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Top St Maarten Sailing Trips

33 Results
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
Private Full-Day Catamaran Sailing Charter in St Maarten

Experience some of the finest sailing, swimming and snorkeling in the turquoise waters of St. Maarten. We can alter our trips to meet your needs, …More

Experience some of the finest sailing, swimming and snorkeling in the turquoise waters of St. Maarten. We can alter our trips to meet your needs,...

8 hours Free Cancellation
5.0 (113)
from
$2,800
St Martin Gd-Case: Private day in all inclusive catamaran

Imagine a perfect day, lulled by the waves and rays of the sun, aboard our exceptional catamaran that transforms every moment into an unforgettable adventure. …More

Imagine a perfect day, lulled by the waves and rays of the sun, aboard our exceptional catamaran that transforms every moment into an unforgettable adventure....

8 hours
5.0 (14)
from
$2,700
Private St. Maarten Cruise - Hakuna Matata Catamaran

Embark on a truly unique journey, where your experience is shaped by your desires. Perfect for families, couples, or groups, our flexible itinerary allows you …More

Likely to Sell Out
Likely to Sell Out

Embark on a truly unique journey, where your experience is shaped by your desires. Perfect for families, couples, or groups, our flexible itinerary allows you...

7 hours
5.0 (71)
from
$1,830
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
Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

Our Captain has 25+ years of experience, 0 incidents and is super helpful. He loves to tell amazing stories and will keep you entertained with …More

Our Captain has 25+ years of experience, 0 incidents and is super helpful. He loves to tell amazing stories and will keep you entertained with...

6 hours Free Cancellation
5.0 (497)
from
$1,750
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
Luxury Catamaran Private Day Sail from St. Maarten to Anguilla

Escape to the tranquil and world-renowned island of Anguilla while you sail aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a …More

Escape to the tranquil and world-renowned island of Anguilla while you sail aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a...

9 hours 30 minutes Free Cancellation
5.0 (11)
from
$397
Luxury Catamaran Private Charter in St. Maarten/St. Martin

Get the mega yacht experience aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a custom-made sailing catamaran appointed with all the …More

Get the mega yacht experience aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a custom-made sailing catamaran appointed with all the...

7 hours 30 minutes Free Cancellation
5.0 (52)
from
$330
Private Catamaran Excursion in Anguilla with its Turquoise Waters

looking for new adventures, unforgettable experience and relaxing beach ? sail with us around Saint-Martin and its neighboring islands. we assure you a memorable experience. …More

looking for new adventures, unforgettable experience and relaxing beach ? sail with us around Saint-Martin and its neighboring islands. we assure you a memorable experience....

8 hours
5.0 (19)
from
$240
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
Don't Worry - Full Day Private Catamaran Cruise - St Maarten

Join us on Don't Worry, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can …More

Join us on Don't Worry, 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 (16)
from
$235
Mojito - Full Day Private Catamaran Cruise - St Maarten

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

Likely to Sell Out
Likely to Sell Out

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

8 hours Free Cancellation
4.8 (24)
from
$230
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
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
The Soul Of Pirates Boat Trip Adventure Caribbean Charter Full Day SXM

Set off from Saint-Martin for a full day on a wind-powered boat, without an engine. With the captain's help, take the helm and help hoist …More

Set off from Saint-Martin for a full day on a wind-powered boat, without an engine. With the captain's help, take the helm and help hoist...

8 hours Free Cancellation
4.8 (24)
from
$193
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
Hakuna Matata - St Maarten Catamaran day cruise

Enjoy a relaxed day perfect for families (kids welcome!), couples, and groups. Captain Robert, with years of experience sailing the world’s oceans, shares captivating stories …More

Likely to Sell Out
Likely to Sell Out

Enjoy a relaxed day perfect for families (kids welcome!), couples, and groups. Captain Robert, with years of experience sailing the world’s oceans, shares captivating stories...

7 hours
5.0 (160)
from
$169
The Original Eco Tour Full-Day Around the Island of Sint Maarten

Enjoy a full day sailing aboard Too Rhum Punch or Quality Time our friendly comfortable and Fun Catamaran around the island of Sint Maarten / …More

Enjoy a full day sailing aboard Too Rhum Punch or Quality Time our friendly comfortable and Fun Catamaran around the island of Sint Maarten /...

8 hours Free Cancellation
4.9 (553)
from
$149
No1SXM Day Sailing Experience 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

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
4.9 (153)
from
$145

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