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All listings in Simpson Bay

Great sailboat rentals near Simpson Bay, Sint Maarten.

Page 1 of 117 listings

SCHAEFER V33 Luxury speedboat 34ft charter from Marigot
Powerboats in Marigot · 8 guests

SCHAEFER V33 Luxury speedboat 34ft charter from Marigot

5.0
$171hour
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
Best of 2023
$1,925day
LEOPARD POWERCAT 51ft 2018 from Marigot
Powerboats in Marigot · 12 guests

LEOPARD POWERCAT 51ft 2018 from Marigot

New
$406-$481hour
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
$2,395day
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
$215person
Boat tour Sailboat 40 feet Saint Martin
Sailing in Marigot · 6 guests

Boat tour Sailboat 40 feet Saint Martin

New
$165person
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
$132hour
Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten
Sailing in Cole Bay · 16 guests

Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten

New
$1,500day
Mambo 40ft Sail Catamaran
Sailing in Simpson Bay · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500day
Private Charters In Simpson Bay or Philipsburg
Sailing in Simpson Bay · 30 guests

Private Charters In Simpson Bay or Philipsburg

5.0
$3,300day
LAGOON 51FT 2023 - SAILING CATAMARN - CHARTER FROM MARIGOT
Sailing in Marigot · 12 guests

LAGOON 51FT 2023 - SAILING CATAMARN - CHARTER FROM MARIGOT

New
$487-$803hour
MoonDance 36' Catalina
Sailing in Simpson Bay · 6 guests

MoonDance 36' Catalina

4.7
$1,000day
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
Opera Yacht 60' boat charter in St Martin
Powerboats in Marigot · 30 guests

Opera Yacht 60' boat charter in St Martin

New
$5,000day
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
$1,337day
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 Simpson Bay

  1. 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!

  2. 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!

  3. 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.

  4. FC

    Fallon

    Luxury 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!

  5. SS

    Shalonda

    Luxury 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

    Luxury 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.