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Insight Vacations

Boston, Cape Cod & The Islands - Small Group (Summer 2026)

Insight Vacations
  • Length

    8 Days

  • Quality
    This indicates the overall quality of the tour operator's products. A low rating does not mean it is not good - it just means that it does not include as much, or perhaps is of a more standard quality than the higher quality tours. For example, a 3 star quality rating means that it is a more standard/economical tour, while 5 stars is a very luxurious tour that often includes a lot of amenities.

  • Starts in

    Boston (Massachusetts)

  • Ends in

    Boston (Massachusetts)

  • Available Tour Start Dates

    MAY 8, 2026 to AUG 21, 2026 These are the tour start dates for instances of this tour that were available the last time Insight Vacations sent us such information. There may be other departures for this tour that are not available (i.e. sold out or cancelled).

  • Activity Level

    No Rating Provided These are tours that the vendor has not electronically communicated an activity level for. Contact us if you would like to know the activity level for any of these tours.

  • Language

    English

  • Guaranteed Date(s)
    Yes means that there is at least one tour date that the vendor guarantees will occur. No means that there is not at least one tour date that the vendor guarantees will occur, which usually means that the vendor wants a certain amount of reservations on each tour in order for each one to occur. Of course, the terms and conditions of the vendor do allow for the vendor to cancel guaranteed tour dates for certain reasons (for example, a natural disaster).

    No

  • Special Interest(s)

    Small Group
    There is at least one season during which this tour is offered as a Small Group. Such seasons are noted as being Small Group within the related date range.

From
Pricing listed is per person, based on double occupancy, and is the least expensive price for at least one departure date of this tour. Price is for the tour only. Additional items, including but not limited to, airfare (unless noted otherwise), travel insurance, and more, are additional.
$4,987.50

Overview

This 8-Day guided tour blends history with glamour as you travel from Massachusetts to Rhode Island. Follow the red-brick Freedom Trail in Boston to see where the U.S. took shape. On the shores of Cape Cod Bay, see Sandwich, a coastal town famous for its glassmakers; here, visit the Sandwich Glass Museum, where you can learn tricks of the trade. At Martha's Vineyard, a driver will take you past the former home of Jacqueline Kennedy Onassis and to Oak Bluffs, an idyllic town with gingerbread-like cottages. Indulge in a sea-to-table feast filled with fish caught from local fishermen, fresh produce from nearby farms and delicacies picked by foragers. In the seaside city of Newport, board an 80-foot schooner to cruise the coastline, taking in views of historical buildings and the homes of the rich and famous — and learn about the area’s past as a pirates’ haven.

Visited During Tour

Boston (Massachusetts) | Cape Cod (Massachusetts) | Martha's Vineyard (Massachusetts) | Nantucket (Massachusetts) | Newport | Sandwich (Massachusetts)

Dates, Offers & Prices
Tour Itinerary
More Details
Dates, Offers & Prices

The following are Boston, Cape Cod & The Islands - Small Group (Summer 2026) tour dates available from Insight Vacations. Select a bonus offer graphic to view its details, including its terms.

Pricing Type: Double Occupancy
Pricing is per person, based on two people per reservation
Start Date  End Date  Bonus Offers From
Pricing listed is per person, based on double occupancy, and is the least expensive price available on this tour date. Price is for the tour only, unless noted otherwise. Additional items, including but not limited to, airfare, travel insurance, and more, are additional.
Guaranteed?
Yes means that that the vendor guarantees that tour date will occur. No means that the vendor does not guarantee the tour will occur on that date, which usually means that the vendor wants a certain amount of reservations on that date in order to confirm it. Of course, the terms and conditions of the vendor do allow for the vendor to cancel guaranteed tour dates for certain reasons (for example, a natural disaster).
Friday May 8, 2026 Friday May 15, 2026 Insight Vacations Sale
Exclusive Rates on all Insight Vacations Tours!

