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 €4,799 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)

Women's-Only Tour Option
As well as the standard tour, there is the option of travelling on a Women's-Only Tour. Combining existing tours tailored to cater to women travellers, led by female tour guides and enriched by local female experts. As well as couples, solo travellers are very welcome facilitating easier connections within small groups of up to 24 people. This approach offers a delightful travel experience, building connections among women and instilling confidence in solo travellers.


  • 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

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

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

2024 Definite Departure Dates
May: 10
Jun: 14, 21
Sept: 13, 20 27
Oct: 11

Last day transfer will arrive at the airport at 12pm, please be aware when booking your flights that the departure flight should be no earlier than 3pm

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
  • Low deposits
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Day 1


Upon arrival in Boston Logan International Airport, transfer independently to your downtown hotel, ready for a Welcome Dinner with your tour director at 6pm. For ease of travel, we can pre-book your overseas airport transfers to your hotel.

Overnight: Hyatt Regency Boston or similar. Dinner with wine included.

Day 2


Today traverse the iconic red-brick Freedom Trail, tracing the footsteps of the American Revolution. Highlights include Boston Common, the Old Corner Bookstore, and the imposing Bunker Hill Monument. Admire the vibrant Back Bay and historic North End, renowned as Boston's Little Italy. Indulge in delectable cannoli and espresso, then opt to explore Fenway Park, home of the Red Sox, or visit the John F. Kennedy Presidential Library and Museum. Enjoy the afternoon at your leisure, pursuing personal interests.

Overnight: Hyatt Regency Boston or similar. Breakfast included

Day 3

Boston - 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, visit the Plimoth Patuxet Museum, a living memorial dedicated to the early settlers and the Wampanoag people. Later 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 and enjoy dinner.

Overnight: 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.

Overnight: Dan'l Webster Inn and Spa, Sandwich or similar. Breakfast included.

Day 5

Sandwich - 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 Menemsha Room for a fabulous sea-to-table experience.

Overnight: Harbor View Hotel or similar. Breakfast and dinner with wine included.

Day 6

Matha's Vineyard - Nantucket Island

Heading to picturesque Nantucket Island today on board a high-speed catamaran. Take in the quaint cobbled streets and spectacular architecture as you walk through on a guided walking tour of downtown. 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.

Overnight: Hotel Viking, Newport or similar. Breakfast included.

Day 7

Nantucket Island - Newport

This morning, choose between Breakers Mansion or Elms Estate for a landmark visit in Newport. Then, sail around Newport Harbor on Rum Runner II, passing mansions, speakeasies, and lighthouses. Enjoy a Celebration Dinner at La Forge Casino Restaurant, dating back to 1880, with fellow travellers, marking the end of our New England journey.

Overnight: Hotel Viking or similar. Breakfast and dinner with wine included.

Day 8

Newport - Boston

Today you have a relaxed start before returning back to Boston for your transfer to Boston Logan International Airport.

Last day transfer will arrive at the airport at 12pm, please be aware when booking your flights that the departure flight should be no earlier than 3pm

Breakfast included.

  • International return flights
  • Internal travel: luxury air-conditioned coach with on-board restroom and extended leg room
  • 7 nights hotel accommodation as described or similar
  • Overseas airport transfer on the last day
  • 7 breakfasts and 4 dinners with wine
  • Boston Freedom Trail
  • Visit Boston's Fenway Park or tour The John F. Kennedy Presidential Library and Museum
  • Visit Pilgrim Hall Museum
  • Visit Plimoth Patuxet Museum
  • Tour the Sandwich Glass Museum and watch glassblowers in action
  • Visit Cape Cod's National Seashore
  • Ferry to Oak Bluffs in Matha's Vineyard with dinner
  • High-speed Catamaran from Matha's Vineyard to Nantucket Island
  • Nantucket Island Downtown Walking Tour
  • Choose between Breakers Mansion or Elms Estate in Newport
  • Visit Newport and Cruise onboard the Adirondack II

What's not included

  • Meals unless stated otherwise
  • Optional excursions
  • Overseas arrival airport transfer on first day (available to pre-book at an additional cost)

Brendan White
Book today

Talk to our travel experts for more information and to book or tailor-make your holiday

01 6649900 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun

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