Sailing Charters & Trips (Near You) 2024

Choose your sailing trip or private charter on Sint Maarten | Saint Martin – Monohull Sailing, Sail Catamaran

Below you find all sailing trips, tours and private charters. Choose your preferred company and enjoy a fun day on the water! You can now book each trip, tour or charter directly via We Are SXM at the best rate.

Book all charters directly on (We Are SXM) and enjoy an exclusive rate! Our rates are always guaranteed to be the lowest, so you don’t have to worry about overpaying. Plus, by booking with us, you’ll be contributing to the local economy. Don’t rely on big travel companies like TripAdvisor, GetYourGuide, or Viator – book with the locals at We Are SXM and keep your funds on the island.

If you already contacted a company directly make sure to mention (We Are SXM) in order to receive our exclusive rate!

Need help choosing which boat fits your party most, feel free to contact us.*

*Please do not delete the subject title for us to know which activity/service you inquire about.

Click on the “FREE ASSISTANCE” or “ASSISTANCE BY WHATSAPP” button below for us to help you find the perfect boat. For last minute requests WhatsApp is preferred.

Sailing Tours & Trips | Water Activities with Wind

12 Metre Regatta - St. Maarten/ St. Martin -America's Cup Sailing Challenge

The ultimate yachting challenge, crewing a real America’s Cup boat. A thrilling head-to-head battle between two genuine giants of the ocean -10%!

Renegades Luxury Catamaran Charter in St Martin, St Barths, Anguilla I

A family affair with Renegades! Sometimes when you go on vacation, the best experience is one that feels like you are traveling with friends.

Celine Charters - Enigma Lagoon 62 Luxury Catamaran - High-end Boat Excursion I

Captain Neil’s “Enigma”, a Lagoon 62 luxury catamaran will bring you around in full comfort. Shared boat trips Wednesday & Friday!

PyratZ Gourmet Sail - Private Charter, 4-Course Chef Lunch, Luxury, Hand Crafted Cocktails, Top-Class Service Google

Outstanding food, drinks and service on a very comfortable Catamaran. Your own yacht without the price tag, exclusive 10% discount dinner cruise!

Random Wind - Luxury Catamaran charter - Family friendly, high quality food and top shelf drinks! We Are SXM - Watersports

SXM is known as the friendly island and Random Wind has the Spirit of SXM. Enjoy a unforgettable Catamaran trip with 10% discount!

Sail The Phoenix - Luxury Day Charter Sint Maarten - Luxurious Catamaran Shared and Private Charter

Unwind with Guided Snorkeling, Home-cooked meals, & Exclusive Amenities! Exclusive 10% discount with promo WEARESXM!

Eagle Catamaran Tours - Boats - Sailing Cat - Day Trip, Sunset Tour, Private Charter

Lots of shared charter options for individuals or groups, around the island of SXM, or to St. Barth’s or Anguilla! FREE TAXI SERVICE

Blue Pelican Boat Charter - Scarab 32 Sport with 2 Mercury Verado 300 engines I

Discover the essence of St. Maarten with Aqua Mania Adventures: pristine dives, breathtaking beaches, and unforgettable moments.

No1SXM Sailing Excursion - Day, Sunset or Private Sail trip - Only on the wind energy, a calming day on the water I

Mirian & Pieter are lifelong sailors, making this a business of passion! Day Sail, Tintamarre Sail or Sunset Sails starting from Nowhere Special.

Spellbound Charter - Small groups only, Custom Trips, groupm private, overnight and cruise ship charters

Scheduled tours, private and overnight charters. Family-friendly and perfect for special events! Catering to Island & Cruise Ship Guests.

Voodoo Sailing - Sail Race - Regatta - Sailing Charter - Monohull Boat Rental with Captain

Join Andre & Sam on a relaxing sailing trip or actual sail race, the choice is yours. Have a magical experience on board this mono-hull.

Spirit of St. Maarten Intro - Day or Dinner Cruise PAGE

Board thist hand-built Brazilian wooden schooner. Full-Day Cruise or 4-Course Sunset at Sea & Dinner Cruise (SXM’s #1 Boat tour)

SXM Kiteschool - Professional Instructor Toon - Kite-Surfing Lessons - Equipment Rental - Orient Bay St Martin - St Maarten

Kitesurfing in Orient Bay; learn kiting within no time, and in a safe & comfortable environment with a Professional Intructors.

