Skylines of Boston & New York City
Skylines of Boston & New York City
Waterfront scenery of Boston, Massachusetts
Waterfront scenery of Boston, Massachusetts
Cape Cod, Hyannis & Provincetown
Cape Cod, Hyannis & Provincetown
Martha's Vineyard
Martha's Vineyard
New York City
New York City

Self-Drive Boston to New York by the Beaches

8 nights from €1,699 per person Including Flights


This self-drive tour starts in the historic city of Boston, journeying to one of the world’s most famous summer vacation destinations, Cape Cod and its magnificent beaches, and where you will enjoy a whale-watching cruise. You’ll take ferry over to Martha’s Vineyard for a couple of days on this beautiful island retreat, explore Mystic Seaport and venture to the grand old mansions of Long Island, before ultimately reaching your final destination: New York City. Tailormade (Tourmappers)

Further reading: Top 10 coastal towns in New England


  • Take in spectacular views of Boston and visit iconic historic sites like Plymouth Rock
  • Stroll the sand dunes, tour lighthouses and watch for whales on Cape Cod
  • Explore the famous gingerbread cottages, ride the world’s oldest carousel and dine on fresh lobster you just watched the lobstermen bring in on Martha’s Vineyard
  • Visit Mystic Seaport, the largest maritime museum in the world and enjoy wine tasting along Long Island’s North Fork Wine Route
  • See the historic Hamptons mansions, browse the shops and art galleries that line Main Street Southampton, and relax on pristine white sand beaches

Itinerary Overview

Fly into Boston 1 night – Yarmouth 2 nights – Martha's Vineyard 2 nights – Mystic 1 night – Riverhead 2 nights – Fly home

Our holidays include
  • Flights & taxes
  • Accommodation
  • Checked baggage
  • CAR licensed & bonded
  • In resort assistance & 24 hour contact centre
Why Book with American Sky?
  • Hassle-free - book direct quickly and easily
  • Choice of airlines and the option to switch
  • A friendly, family run business with a wealth of experience.
  • Great deals on offer for multiple destinations
  • No amendment fees
  • Low deposits
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Day 1

Boston, MA

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: Doubletree by Hilton Boston Bayside 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. On your second day on Cape Cod, enjoy a half-day whale-watching cruise and take time to explore the rest of the peninsula with its beaautiful beaches and iconic lighthouses.

Overnight: Ocean Mist 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: Mansion House or similar

Day 6

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: Hampton Inn & Suites 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 Long Island East End or similar

Day 9

Riverhead - New York JFK Airport - fly home (65 miles)

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.


  • Return transatlantic flights
  • Hotel accommodation as shown or similar
  • Car hire for the duration of the trip included fully inclusive insurance
  • Electronic roadbook
  • Half day whale watching cruise from Cape Cod

Whats not included

  • Activities and attractions
  • Passenger and Vehicle Fare for the Orient Point Ferry and Martha’s Vineyard ferry

Rachel McAnaspie
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