Arrive into Boston and check into your hotel – if time and energy allow, take in one of the best views of the city from the 50th floor of Prudential Tower. See the sailboats gliding across the Charles River, the gold of the Massachusetts State House glistening in the sun, the Harbor Islands in the distance, and even down into Fenway Park.
Overnight: Boston Park Plaza or similar
Day 2 & 3
Yarmouth, MA (92 miles)
Today’s journey will take you to Cape Cod, but you’ll want to stop at the village of Plymouth first. Founded in 1620, it’s most famous as the site of the landing of the Pilgrims, with Plymouth Rock purportedly marking the very spot they disembarked. Explore more history by visiting Plimouth Plantation, a living history museum, and the Mayflower, a full-scale replica of the ship, complete with costumed guides. Enjoy time on the water by taking a Hyannis Harbor Cruise in Hyannis before reaching your final destination of Yarmouth. Your second day on The Cape will be filled with beautiful beaches along the Cape Cod National Seashore, lighthouses and whales. Take a stroll across the dunes, tour one of the five historic Cape Cod lighthouses, open to the public. You can book a tour to watch for whales, with humpbacks and other marine life frequently spotted.
Overnight: Sea Crest Beach Hotel or similar
Day 4 & 5
Martha’s Vineyard, MA (28 miles)
Your morning begins with a short and scenic ferry ride to Martha’s Vineyard, an island just seven miles from the Cape Cod coast. The busy main port, Vineyard Haven, offers great shopping for sea glass jewellery and other treasures, and in Menemsha, you can watch the lobstermen unload their catch. Oaks Bluff, renowned for its unique, vibrant-coloured gingerbread cottages that give the town a storybook feel, is home to the world’s oldest carousel, while Edgartown is considered one of the island’s most picturesque villages, with its brick paths and grand old captain’s homes. Before the day is done, capture the grandeur of an island sunset from the stunning terra cotta-hued clay Gay Head Cliffs overlook. Spend your second day on Martha’s Vineyard taking part in outdoor adventures, like horseback riding or renting a bike and exploring the island on two wheels, or visiting many idyllic stretches of sand. Protected, shallow, clear waters can be found at beaches on the northern and eastern sides of the island.
Overnight: Kelley House or similar
Mystic, CT (133 miles)
Return to the Cape via ferry, and then drive to Mystic, a fabulous coastal town home to Mystic Seaport, the nation's leading maritime museum. It features a working preservation shipyard, a recreated 19th-century seafaring village, fascinating exhibits, a planetarium and four National Historic Landmark vessels, including the last wooden whaleship in the world.
Overnight: Hilton Mystic or similar
Day 7 & 8
Riverhead, NY (108 miles)
Drive to New London, where you’ll take the Orient Ferry to Long Island. Travel the North Fork toward the north shore town of Riverhead - this popular wine route features a bounty of vineyards for tasting and touring, like Jamesport Vineyards which also offers complimentary olives and cheeses to help fortify the afternoon.
The Hamptons is world-renowned for its beaches with fine white sands, gorgeous sunsets and top-notch eateries. On your second day here, take time to explore the best it has to offer, spending time at the Village of Southampton’s main beach, where you can rent and chair and an umbrella, tossing your cares away. Afterwards, take time to stroll the especially charming village of Southampton, with its wide, tree-lined Main Street lined with boutiques and art galleries before taking a tour of the island’s iconic, extravagant mansions.
Overnight: Hyatt Place or similar
New York City marks the end of the tour – or, it could be the beginning of yet another adventure. Either way, be sure to experience some of its highlights, like walking through Central Park, riding the lift to the top of the Empire State Building and exploring the Metropolitan Museum of Art. Just ask to add a few nights on in New York.