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All listings in Sint Maarten

Awesome sailboat rentals in Sint Maarten.

5.0(Average of 33 reviews in this area)
14 listings
Sailing Catamaran Trips in St Maarten and surrounding islands.
Sailing in Simpson Bay · 25 guests

Sailing Catamaran Trips in St Maarten and surrounding islands.

5.0
$215person
Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull
Sailing in Simpson Bay · 10 guests

Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

5.0
$131hour
Discover St Maarten on this beautiful catamaran
Sailing in Upper Prince's Quarter · 12 guests

Discover St Maarten on this beautiful catamaran

5.0
$1,600day
Crewed sail catamaran for a comfortable and fun day at sea!
Sailing in Upper Prince's Quarter · 12 guests

Crewed sail catamaran for a comfortable and fun day at sea!

5.0
$1,450day
MoonDance 36' Catalina
Sailing in Simpson Bay · 6 guests

MoonDance 36' Catalina

4.7
$118hour
Mambo 40ft Sail Catamaran
Sailing in Simpson Bay · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500day
Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten
Sailing in Lowlands · 8 guests

Charter 47' Leopard Cruising Catamaran in Cupe Coy, Sint Maarten

5.0
$1,000day
25% off Luxury Catamaran Day Charter (All-inclusive) in St. Maarten
Sailing in Cole Bay · 10 guests

25% off Luxury Catamaran Day Charter (All-inclusive) in St. Maarten

New
$1,800day
Luxury Catamaran Charter around St Maarten, St Barth and Anguilla
Sailing in Upper Prince's Quarter · 14 guests

Luxury Catamaran Charter around St Maarten, St Barth and Anguilla

New
$2,200day
Private Catamaran Cruise in the beautiful Caribbean
Sailing in Upper Prince's Quarter · 16 guests

Private Catamaran Cruise in the beautiful Caribbean

New
$1,700day
The Best Day Sail in St. Maarten
Sailing in Simpson Bay · 30 guests

The Best Day Sail in St. Maarten

New
$129day
Immerse yourself in paradise on Earth!
Sailing in Simpson Bay · 8 guests

Immerse yourself in paradise on Earth!

New
$2,587day
Private Charters In Simpson Bay
Sailing in Simpson Bay · 30 guests

Private Charters In Simpson Bay

New
$3,300day
Cruising Catamaran Charter for Up to 65 People in St Maarten
Sailing in Simpson Bay · 65 guests

Cruising Catamaran Charter for Up to 65 People in St Maarten

New
$1,800day

Sailing Reviews in Sint Maarten

  1. CT
    Cassie
    Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

    We had a great experience with Garth and Byron! They shared lots of fun information about the island and we had a great day of snorkeling and sailing. Would definitely recommend for a group of 6-8 versus jumping on a big boat with lots of people.

  2. AW
    Angela
    Sailing Catamaran Trips in St Maarten and surrounding islands.

    Choose this boat!!! I booked an 8 hour PRIVATE charter to accommodate 18 people to celebrate my husband's 50th birthday. Upon booking, Captain Neal was immediately in contact and worked to meet all of my needs. A few things to note... * If you need transportation to the dock, the Captain can recommend * The catamaran is large, to board you'll arrive by a small shuttle boat * The boat is as pictured. There is a large upper deck, under shade, with lots of seating and a lounge pad that I did not see in the pictures when I booked. It was a welcomed surprise * The food was AMAZING!!!!!!! Literally everything prepared was delicious. No one asked for additional seasoning or condiments. Everyone had seconds. I belive we had Chef Andrew. One of the best meals of our trip. * Our mate was Anna. Excellent service. She kept a drink in everyone's hands at all times without having to be asked. Pro tip... bring tumblers for your drinks to avoid spills and melting ice. * Alcohol was premium, not rail * We were able to connect our devices to the speakers on the boat. Good sound system that you can hear all over the boat. Overall excellent charter. I highly recommend and would book again.

  3. FC
    Fallon
    Sailing Catamaran Trips in St Maarten and surrounding islands.

    I cannot say enough about our experience. When I say top notch service, captains, food and all the amenities…it was AMAZING! Book this boat if you are looking. Worth every penny. Unbelievable day on the water! This is the best way to see SM in just a day trip!

  4. DL
    Damione
    Crewed sail catamaran for a comfortable and fun day at sea!

    Was a great time and would do it again. Was my first time getting on a boat that was all for my party. Was a fun time. An experience of an lifetime!

  5. SS
    Shalonda
    Sailing Catamaran Trips in St Maarten and surrounding islands.

    Capt. Neil and his crew made my 35th Birthday yacht ride one to remember. We were able to play our music, take plenty of pictures and videos, get in the water and relax. Lunch was AMAZING😋. Everything was so good. I could not have asked for a better experience🧡🧡🧡🧡

  6. SG
    Stephanie
    Sailing Catamaran Trips in St Maarten and surrounding islands.

    Neil was an adept captain and this was the highlight of our experience during this trip to St Marten! Neil and Anna and Bob were very helpful and accommodating during our trip, even letting us DJ for a bit of the ride. Bob is a great chef and the food was incredible for lunch (which included barbecue ribs, roasted veggies, a seafood paella, and mahi mahi) while Anna kept our drinks full. The itinerary was well timed and kept the day moving right along. This would be a great addition to anyone’s itinerary, in particular for people looking for a more mellow and relaxing day trip.