Holiday Overview
Journey through some of North America's favourite summer vacation spots, Cape Cod and its fantastic beaches. Ferry to Martha's Vineyard and experience the Hamptons, long established as a bolt hole for New York's rich and famous.
9 days / 8 nights
Start: Boston
Finish: New York City
US States you will visit: Massachusetts, Rhode Island, Connecticut, New York
Highlights of this trip are:
- Boston Sightseeing
- The Gingerbread Cottages and fine seafood of Martha's Vineyard
- Seeing the Playground of New York's elite in The Hamptons
Boston to New York By The Beaches Road Trip includes:
- Return flights from the UK
- Compact Car with Gold Cover - Unlimited mileage, Full tank of fuel, 3 additional drivers, Collision Damage Waiver (CDW), $1 million liability coverage, Zero excess in the USA
- Self-Drive Directions and Information Packet at hotel upon arrival
- 1 night hotel accommodation in Boston
- 2 nights hotel accommodation in Yarmouth
- 2 nights hotel accommodation in Martha's Vineyard
- 1 night hotel accommodation in Mystic
- 1 night hotel accommodation in Riverhead
- 1 night hotel accommodation in The Hamptons
- Ticket for Hyannis Harbour Cruise and Dolphin Fleet Whale Watching
- Passenger and Vehicle Fare for the Orient
- Point Ferry and Martha’s Vineyard ferry
Day 1 - Arrive in Boston
Arrive Boston and check into your hotel.
Day 2 - Boston-Hyannis-Yarmouth 76 Miles
Travel to Cape Cod. Visit Plymouth en route. Take a Hyannis Harbour boat cruise
Day 3 - Yarmouth-Provincetown-Yarmouth 93 Miles
Explore Cape Cod Nat’l Seashore, see lighthouses, coastal villages, take a whale Watch in Provincetown
Staying at Blue Water Resort On The Ocean
Day 4 - Yarmouth-Martha's Vineyard 28 Miles
Take the ferry to Martha’s Vineyard. Explore the island: Edgartown, Vineyard Haven, Aquinnah Cliffs, Oak Bluffs’ Gingerbread cottages
Day 5 - Martha's Vineyard
Rent a bicycle or moped, go horseback riding, or enjoy one of the may beaches
Staying at Kelley House Hotel
Day 6 - Martha's Vineyard-Mystic 139 miles
Visit Mystic Seaport, set on 17 acres it depicts 17th century seafaring
Day 7 - Mystic-Riverhead 58 Miles
Ferry to Long Island, travel the North Fork stopping at wineries en route.
Day 8 - The Hamptons
Relax on beautiful beaches, stroll charming villages with boutiques and art galleries; tour historic mansions.
Day 9 - Riverhead-New York City 124 Miles - Depart from New York City
Finish in New York City
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Image Gallery
The Hampton's Beach
Aquinnah spring, Martha's Beach
Bourne Beach, Cape Cod
Boston
Liberty Island, NYC
Town Beach, Martha's Vineyard
New York City
Pleasant Bay, Cape Cod
Riverhead, New York
The Hampton's
Martha's Vineyard
USA Holiday Stopovers
Why not add in the 'Land of Fire and Ice' - Iceland -on your way to your holiday in the USA. We have put together a great stopover in Iceland for 2 or 3 nights which includes accommodation and the Golden Circle Trip which includes visits to the Gullfoss Waterfall, the geo thermal area of Geysir and Thingvellir National Park.
If you are travelling to the west coast of America, why not add a couple of nights stay in New York which includes accommodation and tickets for the 'Top of the Rock' observation platform for an iconic view of the city skyline. This can be done either on your way out or on the way back.
Alternative Holidays That May Interest You
Below you will find a small selection of 2026, 2027 holidays that may interest you. Remember, we tailor-make each holiday to your exact needs, so please call us on 0800 917 5742 and let one of our Holiday experts design the perfect trip for you
Best of New England Fly Drive
- Boston
- Portland Maine
- Bar Harbor
- White Mountains
- Killington
- The Berkshires
- Mystic
- Yarmouth MA
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Visit beautiful maritime towns
- See the beautiful mountains of New Hampshire & Vermont
- Experience historic Boston
14 Nights from £2985pp
Boston to New York By The Beaches Road Trip
- Boston
- Yarmouth
- Martha's Vineyard
- Mystic
- Riverhead
- The Hamptons
- New York City
- Receive a free case of wine
- Save £300 per booking book by 31 October
- See the sights of Boston
- The Gingerbread Cottages and fine Seafood of Martha's Vineyard
- See the Playground of New York's elite in the Hamptons
8 Nights from £2050pp
Route 66 Fly Drive Holiday
- Chicago
- St Louis
- Springfield
- Oklahoma City
- Amarillo
- Albuquerque
- Holbrook
- Williams
- Las Vegas
- Los Angeles
- Receive a free case of wine
- Save £300 per booking book by 31 October
- An epic journey across the USA
- Visit 8 States
- See the awesome Grand Canyon
- Hit the bright lights of Las Vegas
15 Nights from £2935pp
Best of Florida Self Drive Holiday
- Orlando
- Clearwater
- Naples
- Miami
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Exciting Orlando
- The Beautiful Gulf Coast
- Vibrant Miami
9 Nights from £1890pp
Coasts and Mountains of the South Road Trip
- Atlanta
- Asheville
- Charlotte
- Myrtle Beach
- Charleston
- Savannah
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Visit the 'World of Coca-Cola'
- Discover the Blue Ridge Parkway, one of the USA’s most scenic drives
- Relax on incredible beaches
7 Nights from £2135pp
The Florida Keys Fly Drive Holiday
- Miami
- Islamorada
- Key West
- Key Largo
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Vibrant Miami
- The famous and scenic Overseas Highway
- Ernest Hemingway's home in Key West
7 Nights from £2400pp