This Massachusetts Road Trip Along The Coast Is Full Of Seaside New England Towns And Charm

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.

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.

From Hyannis, head to Chatham. If you're on Nantucket, you could also take the ferry to Harwich Port. The drive will take you along either Route 6 or the seaside Route 28, two routes that should take between 30 and 40 minutes. Chatham, a picturesque town, is known for its upscale atmosphere and scenic beauty. Stop by the Chatham Lighthouse for a classic New England photo op, and learn about the region's maritime history. You'll find the freshest seafood at Chatham Pier Fish Market, where you can also watch the fishing boats unload their catches. If you need to stay overnight here, check in to the Chatham Bars Inn, a luxurious resort that offers sweeping ocean views and a private beach.

From here, head 35 miles up Route 6 to Provincetown, a nearly hourlong journey where you can enjoy Cape Cod's charming landscapes and a smattering of cute towns and villages on the way. Provincetown is a vibrant, LGBTQ-friendly town is known for its thriving art community, sandy dunes, and picturesque lighthouses. A must-visit spot is the Pilgrim Monument, the tallest all-granite monument in the U.S., and visitors should check Commercial Street, packed with boutiques, cafes, and art galleries. You can also take a tour to the stunning Provincetown sand dunes, and you can book a buggy tour to see them in an unforgettable way. For food, the Lobster Pot is a local favourite serving fresh lobster rolls and clam chowder with a waterfront view. Stay the night at The Brass Key Guesthouse, which offers boutique accommodations with coastal flair. For a budget-friendly option, try the Seaglass Inn & Spa.