Simpson Bay Boat Tours
The best out of 12 boat tours in Simpson Bay - enter dates to check availability
33 ft
Up to 10 people
5.0
/5
(1 review)
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 people
Cole Bay (16 min drive from Simpson Bay)
Experience the turquoise waters of the Caribbean with Timeless Boat Charters.
trips from
US $900
48 ft
Up to 17 people
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 10 people
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 $684
31 ft
Up to 8 people
5.0
/5
(1 review)
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.
"From the beginning of the booking until we returned from our cruise, Captain Dilan was amazing!" — Kirsten,
"From the beginning of the booking until we returned from our cruise, Captain Dilan was amazing!" — Kirsten,
trips from
US $500
8 ft
Up to 4 people
Just added to our fleet
5+ external reviews
Simpson Bay
Seas The Day – Inflatable Dinghy is a brand-new 2026 AB Marine inflatable outboard, based in Simpson Bay and perfect for exploring the surrounding waters in a fun, flexible, and intimate way.
trips from
US $120
26 ft
Up to 5 people
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
25 ft
Up to 10 people
Just added to our fleet
Cole Bay (2.1 miles from Simpson Bay)
Experience the best of St. Maarten on board this 2006 Hydra Sport Vector 2500, departing from Cole Bay and operated by Bliss Boat Charter.
+2
trips from
US $800
44 ft
Up to 16 people
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 people
5.0
/5
(1 review)
•
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.
"excellent charter. great skipper and forst mate attended the fove of us well." — John,
"excellent charter. great skipper and forst mate attended the fove of us well." — John,
+2
trips from
US $900