Boston, Cape Cod & the Islands - Insight Vacations

Boston Cape Cod and the Islands (Summer 2018)

Duration: 8 days Visiting: United States

Prices from {{lowPrice}}

  • Overview
  • Itinerary
  • Highlights
  • Optional experiences
  • Accommodation
  • Reviews
  • Dates & prices

You're constantly reminded of the sea in this fish-hook shaped corner of New England. From "Ocean State" Rhode Island, steeped in sailing history, to the chic waterfront resorts of Martha's Vineyard and summer playgrounds of the Cape.

  1. Day 1

    Boston, the Cradle of Liberty.

    Welcome to Boston. Upon arrival at Boston Logan International Airport, transfer to your downtown hotel. At 18:00, gather with your Tour Director for a Welcome Dinner with wine and an opportunity to mingle, during a pleasant evening.

  2. Day 2 - Relaxed Start

    Historic Boston.

    (Relaxed Start) Your Tour Director will provide you with a fascinating insight into 'Beantown' during a historical sightseeing tour. At several stops along Boston's famed Freedom Trail, hear about the struggle and courage of the American colonists during revolutionary times. View the colourful neighbourhoods of Back Bay and historic North End. The afternoon is free to pursue your own interests.

  3. Day 3

    Newport, the Queen of Summer Resorts.

    South of Boston is Rhode Island, America's smallest state packed with big league attractions. Its star player is the elegant town of Newport, lined with the Gilded Age mansions of America's wealthiest families. Visit The Breakers, the grandest of Newport's summer ‘cottages’ and a symbol of the Vanderbilt family's social and financial preeminence during the late 19th century. Newport was home to the America's Cup for more than 50 years and is widely known as the Sailing Capital of the World. Embark on a nautical discovery on-board an 80-foot (24 metre) schooner for a scenic cruise around the coastline. In the evening, dinner is served at a local restaurant.

  4. Day 4

    On to Sandwich.

    In the morning, travel back in time to visit the stunning New Bedford Whaling Museum, where a Local Expert will enlighten you on the extensive impact whaling had on the region. See the largest model ship in the world, a beautiful scrimshaw collection, and the many exhibits, including the material that inspired Herman Melville to pen his classic work, ‘Moby Dick.’ Travel on to the town of Sandwich, the oldest town on Cape Cod. Continue to the Heritage Museums and Gardens, where in one beautiful location, you'll find sweeping lawns, stunning gardens, a windmill, art gallery, museum of Americana, and an amazing collection of antique cars. Visit the Sandwich Glass Museum to experience the techniques of the English and Irish glassmakers that founder Deming Jarvis developed during the early 19th century.

  5. Day 5

    Martha’s Vineyard, a Presidential Paradise.

    Board your morning ferry to Martha's Vineyard, home to pristine sandy beaches, and diverse outdoor attractions. No stranger to presidential visits, the island has hosted Bill Clinton and the Obamas, while the former U.S. First Lady Jacqueline Kennedy Onassis maintained a home here. After disembarking, make your way to Oak Bluffs, known for its rainbow-coloured, gingerbread-like cottages with storybook decorations, high-peaked roofs, and dainty verandahs. Get acquainted with the island on a tour, before reaching your hotel which overlooks Edgartown's beautiful harbour, lighthouse and Chappaquiddick Island.

  6. Day 6

    Cape Cod National Seashore, Provincetown and North Falmouth.

    Take the ferry back to Woods Hole before an excursion to the Cape Cod National Seashore, a National Park that encompasses much of the Outer Cape. Travel to the extreme tip of Cape Cod, to Provincetown – a small coastal resort known for its beaches, cool boutiques, restaurants and art galleries, giving this town a fun and funky vibe. Then, it's on to the cottage-lined streets of North Falmouth and your beachside hotel. Step outside to feel the sun on your face and the sand between your toes.

  7. Day 7

    Nantucket Island.

    Depart Hyannis in style on a high-speed catamaran for the quaint island of Nantucket. Not only has it retained the charm of a bygone era, it is one of the most exclusive coastal communities in the US. During your visit, take in the beauty of the quaint cobblestone streets, simple Quaker-style homes and handsome houses dating back to the whaling days. Return to the mainland in the late afternoon to relax at your beachfront hotel, before meeting in the evening for a Celebration Dinner with wine.

  8. Day 8 - Relaxed Start

    Berries, Bogs and Back to Boston.

