All 106 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 $4,053 $579 / night |
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| 14-Day Yachtsman's Caribbean in Depth | Dec 5, 2026 | 14 | Seabourn Ovation |
from $6,818 $487 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Dec 19, 2026 | 14 | Wind Surf |
from $7,680 $548 / night |
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| Beach Fun & Sun: A Remote Caribbean Getaway - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Dec 19, 2026 | 7 | Wind Surf |
from $3,638 $519 / night |
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| 7-Day Yachtsman's Caribbean | Dec 26, 2026 | 7 | Seabourn Ovation |
from $5,848 $835 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Dec 26, 2026 | 14 | Wind Surf |
Call for price |
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| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Dec 26, 2026 | 7 | Wind Surf |
from $4,392 $627 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 2, 2027 | 14 | Wind Surf |
from $5,440 $388 / night |
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| Philipsburg, St.Marteen to Philipsburg, St.Marteen | Jan 2, 2027 | 7 | Wind Surf |
from $2,728 $389 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 9, 2027 | 14 | Wind Surf |
from $6,210 $443 / night |
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| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 9, 2027 | 7 | Wind Surf |
from $2,922 $417 / night |
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| 14-Day Caribbean Gems in Depth | Jan 16, 2027 | 14 | Seabourn Ovation |
from $11,008 $786 / night |
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| 7-Day Yachtsman's Caribbean | Jan 16, 2027 | 7 | Seabourn Ovation |
from $5,648 $806 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 16, 2027 | 14 | Wind Surf |
Call for price |
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| Beach Fun & Sun: A Remote Caribbean Getaway - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 16, 2027 | 7 | Wind Surf |
from $3,428 $489 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 23, 2027 | 14 | Wind Surf |
Call for price |
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| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 23, 2027 | 7 | Wind Surf |
from $4,672 $667 / night |
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| 7-Day Yachtsman's Caribbean | Jan 30, 2027 | 7 | Seabourn Ovation |
from $4,748 $678 / night |
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| Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 30, 2027 | 7 | Wind Surf |
from $3,253 $464 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Jan 30, 2027 | 14 | Wind Surf |
from $7,330 $523 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 6, 2027 | 14 | Wind Surf |
from $5,790 $413 / night |
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| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 6, 2027 | 7 | Wind Surf |
from $2,782 $397 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 13, 2027 | 14 | Wind Surf |
from $6,490 $463 / night |
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| Philipsburg, St.Marteen to Philipsburg, St.Marteen | Feb 13, 2027 | 7 | Wind Surf |
from $3,183 $454 / night |
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| 14-Day Caribbean Gems in Depth | Feb 20, 2027 | 14 | Seabourn Ovation |
from $10,308 $736 / night |
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| 7-Day Yachtsman's Caribbean | Feb 20, 2027 | 7 | Seabourn Ovation |
from $5,848 $835 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 20, 2027 | 14 | Wind Surf |
from $6,420 $458 / night |
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| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 20, 2027 | 7 | Wind Surf |
from $3,972 $567 / night |
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| Antigua to the British Virgin Islands: Hidden Cays and Azure Seas Aboard Sea Cloud II | Feb 26, 2027 | 7 | Sea Cloud II |
from $24,000 $3,428 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 27, 2027 | 14 | Wind Surf |
from $6,070 $433 / night |
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| Beach Fun & Sun: A Remote Caribbean Getaway - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Feb 27, 2027 | 7 | Wind Surf |
from $3,113 $444 / night |
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| 14-Day Caribbean Gems in Depth | Mar 6, 2027 | 14 | Seabourn Ovation |
from $10,008 $714 / night |
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| 7-Day Yachtsman's Caribbean | Mar 6, 2027 | 7 | Seabourn Ovation |
from $4,948 $706 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Mar 6, 2027 | 14 | Wind Surf |
from $6,350 $453 / night |
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| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Mar 6, 2027 | 7 | Wind Surf |
from $3,412 $487 / night |
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| Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Mar 13, 2027 | 14 | Wind Surf |
