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a beach with a lot of people on it

Explore Sailing Voyages in Sint Maarten 🇸🇽

Cover photo by @tomaltomasz on Unsplash

Voyage photo from MSWI IYT Day Skipper course - Passage 6Voyage photo from MSWI IYT Day Skipper course - Passage 6Voyage photo from MSWI IYT Day Skipper course - Passage 6
Matthew Van Ernest
Nicole Denett

Nicole Denett & Matthew Van Ernest

9 October 2026 at 10:23

LTD SXM Flotilla - Day 6
Cachucha
LTD SXM Flotilla - Day 6
17.7NM
3h 38m

Koolbaai, Sint Maarten to Friar’s Bay, Saint Martin

Matthew Van Ernest
Nicole Denett

Nicole Denett & Matthew Van Ernest

8 October 2026 at 09:03

LTD SXM Flotilla - Day 5
Cachucha

Bill (green beret guy) Shelley Matt Bob Tim Peggy

LTD SXM Flotilla - Day 5
23.9NM
4h 26m

Anse des Flamands, Saint Barthélemy to Koolbaai, Sint Maarten

Bradley St Croix

Bradley St Croix

8 September 2026 at 21:43

Oceans 8
Voyage map
77.5NM
21h 9m

Caribbean Sea, Bonaire, Sint Eustatius, and Saba to Simson Bay Village, Sint Maarten

Jamie

Jamie , Jeffrey Tyrrell & 1 other

17 September 2026 at 22:47

kelea
Voyage map
103.4NM
13h 11m

Simson Bay Village, Sint Maarten to Fish Cay, U.S. Virgin Islands

Knoxville Grant

Knoxville Grant

8 September 2026 at 20:01

Voyage map
92.2NM
13h 26m

Belle Tete, St Kitts and Nevis to Simson Bay Village, Sint Maarten

Tabby

26 January 2026 at 16:53

St Maarten-Panama
St Maarten-Panama
1138.7NM
4 days 22 hours

Koolbaai, Sint Maarten to Punta Shelter, Panama

Bradley St Croix

Bradley St Croix

25 August 2026 at 16:47

Oceans 8
Voyage map
88.6NM
18h 58m

Dead Chest, British Virgin Islands to Koolbaai, Sint Maarten

Stephen Cork

17 August 2026 at 15:37

It’s chemistry
Voyage map
88.3NM
17h 49m

Philipsburg, Sint Maarten to Brades, Montserrat

Maxwell Boise
Craig Boise

Craig Boise & Maxwell Boise

7 August 2026 at 12:03

St. Maarten - Day 7
Sybaris
St. Maarten - Day 7
11NM
2h 36m

The Corner, Sint Maarten to Friar’s Bay, Saint Martin

Craig Boise

Craig Boise - We're were ghosting along with 5-9 kts of wind. 🥱

Add a comment...

Emma  Bauer

Emma Bauer

7 August 2026 at 09:26

MSWI IYT Day Skipper course - Passage 6
Imagine A

About a 2 meter swell coming around the north side of the island and down the windward side, flew up the leeward side. Sunny, consistent wind, beautiful sailing!

3

MSWI IYT Day Skipper course - Passage 6
22.1NM
3h 19m

Grand-Case, Saint Martin to Koolbaai, Sint Maarten

Baylee

Baylee

4 August 2026 at 08:19

SXM to Barths
SXM to Barths
19NM
4h 48m

Koolbaai, Sint Maarten to Gustavia, Saint Barthélemy

Baylee

Baylee

3 August 2026 at 12:26

Simpson Bay to KoolBaai
Simpson Bay to KoolBaai
3.8NM
44min

Simson Bay Village to Koolbaai, Sint Maarten

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