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Top St Maarten Sailing Trips

33 Results
Be Happy - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Be Happy for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private sailing experience with your group, …More

Join us aboard Be Happy for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private sailing experience with your group,...

4 hours Free Cancellation
5.0 (10)
from
$195
Be Happy - Full Day Private Catamaran Cruise - St Maarten

Join us on Be Happy, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can …More

Join us on Be Happy, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can...

8 hours Free Cancellation
5.0 (9)
from
$235
Half-Day The Soul Of Pirates Private Boat Trip Adventure Caribbean Charter SXM

A timeless adventure aboard DE our sailboat. Come live an unforgettable experience on a sailboat. No DE engines, sail like pirates. Things to do: snorkel, …More

A timeless adventure aboard DE our sailboat. Come live an unforgettable experience on a sailboat. No DE engines, sail like pirates. Things to do: snorkel,...

3 hours 30 minutes Free Cancellation
5.0 (7)
from
$1,538
No1Sxm Private Intimate Day Sail in St. Maarten

Are you ready to go Sailing? True sailing on board of No1Sxm Trimaran: stable, smooth, fast. The 5 hour experience takes you along the south west …More

Likely to Sell Out
Likely to Sell Out

Are you ready to go Sailing? True sailing on board of No1Sxm Trimaran: stable, smooth, fast. The 5 hour experience takes you along the south west...

5 hours 30 minutes Free Cancellation
4.8 (5)
from
$124
Don't Worry - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Don't Worry, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a …More

Join us aboard Don't Worry, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a...

4 hours Free Cancellation
5.0 (5)
from
$210
No1Sxm Half Day Sail Snorkeling and Sunset Experience

On this 4-hour sail we have combined the excitement of Sailing on a great trimaran, Swimming/Snorkeling in turquoise waters of a calm bay on the …More

On this 4-hour sail we have combined the excitement of Sailing on a great trimaran, Swimming/Snorkeling in turquoise waters of a calm bay on the...

4 hours Free Cancellation
5.0 (4)
from
$128
2 days 1 night by private catamaran from St Martin to St Barth

Treat yourself to a private and exclusive stay in Saint Barthélémy from Grand-Case Combine sailing, discovering a part of St Martin by sea, magical night …More

Treat yourself to a private and exclusive stay in Saint Barthélémy from Grand-Case Combine sailing, discovering a part of St Martin by sea, magical night...

2 days
5.0 (2)
from
$4,798
Full-Day Private Boat Charter Caribbean adventure

A timeless adventure aboard DE our sailboat. Come live an unforgettable experience on a sailboat. No DE engines, sail like pirates. Decks DE stern and …More

A timeless adventure aboard DE our sailboat. Come live an unforgettable experience on a sailboat. No DE engines, sail like pirates. Decks DE stern and...

6 hours Free Cancellation
5.0 (2)
from
$1,779
Mojito - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Mojito, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private …More

Likely to Sell Out
Likely to Sell Out

Join us aboard Mojito, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private...

4 hours Free Cancellation
5.0 (1)
from
$190
Tango Caribbean Dinner Cruise

Experience the true Caribbean way on this evening dinner cruise! Guests are treated to an open bar and snacks as the catamaran sails along the …More

Experience the true Caribbean way on this evening dinner cruise! Guests are treated to an open bar and snacks as the catamaran sails along the...

3 hours Free Cancellation
4.7 (515)
from
$85
Prickly Pear Catamaran Trip from St Maarten Including Lunch

Discover the paradise shores of Prickly Pear Islands on this full-day trip from St Maarten. Sail aboard Lambada catamaran and stop at Prickly Pear Island, …More

Discover the paradise shores of Prickly Pear Islands on this full-day trip from St Maarten. Sail aboard Lambada catamaran and stop at Prickly Pear Island,...

8 hours Free Cancellation
4.7 (422)
from
$135
St. Martin Sunset Sail

Nothing compares to the exquisite colors of a Caribbean sunset. Enjoy the romantic mood that is automatically set as the sun disappears into the waters …More

Nothing compares to the exquisite colors of a Caribbean sunset. Enjoy the romantic mood that is automatically set as the sun disappears into the waters...

1 hour 30 minutes Free Cancellation
4.7 (230)
from
$45
Sunset Champagne Cruise in St. Maarten

Experience the romance of a Caribbean sunset on a Champagne cruise in St Maarten. While you sail along the coast on a luxury catamaran, enjoy …More

Experience the romance of a Caribbean sunset on a Champagne cruise in St Maarten. While you sail along the coast on a luxury catamaran, enjoy...

1 hour 30 minutes Free Cancellation
4.7 (83)
from
$55

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