Exclusive Rates on all Insight Vacations Tours!

Book any Insight Vacations tour with us and you'll get the best deal possible!

Contact us for pricing and availability.
Available for new bookings made starting 10/22/20. Subject to expire without advanced notice.

Bonus Offers are not combinable, unless noted otherwise. Pricing may already reflect the application of any applicable promotions. Additional restrictions apply. Certain terms and conditions apply to each offer. Additional restrictions apply. We reserve the right to correct errors.

Insight Vacations Sale
No Booking Fees!

No Booking Fees!

We do not charge booking fees on any Insight Vacations tours.

You're sure to enjoy an affordable Insight Vacations tour package when booking with us!

Contact us for pricing and availability.
Available for new bookings made starting 10/22/20. Subject to expire without advanced notice.

Bonus Offers are not combinable, unless noted otherwise. Pricing may already reflect the application of any applicable promotions. Additional restrictions apply. Certain terms and conditions apply to each offer. Additional restrictions apply. We reserve the right to correct errors.

$4,987.50
No
(Departure #20260508)
Friday Aug 21, 2026 Friday Aug 28, 2026 Insight Vacations Sale
Exclusive Rates on all Insight Vacations Tours!

Exclusive Rates on all Insight Vacations Tours!

Book any Insight Vacations tour with us and you'll get the best deal possible!

Contact us for pricing and availability.
Available for new bookings made starting 10/22/20. Subject to expire without advanced notice.

Bonus Offers are not combinable, unless noted otherwise. Pricing may already reflect the application of any applicable promotions. Additional restrictions apply. Certain terms and conditions apply to each offer. Additional restrictions apply. We reserve the right to correct errors.

Insight Vacations Sale
No Booking Fees!

No Booking Fees!

We do not charge booking fees on any Insight Vacations tours.

You're sure to enjoy an affordable Insight Vacations tour package when booking with us!

Contact us for pricing and availability.
Available for new bookings made starting 10/22/20. Subject to expire without advanced notice.

Bonus Offers are not combinable, unless noted otherwise. Pricing may already reflect the application of any applicable promotions. Additional restrictions apply. Certain terms and conditions apply to each offer. Additional restrictions apply. We reserve the right to correct errors.

$4,987.50
No
(Departure #20260821)
Tour Itinerary
Insight Vacations Tour Code 19-1526

Boston, Cape Cod & The Islands - Small Group (Summer 2026)

Insight Vacations Tour Code 19-1526

Map of Boston, Cape Cod & The Islands - Small Group (Summer 2026) from Insight Vacations
  • Day
    1

    Boston, the Cradle of Liberty

    Welcome to Boston, described by many as the most European city in the U.S., you can expect a thriving art scene, delicious variety of seafood delicacies and plenty of charm. Arrive to the Hyatt Regency Boston, just steps from Boston's most desirable area-attractions such as the Boston Common, Faneuil Hall, and Boston's famous shopping destination, Newbury Street. A 10-to-15 minute walk will bring you to the South End, Back Bay or the Charles River Esplanade. At 18:00, join your Travel Director for a Welcome Dinner with wine and an opportunity to mingle with fellow guests.

    • Meals Included:
    • Dinner with Wine
    • Accommodations: Hyatt Regency, Boston
  • Day
    2

    Historic Boston

    Explore the city with your Travel Director and learn about its transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. See Bunker Hill Monument, Boston Common, Boston Public Garden, Trinity Church and Copley Square. Later, with Insight Choice choose to visit the John F. Kennedy Presidential Library and Museum dedicated to the memory of the nation's thirty-fifth president, or tour Boston's oldest and largest Museum of Fine Arts, which is home to over 500,000 works of art, making it one of the largest art collections in the Americas. The rest of the day is at leisure.

