New England Island fly drive


This scenic fly and drive trip will take you through bustling Boston, way into the picturesque towns of Chatham, Nantucket & Martha's Vineyard. These towns are known for their colonial style architecture and being well preserved they are a lovely sight to see. As you are driving it gives you the freedom to stop and take in the view wherever you may feel like. Go on a whale watching cruise and see the water blow out as the whales come up from their dives. Enjoy a spot of fishing looking for Bluefin Tuna and sharks. 

The hotels booked are luxurious and comfortable, giving you enough luxury to recuperate from every drive to explore the town. This will be a beautiful drive through traditional and beautiful towns of New England.


11 Days


From $4,557.70 per person based on two adults sharing

Best time to go

Summer times (late May to August) is the best time to go on this tour and enjoy the lovely weather that New England offers.

Tour Highlights

  • Go whale watching in Nantucket
  • 2.5-mile Redbrick Freedom Trail
  • Go fishing for Bluefin Tuna and Sharks
  • Explore the breathtaking Aquinnah Cliffs

Day 1: Departure
Fly into Boston & upon arrival make your own way to the hotel for a 3-night stay. From the moment you’re greeted by the brass-buttoned bellhop by the door, you can tell that XV Beacon takes its traditional values seriously. Set in a peaceful, leafy stretch of Boston’s historic centre by the common, this classic hotel hides original cage elevators, art deco furnishings and impeccably friendly service behind a beautiful Beaux-Arts façade. Whatever you do, don’t miss the wine list.

Overnight at: Boston XV Beacon

A New England island fly drive tour


Day 2: Boston

A day at leisure. The number one thing you should do while in Boston is to follow the 2.5-mile Redbrick Freedom Trail from Boston Common to Bunker Hill. Set aside 1 to 3 hours and be sure to make a pit stop for a "beah" at America’s oldest bar, the Bell in Hand Tavern.

Overnight at: Boston XV Beacon
Boston XV Beacon accomodation


Day 3: Boston

A day at leisure. There’s nothing quite like taking in a game at Fenway Park, one of America’s most beloved baseball stadiums since it opened in 1912. But even if the Red Sox aren’t playing, you’ll want to swing by. Savour the clam chowder and enjoy the many historical and modern attractions this city has to offer.

Overnight at: Boston XV Beacon

A New England Island fly drive tour


Day 4: Chatham
Distance travelled: Boston – Cape Cod/Chatham, MA (91 mi/146 km)
This morning collect your 4 doors intermediate car rental from the downtown depot. Chatham is situated on the “elbow” of Cape Cod, a popular summer resort boasting a quaint and walkable Main Street, a stretch of white sand beach, the Chatham Lighthouse and the Chatham Bars Inn, a luxury Cape Cod oceanfront resort. Spend two nights at this idyllic retreat, set in 25 acres of beautifully landscaped grounds and sandy ocean beaches. Wake up to the sound of the surf breaking against the shore and unwind watching the sunset from the private balcony overlooking the ocean. The privacy, luxurious accommodations, and spa treatment options make this an ultimate retreat.

Overnight at: Chatham Bars Inn

Chatham Bar Inn accommodation in new England

Day 5: Chatham
A day at leisure. Some of the finest fishing grounds are located just a short boat ride away, whether it’s light tackle, targeting Striped Bass, Bluefish and Black Sea Bass, or a full day offshore in search of Bluefin Tuna and Sharks. Go exploring a quintessential New England village by the sea, with colonial style structures and a lighthouse with a breathtaking view of Cape Cod. 

Overnight: Chatham Bars Inn

Chatham holidays


Day 6: Nantucket
Distance travelled: Chatham –Nantucket (18 mi/29 km)
Board the ferry in Hyannis for the hour-long trip to this exclusive resort off the coast of Massachusetts and stay at the White Elephant for two nights. Nantucket has been named a National Historic District and has architecturally changed little since the 17th century, as seaside cottages and old-fashioned lamps still line its streets. It is one of the most unique, historic, and visually stunning places in the northeast U.S. Not only is Nantucket a popular summer resort, it is also renowned for its famous Christmas Stroll. The White Elephant sits serenely on the waterfront. The Harborside Lawn offers the perfect setting for sipping a cool glass of lemonade in the afternoon or relax by the fire in the evening in the hotel’s comfortable Library. Just steps away from the hotel one can meander among the unique boutiques and art galleries, restaurants, and fascinating museums for which the island is known.
Once the whaling capital of the world, Nantucket is now a tourist’s delight.

Overnight at: The White Elephant

The White Elephant hotel

Day 7: Nantucket
A day at leisure. Go on a guided tour of the town to learn about the interesting history this pretty little town has. You can also book a whale watching cruise, which is an unforgettable experience when you see them blow water after a dive. A tour guide will be on hand to answer any questions you may have on these majestic mammals. 

Overnight at: The White Elephant

Nantucket holidays fly driv

Day 8: Martha's Vineyard

Distance travelled: Nantucket - Martha’s vineyard (43 mi/69 km)
Board the ferry in Nantucket for the hour-long trip to Martha's Vineyard and stay at the Menemsha Inn for two nights. Far less developed than Cape Cod—thanks to a few local conservation organizations—yet more cosmopolitan than neighbouring Nantucket, Martha's Vineyard is an island with a double life consisting of woods, fields, hillsides and the breathtaking Aquinnah Cliffs.

Overnight at: Menemsha Inn

A new england fly drive tour

Day 9: Marthas Vineyard
A day at leisure. Menemsha Harbor has some of the world's best fishing guides to lead you to monster striped bass, peaceful beachcombing, golf courses, charming shopping and sightseeing, and unforgettable dining at the next door Beach Plum Inn and the Homeport Restaurant in Menemsha Harbor.

Overnight at: Menemsha Inn
Menemsha Inn hotel accommodation


Day 10: Boston

Distance travelled: Martha’s Vineyard - Boston (71 mi/114 km)
Return to Boston via ferry and car. Return the car upon arrival at Boston Airport. Fly overnight to the UK.

A New England Island Fly Drive

Day 11: Arrival
Arrive in the morning, local time

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