Private Catamaran Charters fleet:

Discover the best catamaran charters in Sint Maarten | Saint Martin for your next water adventure. Our catamarans are budget-friendly, and perfect for larger groups up to 28 passengers. With different types of catamarans to choose from and the best rates guaranteed, book your preferred catamaran today and explore the region in style.

Lagoon (62 FT)

Celine Charters - Enigma Lagoon 62 Luxury Catamaran - High-end Boat Excursion I

Day Charter SXM from $3800
Day Charter ANG from $3800
Day Charter SBH from $3800
Shared Charters from $215 p.p.

Maximum 24 Guests

Nautitech (40ft)

Be Happy, Nautitech 40 Open Sail Catamaran - Day Charter SXM I

Half-Day Charter from $1200
Day Charter SXM from $1500

Maximum 15 Guests

2022 Lagoon (43ft)

Luxury Sailing Catamaran Charter - Custom-made 2022 Lagoon 42FT

Sunset Charter from $ 1095
Half-Day Charter from $1895
Day Charter SXM from $2395
Day Charter ANG from $2795

Maximum 10 Guests

BRAND-NEW 45FT Leopard Sailing Catamaran from 2023

Half-Day Charter from $1600
Day Charter SXM from $2000
Day Charter ANG from $2290

Maximum 14 Guests

Sunkiss (38ft)

Sunkiss 38 FT - Luxury Catamaran - Day Charter, 3 Cabins, St. Barths Boat Rental, St. Martin, Anguilla - BVI

Half-Day Charter from $1000
Day Charter SXM from $1250
Overnight Charter from $2750

Maximum 8 Guests

Leopard (51FT)

Vogue - Leopard 51FT Luxury Power Catamaran Charter with lots of Water Toys I

Half-Day Charter from $1790
6H Charter from $2090
8H Charter from $2511

Maximum 14 Guests

Bali (45 FT)

Bali 45 FT Gourmet Sail - Private Charter, 4-Course Chef Lunch, Luxury, Hand Crafted Cocktails, Top-Class Service

Sunset Dinner Charter $2000
5H Charter SXM from $1800
Day Charter SXM from $2280
Day Charter ANG from $2640

Maximum 12 Guests

Mojito (44ft)

Boomerang Charter - Fun Catamaran trip/tour St. Martin-St. Maarten-Anguilla-St. Barths-including food and drinks!

Half-Day Charter from $1400
Day Charter SXM from $1750
Day Charter ANG from $2261

Maximum 16 Guests

Lagoon 450S (45 FT)

Lagoon 450S - 45 Feet Luxury Power Catamaran operated by Pyratz and including Gourmet Lunch

Sunset Dinner Charter $2000
5H Charter SXM from $1800
Day Charter SXM from $2280
Day Charter ANG from $2640

Maximum 12 Guests

Boomerang charter

Boomerang Charter - Fun Catamaran trip/tour St. Martin-St. Maarten-Anguilla-St. Barths-including food and drinks!

Day Charter SXM from $2620
Day Charter ANG from $3060
Day Charter SBH from $3325
Shared Charters from $145 p.p.

Maximum 30 Guests

No1SXM Sailing

No1SXM Sailing Excursion - Day, Sunset or Private Sail trip - Only on the wind energy, a calming day on the water I

Sunset Sail Charter $595
5H Day Sail Charter SXM $1150
Tintamarre Sail SXM $1400
Shared Charters from $55 p.p.

Maximum 14 Guests

Voodoo sailing

Voodoo Sailing - Sail Race - Regatta - Sailing Charter - Monohull Boat Rental with Captain, Food and Drinks

Private Sail Charter $500
Anguilla Day Sail $115 p.p.
Sunset Sail SXM $50 p.p.

Maximum 10 Guests

Sunreef (62ft)

Sunreef 62 - Luxury Catamaran - Caribbean Week Charter, 4 Cabins, St. Barths, St. Martin, BVI

Max 8 persons – From: $34,000 p/w