    • Meals Included:
    • Breakfast
    • Accommodations: Hyatt Regency, Boston
  • Day
    3

    Pilgrim Heritage and on to Sandwich

    This morning, discover Plymouth's history at the first Pilgrim settlement. Visit Pilgrim Hall Museum, the oldest continuously operating public museum in the country and America’s museum of Pilgrim possessions. Join a MAKE TRAVEL MATTER® Experience as you visit the Plimoth Patuxet Museum. This living memorial is dedicated to preserving the histories of the Native and English inhabitants of this region and educating the public on early settlers and the Wampanoag People in an immersive and engaging environment. Later you'll get to know the Cape more intimately as you make your way to the coastal haven of Sandwich. This afternoon, discover the art and science of glass making at Sandwich Glass Museum where you can watch glassblowers in action and explore exhibits spanning over three centuries. Enjoy a dinner back at your hotel later this evening featuring local favorites.

    • Meals Included:
    • Breakfast
    • Dinner with Wine
    • Accommodations: Dan'l Webster Inn and Spa, Sandwich
  • Day
    4

    Explore Cape Cod

    Head out to Salt Pond on Cape Cod's National Seashore and learn about the natural wonder and human history represented on the Cape, from its First People and European settlement to modern lifestyles and communication technology. An optional experience on the Sand Dunes of the National Seashore may present itself later today. Roll through the Dune Shacks of Peaked Hill Bars Historic District, catching sight of Pilgrim Lake and the famed artists’ dune shacks while Local Experts share the history and ecology of these striking and inspiring dunes.

    • Meals Included:
    • Breakfast
    • Accommodations: Dan'l Webster Inn and Spa, Sandwich
  • Day
    5

    Martha's Vineyard, a Presidential Paradise

    Board a ferry this morning to Martha's Vineyard (seasonal). Home to pristine sandy beaches, outdoor attractions and heavenly harbor towns, this summer hangout is no stranger to presidential visits. The island has hosted the Clintons 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-colored, gingerbread-like cottages with gothic storybook decorations, high-peaked roofs, and dainty verandas. You’ll also find the oldest operating platform carousel in America here. Get acquainted with the island, before reaching your hotel. Tonight's dinner is sure to delight with the season’s freshest offerings from local farms, fishing boats, foragers and markets.

    • Meals Included:
    • Breakfast
    • Dinner with Wine
    • Accommodations: Harbor View, Martha's Vineyard
  • Day
    6

    Nantucket Island

    Depart Martha's Vineyard in style on a high-speed catamaran for the picturesque 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 U.S. During your visit, take in the beauty of the antique cobblestone streets, lined with high- end boutiques and breathtaking architecture during a guided walking tour. The homes date back to its whaling days which also influenced much of the culture on the island. In the past, the style of home directly correlated to a whaler's ranking. Return to the mainland in the evening to relax at your luxurious hotel.

    • Meals Included:
    • Breakfast
    • Accommodations: Viking, Newport
  • Day
    7

    Newport, the Queen of Summer Resorts Relaxed Start

    This morning, you'll enjoy a visit to The Breakers, a Gilded Age mansion and summer residence of Cornelius Vanderbilt II. The 70-room estate is the grandest of Newport's summer cottages. Today, it is a National Historic Landmark that serves as a symbol of the Vanderbilt family's social and financial pre-eminence in the Gilded Age. This afternoon, sail around Newport Harbor aboard the Rum Runner II cruising by Newport mansions and former speakeasies, lighthouses, islands, and many other points of interest along the waterfront. Our journey through New England is almost at its end, but not before you join your fellow travelers for a Celebration Dinner at La Forge Casino Restaurant originally established in 1880.

    • Meals Included:
    • Breakfast
    • Dinner with Wine
    • Accommodations: Viking, Newport
  • Day
    8

    Back to Boston Relaxed Start

    It's time to say goodbye to your fellow travelers as you return to Boston. For those heading home there will be complimentary transfers to Boston Logan International Airport, arriving at 12:00. Alternatively, you may return to the Hyatt Regency Boston if you wish to extend your stay.

