We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

All listings in Sint Maarten

Incredible sailboat rentals in Sint Maarten, Sint Maarten.

Page 1 of 117 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
Best of 2023
$1,957day
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
$230person
Sail Ocean Science, Instructional Sailing Trips, Book a Cabin or the boat.
Sailing in Simpson Bay · 10 guests

Sail Ocean Science, Instructional Sailing Trips, Book a Cabin or the boat.

New
$950person
Discover St Maarten on this beautiful catamaran
Sailing in Upper Prince's Quarter · 15 guests

Discover St Maarten on this beautiful catamaran

5.0
$1,750day
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
$1,500day
Mambo 40ft Sail Catamaran
Sailing in Simpson Bay · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500day
The Best Day Sail in St. Maarten
Sailing in Simpson Bay · 30 guests

The Best Day Sail in St. Maarten

5.0
$129day
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
$1,200day
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
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
Private Charters In Simpson Bay or Philipsburg
Sailing in Simpson Bay · 30 guests

Private Charters In Simpson Bay or Philipsburg

5.0
$3,300day
MoonDance 36' Catalina
Sailing in Simpson Bay · 6 guests

MoonDance 36' Catalina

4.7
$1,000day
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
Immerse yourself in paradise on Earth!
Sailing in Simpson Bay · 8 guests

Immerse yourself in paradise on Earth!

New
$1,359day
Private Catamaran Cruise in the beautiful Caribbean
Sailing in Upper Prince's Quarter · 16 guests

Private Catamaran Cruise in the beautiful Caribbean

New
$2,000day
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

Top Destinations Nearby

Sailing Reviews in Sint Maarten

  1. DV

    Diamond

    Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends

    Look no further- Book Today! The boat is super fabulous, the Captain is so friendly and nice and Rebecca makes the best drinks. They cater to your every need and make your trip so memorable. We truly had a blast!!

  2. RB

    Roberto

    Mambo 40ft Sail Catamaran

    Peofessional, friendly, easy going crew with all goodies on board. We had a day to remember!!!

  3. DS

    Dana

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

    I celebrated my 36th birthday with 7 of my close friends and family. This experience was a real treat! We had an unforgettable trip to Anguilla filled with great vibes, great food, unlimited drinks, paddle boarding, snorkeling, and more. 11/10

  4. ME

    Meschel

    The Best Day Sail in St. Maarten

    Great experience! Highly recommend!

  5. 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!

  6. 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!