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 trips. Please note, many Optional Experiences are operated by independent third party suppliers, not Insight Vacations. The Optionals and pricing listed here are a guideline only and 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
11289 independent user reviews received during the past year.

  • 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.

  • 05 October, 2018


    Trip: Just a really great trip … don't know what else to say

    Service: everything was just wonderful … loved the tour director

  • 05 October, 2018


    Trip: Would rather have had more time in Boston and less in Sandwich and the Glass Museum. Nantucket was spectacular and would have liked a longer day there.

    Service: Our tour guide, Howell Geib, and bus driver, Hardy, we're exceptional. Howie was very knowledgeable about the area and that made the whole trip so enjoyable. We always felt very safe with Hardy behind the wheel.

  • 05 October, 2018


    Trip: We got to see all of the New England highlights!

    Service: Howie and Hardy were a great guide/driver team. Howie was very knowledgeable and it was obvious that he was very passionate about his work!

  • 05 October, 2018


    Trip: Exciting, knowledgeable, humorous, and caring tour director - Howie Geib. I have food allergies and I received excellent attention and my food was always safe and delicious.

    Service: Attention to detail. Care and understanding.

  • 05 October, 2018


    Trip: All the destinations, hotels, food, places we stopped & visited,variety of modes of transportation, sights, speakers, information, the different islands & things we saw, heard & did with a bus full of delightful fellow passengers & excellent tour guide & bus driver made this trip a 5 star tour.

    Service: Our tour director, Howie Geib, was the best part of the tour & he made it great. The hotels, food, activities, sites, destinations, people, bus, bus driver, etc. etc. was wonderful, fun, informative, educational, beautiful, interesting, comfortable,etc, etc.

  • 05 October, 2018


    Trip: I wanted to see more of Martha's Vineyard and not just the gingerbread houses. Where were the estates everyone hears about in the papers? I know it rained but a bus ride would have been nice. And, the garden in Sandwich wasn't that great with no signage inside or flowers.

    Service: The documents were delivered on time. Howie was a terrific guide and we were always looked after even when it started to rain. I liked the location of the Westin in Boston but the toilet was made for a 5 year old like in kindergarten; so low and others on the tour also complained. I haven't seen a toilet like that in years; what gives?

  • 01 October, 2018


    Trip: The only suggestion would be to remove the day going to Provincetown. It was a 2 hour drive there and back taking up most of the day with very little to see and enjoy at the destination.

    Service: The tour director, Jackie Lappen, not only shared information but with caring and sometimes a little humor. Her love for Boston made us see the city through her eyes. If Jackie didn't know an answer offhand, she searched for the answer and shared it with the group. Rocky was a great driver with a great sense of humor and a ready smile at all times. The lodging and meals were very good.

  • 29 September, 2018


    Trip: We loved where we went & what we daw.

    Service: Hotels, tour director, bus driver, & places we visited. All were great.

  • 28 September, 2018


    Trip: Weather constraints & room assignment confusion at Sandwich hotel, but handled with professional expertise of tour director.

    Service: Everything! Tour director & driver the best.

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