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Overnight, Multi-Night, Weekly Experiences

While the possibilities and destinations for your yachting overnight experiences are endless, here are a few curated suggestions to inspire your itinerary:

Sunset showcasing the scenic beauty of a Hamptons escape on a luxury yacht charter.”

The Hamptons Escape (2-3 days)
Sag Harbor→Shelter Island→Montauk

  • Begin with a sunset departure from Sag Harbor, cruising past the bluffs, beaches and estates.

  • Anchor off Shelter Island for a serene overnight stay, with the option to dine aboard or at Sunset Beach

  • Continue to Montauk for fishing, swimming, or a waterside lunch at Duryea's.

  • End the trip docked or moored in Montauk Harbor with cocktails aboard.

Nantucket & The Vineyard (5-7 days)
Newport→Martha's Vineyard→Nantucket

  • Depart from historic Newport, RI and cruise through open waters to Martha's Vineyard, where you can explore Edgartown, enjoy vineyard tours, or bike along the coast.

  • Spend two nights in Nantucket, docking at the marina or mooring just offshore

  • Wander cobblestone streets, dine at Topper's, and experience the island's timeless charm.

Scenic view capturing the charm of classic New England coastal destinations
Scenic view of on Long Island Sound, perfect for a peaceful getaway and coastal exploration.

The Long Island Sound Getaway (3-4 days)
Greenport→Old Saybrook→Mystic Seaport→Orient Point

  • Begin in Greenport, with its boutique charm and maritime culture.

  • Cruise to Old Saybrook or Mystic, CT, where history meets fine dining

  • Explore Mystic Seaport Museum or stroll the town's quaint streets.

  • Spend your final evening anchored near Orient Point, with a private dinner and coastal views.

The Northeast Grand Tour (7-10 days)
New York City→Block Island→Newport→Nantucket→Martha's Vineyard

  • Start in NYC with a dramatic departure past the skyline

  • Cruise to Block Island for a laid-back first night.

  • Spend time in Newport, then head east to Nantucket and Martha's Vineyard, enjoying a blend of cultural elegance and island charm.

Stunning view of the New York City skyline from the water, showcasing iconic landmarks on the Northeast Grand Tour yacht itinerary.
Luxurious poker table setup highlighting upscale entertainment during coastal yacht charter.

Casino & Coastal Luxury (2-3 days)
Orient Point→Mohegan Sun→Mystic Seaport

  • From Orient Point, set course for the Thames River and arrive at Mohegan Sun Marina, where high-end gaming, dining, and nightlife await.

  • The next day, head to Mystic Seaport for a quieter, more historic contrast.

  • Return via scenic cruise along Long Island Sound.

Florida & Exuma Retreat (5-10 days)
Palm Beach→The Bahamas→Exumas

  • Depart from Palm Beach and cross to West End, Bahamas, clearing customs.

  • Continue south through the Abacos or fly directly to the Exumas.

  • Spend your days island-hopping to secluded beaches, snorkeling Thunderbolt Grotto, and dining barefoot under the stars.

  • Overnight stays may be at exclusive marinas or moored off private islands.

Snorkelers exploring the crystal-clear waters of Thunderbolt Grotto in the Exumas, perfect for a Florida and Exumas luxury yacht retreat.
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