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All listings in Simpson Bay

Great sailboat rentals near Simpson Bay, Sint Maarten.

Page 1 of 115 listings

Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends
Sailing in Simpson Bay · 20 guests

Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends

5.0
$1,957/day
Private Luxury Catamaran Day Charter (All-inclusive) in St. Maarten
Sailing in Cole Bay · 10 guests

Private Luxury Catamaran Day Charter (All-inclusive) in St. Maarten

5.0
$2,395/day
Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten
Sailing in Cole Bay · 12 guests

Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten

5.0
$1,500/day
Luxury Catamaran Trips in St Maarten and Surrounding Islands
Sailing in Simpson Bay · 22 guests

Luxury Catamaran Trips in St Maarten and Surrounding Islands

5.0
$475/hour
The Best Day Sail in St. Maarten
Sailing in Simpson Bay · 30 guests

The Best Day Sail in St. Maarten

5.0
$129/day
Mambo 40ft Sail Catamaran
Sailing in Simpson Bay · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500/day
Boat tour Sailboat 40 feet Saint Martin
Sailing in Marigot · 6 guests

Boat tour Sailboat 40 feet Saint Martin

New
$140/hour
Sailing Catamaran Amari - Overnight Charter All Inclusive Fully Crewed
Sailing in Simpson Bay · 6 guests

Sailing Catamaran Amari - Overnight Charter All Inclusive Fully Crewed

New
$3,360+/night
Adventures in the Caribbean
Sailing in Simpson Bay · 10 guests

Adventures in the Caribbean

New
$500/hour
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

5.0
$1,800/day
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
$1,200/day
Sailing in the Caribbean St. Martin
Sailing in Marigot · 10 guests

Sailing in the Caribbean St. Martin

New
$1,087/day
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
$1,000/day
Private Charters In Simpson Bay or Philipsburg
Sailing in Simpson Bay · 30 guests

Private Charters In Simpson Bay or Philipsburg

5.0
$3,300/day
Tours & weekly rentals Bahia 46 (Fountaine Pajot)
Sailing in Marigot · 12 guests

Tours & weekly rentals Bahia 46 (Fountaine Pajot)

New
$217/hour

Sailing Reviews in Simpson Bay

  1. DC

    DeAvionne

    Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten

    Garth's boat was an amazing experience! My friends and I had such an enjoyable sail, thanks to Ross and Byron, who made us feel so welcome and comfortable. Their exceptional service ensured that our trip was tailored to the activities we wanted to do, and they truly went above and beyond. The boat was absolutely beautiful, and the captains felt like family by the end of the trip. We can’t wait to sail with them again whenever we’re back in SXM!

  2. khadijah

    khadijah

    Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends

    Overall great experience. Communication could have been better but overall my crew had an amazing time. Drinks were good staff was friendly. They took us to Anguilla and we pretty much had a private beach and pool experience and amazing food. Best day of our trip.

  3. LG

    Lesli

    Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends

    Ludo and Tom were great! Seas were a little rough but you could tell Ludo had experience with this as the way he navigated the boat minimized the rocking. Tom was a great host and always made sure we were taken care of! I would highly recommend this team!

  4. Mark

    Mark

    Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends

    Communication could have been a little better with the captain before our trip but once on board David and Stephanie were awesome. Definetly 5 star service. The snacks and wide variety of alcohol and soft drink choices were excellent. Would book again for sure!

  5. JF

    Joanna

    Private Luxury Catamaran Day Charter (All-inclusive) in St. Maarten

    We had an amazing time! The catamaran is clean, spacious and beautiful. The captain and Diane were the best and took very good care of us! The drink options available were good!! The light breakfast and lunch served were fresh and delicious! I highly recommend them, don't hesitate to book!

  6. AW

    Angela

    Luxury 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.