American Beauty | Newport to Boston

Day 1

Newport has long been the gateway to New England, especially for yachtsmen. Longtime home of the America’s Cup, the quintessential New England seaside town is a bastion of sailing. Experience the wealth and power of those who made Newport a center of grand society with a visit to one of the Newport Mansions. Spend the afternoon strolling along Cliff Walk before joining the yachting crowd in the bars and the restaurants that line the yachting capital’s lively waterfront.

Days 2 & 3
Newport to Martha’s Vineyard (60 nautical miles)

Set a compass for the exclusive summer destination of Martha’s Vineyard, known for its beaches, boardwalks and quaint towns. Bike along the paths that line the wild coastline. Step ashore to Edgartown for an island clambake – a Vineyard tradition. Browse the shops and restaurants, or buy some fresh fish from the fishmonger on the dock for an evening-feast on board.

Day 4
Martha’s Vineyard to Nantucket (20 nautical miles)

Cruise to the crescent shaped Nantucket Island. Dock in Nantucket Boat Basin and explore the wonderful restaurants, antique shops and galleries in Nantucket Town. Roam this crescent-shaped island on bicycle, taking in its lighthouse and stately 18th and 19th century homes. Take a refreshing dip in the Atlantic Ocean from one of the many beautiful wild beaches.

Day 5
Nantucket to Provincetown (58 nautical miles)

Located at the most northerly point of Cape Cod, Provincetown is edged with beaches that disappear into the open sea. Discover the Outer Cape by bicycle. The fishing village and artistic community is both scenic and welcoming and the surrounding areas offer plenty of opportunities to explore the vast stretches of sand dune, forests, beaches and open sea.

Day 6
Provincetown to Plymouth (20 nautical miles)

Cruise across the bay of Cape Cod to Plymouth. The town is supposedly where the Pilgrim Fathers first settled. Visit the Mayflower II – a replica of the 17th-century ship Mayflower, celebrated for transporting the Pilgrims to the New World in November 1620.

Day 7
Plymouth to Boston (25 nautical miles)

Watch for whale pods as you cruise to the university town of Boston. Rich in history and tradition, Boston successfully combines big city style with a small-town ambience and atmosphere. Hook up with the Freedom Trail – a red brick line that winds around 2.5 miles of the city, linking 16 of the most historic sites.

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