    (Relaxed Start) As one of the few fruits native to North America, it is said that the cranberry is more American than apple pie. Meet a local cranberry bog farmer. With generations of knowledge behind him, he will share with you the lifecycle and cultural impact of this truly American berry. Return to Boston, where there are complimentary transfers to Boston Logan International Airport, or the Boston tour hotel for guests wishing to extend their stay. Airport arrival will be at 14:00.




  • Nantucket: Take an excursion to this idyllic island, characterised by cobblestone streets and lighthouses.
  • New Bedford: With a Local Expert, journey back to the great age of Moby Dick and castaway crews from around the globe, at the engaging New Bedford Whaling Museum.


  • Boston: See Boston’s red-brick Freedom Trail come to life as your Tour Director leads you through this historic walking tour.
  • Newport: Step aboard an 80-foot schooner for a scenic cruise around the Newport coastline.
  • Sandwich: There’s something for everyone at the Heritage Museums and Gardens – a fascinating complex of Americana museums, located within a 100-acre garden setting.


  • Boston: View the neighbourhoods of Back Bay and North End.
  • Martha's Vineyard: Visit Oak Bluffs with its ‘gingerbread cottages’ and tour the island.
  • Cape Cod: Tour the Cape Cod National Seashore. Taste the goodness of Massachusetts’ number one agricultural commodity crop at a cranberry bog.
  • Scenic Drives: Travel along Ocean Drive in Newport, Rhode Island. Enjoy the natural beauty of Martha’s Vineyard and Nantucket.


  • Cape Cod: Meet a local farmer and taste the goodness of the all-American cranberry fruit at a working cranberry bog.
  • North Falmouth: Join your Tour Director and celebrate the culmination of your tour with wine and classic New England cuisine.
  • Included Quality Dining: 7 Full Breakfasts (FB), 4 Dinners (D) with wine (DW).


  • Newport: Experience warmth and character at the boutique Hotel Viking, registered with the Historic Hotels of America.
  • Sandwich: Visitors to the boutique Dan'l Webster Inn are treated to the romance of the past, combined with today's conveniences.
  • Martha's Vineyard: The refined Harbor View Hotel embodies timeless character with modern comforts.
  • Cape Cod: While the views and sunsets are fabulous at the Sea Crest Beach Hotel, so are the facilities and warm hospitality of the staff.
  • Boston: The Westin Copley Place is a tranquil haven of classic luxury in the centre of the city.


  • Our highly-skilled Insight Tour Director will ensure your journey is seamless, serving as your expert guide, consummate organiser, and friend in a foreign land.
  • Enjoy the comfort of Insight's luxury, air-conditioned, 40-seat touring coach, with extended Business Class legroom and on-board restroom.
  • Personal radio headsets give you the freedom to wander during visits to famous highlights, without missing any of your Local Expert's fascinating commentary.
  • We carry your bags for you and promptly deliver them to your hotel door.
  • Hotel and restaurant tips are included; you'll never have to worry about how much to give, nor search for foreign currency. Plus, we include all taxes and porterage charges at hotels.
  • Stay connected with friends and family with our complimentary coach and hotel Wi-Fi (where available).
  • From time to time, your Tour Director will enchant you with an Insight Flourish - a local tidbit representing authentic food or beverages unique to the destination.
  • Complimentary transfers from and to Boston Logan International Airport are available only on arrival and departure days. Should your flights not coincide with these transfers, or additional accommodation has been booked through Insight Vacations, charged transfers are available. Alternatively, please make your own way from/to the airport.

Optional experiences

Most Insight trips already include a host of bonus highlights and comprehensive sightseeing. There may also be an exciting array of Optional Experiences which will turn an already amazing experience into the trip of a lifetime! These are entirely optional and can be booked through your Travel Director/Local Representative at the commencement of your trip. Please note, many Optional Experiences are operated by independent third party suppliers, not Insight Vacations.

Prices and availability of Optional Experiences are subject to change.