from $6,140 $438 / night |
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| Philipsburg, St.Marteen to Philipsburg, St.Marteen | Mar 13, 2027 | 7 | Wind Surf |
from $3,428 $489 / night |
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| 7-Day Yachtsman's Caribbean | Mar 20, 2027 | 7 | Seabourn Ovation |
from $5,948 $849 / night |
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| 19-Day Yachtsman's Caribbean & Atlantic Passage | Mar 20, 2027 | 19 | Seabourn Ovation |
from $10,898 $573 / night |
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| Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten | Mar 20, 2027 | 7 | Wind Surf |
from $3,307 $472 / night |
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| Atlantic Interludes & Iberian Indulgences - Philipsburg, St.Maarten to Barcelona | Mar 27, 2027 | 23 | Wind Surf |
from $5,919 $257 / night |
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| Ocean Crossings - Philipsburg, St. Maarten to Lisbon | Mar 27, 2027 | 15 | Wind Surf |
from $2,805 $187 / night |
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| Star Collector: Caribbean Explorations | Nov 20, 2027 | 15 | Wind Surf |
from $4,845 $323 / night |
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| Beach Fun & Sun: A Remote Caribbean Getaway | Nov 20, 2027 | 8 | Wind Surf |
from $3,028 $378 / night |
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| Star Collector: Caribbean Explorations | Nov 28, 2027 | 14 | Wind Surf |
from $4,530 $323 / night |
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| Classic Caribbean | Nov 28, 2027 | 7 | Wind Surf |
from $2,537 $362 / night |
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| 7-Day Yachtsman's Caribbean | Dec 4, 2027 | 7 | Seabourn Ovation |
from $4,543 $649 / night |
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| Star Collector: Caribbean Explorations | Dec 5, 2027 | 14 | Wind Surf |
from $4,460 $318 / night |
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| Beach Fun & Sun: A Remote Caribbean Getaway | Dec 5, 2027 | 7 | Wind Surf |
from $2,693 $384 / night |
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| Star Collector: Caribbean Explorations | Dec 12, 2027 | 15 | Wind Surf |
from $5,145 $343 / night |
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| Classic Caribbean | Dec 12, 2027 | 7 | Wind Surf |
from $2,747 $392 / night |
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| Tropical Charms of the Caribbean | Dec 18, 2027 | 9 | Emerald Sakara |
from $6,351 $705 / night |
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| Star Collector: Caribbean Explorations | Dec 19, 2027 | 15 | Wind Surf |
from $5,370 $358 / night |
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| Beach Fun & Sun: A Remote Caribbean Getaway | Dec 19, 2027 | 8 | Wind Surf |
from $3,508 $438 / night |
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| Tropical Charms of the Caribbean | Dec 27, 2027 | 9 | Emerald Sakara |
from $6,801 $755 / night |
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| Star Collector: Caribbean Explorations | Dec 27, 2027 | 13 | Wind Surf |
from $4,280 $329 / night |
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| Classic Caribbean | Dec 27, 2027 | 7 | Wind Surf |
from $3,062 $437 / night |
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| 11-Day Yachtsman's Holiday in Aruba, Bonaire & Curacao | Dec 28, 2027 | 11 | Seabourn Ovation |
from $7,788 $708 / night |
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| Star Collector: Caribbean Explorations | Jan 3, 2028 | 13 | Wind Surf |
from $4,085 $314 / night |
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| Beach Fun & Sun: A Remote Caribbean Getaway | Jan 3, 2028 | 6 | Wind Surf |
from $2,108 $351 / night |
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| Star Collector: Caribbean Explorations | Jan 9, 2028 | 14 | Wind Surf |
from $4,320 $308 / night |
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| Classic Caribbean | Jan 9, 2028 | 7 | Wind Surf |
from $2,642 $377 / night |
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| Caribbean Island Hopping: Sint Maarten to Barbados | Jan 12, 2028 | 10 | Emerald Sakara |
from $8,012 $801 / night |
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| Star Collector: Caribbean Explorations | Jan 16, 2028 | 14 | Wind Surf |
from $3,900 $278 / night |
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| Beach Fun & Sun: A Remote Caribbean Getaway | Jan 16, 2028 | 7 | Wind Surf |
from $2,378 $339 / night |
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| 7-Day Yachtsman's Caribbean | Jan 22, 2028 | 7 | Seabourn Ovation |
from $5,143 $734 / night |
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| Star Collector: Caribbean Explorations | Jan 23, 2028 | 14 | Wind Surf |
from $3,830 $273 / night |
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| Classic Caribbean | Jan 23, 2028 | 7 | Wind Surf |
from $2,362 $337 / night |
