Cape Cod, Massachusetts
Cape Cod, Massachusetts
Boston, Massachusetts
Boston, Massachusetts
Newport, Rhode Island
Newport, Rhode Island
Martha's Vineyard & Oak Bluff
Martha's Vineyard & Oak Bluff
Cape Cod & Lewis Bay Lighthouse, Massachusetts
Cape Cod & Lewis Bay Lighthouse, Massachusetts

Boston, Cape Cod & the Islands

7 Nights from €3,059 Including Flights


Discover some of New England’s most beautiful and quintessential cities and towns on this wonderful seven-night escorted tour. Starting and ending in Boston, you’ll have the chance to discover everything that makes this region so lovable, including stays in Cape Cod, Newport, Nantucket Island and Martha’s Vineyard.

From kooky villages with rainbow-coloured cottages and cool towns brimming with culture, to brilliant museums infused with deep history and little islands home to stunning natural beauty, there is much to see and do on this trip. Whether you fancy trying succulent seafood straight from the sea, delving into the region’s past, relaxing on dazzling beaches or exploring the coast by catamaran, there’s something for everyone on this coastal adventure.


  • Explore Boston’s Freedom Trail
  • Visit ‘The Breakers’, the most splendid of Newport’s summer cottages
  • Discover Herman Melville’s inspiration for Moby Dick at the New Bedford Whaling Museum
  • Journey to the naturally pretty Nantucket Island on board a speedy catamaran
  • Explore Martha Vineyard’s gingerbread-like cottages
  • Cruise along Newport’s coast on board an 80-foot schooner

Itinerary Overview

Boston 2 nights – Newport 1 night – Sandwich 1 night – Martha's Vineyard 1 night – Nantucket Island 1 night – North Falmouth 1 night – Fly home from Boston.

Our holidays include
  • Flights & taxes
  • Accommodation
  • Checked baggage
  • CAR licensed & bonded
  • In resort assistance & 24 hour contact centre
Why Book with American Sky?
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  • 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


Upon arrival in Boston Logan International Airport, you will transfer to your downtown hotel, ready for a Welcome Dinner with your tour director at 6pm.

Hotel: Hyatt Regency Boston
Dinner with wine included.

Day 2


Today is a relaxed insight into this eclectic city. Enjoy a city sightseeing tour including several stops along Boston’s Freedom Trail and the colourful neighbourhoods of Back Bay and Bunker Hill, before spending the afternoon exploring as you please.

Hotel: Hyatt Regency Boston
Breakfast included.

Day 3


Adorned with the Gilded Age mansions of America’s richest families, we’re certain your day in Newport will take your breath away. Visit ‘The Breakers’, the grandest of Newport’s summer ‘cottages’, and discover why the city has been named the Sailing Capital of the World. In the afternoon, you will board an 80-foot schooner for a picturesque cruise along the coast. Dinner will be served at 22 Bowens Wine Bar & Grill.

Hotel: Hotel Viking
Breakfast and dinner with wine included.

Day 4


This morning travel to the New Bedford Whaling Museum, to discover the material that inspired Herman Melville to pen his classic work, Moby Dick. Afterwards, you will travel to the charming town of Sandwich, the oldest on Cape Cod, to explore the Heritage Museums and Gardens, museum of America, and the old-school vintage cars. End the day with a visit to the Sandwich Glass Museum to see the techniques of the English and Irish glassmakers developed by Deming Jarvis during the early 19th century. The rest of the day is at your leisure.

Hotel: Dan’l Webster Inn and Spa
Full breakfast included.

Day 5

Martha’s Vineyard

In the morning, you will board the ferry to Martha’s Vineyard, a pretty area characterised by its pristine beaches and fantastic outdoor recreation. Many presidential visits have taken place here, including that of Bill Clinton and the Obamas. Here, you will travel to Oak Bluff, which will bring a smile to your face with its kaleidoscope of coloured, gingerbread like cottages adorned with story book decorations. There’s a great tour of the island included, with gorgeous views of the harbour, lighthouse and Chappaquiddick Island from your hotel.

Hotel: Harbor View Hotel
Full breakfast and dinner with wine included.

Day 6

Nantucket Island

Heading to picturesque Nantucket Island today on board a high speed catamaran. Take in the quaint cobbled streets and spectacular architecture. Nantucket is one of the most exclusive coastal communities in the US. Return to the mainland in the late afternoon to enjoy the amenities of your beachside hotel.

Hotel: Sea Crest Beach Hotel (Oceanview room)
Breakfast included.

Day 7

Cape Cod National Seashore – Provincetown - North Falmouth

Begin the day with a ferry to Woods Hole, before a great exploration of the Cape Cod National Seashore. You’ll then travel to the extreme tip of Cape Cod – Princetown – which is a lovely coastal resort well-loved thanks to its funky boutiques, stunning beaches, and thriving restaurant and art scene. Return back to North Falmouth before a lovely Celebration Dinner with wine in the evening.

Hotel: Sea Crest Beach Hotel (Oceanview room)
Breakfast and dinner with wine included.

Day 8


Today you will visit a local cranberry bog to learn about one of Massachusetts’ most important crops – a fruit that is said to be one of only a few native fruits in North America. You’ll then return to Boston for your transfer to Boston Logan International Airport. Please note not to book flights before 4pm, as airport arrival will be at 2pm.

  • International flights
  • Hotel accommodation for seven nights
  • Airport transfers
  • 7 breakfasts and 4 dinners with wine
  • Activities: Boston's Freedom Trail, The Breakers in Newport, cruise on the 80-foot schooner around Newport, New Bedford Whaling Museum, ferry to Martha's Vineyard and tour of Oak Bluffs, Nantucket Island, Heritage Museums and Gardens in Sandwich, cranberry bog in Cape Cod, tour of Cape Cod National Seashore.

Jackie Sheehan
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