Simpson Bay Boat Tours
The best out of 11 boat tours in Simpson Bay - enter dates to check availability

33 ft
Up to 10 persons
Just listed
Cole Bay (21 min drive from Simpson Bay)
Offshore Boats Charter SXM offers premium private charters from Cole Bay aboard a powerful 33’ Contender, designed for speed, comfort, and performance in the crystal-clear waters of St. Maarten, St. Barths, and Anguilla.
+1
Trips from
US $650

33 ft
Up to 6 persons
Cole Bay (16 min drive from Simpson Bay)
Experience the turquoise waters of the Caribbean with Timeless Boat Charters.
Trips from
US $900

35 ft
Up to 10 persons
5+ external reviews
Cole Bay (16 min drive from Simpson Bay)
Suneeta Sxm – Private Boat Charter is your gateway to exploring the stunning waters of St. Martin aboard a 2018 Jefferson Yachts Marlago Center Console.
+1
Trips from
US $690

48 ft
Up to 17 persons
Just listed
Simpson Bay
Pura Vida SXM is a stunning 48-foot catamaran built in 2005, based in the beautiful waters of Simpson Bay.
Trips from
US $950

35 ft
Up to 14 persons
Just listed
5+ external reviews
Simpson Bay
Experience the ultimate day on the water with All About Boat Charters, a beautifully restored 1992 Rabco 35 Center Console (restored in 2025) based in vibrant Simpson Bay.
Trips from
US $1,400

31 ft
Up to 8 persons
Cole Bay (16 min drive from Simpson Bay)
Set out from Cole Bay aboard DeepSea Exotic Charters, a beautifully restored 2010 Vendette Guepard G31 Center Console, upgraded in 2025 and designed for speed, comfort, and unforgettable Caribbean adventures.
Trips from
US $500

26 ft
Up to 5 persons
5+ external reviews
Cole Bay (15 min drive from Simpson Bay)
Experience the ultimate island adventure with Captain Flint Boat Charters, aboard a beautifully restored 2000 Mako 253 Cruiser (refreshed in 2025) in Cole Bay.
Trips from
US $800

40 ft
Up to 12 persons
5.0
/5
(1 review)
•
5+ external reviews
Philipsburg (28 min drive from Simpson Bay)
Knot At Work – a Nautitech Open 40 is a 2015 sailing catamaran based in Philipsburg, accommodating up to 12 guests. Onboard amenities include an audio system, inside and outside speakers, an ice box, and a refrigerator for your comfort.
"knot at work was very clean and enjoyable, what made the boat even more enjoyable was nika and david." — Paola,
"knot at work was very clean and enjoyable, what made the boat even more enjoyable was nika and david." — Paola,
+2
Trips from
US $900

44 ft
Up to 16 persons
5.0
/5
(2 reviews)
•
5+ external reviews
Philipsburg (28 min drive from Simpson Bay)
Mojito – Leopard 44 Sail Catamaran is a 2017 Robertson & Caine Leopard Catamaran based out of Philipsburg. It can take up to sixteen guests.
"Our sailing experience with Charlie and Janel on the Mojito catamaran was absolutely amazing!" — Bodo,
"Our sailing experience with Charlie and Janel on the Mojito catamaran was absolutely amazing!" — Bodo,
+3
Trips from
US $1,000

40 ft
Up to 12 persons
5+ external reviews
Philipsburg (28 min drive from Simpson Bay)
Be Happy – Nautitech 40 is a 2014 sailing catamaran based in Philipsburg, accommodating up to 12 guests. Onboard amenities include an audio system, inside and outside speakers, an ice box, and a refrigerator for your comfort.
+2
Trips from
US $900
