star Collector: Caribbean Explorations | Feb 27, 2028 | 14 | Wind Surf |
from $4,228 $302 / night |
|
| A Remote Caribbean Getaway | Feb 27, 2028 | 7 | Wind Surf |
from $2,590 $370 / night |
|
| 14-Day Caribbean Yacht Harbors in Depth | Mar 4, 2028 | 14 | Seabourn Ovation |
from $7,504 $536 / night |
|
| 7-Day Yachtsman's Caribbean | Mar 4, 2028 | 7 | Seabourn Ovation |
from $4,039 $577 / night |
|
| Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing | Mar 12, 2028 | 22 | Wind Surf |
from $4,112 $186 / night |
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| Beach Fun & Sun: A Remote Caribbean Getaway | Mar 12, 2028 | 7 | Wind Surf |
from $2,625 $375 / night |
|
| 19-Day Yacht Harbors & Atlantic Crossing | Mar 18, 2028 | 19 | Seabourn Ovation |
from $10,308 $542 / night |
|
| 7-Day Yachtsman's Caribbean | Mar 18, 2028 | 7 | Seabourn Ovation |
from $4,549 $649 / night |
|
| 7-Day St. Barts & Caribbean Yacht Harbors | Dec 16, 2028 | 7 | Seabourn Ovation |
from $4,244 $606 / night |
|
| 14-Day St. Barts & Boutique Yacht Harbors Holiday | Dec 16, 2028 | 14 | Seabourn Ovation |
from $8,409 $600 / night |
|
| 7-Day Caribbean Yacht Harbors Holiday | Dec 30, 2028 | 7 | Seabourn Ovation |
from $5,044 $720 / night |
|
| 14-Day Exploring Boutique Yacht Harbors on Holiday | Dec 30, 2028 | 14 | Seabourn Ovation |
from $9,009 $643 / night |
|
| 7-Day Exploring Aruba, Bonaire & Curacao | Jan 13, 2029 | 7 | Seabourn Ovation |
from $4,654 $664 / night |
|
| 14-Day Boutique Yacht Harbors & Southern Caribbean Isles | Jan 13, 2029 | 14 | Seabourn Ovation |
from $8,624 $616 / night |
|
| 7-Day St. Barts & Caribbean Yacht Harbors | Jan 27, 2029 | 7 | Seabourn Ovation |
from $4,644 $663 / night |
|
| 14-Day Southern Caribbean Isles & Boutique Yacht Harbors | Jan 27, 2029 | 14 | Seabourn Ovation |
from $8,614 $615 / night |
|
| 7-Day St. Barts & Caribbean Yacht Harbors | Feb 17, 2029 | 7 | Seabourn Ovation |
from $4,844 $692 / night |
|
| 14-Day St. Barts & Boutique Yacht Harbors | Feb 17, 2029 | 14 | Seabourn Ovation |
from $8,609 $614 / night |
|
| 7-Day St. Barts & Caribbean Yacht Harbors | Mar 3, 2029 | 7 | Seabourn Ovation |
from $4,844 $692 / night |
|
| 14-Day St. Barts & Boutique Yacht Harbors | Mar 3, 2029 | 14 | Seabourn Ovation |
from $8,609 $614 / night |
|
| 7-Day St. Barts & Caribbean Yacht Harbors | Mar 17, 2029 | 7 | Seabourn Ovation |
from $4,844 $692 / night |
