Sint Maarten
Discover the ultimate 7-day sailing yacht itinerary from Sint Maarten, with stops in Anguilla, St. Barth’s, and hidden Caribbean island gems.
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 1: Arrival in Sint Maarten – Simpson Bay
- Arrive at Princess Juliana Airport (SXM)
- Transfer to the marina (Simpson Bay or Port de Plaisance)
- Welcome aboard, meet the crew, safety briefing, and settle in
- Optional short sail to Mullet Bay for a sunset swim
- Dinner onboard or at a local restaurant in Simpson Bay
Day 2: Sint Maarten to Anguilla (Road Bay)
- Breakfast on board
- Clear customs and sail to Road Bay, Anguilla (~2-3 hours)
- Afternoon swim/snorkel at Sandy Island or Prickly Pear Cays
- Explore Shoal Bay or relax on the beach
- Dinner on board or at da’Vida beachfront restaurant
Day 3: Anguilla – Little Bay and Meads Bay
- Morning swim/snorkel at Little Bay (cliff jumping available!)
- Cruise to Meads Bay – one of Anguilla’s best beaches
- Lunch at Blanchards Beach Shack or Jacala
- 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
- Boutique shopping or hike to Colombier Beach
- Dinner ashore at Bonito or Orega
Day 5: St. Barth’s – Colombier & Shell Beach
- Breakfast on board, then sail to Colombier Bay for snorkeling
- Beach picnic or return to Gustavia for lunch
- 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