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.
Featured accommodation
The Revolution Hotel
Day 2 - Boston-Hyannis-Yarmouth 76 Miles
Travel to Cape Cod. Visit Plymouth en route. Take a Hyannis Harbour boat cruise
Featured accommodation
Blue Water Resort On The Ocean
Unmissable Experiences
Yarmouth Experiences
Day 3 - Yarmouth-Provincetown-Yarmouth 93 Miles
Explore Cape Cod Nat’l Seashore, see lighthouses, coastal villages, take a whale Watch in Provincetown
Featured accommodation
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
Featured accommodation
Kelley House Hotel
Day 5 - Martha's Vineyard
Rent a bicycle or moped, go horseback riding, or enjoy one of the may beaches
Featured accommodation
Kelley House Hotel
Unmissable Experiences
Marthas Vineyard Experiences
Day 6 - Martha's Vineyard-Mystic 139 miles
Visit Mystic Seaport, set on 17 acres it depicts 17th century seafaring
Featured accommodation
Inn at Mystic
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
The Revolution Hotel
The Revolution Hotel in Boston, Massachusetts, offers a unique blend of modern style and historic charm, making it a perfect choice for guests seeking a vibrant yet comfortable stay. Located in the heart of Boston’s South End, the hotel reflects the city’s revolutionary spirit, both in design and atmosphere. With eclectic, art-filled interiors and rooms that range from chic micro rooms to spacious suites, guests will find something to suit their needs. The hotel also features co-working spaces, a fitness centre, and a cosy cafe.
Blue Water Resort On The Ocean
Offering a private beach area, an outdoor pool and a seasonal restaurant, this oceanfront resort in Cape Cod is located on Nantucket Sound.
Kelley House hotel
Over two centuries of Vineyard charm. By far the most iconic Edgartown hotel, the Kelley House opened its doors in 1742 and has since been celebrated as one of the oldest hotels in America. The town of Edgartown has been known throughout the ages as a colonial settlement, whaling community, and an elegant vacation destination. The Kelley House hotel encompasses a long line of tradition and stands as one of the most distinguished historic hotels in all of New England.
Inn at Mystic
Situated on fourteen green acres overlooking Fishers Island Sound and Mystic Harbour, the Inn offers relaxing accommodations including rooms with ocean views, jacuzzis, and wood burning fireplaces. Inn at Mystic was once a private estate but it now consists of a hotel, restaurant, mansion, and full service banquet operations. The Inn at Mystic been welcoming guests for over fifty years.
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 Canada Holidays that may interest you. Remember, we tailor-make each holiday to your exact needs, so please call us on 0800 917 5724 and let one of our Travel Specialists 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
- Visit beautiful maritime towns
- See the beautiful mountains of New Hampshire & Vermont
- Experience historic Boston
- Receive a free case of wine
- Save £250 per person book by 30 September
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
- 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
- Receive a free case of wine
- Save £250 per person book by 30 September
8 Nights from £2050pp
Route 66 Fly Drive Holiday
- Chicago
- St Louis
- Springfield
- Oklahoma City
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- An epic journey across the USA
- Visit 8 States
- See the awesome Grand Canyon
- Hit the bright lights of Las Vegas
- Receive a free case of wine
- Save £250 per person book by 30 September
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Best of Florida Self Drive Holiday
- Orlando
- Clearwater
- Naples
- Miami
- Exciting Orlando
- The Beautiful Gulf Coast
- Vibrant Miami
- Receive a free case of wine
- Save £250 per person book by 30 September
9 Nights from £1890pp
Coasts and Mountains of the South Road Trip
- Atlanta
- Asheville
- Charlotte
- Myrtle Beach
- Charleston
- Savannah
- Visit the 'World of Coca-Cola'
- Discover the Blue Ridge Parkway, one of the USA’s most scenic drives
- Relax on incredible beaches
- Receive a free case of wine
- Save £250 per person book by 30 September
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The Florida Keys Fly Drive Holiday
- Miami
- Islamorada
- Key West
- Key Largo
- Vibrant Miami
- The famous and scenic Overseas Highway
- Ernest Hemingway's home in Key West
- Receive a free case of wine
- Save £250 per person book by 30 September
7 Nights from £2400pp
