St. Martin Sailing Itinerary

Fancy an adventure with long, challenging sails and wide-open Caribbean waters? Or maybe just a quick hop to a deserted island? Or a taste of Caribbean culture with a dash of designer shopping thrown in? Whatever your wish, the seductive sailing of a St. Martin charter vacation offers you the ultimate in flexibility.

Ready to set sail? Browse our suggested St. Martin itineraries, pick the perfect time to sail, and secure your dream St. Martin yacht charter today. Questions? Our team is just a call away to assist you!

Please note: Moorings and marinas may have an associated fee dependent on location. 

7 Day St. Martin Bareboat Itinerary

Day 1

Marina Fort Luis to Grand Case, St. Martin

Start your St. Martin sailing holiday in our base at Marina Fort Luis in Marigot. Located 20 minutes from the airport and surrounded by many great restaurants and shopping, this is the ideal place to start your sail.

The day’s sailing

• 1 Hr Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.

Day 2

Grand Case to Orient Bay, St. Martin

Less than three miles from St. Martin, tiny, deserted Tintamarre is the perfect spot to enjoy lunch on the boat. With Tintamarre portside, then head to the eastern coast of St. Martin towards lively Orient Bay. The bay is caressed by a two-mile-long white sand beach and protected by a reef, making it perfect for the numerous water activities that you’ll find here. Enjoy dancing to live music or relax on a sun lounger—Orient Bay has something for everyone.

The day’s sailing

• 1 Hr Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.

Day 3

Orient Bay to Gustavia

Point your bow toward Saint-Barthélemy Channel and enjoy a few hours of blue-water sailing. Anchor at glamorous Gustavia, on St. Barts’ east coast, and head ashore for the chic French atmosphere and delectable cuisine. Explore this red-roofed Caribbean capital and hit the numerous historic sites that line the harbor, stopping for lunch at any of the fine French restaurants.

The day’s sailing

• 3 Hr Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.

Day 4

Gustavia to Anse de Colombier

Cruise north from Gustavia along St. Barts’ coast to the ethereal turquoise waters of Anse de Colombier. Part of St. Barts Marine Reserve, the shallow reefs around Anse de Colombier are perfect for snorkeling with turtles, rays, and even dolphins. The beach is known for its seclusion, only accessible by sea or a 20-minute walk from the main road.

The day’s sailing

• 1 Hr Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.

Day 5

Anse de Colombier to Philipsburg

Today your destination is Philipsburg, St. Martin’s lively Dutch capital. This bustling town is alive with chic boutiques, vibrant nightlife, and a cosmopolitan atmosphere. Famous for shopping, you’ll find everything from designer shops to local boutiques and world-class duty-free shopping.

The day’s sailing

• 2 Hr Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.

Day 6

Philipsburg to Road Bay, Anguilla

Today you’ll sail to bustling Road Bay. One of the most popular anchorages in the Leeward Islands, Road Bay is vibrant yet laid back and unpretentious. You’ll find a beautiful stretch of white sand beach decorated with lovely, relaxed restaurants and bars. Anguilla is known as the wreck diving capital of the Caribbean, with seven sunken wrecks home to colorful fish and corals that are perfect for snorkeling and scuba diving.

The day’s sailing

• 4 Hr Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.

Day 7

Road Bay to Crocus Bay, Anguilla

Cruise along the spectacular coast of Anguilla from Road Bay to Crocus Bay. Backed by lush greenery and soft white sand tumbling to the turquoise Caribbean, Crocus Bay is famous for its beautiful sunsets. Spend the day collecting seashells from the pristine white sands and in the evenings sip a rum punch and watch the blazing sun sink over the water.

The day’s sailing

• 0.5 Hr Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.

Day 8

Return to the base – Marigot

Time to head back to the base. Once you arrive relax in the warm Caribbean sun and enjoy your last day of sailing before arriving at Marina Fort Louis and enjoying cocktails or fresh seafood for your final Caribbean lunch.

The day’s sailing

• 2 Hr Sailing time

To be used as a guide only. Based on suggested sailing lanes and average wind speed for the area.

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