From Newport to Newport.

Newport, Rhode Island, is a prime yachting destination located on the historic Narragansett Bay. With its picturesque shorelines, bustling harbors, and hidden beaches, it is a perfect place for sailing and exploring the area. Boaters can take part in the Newport Harbor Boat Parade, an annual tradition spanning more than a hundred years that features creative and elaborate decorations from each vessel. Marinas in Newport range from small to large, with every amenity a boater could need. Stop at lively anchorages like Brenton Cove or Coddington Cove, or slip into more intimate settings such as Sakonnet Point and Potter Cove. For those onshore, walk or bike the Cliff Walk for sweeping views, or explore the charming shops, galleries, and restaurants of historic downtown. Newport truly is an oasis for yachting enthusiasts of all levels.

DAY TWO
Newport to Block Island
DISTANCE: 22nm DURATION: 2h 50m

Block Island is a conservation paradise with 40 percent of the island permanently protected. There are about 25 kilometers of beaches, and the laid-back feel makes it a natural stop for yacht guests seeking sand and sea. Onshore, you’ll find Victorian houses and quaint shops sharing the island with local seafood restaurants. Outdoor entertainment reigns here: hiking, cycling, horse riding, sailing, and fishing. Golfers can play the full 18-hole course attached to the Brenton Hotel, though a tee time is essential. Block Island is ideal for those who want their charter to be filled with natural beauty and active days.

Cuttyhunk, south of Cape Cod, has long been a dream destination for New England’s boating elite. Known for its shellfish, especially bass and oysters, the island is as much about good food as it is about quietude. Order from the floating raw bar, which delivers your seafood straight to the boat, or pick up fresh lobster at the dockside market. Ashore, Avalon offers luxurious accommodation, while the island itself is a slow, simple place to unwind. Bicycles and golf carts replace cars, and Lookout Hill’s WW2 bunkers are now scenic picnic sites. This is a spot for relaxed afternoons and a true sense of being away from it all.

Martha’s Vineyard, or simply “The Vineyard,” is a quintessential New England summer destination. Known worldwide as the setting for Jaws, the island has six towns, each with its own flavor, best explored by bike, cab, or bus. Stop at Bad Martha Farmer’s Brewery in Edgartown for craft beer and locally sourced platters, or indulge in wine labeled Martha’s Vineyard AVA. The island hosts numerous film festivals across the year, focusing on arthouse and independent films. The Vineyard is less about nightlife and more about beaches, oyster farms, picnics, and leisurely exploration.

Nantucket is steeped in maritime history and is celebrated every spring with fields of blooming daffodils. Once the world’s whaling capital, its story is preserved in the Nantucket Whaling Museum and other galleries. Today, the island balances heritage with refined living. It has several beaches and lighthouses, local restaurants serving fresh seafood, and even its own winery and craft brewery. The historic district encompasses the whole island, making it the largest National Historic Landmark District in the contiguous United States. Nantucket is pure classic New England charm.

Woods Hole is a seaside village with a rich scientific and cultural reputation. Visitors can explore the Woods Hole Science Aquarium, stroll scenic Eel Pond, or tour the world-renowned Oceanographic Institution. Its harbors and beaches are perfect for outdoor adventures, while onshore, small shops, restaurants, and cafes bring New England hospitality to life. For charter guests, Woods Hole offers a balance of ocean activities and leisurely cultural experiences.

Return to Newport for one more chance to soak in Rhode Island’s premier yachting culture. Enjoy another stroll through the historic streets, visit a gallery or boutique, or indulge in fresh seafood ashore. By evening, toast your week in New England with a farewell dinner along Thames Street or Bannister’s Wharf. Newport, with its combination of maritime tradition and modern vibrancy, makes for the perfect bookend to the journey.

Relax onshore before departure. Do some last-minute shopping, or join one of the town’s summer festivals celebrating jazz, folk music, film, wine, or art. Newport’s energy, history, and sailing heritage ensure your journey ends on the same high note on which it began.