The Westin Copley Place

Boston (Contemporary) - USA

Hotel Viking

Newport (Heritage) - USA

Built by the citizens of Newport in the 1920s to accommodate their guests and visitors, the Hotel Viking, “the people’s hotel,” will charm you with its mix of classic elegance and modern amenities.This Newport luxury hotel, centrally located on historic Bellevue Avenue, has proudly hosted many famous guests including President and Mrs. John F. Kennedy, the Astors, the Vanderbilts, as well as many entertainers and celebrities m

Dan'l Webster Inn and Spa

Sandwich (Heritage) - USA

Harbor View Hotel & Resort

Martha’s Vineyard/Edgartown (Central) - USA

The historic Harbor View Hotel on Martha’s Vineyard, located in the very heart of Edgartown, Massachusetts, has been the second home for generations of families. Martha’s Vineyard getaways to Harbor View are more than mere vacations. They are beloved traditions where family customs are passed down, fun activities are shared and the cherished heritage of the past comes alive every day. With stunning ocean views and refined Martha’s Vineyard décor, the Harbor View delivers the attentive personal service you thought had disappeared forever.

Sea Crest Beach Hotel

Falmouth (Scenic) - USA

Just minutes over the Bourne or Sagamore bridges, the Sea Crest Beach Hotel in North Falmouth provides the perfect backdrop for relaxing romantic escapes, adventurous getaways and unforgettable events. Discover a location of pristine white sand beaches at Old Silver Beach, iconic cottage-lined streets, barefoot luxury and a casual, welcoming vibe just about anywhere you go. Sea Crest Beach Hotel is home to 263 guest rooms and suites all designed in classic Cape Cod style with neutral tones and retro motifs.

Guest Reviews & Experiences

Our guests rate us 4.5 out of 5 based on
11509 independent user reviews received during the past year.

  • 07 November, 2018


    Trip: Most of the people on tour thought that we should have spent less time at Nantucket and more time at Martha's VIneyard.

    Service: I took the Boston/Cape Cod tour and absolutely loved it! The tour director was fun and knowledgeable about the areas we visited. The high speed ferry ride was a highlight for me. I am planning on going on another Insight vacation in the near future.

  • 02 November, 2018


    Trip: My only request is that optional sight seeing be offered for people who don’t care to spend time shopping.

    Service: My husband and I had a great time on our last Insight vacation. Our tour guide was very attentive to everyone and the group enjoyed each other’s company, making it a really fun time. I highly recommend touring with Insight to others and plan to do so again myself.

  • 28 October, 2018


    Trip: Same as previous comments.

    Service: Courtesy and politeness were abundant.

  • 19 October, 2018


    Trip: We did not need a full day in Nantucket. Once we toured the entire Island(which only took almost an hour) we could have eaten then left. After we ate, we walked around. We were there about TWO more hours after that. We did not need that much time there in Nantucket. My suggestion is that we start that tour with two days in Boston and two days on the end of the tour in Martha's Vineyard. There is no reason to stay the last two nights in South Falmouth. That can be done in the middle along with Nantucket. Other than that, everything was great.

    Service: Everything went well. Very thorough.

  • 19 October, 2018


    Trip: Did not care for the glass museum and a little to much free time in New Bedford. Otherwise loved everything & everywhere!!!

    Service: Great trip! Only trouble was a strike at the Westin hotel in Boston. NOT GOOD!! We should have been moved. Tour director, Jackie Lappen was wonderful as was a he bus driver, Hardy. They made the trip so much fun.

  • 19 October, 2018


    Trip: All trips on time and well thought out.

    Service: Excellent customer service. By the way, my last name is Horton not hornton. Tks

  • 19 October, 2018


    Trip: every thing was excellent

    Service: yes

  • 19 October, 2018


    Trip: Enjoyed the sights but felt rushed. Early departures, would have liked to stay more than one day in Martha's vineyard. Didn't get to enjoy my balcony and ocean at Seacrest. Didn't enjoy dinner there.

    Service: I liked that transfers, tickets, luggage and transportation was arranged and comfortable.

  • 19 October, 2018


    Trip: Love the food. Entire area is rich with history, which is a forte of our guide. All questions were answered to our satisfaction.

    Service: Very knowledgeable guide and great driver. Comfortable accommodations. Never rushed but never bored. Just enough time on our own to explore restaurants and local sights.

  • 06 October, 2018


    Trip: Very informative and pleasant.

    Service: Great Guide and Driver ... very informative and pleasant.

  • 06 October, 2018


    Trip: I loved the choice of places we visited, although I would have preferred more time in Martha's Vineyard

    Service: I would definitely recommend then again, our tour director, Howie Geib was the best I have ever had in my travels. He was very knowledgeable of the area, and went out of his way to accommodate everyone's specific needs.

  • 06 October, 2018


    Trip: The hotels we stayed at were nice but some of them we had to go outside to get to the dining room and we had quite a bit of rain.

    Service: The tour director was very knowledgeable and took wonderful care of the group.

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