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 £2,929 per person 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. (IN)


  • Explore Boston’s Freedom Trail
  • Visit ‘The Breakers’, the most splendid of Newport’s summer cottages
  • Experience the techniques of the glassmakers at the Sandwich Glass Museum
  • Visit the Pilgrim Hall Museum and meet a descendant of the Mayflower Party
  • Explore Martha Vineyard’s gingerbread-like cottages
  • Cruise along Newport’s coast on board an 80-foot schooner
  • Tour the Cape Cod National Seashore

Itinerary Overview

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


Tour departs Fridays between May - October. Speak to our sales experts today to discuss your tour (IN).

Our holidays include
  • Flights & taxes
  • Accommodation
  • Checked baggage
  • ATOL protection
  • In resort assistance & 24 hour contact centre
Why Book with American Sky?
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  • 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 (or similar) 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 (or similar) Breakfast included

Day 3

Pilgrim Heritage - Sandwich

This morning discover the history behind the first pilgrim settlement with a visit to Pilgrim Hall Museum, and meet a descendant of the Mayflower party. Afterwards, you will travel to the charming town of Sandwich, the oldest on Cape Cod. Experience the English and Irish glassblowing techniques at the Sandwich Glass Museum, before ending your day at your charming inn.

Hotel: Dan'l Webster Inn and Spa, Sandwich (or similar) Breakfast and dinner with wine included.

Day 4


Today you’ll explore Cape Cod’s National Seashore, meeting a park ranger as Salt Pond who’ll teach you all about the natural wonder and human history on the cape. The rest of the day is at your leisure, with optional experiences of whale watching, or a visit to the Peaked Hill Bars Historic District Sand Dunes.

Hotel: Dan'l Webster Inn and Spa, Sandwich (or similar) 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. Tonight, you’ll dine at Bettini Restaurant for a fabulous sea-to-table experience.

Hotel: Harbor View Hotel (or similar) 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: Hotel Viking, Newport  (or similar) Breakfast included.

Day 7


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 (or similar) Breakfast and dinner with wine included.

Day 8


Today you have a relaxed start before returning back 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 (as described above or similar)
  • 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, ferry to Martha's Vineyard and tour of Oak Bluffs, Nantucket Island, Sandwich Glass Museum, tour of Cape Cod National Seashore.

Julie Leggatt
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