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European heritage, Caribbean charm

From short, relaxing island hops to open, blue water cruising, sailing St. Martin is as diverse as the split personality of the island itself. Half Dutch, half French, St. Martin offers that perfect combination of chic European sophistication and laid-back Caribbean charm.

Explore remote, untouched islands, dive kaleidoscope reefs and underwater shipwrecks and relax on white sand beaches. Delectable food, pristine anchorages and enchanting island culture are waiting for you on your St. Martin bareboat sailing adventure.

St. Martin itinerary

8
Days

Highlights

  • Designer shopping
  • Wreck diving Anguilla
  • Watersports at Creole Rock
  • Grand Case’s French cuisine
  • Snorkelling with colourful tropical fish
  • Secluded beaches, seductive coastline
Day 1

Marina Fort Luis to Grand Case, St. Martin

The day's sailing

1.5 hr
Sailing time

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

Suggested activities

  • Shopping Shopping
  • Sunbathing Sunbathing
  • Exploring Exploring
Marina Fort Luis - 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.

Discover Grand Case

Spend Your Day

Head north along the island’s seductive coastline to Grand Case, the gourmet capital of the Caribbean. Indulge in a decadent French or Creole-inspired meal, capping off the day with a sip of local rum as you watch the sun set on the horizon.

Suggested lunch spots

Enjoy a swim and a local lunch at the “Lolo’s”. Take the dinghy and go to Creole Rock for a some nice snorkeling. Grand Case is small village with her large bay with crystal clear water and a long beach.

Day 2

Grand Case to Orient Bay, St. Martin

The day's sailing

2.5 hr
Sailing time

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

Suggested activities

  • Shopping Shopping
  • Sunbathing Sunbathing
  • Exploring Exploring

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.

Discover Orient Bay

Seek serenity

Head north and you’ll find the quieter, more family friendly Friar’s Bay. Here the gently rolling waves of the bay are warm and filled with colorful fish, while the bright white strip of sand is fringed with quietly swaying palms.

Day 3

Orient Bay to Gustavia

The day's sailing

2.5 hr
Sailing time

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

Suggested activities

  • Shopping Shopping
  • Sunbathing Sunbathing
  • Exploring Exploring

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.

Discover Gustavia

Culture in glamorous Gustavia

Explore the 17th century forts that line the harbour, from Fort Karl in the north to the lighthouse and cannons of Fort Gustaf in the south. Near Fort Gustaf is Shell Beach, a popular spot for beachcombers seeking beautiful seashells.

Suggested lunch spots

Drop anchor at tranquil Ile Fourchue and enjoy a picnic on board in the clear, calm Caribbean waters.

Day 4

Gustavia to Anse de Colombier

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 area.

Suggested activities

  • Shopping Shopping
  • Sunbathing Sunbathing
  • Exploring Exploring

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 snorkelling 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.

Discover Anse de Colombier

Swimming with dolphins

An important part of the St. Barts Marine Reserve, Anse de Colombier is perfect for snorkelling with colourful tropical fish, turtles, rays, lobster and even dolphins.

Day 5

Anse de Colombier to Philipsburg

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 area.

Suggested activities

  • Shopping Shopping
  • Sunbathing Sunbathing
  • Exploring Exploring

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.

Discover Philipsburg

Designer shopping

Stroll Front Street, the mile-long shopping street fringed with palm trees and filled with an array of designer and boutique shops.

Day 6

Philipsburg to Road Bay, Anguilla

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 area.

Suggested activities

  • Shopping Shopping
  • Sunbathing Sunbathing
  • Exploring Exploring

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.

Discover Road Bay

Local rum and golden sun

Sit back and enjoy live jazz music on the beach while sipping a local rum cocktail as the golden sun sets over the water

Suggested lunch spots

Sample fresh lobster, crayfish or snapper at one of the beachside restaurants Sandy Island, a spit of white sand floating serenely off the coast of Anguilla.

Day 7

Road Bay to Crocus Bay, Anguilla

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 area.

Suggested activities

  • Shopping Shopping
  • Sunbathing Sunbathing
  • Exploring Exploring

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.

Discover Crocus Bay

Snorkelling caves and reefs

On the eastern edge of the bay you’ll find spectacular snorkelling, with the cliffs and caves along the shoreline filled with colourful fish.

Suggested lunch spots

Stop for lunch at Prickly Pear Cays, just six miles north of Road Bay, for a beautiful white sand beach crowned by coral reefs teeming with colourful fish.

Day 8

Return to the base – Marigot

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 area.

Suggested activities

  • Shopping Shopping
  • Sunbathing Sunbathing
  • Exploring Exploring
Marigot Bay

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 cocktail or fresh seafood for your final Caribbean lunch.