St. Maarten / St. Martin Sailing Blog

St. Maarten has one of the most active sailing communities of the Caribbean. Sailing charters or tours can be booked here year round, but many sail in with their own ship. Around the Simpson Bay Lagoon, one finds a variety of marinas, services and restaurants with dinghy harbors for hungry and thirsty sailors. Most famous are St. Maarten sailing events like the annual Heineken Regatta and the Caribbean Multihull Challenge. Let us keep you in the loop with this blog!

boats on the water for the heineken regatta

August 13, 2026

Caribbean Sailing Association Launches New Five-Year Racing Calendar for Region

Five year outlook, new Caribbean Trophy   This week, the Caribbean Sailing Association (CSA) launched a five-year racing agenda. This provides the five major Caribbean regattas with an overview to plan ahead. Additionally, it makes the agenda more concentrated, so

Dive Sint Maarten padi certified courses

August 3, 2026

ACTIVITY OF THE WEEK: DIVE SINT MAARTEN

Explore the island’s unique dive sites!     Dive Sint Maarten is a professional dive center offering a comprehensive range of services, including fun dives and PADI dive courses and tours. With the highest quality of professional dive gear, equipment,

July 10, 2026

How Long Should Your St. Maarten Getaway Be? What Timeframe Should You Book?

If you are planning a St. Maarten holiday, one of the most frequently asked questions is how long you should book your stay to really get to know the island. The short answer is that most visitors choose to spend around

Auction items June collage

July 1, 2026

The St. Maarten Auction July Specials!

The St. Maarten Auction July Specials! | St. Maarten / St. Martin   Looking for something exciting to do this month? Let us help you plan the perfect escape!   Discover a curated selection of incredible auction items, starting at

June 8, 2026

Activity Of The Week: Full Day Gourmet Sailing with Pyratz Gourmet Sailing

Pyratz Gourmet Sailing offers the ultimate catamaran experience, blending the timeless pleasure of sailing with refined gastronomy on a full day of gourmet sailing. Designed for travelers who prefer elegance over crowds, their cruises are limited to just eight guests,

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