Sint Maarten

Embark on an unforgettable week-long sailing adventure around the pristine waters of Sint Maarten, Saint Martin and their neighboring Caribbean gems. This 7-day luxury yacht charter itinerary blends serene anchorages, world-class beaches, vibrant island culture, and upscale dining, all at your own pace. From the laid-back charm of Anguilla to the chic sophistication of St. Barth’s, each day offers a new horizon to explore. Whether you're snorkeling secluded coves, sipping cocktails at sunset, or discovering hidden beaches only accessible by boat, this itinerary promises the perfect balance of relaxation and exploration.

Day O: Pre Game

• Good hotel options if you decide to arrive a few days early...The Morgan Resort (https://www.themorganresort.com) in Simpson Bay, Sint Maarten and Hommage Hotel in Marigot, Saint Martin

Day 1: Arrival in Sint Maarten – Simpson Bay

• Arrive at Princess Juliana Airport (SXM)
• Transfer to Simpson Bay Marina - an airport taxi is a good option, and tender works too!
• Welcome aboard, meet the crew, safety briefing, and settle in
• Options: a shopping trip to Philipsburg (Holland House for cocktails), a swim in the Marina pool next to the docks, or get going with a short sail to Mullet Bay for a sunset swim!
• Dinner onboard or at a local restaurant in Simpson Bay (the burgers are amazing at The Tap & Still, a five minute walk from the dock)

Day 2: Sint Maarten to Anguilla (Road Bay)

• Breakfast on board - and check the bridge times to plan your exit from Simpson Bay
• Clear customs and sail to Road Bay, Anguilla (~2-3 hours). You will pass Marigot and Grand Casse - both good options for a stop, if you have the time
• Afternoon swim/snorkel at Sandy Island or Prickly Pear Cays (both have great beach bars!)
• Explore Shoal Bay or relax on the beach
• Dinner on board or at da’Vida beachfront restaurant

Meads Bay in Anguilla

Day 3: Anguilla – Little Bay and Meads Bay

• Morning swim/snorkel at Little Bay (cliff jumping available!)
• Cruise to Rendezvous Bay – one of Anguilla’s best beaches
• Lunch, drinks and music at Sunshine Shack (https://sunshineshack.net) or Bankie Banks (https://www.bankiebanx.net)
• Paddleboard or kayak in the calm bay
• Sunset cocktails and BBQ dinner on board

Day 4: Anguilla to St. Barth’s (Gustavia)

• Early morning sail to St. Barth’s (~4-5 hours)
• Check-in at Gustavia and explore the chic harbor town, take a taxi to see the craziest airport runway in the world!
• Boutique shopping or have a music and "boozy" lunch at Nikki Beach (https://nikkibeach.com/saint-barth/)
• Dinner ashore at Bonito or Orega

Gustavia Saint Barthélemy

Day 5: St. Barth’s – Colombier & Shell Beach

• Breakfast on board, then sail to Colombier Bay for snorkeling - much calmer than Gustavia
• Beach picnic and afternoon swim at Shell Beach
• Optional: beach party at Shellona or sunset cocktails
• Night onboard or evening out in Gustavia

Day 6: St. Barth’s to Tintamarre & Pinel Island

• Morning sail to Tintamarre Island (a nature reserve near St. Martin)
• Snorkeling with turtles and a natural clay mud bath
• Continue to Pinel Island for lunch and beach time
• Try Yellow Beach or Karibuni restaurants
• Anchor overnight in Orient Bay

Day 7: Return to Sint Maarten (Marigot or Simpson Bay)

• Leisurely breakfast, swim, and paddleboard in Orient Bay
• Day at sail, waterskiing or on an e-foil
• Return sail to Simpson Bay Lagoon (~2-3 hours)
• Final night BBQ dinner

Day 8: Departures

• Final breakfast onboard
• Disembark by mid-day, potentially enjoy the local harbor for the day and night