Sinner or Saint Martin 8-day Caribbean Nude Gay Sailing. Whether you’re feeling more saint or sinner this week is entirely up to you - and honestly, by middle of the week most of our guests have tried both. St. Martin’s split French-Dutch personality practically demands it: a little devotion to Orient Bay’s bare beaches, a little penance at Sunday brunch, and a whole lot of temptation hopping between the French and Dutch halves of the island and chic St. Barth. Confession is optional. Clothing is too.

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 gay sailing adventure.

St.Maarten Caribbean Nude Gay Sailing Itinerary

Day 1 - All Aboard in Anse Marcel — Still On Your Best Behavior
• Embarkation:
Settle into your catamaran at Anse Marcel Marina after 18:00.

• Welcome Drinks & Briefing:
Toast the week ahead with welcome cocktails as the crew runs through the boat, safety basics, and the route.

• Attractions:
Explore Anse Marcel’s sheltered bay and beach, then turn in early - sainthood lasts exactly one more day.

• Travel Tip:
Fly to Princess Juliana International Airport (SXM) (directly from Europe or Americas), then grab a taxi or pre-order transfer to Marina Anse Marcel (40-45 min ride).

Day 2 - Anse Marcel to Orient Beach, St. Martin
• Morning:
Set sail down St. Martin’s northeast coast, stopping at Île Pinel - or, if conditions favor it, remote Tintamarre - for a lunch break before continuing on to Orient Bay.

• Gay/Nude Beaches:
Orient Bay, anchoring off the beach’s long-established clothing-optional stretch, with a beach bar still pouring frozen drinks for naturists.

• Evening:
Sunset drinks and dinner on deck, night at anchor.

Day 3 - Orient Beach to Gustavia, St. Barth
• Morning:
Cross the channel southeast to Île Fourchue, an uninhabited nature-reserve islet off St. Barth’s north coast, for a snorkel stop in its sheltered volcanic bay.

• Afternoon:
Continue on to Gustavia, St. Barth’s chic little capital - boutique-lined streets straight out of the French Riviera, with a harbor-side terrace made for a long lunch and watching the shopping bags go by.

• Attractions:
Spend the afternoon poking around the harbor front and its yacht-watching cafes, then settle in for cocktail hour on deck as the sun goes down.

Day 4 - Round the Island to Anse de Gouverneur & Anse de Colombier
• Morning:
Sail south around St. Barth’s dramatic coastline to Anse de Gouverneur, on the island’s south shore.

• Gay/Nude Beaches:
Anse de Gouverneur, where clothing is tolerated as optional toward the beach’s far ends.

• Afternoon:
Continue anti-clockwise around the island to Anse de Colombier for the night - snorkel or dive in search of sea life, go on a sunset or next early morning hike.

Day 5 - Colombier back to Philipsburg, Sint Maarten
• Morning:
Cross northwest from Colombier back to St. Martin, anchoring in Great Bay off Philipsburg on the Dutch side.

• Attractions:
Stroll the Great Bay boardwalk and Front Street’s shops and bars, or climb to Fort Amsterdam for views over the bay.

• Optional Activity:
Snorkel or paddleboard off Great Bay Beach.

Day 6 - Philipsburg via Maho Beach to Cupecoy
• Morning:
Sail west along the Dutch coastline, stopping just off Maho Beach to watch jets roar in low over the water on final approach to Princess Juliana Airport.

• Afternoon:
Continue to Cupecoy, anchoring off its cliff-framed coves for the afternoon.

• Gay/Nude Beaches:
Cupecoy’s clothing-optional beach, with its nude section toward the far western end and a long-time LGBTQ+ following.

Day 7 - Cupecoy to Anse Marcel
• Homeward Bound:
Sail north back up St. Martin’s western coastline toward Anse Marcel.

• Lunch Stop:
Drop anchor off Grand Case, the island’s gourmet capital, for a relaxed lunch ashore.

• Last Night Aboard:
Toast the week’s adventures with one final sunset on deck after tying up at Anse Marcel Marina.

Day 8 - The Morning After in Anse Marcel - Sinner Confirmed
• Bittersweet Goodbye:
Disembark before 09:00, sun-kissed, a little sad it’s over, and no longer eligible for sainthood.

• Walk of Fame:
Say farewell to your fellow sailors - bound together by a week’s worth of sunshine, saltwater, and stories best left unconfessed.

• Onward Travels:
Head out to explore the rest of St. Martin, or make your way to the airport with a ton of new memories and connections.

• Safe Travels
Safe travels, and thank you for sailing bare with us!

This itinerary is subject to change. Local circumstances such as weather may influence the itinerary.