If you’re craving a quintessential New England road trip, Massachusetts’ coastline is the perfect route. Boasting pretty beach towns with picturesque sand dunes and seafood, this coastal route takes you from Boston to the idyllic islands of Martha’s Vineyard and Nantucket.
Massachusetts is a state where history and coastal beauty intertwine seamlessly. From the arrival of the Pilgrims in 1620 to the bustling maritime trade of the 18th and 19th century, the coastline of Massachusetts has been at the heart of American history.
Today, the state’s seaside towns retain the charm of their storied past, with cobblestone streets, historic lighthouses, and New England architecture. Over nine days, you’ll wind through seaside towns, historic landmarks, and scenic drives. Here’s a detailed itinerary for a road trip full of coastal charm, local culture, and delicious food that promises an unforgettable New England experience.
Drive from Boston to Hyannis and the islands
Your coastal road trip begins in Boston, a bustling city rich in history and modern flair. You can begin by exploring historic landmarks along the Freedom Trail, a 2.5-mile route that passes 16 historic sites, including the Paul Revere House, Old North Church, and the Boston Common. For a deeper dive into American history, head to the Boston Tea Party Ships and Museum (which, ironically, also has a tea room). Grab a bite at Union Oyster House, the oldest continuously operating restaurant in the U.S., serving clam chowder, delicious oysters, and other fresh seafood. For Italian fare, stroll over to the North End and indulge in a meal at Giacomo’s, or seek out Mike’s Pastry for a classic cannoli. For a comfy stay, try The Langham Hotel, which blends historic charm with modern luxury. Alternatively, stay at the more budget-friendly YOTEL Boston, conveniently located near the Seaport District.
From there, drive along the Cape to Hyannis, Cape Cod’s largest town and a hub for ferries to the islands. Visit the John F. Kennedy Hyannis Museum to learn about the Kennedy family’s connection to the Cape. You’ll find a great spot to try some local clam chowder and lobster rolls at The Black Cat Tavern, and check out the Anchor In Hotel for budget-friendly lodging.
Here, you could also take a ferry to the iconic island of Martha’s Vineyard, a beloved summer retreat full of charming towns and sandy beaches. Explore the island’s historic lighthouses and boutiques, and head to Aquinnah for breathtaking ocean views. The Christopher in Edgartown offers laid-back, island-chic lodging. You can also head to Nantucket, a two-hour-plus ferry ride away. There, explore historic whaling captains’ houses, cobblestone streets, and upscale boutiques. Rent a bike and ride to Siasconset, a postcard-perfect village with rose-covered cottages.
Drive up the Cape to Chatham and Provincetown