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| Star Collector: Caribbean Explorations | Jan 30, 2028 | 14 | Wind Surf |
from $4,110 $293 / night |
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| Beach Fun & Sun: A Remote Caribbean Getaway | Jan 30, 2028 | 7 | Wind Surf |
from $2,273 $324 / night |
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| 14-Day Caribbean Yacht Harbors in Depth | Feb 5, 2028 | 14 | Seabourn Ovation |
from $10,008 $714 / night |
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| 7-Day Yachtsman's Caribbean | Feb 5, 2028 | 7 | Seabourn Ovation |
from $5,643 $806 / night |
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| Star Collector: Caribbean Explorations | Feb 6, 2028 | 14 | Wind Surf |
from $4,460 $318 / night |
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| Classic Caribbean | Feb 6, 2028 | 7 | Wind Surf |
from $2,677 $382 / night |
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| Star Collector: Caribbean Explorations | Feb 13, 2028 | 14 | Wind Surf |
from $4,250 $303 / night |
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| Beach Fun & Sun: A Remote Caribbean Getaway | Feb 13, 2028 | 7 | Wind Surf |
from $2,483 $354 / night |
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| 14-Day Caribbean Yacht Harbors in Depth | Feb 19, 2028 | 14 | Seabourn Ovation |
from $9,708 $693 / night |
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| 7-Day Yachtsman's Caribbean | Feb 19, 2028 | 7 | Seabourn Ovation |
from $5,343 $763 / night |
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| Star Collector: Caribbean Explorations | Feb 20, 2028 | 14 | Wind Surf |
from $4,040 $288 / night |
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| Classic Caribbean | Feb 20, 2028 | 7 | Wind Surf |
from $2,432 $347 / night |
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| Star Collector: Caribbean Explorations | Feb 27, 2028 | 14 | Wind Surf |
from $4,040 $288 / night |
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| A Remote Caribbean Getaway | Feb 27, 2028 | 7 | Wind Surf |
from $2,448 $349 / night |
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| 14-Day Caribbean Yacht Harbors in Depth | Mar 4, 2028 | 14 | Seabourn Ovation |
from $9,408 $672 / night |
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| 7-Day Yachtsman's Caribbean | Mar 4, 2028 | 7 | Seabourn Ovation |
from $4,743 $677 / night |
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| Star Collector: Caribbean Explorations | Mar 5, 2028 | 14 | Wind Surf |
from $4,040 $288 / night |
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| Classic Caribbean | Mar 5, 2028 | 7 | Wind Surf |
from $2,432 $347 / night |
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| Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing | Mar 12, 2028 | 22 | Wind Surf |
from $4,168 $189 / night |
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| Beach Fun & Sun: A Remote Caribbean Getaway | Mar 12, 2028 | 7 | Wind Surf |
from $2,448 $349 / night |
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| 19-Day Yacht Harbors & Atlantic Crossing | Mar 18, 2028 | 19 | Seabourn Ovation |
from $11,708 $616 / night |
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| 7-Day Yachtsman's Caribbean | Mar 18, 2028 | 7 | Seabourn Ovation |
from $5,843 $834 / night |
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| Ocean Crossings | Mar 19, 2028 | 15 | Wind Surf |
from $2,580 $172 / night |
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| Star Collector: Spanish Shores Transatlantic Crossing | Mar 19, 2028 | 23 | Wind Surf |
from $5,689 $247 / night |
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| 7-Day St. Barts & Caribbean Yacht Harbors | Dec 16, 2028 | 7 | Seabourn Ovation |
from $4,743 $677 / night |
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| 14-Day St. Barts & Boutique Yacht Harbors Holiday | Dec 16, 2028 | 14 | Seabourn Ovation |
from $9,308 $664 / night |
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| 7-Day Caribbean Yacht Harbors Holiday | Dec 30, 2028 | 7 | Seabourn Ovation |
from $5,543 $791 / night |
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| 14-Day Exploring Boutique Yacht Harbors on Holiday | Dec 30, 2028 | 14 | Seabourn Ovation |
from $9,908 $707 / night |
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| 7-Day Exploring Aruba, Bonaire & Curacao | Jan 13, 2029 | 7 | Seabourn Ovation |
from $5,153 $736 / night |
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| 14-Day Boutique Yacht Harbors & Southern Caribbean Isles | Jan 13, 2029 | 14 | Seabourn Ovation |
from $9,523 $680 / night |
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| 7-Day St. Barts & Caribbean Yacht Harbors | Jan 27, 2029 | 7 | Seabourn Ovation |
from $5,143 $734 / night |
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| 14-Day Southern Caribbean Isles & Boutique Yacht Harbors | Jan 27, 2029 | 14 | Seabourn Ovation |
from $9,513 $679 / night |
The Captain's Log
Exceptional cruises. Intelligent prices.
The Captain's Log