    • Meals Included:
    • Breakfast
More Details

Insight Vacations is informing us of the following additional details regarding their Boston, Cape Cod & The Islands - Small Group (Summer 2026) tour:

Travelers Notes

NOTE: This Trip falls under Tour Deposit Level 2. Please refer to the Deposit, Payment and Cancellations policies on our website. DAY 1: On the first day of the itinerary guests to arrive into Boston General Edward Lawrence Logan International Airport (BOS). Guests make their own arrival transfer arrangements or can purchase private transfer. It is not recommended to book flights arriving after 15:00 on the first day of the trip. Guest meet their Travel Director at approximately 18:00 for a Welcome Reception and a short introduction on the first day of the tour, please be aware when booking your flights. DAY 8: On the last day of the itinerary guests to depart from Boston General Edward Lawrence Logan International Airport (BOS). Complimentary transfer will arrive at 12:00 on last day only, please be aware when booking flights.TRANSFERS: Private chargeable transfers are available at an additional charge on the arrival and departure days of the itinerary or in conjunction with pre-trip or post-trip accommodation booked through Insight Vacations. Guests who purchase private sedan transfers through Insight Vacations will be responsible to make a reservation directly with RMA 30 days to 7 days prior to departure. Additional information will be included with documents. GROUND HANDLER: This trip is operated by Ground Handler, Destination America.
Pricing listed above for tours is per person, in US Dollars, and is based on double occupancy. Pricing may change for other occupancy types. Pricing is based on the last time the vendor electronically sent us pricing data, which varies by vendor (usually occurs overnight or multiple times throughout each day). Pricing and availability are subject to change and must be confirmed by one of our travel advisors, who can contact the vendor to do so. Intra-vacation air (also referred to as internal air) is usually based on economy class seating (do not assume otherwise, unless explicity noted otherwise) and may be 100% non-refundable at time of final payment. Air quotes (including intra-vacation airfare) may be subject to change until final payment has been received by the vendor. Flight confirmation may be based on availability. Air reservations may not be able to be confirmed until a passport copy is received by the vendor. The following charges are not included in the vacation price unless otherwise noted: airfare to and from the start of your vacation; airline baggage fees including checked and/or excess baggage fees; Federal inspection fees for the Federal U.S. Customs and Immigrations; International Air Transportation tax; agricultural tax; other per person taxes imposed by government entities; airport taxes and fees, including the September 11th Security fee, passenger facility charges, Federal domestic flight segment fees, and U.S. and international arrival and departure and other government-imposed fees added by the airline and applicable at time of booking; port taxes; passports; visas and vaccinations; tips to your Cruise Director, Local Host, driver, Local Guides, and/or ship's crew; gratuities on ferries, trains, and cruise ships; laundry; telephone; minibar; alcohol, beverages, and food outside of the contracted menu as presented at a hotel or restaurant or onboard your vessel (these extra items will be billed to you before leaving the hotel, ship, or restaurant); airport transfers on non-qualifying flights; optional excursions; additional activities and excursions purchased online; porterage at airports and train stations; Travel Protection; and all other items of a personal nature. Itinerary details are provided by the vendor. Vendors may reserve the right to change itineraries, even on existing reservations. There may be instances where the name of a tour contains a tour length in it, but where there is a version of the tour that is a different number of days in length. You can check the true length of a tour by referring to the length value listed in association with that tour. Destination images displayed on this web page, some which are supplied by the related vendor and some which are not, are intended to simply give a general representation of the region of the world being visited during the tour. Such images are not necessarily of the exact areas being visited during the tour. Hotel details (including, but not limited to: rating/class, descriptions, images, amenities and addresses) are provided by Insight Vacations. Hotel amenities may be communicated in shorthand by Insight Vacations (for example, if "Laundry" is listed that may only mean that the hotel has an optional fee-based service that would allow for your laundry to be done by their staff). We reserve the right to correct errors.