7 Days in Massachusetts

Discover cedar-shingled towns, sheltered island harbours, and refined summer cruising across Cape Cod and the Islands.

7 Days 6 Nights

Hyannis to Hyannis

Itinerary Overview

The coast of Massachusetts extends across Cape Cod, Nantucket Sound, Martha’s Vineyard, and the Elizabeth Islands, creating one of New England’s most established summer cruising regions. This seven-day route begins and ends in Hyannis, connecting historic harbours, secluded anchorages, island towns, and Atlantic beaches. From Nantucket to Edgartown, and from Vineyard Haven to Cuttyhunk, each destination offers a different perspective on coastal New England. The route is ideal for guests looking for boutique shopping, cycling, waterfront dining, swimming, quiet anchorages, and leisurely days on the water. Nantucket, Martha’s Vineyard, and Cape Cod are among the region’s best-known coastal destinations, with Nantucket Harbour particularly established among luxury yachts and visiting sailors.

Itinerary Starting Point

Hyannis

A classic Cape Cod beginning

Begin in Hyannis, one of Cape Cod’s best-known maritime centres and a convenient gateway to Nantucket Sound. Guests can settle onboard, explore the waterfront, visit nearby beaches, and enjoy fresh seafood ashore. An afternoon cruise around the harbour provides an easy introduction to the region before dinner and a relaxed first evening onboard.
27 NM

Nantucket

Cobblestone streets and coastal refinement

Cruise across Nantucket Sound to Nantucket, known for its historic whaling heritage, cedar-shingled buildings, elegant boutiques, and polished dining scene. Guests can cycle towards Siasconset, visit the island’s beaches and lighthouses, or stroll through the historic town centre. End the day with dinner ashore or cocktails overlooking Nantucket Harbour.
25 NM

Edgartown

Martha’s Vineyard at its most elegant

Continue to Edgartown on Martha’s Vineyard, recognised for its white-clapboard homes, historic streets, boutiques, and scenic harbour. Spend the afternoon cycling, exploring South Beach, visiting Edgartown Lighthouse, or tendering towards Chappaquiddick. The evening is ideal for refined waterfront dining followed by a peaceful night in the harbour.
8 NM

Vineyard Haven

Sailing heritage and relaxed island life

Enjoy a gentle cruise to Vineyard Haven, a sheltered harbour with a strong sailing tradition and an inviting town centre. Guests can browse independent shops, explore the island by car or bicycle, and visit nearby beaches before returning to the yacht. Spend the evening dining onboard or enjoying a relaxed restaurant ashore.
15 NM

Hadley Harbor

A secluded Elizabeth Islands anchorage

Cruise towards Hadley Harbor, a peaceful and protected anchorage surrounded by the natural landscapes of the Elizabeth Islands. The day can be spent kayaking, paddleboarding, swimming, or simply relaxing on deck away from busy towns. With limited development nearby, this stop is ideal for a private onboard dinner and a quiet night beneath the stars.
17 NM

Cuttyhunk

Remote New England island character

Continue to Cuttyhunk, the outermost of the Elizabeth Islands and a favourite stop for yachts seeking a quieter side of Massachusetts. Guests can walk through the small island community, swim from a secluded beach, explore by tender, or enjoy freshly prepared seafood onboard. Finish with sunset views across Buzzards Bay.
45 NM

Hyannis

A final passage across Nantucket Sound

Cruise back towards Hyannis, passing the southern coastline of Cape Cod along the way. Spend the morning enjoying breakfast on deck, relaxing in the sun, or stopping for a final swim when conditions allow. Arrive in Hyannis for disembarkation, concluding a charter shaped by elegant island towns and peaceful coastal anchorages.