7-Day Philipsburg Yacht Charter Itinerary: St. Maarten & Anguilla Exploration
Embark on a captivating Philipsburg yacht charter, a journey through the vibrant dual-nation island of St. Maarten and its tranquil neighbour, Anguilla. Imagine waking to the gentle lapping of waves against your hull, the Caribbean sun warming your skin as you prepare for a day of exploration. This Philipsburg yacht charter itinerary promises a blend of lively island culture, exquisite dining, and the serene beauty of secluded coves. Discover hidden gems, snorkel in crystal-clear waters, and savour the unique charm of these Leeward Islands.
Cruising region: Caribbean Yacht Charter
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Plan this charter
- First planned stop
- Philipsburg, St. Maarten
- Final planned stop
- Simpson Bay, St. Maarten
Shore plans to discuss with your crew
- Day 1Duty-free shopping on Front Street
- Day 1Relaxing on Great Bay Beach
- Day 1Visiting the historic Fort Amsterdam
- Day 1Sampling local Dutch Caribbean cuisine
- Day 2Gourmet dining at waterfront restaurants
- Day 2Strolling along Grand Case Beach
Confirm joining and departure ports, yacht availability and the daily passage plan before paying a deposit. The captain decides anchorages and any route changes for weather, sea conditions and local restrictions. Shore venues, marine-park permissions and activity bookings require separate confirmation.
Map connections are schematic, not a navigable passage plan. Distances, safe approaches and passage times must be checked by the captain.
Ask for an itemised quotation covering the charter fee, taxes, APA or package expenses, berth charges and any delivery or redelivery costs.
- DAY 01
Philipsburg, St. Maarten
Begin your Philipsburg yacht charter adventure in the bustling capital of Dutch St. Maarten. Explore the duty-free shops along Front Street and soak in the vibrant atmosphere of Great Bay.
- Duty-free shopping on Front Street
- Relaxing on Great Bay Beach
- Visiting the historic Fort Amsterdam
- Sampling local Dutch Caribbean cuisine
- Anchorage
- Great Bay
- Dining
- Holland House Beach Hotel Restaurant
- DAY 02
Grand Case, St. Martin
Sail north to the culinary capital of the French side, Grand Case. Enjoy gourmet dining and the relaxed charm of this picturesque village.
- Gourmet dining at waterfront restaurants
- Strolling along Grand Case Beach
- Snorkelling in the calm bay
- Visiting local art galleries
- Anchorage
- Grand Case Bay
- Dining
- Le Pressoir
- DAY 03
Tintamarre Island
A short sail brings you to the uninhabited Tintamarre Island, part of the French Nature Reserve. Enjoy pristine beaches and excellent snorkelling.
- Swimming with sea turtles
- Relaxing on the secluded white sand beach
- Exploring the island's walking trails
- Bird watching
- Anchorage
- Tintamarre Bay
- Dining
- Onboard gourmet picnic
- DAY 04
Road Bay, Anguilla
Cross the border into Anguilla, clearing customs at Road Bay. This bay offers a lively atmosphere with beachfront bars and restaurants.
- Clearing customs into Anguilla
- Enjoying live music at 'Elvis' Beach Bar'
- Swimming and sunbathing on Road Bay Beach
- Sampling fresh seafood
- Anchorage
- Road Bay
- Dining
- Dolce Vita
- DAY 05
Little Bay & Crocus Bay, Anguilla
Anchor in the stunning Crocus Bay and tender to the tiny, secluded Little Bay, famous for its dramatic cliffs and excellent snorkelling.
- Snorkelling in crystal-clear Little Bay
- Cliff jumping (for the adventurous)
- Relaxing on Crocus Bay Beach
- Kayaking or paddleboarding
- Anchorage
- Crocus Bay
- Dining
- DaVida Restaurant Bayside Grill
- DAY 06
Sandy Ground, Anguilla
Return to Sandy Ground for a relaxed evening. This charming fishing village transforms into a hub of activity as the sun sets.
- Enjoying a 'rum punch' at a beach bar
- Watching the sunset over the harbour
- Dining at a casual beachfront eatery
- Shopping for local crafts
- Anchorage
- Sandy Ground
- Dining
- Jacala
- DAY 07
Simpson Bay, St. Maarten
Sail back to St. Maarten and spend your final day in the lively Simpson Bay Lagoon. Enjoy watersports or relax on the beach before disembarking.
- Watching planes land at Princess Juliana Airport
- Enjoying watersports in Simpson Bay Lagoon
- Relaxing on Simpson Bay Beach
- Last-minute souvenir shopping
- Anchorage
- Simpson Bay Lagoon
- Dining
- IZI Ristorante Italiano
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