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Fly Drive USA

Boston, Boats & Beaches

Begins in and ends in Boston, Massachusetts

  • 14 Days / 13 Nights
  • All year round

Perfect for those who love to be close to the ocean and have a spirit for adventure. Enjoy a stay in the charming city of Boston, discovering the wealth of attractions it offers, before exploring the delights of Cape Cod and the islands of Nantucket and Martha’s Vineyard. This itinerary includes: 

  • Round-trip scheduled flights from London Heathrow to Boston, Massachusetts
  • Intermediate 4-door car hire including insurance
  • Ferry from Hyannis to Martha’s Vineyard
  • Ferry from Martha’s Vineyard to Nantucket
  • Ferry from Nantucket to Hyannis
  • All Island Tour by Bus in Oak Bluffs (Martha’s Vineyard)
  • Nantucket Island Bus Tour
  • Accommodations as stated

Pricing Information

With airlines and hotels regularly introducing special offers, we’ve elected to not display pricing on our website. In order to ensure that we give you the most competitive price for the itinerary you’re interested in we’ll apply the best rates, promotions and offers that are available when we receive your enquiry. Please contact us via email, telephone or our websites ‘make an enquiry’, and we’ll endeavour to provide you with a tailor-made quotation within one working day.

Day 1

Arrive Boston

Depart the UK on your chosen scheduled flight to Boston. Upon arrival proceed to your hotel, the Fairmont Copley Plaza, which will provide your base for the first three nights of this wonderful itinerary. A great location, close to shopping and restaurants on Newbury, Boston Common and the Swan Boats in Boston Public Garden, you’re located in the heart of the action.

Fairmont Copley Plaza, Boston
Day 2, 3

Boston

Boston is a city where history truly comes alive – in a fun and engaging way. You can enjoy the myriad of attractions, including Faneuil Hall and the Boston Tea Party Museum. Take a visit to the delightful waterfront area, where sightseeing cruises depart, Boston Aquarium is located and you will find a wealth of seafood restaurants. Boston is also a very green city, filled with parks and landscaped areas. Don’t miss walking on Boston Common and visiting Boston Public Gardens.

Sightseeing in Boston

Fairmont Copley Plaza, Boston
Day 4, 5

Sandwich

58mi / 93km

This morning you collect your rental car and say goodbye to the big city. Heading south, your destination is the town of Sandwich in Cape Cod, which will be your base for the next two nights. On route, we highly recommend a stop in the town of Plymouth, home to the Plimoth Patuxet Museums, where each museum brings to life the history of Plymouth Colony and the Indigenous homeland. When you arrive into Sandwich, you will be greeted by one of the most picturesque towns on Cape Cod. It boasts beautiful old homes, some of which have been converted into inns, charming shops and restaurants. If you enjoy the outdoors, you’ll love Sandwich, home to many pristine beaches including East Sandwich Beach, Sandy Neck Beach, and Town Neck Beach, all offering fun in the sun and water activities.

Dan'l Webster Inn & Spa, Sandwich
Day 6, 7

Chatham

32mi / 51km

After breakfast, you journey further into Cape Cod, to the town of Chatham where you spend a further two nights. Chatham is located at the southeast tip of Massachusetts and halfway down the 75-mile-long Cape Cod Peninsula. This seaside town is blessed with beautiful scenery and offers a diverse range of activities. If you like to get outdoors, Chatham is home to many Nature Trails and Parks for biking and hiking. If golf is your passion, there are beautiful golf courses overlooking the Atlantic. If you enjoy visiting historic places and museums, there are some of the best-preserved homes and buildings in the area. Venturing further afield, Chatham offers the perfect base from which to explore the northern tip of Cape Cod. The quirky town of Provincetown is less than an hour’s drive away and highly recommend as the location from which to take a Whale Watch Cruise. The three hour tours offer a wide spectrum of educational tools that go beyond the average boat trip, designed to enhance your awareness of whales, other marine life, and the marine habitat that surrounds Provincetown.

Chatham Bars Inn, Chatham
Day 8, 9

Martha's Vineyard

60mi / 97km

Today you will make the short drive to Hyannis, where you leave your car at a long-stay car park (paid for locally) and head over to Martha’s Vineyard (Oak Bluff) on a passenger ferry. Once you arrive on Martha’s Vineyard you will independently make your way to the Harbor View Hotel in Edgartown, your centrally located base for the next two nights. To help you aclimatise, on your first day on the island, we have included an All Island Tour leaving from Oak Bluff, which is less than seven miles from Edgartown. This three hour tour covers many of the island’s top attractions including the Aquinnah Cliffs, East Chop Lighthouse, the Menemsham fishing village and so much more. Following the tour, you can explore for yourself. Beautiful beaches ring the island’s outer edge, while the interior is crisscrossed with many biking and walking trails accentuated by natural and cultivated foliage and flowers. Rest assured you’ll never be short of things to see, do and explore on this strikingly beautiful island. 

Harbor View Hotel, Edgartown, Martha's Vineyard
Day 10, 11

Nantucket

38mi / 61km

This morning you will check out of your hotel before independently making your way back to the port in Oak Bluff. Here you will catch another passenger ferry, this time you will be hopping over to Nantucket for a further two night stay. Nantucket is a charming island with an array of golden beaches, sand dunes, lighthouses, historic harbours, quaint inns, and more than half a dozen museums ready to explore. To help enhance your Nantucket experience we have included a one and half hour Island Bus Tour, where you will enjoy a fully narrated historic exploration, covering close to 65% of the island. Stops include The Old Mill, “Sconset” Village with its rose-covered cottages, Low Beach, Sankaty Head Lighthouse, Cranberry bogs, the Nantucket moors and lots more.

White Elephant, Nantucket
Day 12, 13

Falmouth

50mi / 80km

Today you will head back to the port, where you will board your final passenger ferry back to Hyannis on Cape Cod. After picking up your car, you’ll make the short 20 mile journey Falmouth for your final two nights. Falmouth is another one of Cape Cod’s treasures, located in the southwestern part of the Cape which encompasses several small villages, 68 miles of coastline and 10 beaches. Whether its boating, windsurfing, fishing, jet skiing or simply soaking up the sun which tempts you, there is something for everyone on the beaches of Falmouth. We highly recommend visiting either Chapoquoit Beach or Old Silver Beach to catch one of the stunning sunsets. For outdoor adventures, you may choose to hike or bike along many of the paths and trails which offer a natural setting of salt marsh, cranberry bogs, ponds, and woodlands. One further recommendation would be to make time to stroll along Falmouth’s tree-lined Main Street, where you’ll find quaint shops filled with unique gifts and delightful restaurants to suit every palate; from international restaurants to fresh fish and seafood cuisines.

Sea Crest Beach Hotel, Falmouth
Day 14

Journey Home

74mi / 119km

This morning you may have time for some last-minute sightseeing or shopping for those all-important souvenirs before making the 74 mile journey back to Boston International Airport, to return your car and check-in for your flight to the UK. 


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Our team of travel professionals focus on providing you with the very best advice when it comes to planning your holiday to the USA and Canada. They have experienced the destinations, hotels, tours and excursions for themselves, so if its expert advice and guidance backed by faultless customer service that you are looking for, you couldn’t’ be in safer hands. We will listen to your wish list of ideas as well as add our own personal recommendations to create a unique itinerary, personalised just for you.

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