European, 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, unspoilt 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

Oyster Pond 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

Start your St. Martin sailing holiday in our base at Captain Oliver’s Marina at Oyster Pond. Nestled amidst verdant hills between the Dutch and French sides of St. Martin, this protected lagoon is the perfect spot to launch your bareboat holiday. 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.

Discover Grand Case

Get your adrenaline pumping

Take a stroll to Le Petite Bay at the far end of Grand Case Bay and you’ll find an array of water sports available from Creole Rock, including snorkelling, paddleboating, water skiing and kayaking.

Suggested lunch spots

Less than three miles from St. Martin, tiny, deserted Tintamarre is the perfect spot to lunch. Snorkel on the east coast or head to lovely Baie Blanche on the west coast.

Day 2

Grand Case to Road Bay, Anguilla

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

Today you’ll sail from Grand Case into the Anguilla Channel, skirting the southwestern coast of Anguilla and heading for 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 colourful fish and corals that are perfect for snorkelling 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 on paradise Sandy Island, a spit of white sand floating serenely off the coast of Anguilla.

Day 3

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 4

Crocus Bay to Orient Bay, St. Martin

The day's sailing

3.5 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

Skirt the southern tip of Anguilla and set sail across the Anguilla Channel back to St. Martin. With Tintamarre portside, 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 of Orient Bay 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 colourful fish, while the bright white strip of sand is fringed with quietly swaying palms.

Suggested lunch spots

Just off St. Martin’s coast, Green Cay offers spectacular snorkelling opportunities. Alternatively, stick to land and enjoy the butterflies and tropical rainforest atmosphere of The Butterfly Farm.

Day 5

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

Today you’ll enjoy a stretch of blue water sailing across the Saint-Barthélemy Channel. 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 harbour, 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 6

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 7

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

Point your bow toward Saint-Barthélemy Channel and enjoy a few hours of blue water sailing. 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 8

Philipsburg to Oyster Pond

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

It’s just a quick hop from Philipsburg to our base at Oyster Pond, so make use of your extra time to enjoy Oyster Pond and the many restaurants on offer here. Relax in the warm Caribbean sun and enjoy your last day of sailing before arriving at Captain Oliver’s Marina and enjoying a cocktail or fresh seafood for your final Caribbean lunch.