St Martin Sailing Holidays

St. Martin Route


Welcome to St Martin Sailing Holidays

St. Maarten has extraordinary beautiful sailing possibilities. You could spend your sailing holidays in St. Maarten exploring the northern Leeward Islands spending your days sailing and sojourning ashore to shop, sightsee, and eat in various restaurants. You can also have a mix of long and short passages giving you the opportunity to sail farther south to picturesque islands like St. Kitts, Nevis, and Antigua. Combining the Caribbean waters with islands, fair winds, and pleasant days of island-hopping, a sailing holiday in St. Maarten offers a variety of possibilities depending on you.

“I had the best time and probably the best vacation of my life sailing in Greece with Sailing Nations. Met some super nice people and the holiday was chilled and well organized, there was a bit of everything for all different tastes and moods: swimming, relaxing, hiking, sailing, partying, etc. The skippers were experienced which made me feel safe and I would recommend it to everyone, either if you are a sailor or not, you will not regret it! Would do it again for sure!” – Mariana, Switzerland

Example Itinerary

This is an example itinerary. Actually itinerary might differ depending on the wind and weather.

Marigot Bay

As your sailing holiday begins, you start by traveling to Orient Bay to port. Hidden behind two cays, lies the entrance where you are able to enjoy lunch. A little further north is Tintamarre, another nice port, with both areas offering great beaches. Grand Case Bay is usually a pleasant anchorage for the night as it is home to a wide selection of good restaurants and lively bars. It is also home to Creole Rock, which offers superb snorkeling adventures. The port of Marigot is always bustling so if you’d like, you can anchor there and enjoy the nightlife.

Road Bay

 A lower island known for its scuba diving, restaurants, and laid-back Caribbean charm, Road Bay is one of the most pleasant areas in northern Leeward Islands. Furthermore, serving as a port for cruising yachts, it is a great place to go ashore for dinner. Not far away is Sandy Island, one of the many off-lying areas in Anguilla that is protected as a marine reserve. Sandy Island is a good choice for an afternoon spent swimming or snorkeling.

Crocus Bay

Next stop leads you out to Prickly Pear Cays, part of Anguilla’s marine park. These tiny islands offer a good lunch stop in warm weather perfect for a swim or snorkeling along the reef. If you anchor off the south side of East Prickly Pear, you’ll get the chance to see seabirds nesting in the craggy cliffs, a pristine white-sand beach along the cay, and the dazzling colors of the ocean. Go ashore along the north side of the island, enjoy a stroll while listening to the “whistling rocks” as they fall in rhythm with the waves. Going back to the main island will take you to scenic Crocus Bay where you can anchor for the night and explore.

Orient Bay

You may have stopped for lunch here on your first day of your sailing holiday in St. Maarten. It definitely warrants a longer stop as Orient Bay offers two good anchorages, shore side attractions, and plenty of watersports to pass your time.


Next up, you travel to one of the prettiest locales in the Northern Leewards, St. Barts, officially known as St. Barthemey. On the way, stop for some lunch and snorkeling at the privately owned Ile Fourchue, a small, hilly isle off the coast. The picturesque waterfront town of Gustavia is less than two hours away where you can stop and explore.

Anse de Colombier

Steep hills overlook the blue waters of the picture-perfect bay of this stop. A nearby village is situated and is well-worth the hike as you will get a stunning view of surrounding islands, as well as great opportunities to snorkel, swim, sunbathe, and relax.

Great Bay

Philipsburg, the Dutch Capital of St. Maarten, is a thriving waterfront port with a lively nightlife, interesting shops, excellent restaurants, and casinos. There is also a beach boardwalk lined with restaurants worthy of a stroll before you decide where you want to stop for dinner on the last evening of your sailing holiday in St. Maarten.

What's included

  • 7 day yacht rental
  • Dinghy and Outboard engine with gasoline
  • Fully insured Yachts
  • Gas for the kitchen
  • Safety equipment
  • Sheets, blankets & towels
  • GPS & nautical charts
  • Final cleaning
  • Stereo with speakers
  • Tourist taxes
  • Tour planing and administration
  • A fully featured yacht with everything you need for amazing sailing holidays
  • A professional Skipper that will sail you to remote islands and amazing villages
  • Sun, sail, friendships, and unforgettable memories

What's excluded

  • Please bing EUR 150 / USD 170 in cash for a cruising kitty to cover variable cost of Food, Water, Gas, Marina fees
  • Advisable to bring some spending money if you want to go out in the evenings.
  • Flights and transportation to base

Arrival / Departure

Latest embarkation in on Saturday at 4:00 PM
Disembarkation is on Saturday at 9:00 AM

Visa Information

If you need a visa or not really depends on the country. You can see a list of requirements here.

Getting There

Princess Juliana International Airport (IATA: SXM, ICAO: TNCM) (also known as Saint Maarten International Airport)

These are great portals for finding flights:
These are great portals for finding accommodation:

Ready to go?

See below for our individual rates for both our Monohulls and Catamaran yachts.

Currently there are no events scheduled for this destination.

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