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

Boston (Contemporary) - USA

Hotel Viking Newport

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

Danl Webster Inn and Spa Sandwich

Sandwich (Heritage) - USA

Harbor View Hotel and Resort Martha Vineyard_Edgartown

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 North Falmouth

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
10940 independent user reviews received during the past year.

  • 08 July, 2018


    Trip: Martha's Vineyard and Nantucket were highlights. We did not enjoy the day spent traveling to Provincetown nor Provincetown itself.

    Service: It was our first experience doing any kind of group tour. We were impressed with the attention to detail, our accommodations, meals and a fantastic tour guide.

  • 30 June, 2018


    Trip: Learnt all sorts of interesting details about the area--loved seeing the architecture

    Service: Easy to call the office and sort out booking and special meal requests--staff all friendly and helpful

  • 24 June, 2018


    Trip: Stunning scenery and the islands were beautiful. Surpassed expectations.

    Service: Excellent attention to detail to ensure that the trip ran smoothly and on time. The arrival at the hotels was seamless as Cindy ensured that we had our room keys before we even got off the bus so there was no waiting around or time wasted. Nice touches like welcome drink and surprise of trying local food on the bus leaving Provincetown. The hotels were excellent and al had something special whether amazing views, central location or history.

  • 23 June, 2018


    Trip: Didn’t care for all of the stops we made, at some destinations we had too much time for shopping and eating on our own. Provincetown was s place that could be omitted. Great hotels!

    Service: Good info sent out in advance of trip.

  • 22 June, 2018


    Trip: Everything was great except for the 'Cape Cod Experience'. We took the mid-morning ferry from Martha's Vineyard to Hyannis, rode the bus for 3 hours to stop for 30 min. at the Providencetown Cape National Seashore gift station (not even going to the water!) and then directly into Providencetown for 75 min. and back on the bus to drive the 3 hours back to Falmouth, MA. BIG waste of a full day!!!

    Service: I ordered our tour on the Insight website with ease; kept my payment records current on the website; requested travel insurance and filed all my traveler info very conveniently on the Insight website.

  • 22 June, 2018


    Trip: Interesting itinerary. Thought the second day in Boston was wasted. So much more we could have seen and done. No reason to be back at hotel At noon.

    Service: Cyndi Cobb acted in a very professional manner. Made the tour interesting for all.

  • 28 May, 2018


    Trip: The itinerary was well paced and very enjoyable.

    Service: The tour director was excellent and was very thorough in even the tiniest detail of the tour.

  • 28 May, 2018


    Trip: There was a wonderful variety each day -- from a sailboat cruise, a tour of the Vanderbilt mansion, touring a whaling museum, taking a ferry to Martha's Vineyard, a visit to Cape Cod and Nantucket. Absolutely perfect!

    Service: Everything went as planned. Our tour guide was wonderful in explaining where we would be that day. Very knowledgeable.

  • 09 October, 2017


    Trip: As stated in previous statement - first class tour and staff

    Service: Excellent tour giving a taste of many areas in Boston,Cape Cod and the islands.Robin,our tour guide,was just perfect - friendly, helpful and very knowledgeable. John our driver was a first class driver, also friendly and helpful. A thoroughly enjoyable and interesting holiday

  • 08 October, 2017


    Trip: There were plenty of options and opportunity to shop and purchase items that were unique.

    Service: Having to deal with Hurricane Jose and keeping the safety of others first and foremost, but finding alternatives that would be enjoyable was no easy task I am sure. Michelle and John kept us informed every step of the way and did their very best to keep things entertaining and fun.

  • 08 October, 2017


    Trip: Some of the stops were to short and some too long, but you get that with any tour. Fortuneatly we had scheduled more days on our own and saw more in Boston than we had time for on the tirp. would have liked more time at the Whaling Museum and less in Sandwich glass.

    Service: Customer service by our tour leader, driver and hotel staffs wherever we went was excellent. Would recommend to others.

  • 08 October, 2017


    Trip: Quaint. The schedule was not rushed.

    Service: Great guide, wonderful hotels, relaxing schedule.

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