New England Itineraries: Day Charters and Multi-Day Routes

Newport to Block Island

Board your yacht at Newport Shipyard by mid-morning. After a welcome champagne toast on the flybridge with Newport’s harbour spread out below, cruise south-west to Block Island (12 nautical miles, roughly 2 hours). Moor in Great Salt Pond and spend the afternoon exploring: the Mohegan Bluffs and Southeast Lighthouse, the network of hiking trails through rolling meadows studded with wildflowers, and the quiet northern beaches where your crew sets up paddleboards and snorkelling gear. Dinner on the aft deck, your chef prepares local swordfish with summer vegetables and a New England blueberry crumble, as the sun sets over the pond.

Block Island to Martha’s Vineyard

Depart Block Island after a leisurely breakfast and cruise north-east to Martha’s Vineyard (roughly 30 nautical miles, 2 to 3 hours). Arrive at Oak Bluffs Marina by early afternoon. Explore Oak Bluffs’ famous gingerbread cottages, over 300 brightly painted Victorian houses arranged around a central tabernacle, originally built as a Methodist camp meeting ground in the 1860s. Stroll the harbour-front circuit, pick up a cone at Back Door Donuts (a Vineyard institution, open since 1987), and settle in for an afternoon of people-watching and seaside charm. Dinner ashore at Sweet Life Café (Oak Bluffs’ finest, with an outdoor patio for warm evenings) or on board.

Martha’s Vineyard Exploration and Return to Newport

Spend the morning cruising along the Vineyard’s southern coast to Aquinnah (Gay Head), where multicoloured clay cliffs, red, orange, ochre and white, formed over millions of years, rise 45 metres above the sea. The Gay Head Lighthouse (originally built 1799, current structure 1856, moved inland in 2015 to protect it from erosion) stands on the clifftop. Anchor offshore for photos, a swim and a chef-prepared brunch with the cliffs as your backdrop. In the early afternoon, cruise to Edgartown, the Vineyard’s most elegant town, with white-clapboard whaling captains’ houses, the Old Whaling Church (1843, a Greek Revival landmark) and boutique shops. Depart by mid-afternoon for the return to Newport (32 nautical miles), arriving by early evening.

Newport to Martha’s Vineyard

Depart Newport mid-morning and cruise to Martha’s Vineyard (32 nautical miles, 2 to 3 hours). Berth at Vineyard Haven or pick up a mooring in Edgartown harbour. Afternoon exploring Edgartown: the elegant whaling-era architecture, the Vineyard Museum, and a walk along the harbour with views across to Chappaquiddick Island. Dinner at Détente (inventive American cuisine since 2005, in a twinkle-lit courtyard that epitomises Vineyard charm).

Martha’s Vineyard to Nantucket

A morning visit to Menemsha harbour, a working fishing village on the Vineyard’s western tip, famous for its lobster shacks, fresh seafood and the location where Spielberg filmed key scenes for Jaws. Watch the fishermen unload the morning catch, pick up a lobster roll (among the best in New England), and cruise across Nantucket Sound to Nantucket (roughly 30 nautical miles from Oak Bluffs, 2 to 3 hours). Arrive in Nantucket harbour by mid-afternoon. The town is a living museum of 18th- and 19th-century whaling prosperity: cobblestoned Main Street, grey-shingled houses, gas lanterns and a refined, understated elegance. Dinner at Company of the Cauldron, a candlelit, prix-fixe jewel with a nightly-changing menu of French-inflected seasonal cuisine, or Cru on Straight Wharf for harbour-front oysters and chilled rosé.

Nantucket Exploration

A full day on Nantucket. Morning cycling to Sconset (Siasconset), a tiny village of rose-covered cottages on the island’s eastern tip, 7 miles from town. The 1850s Sankaty Head Lighthouse guards the bluff, and the beaches here are wild and uncrowded. Return to town for lunch at TOPPER’S at The Wauwinet (Wine Spectator Grand Award since 1996, modern coastal cuisine in a stunning waterfront setting). Afternoon at one of the town beaches, or a visit to the Whaling Museum (housed in a former spermaceti candle factory, with a 14-metre sperm whale skeleton suspended from the ceiling). Sundowners on the aft deck as the harbour turns golden.

Nantucket to Cape Cod and Return to Newport

Depart Nantucket and cruise north to Hyannis on Cape Cod (roughly 25 nautical miles, 1.5 to 2 hours). Hyannis is the Cape’s central hub and the summer home of the Kennedy family, the Kennedy compound is visible from the harbour. If time and conditions allow, your captain can position the yacht near Stellwagen Bank (north of Provincetown) for whale watching, humpbacks, minke and finback whales feed here from June through September. Alternatively, explore Hyannis’s Main Street, with its galleries, boutiques and waterfront restaurants. After lunch, set course south-west for Newport (roughly 48 nautical miles from Hyannis, 3 to 4 hours), arriving by early evening.

Guests looking for a comprehensive New England experience can combine the 3-day Block Island-Martha’s Vineyard route with the 4-day Nantucket-Cape Cod route for a 7-day charter that visits every major island destination without repeating a single port. Add extra days to extend north toward Maine’s Acadia coast for autumn foliage, lobster bakes and one of the most dramatic shorelines in the United States.

Newport to Block Island

Board at Newport Shipyard mid-morning. Cruise to Block Island (12 nautical miles). Explore the Mohegan Bluffs, Southeast Lighthouse and pristine beaches. Dinner on the aft deck in Great Salt Pond.

Block Island to Martha’s Vineyard

Cruise north-east to Martha’s Vineyard (30 nautical miles). Explore Oak Bluffs’ gingerbread village and harbour-front scene. Dinner ashore at Sweet Life Café or aboard your yacht.

Martha’s Vineyard to Nantucket

Morning at Menemsha’s lobster shacks, then cruise to Nantucket (30 nautical miles). Afternoon exploring the cobblestoned town. Dinner at Company of the Cauldron.

Nantucket Exploration

Full day on Nantucket: cycle to Sconset, visit the Whaling Museum, lunch at TOPPER’S, afternoon at the beaches. Sundowners in the harbour.

Nantucket to Newport

Depart Nantucket and cruise south-west to Newport (64 nautical miles, 4 to 5 hours). Arrive by mid-afternoon. Final exploration of Newport, the Cliff Walk, the mansions, a farewell drink at White Horse Tavern (1673). Dinner on the aft deck with Newport’s harbour twinkling around you.

This 5-day itinerary covers all four of New England’s premier island destinations, Block Island, Martha’s Vineyard, Nantucket and Newport, without repeating a stop. Add it to the 3-day Bimini route from earlier in this guide for an 8-day two-season experience spanning tropical Bahamas waters and New England’s historic coast.