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Boston, Cape Cod & The Islands - Classic Group
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Length
8 Days
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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)
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Ends in
Boston (Massachusetts)
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Available Tour Start Dates
MAY 15, 2026 to OCT 9, 2026
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Activity Level
No Rating Provided
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Language
English
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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
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.
$4,797.50
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 - Classic Group tour dates available from Insight Vacations. Select a bonus offer graphic to view its details, including its terms.
Tour Itinerary
Insight Vacations Tour Code 19-1097
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Day
1Welcome to Boston
Boston, often described as America’s most European city, is a captivating blend of history, art, and culinary delights. Upon your arrival at the Hyatt Regency, nestled in the heart of downtown, you're just moments from sights such as the historic Faneuil Hall and the fashionable Newbury Street. Take a leisurely stroll through the charming South End or along the picturesque Charles River Esplanade. This evening, meet your Travel Director and fellow guests for a delightful dinner, marking the beginning of your unforgettable journey.
- Meals Included:
- Dinner with Wine
Accommodations: Hyatt Regency, Boston -
Day
2Exploring Plymouth's Past
Join your Travel Director for an enriching exploration of Boston’s storied past. Walk along the famous Freedom Trail, where each step brings the American Revolution to life. Visit landmarks like Boston Common, the Old Corner Bookstore, and the Old State House. Continue your historic exploration at the Pilgrim Hall Museum in Plymouth, hosted by a Mayflower descendant, offering personal stories tied to the museum’s fascinating collection of 17th-century artefacts. At the Plimoth Patuxet Museum, immerse yourself in the stories of early English settlers and the Wampanoag Indigenous community during a MAKE TRAVEL MATTER® Experience. From the replica Mayflower II to the recreated homesites, your visit contributes to preserving this vital heritage, supporting pre-industrial crafts, trades, and maritime traditions.
- Meals Included:
- Breakfast
Accommodations: Dan'l Webster Inn and Spa, Sandwich -
Day
3The Wonders of Cape Cod
The windswept shores and pristine landscapes of Cape Cod await as you embark on a journey through the heart of New England’s maritime history. The Cape’s rolling sand dunes, historic lighthouses, and timeless fishing villages set the stage for a day rich in cultural discovery. Explore Cape Cod’s National Seashore, where the stories of the Wampanoag people and European settlers converge against a backdrop of stunning coastal beauty. Later, visit the Sandwich Glass Museum, where you’ll witness demonstrations of glassblowing techniques pioneered by English and Irish craftspersons in the early 19th century. This captivating experience will leave you with a deeper appreciation of Cape Cod's art, history, and natural beauty.
- Meals Included:
- Breakfast
- Dinner with Wine
Accommodations: Dan'l Webster Inn and Spa, Sandwich -
Day
4Nautical History in Nantucket
Set sail from Hyannis to the island of Nantucket, where cobblestone streets and preserved historic homes tell the story of a bygone whaling era. Stroll through the charming downtown, learning how the rise and fall of the whaling industry shaped Nantucket’s social fabric and economy. As you uncover tales of seafaring adventures, witness the island’s transformation into a beloved destination for visitors from across the globe. After a day steeped in maritime history, return to Hyannis by ferry for an evening at leisure.
- Meals Included:
- Breakfast
Accommodations: Dan'l Webster Inn and Spa, Sandwich -
Day
5The Charms of Martha’s Vineyard – An Island Escape
Board a morning ferry to Martha’s Vineyard, an island known for its pristine beaches, charming harbor towns, and storied visitors, including U.S. presidents. Explore Oak Bluffs with its gingerbread cottages, visit the Flying Horses Carousel and see State Beach, made famous by the film Jaws. Discover the island’s colorful past, from whaling to modern-day tourism, as you gain insights into the history of Edgartown harbor lighthouse. Later, enjoy island hospitality with seasonal offerings from local farms, fishing boats and foragers during a dining experience at Bettini, located in your elegant hotel.
- Meals Included:
- Breakfast
- Dinner with Wine
Accommodations: Harbor View, Martha's Vineyard -
Day
6The Timeless Elegance of Newport Relaxed Start
Arrive in Newport, where over 95 years of hospitality and charm characterize the historic Hotel Viking. Set in the heart of this coastal city, your boutique accommodation offers luxurious rooms and stunning views. Enjoy complimentary bike rentals or relax in the hotel’s spa, pool, or café. This evening, take a leisurely stroll through Newport’s vibrant streets, where every corner reveals another piece of its storied past.
- Meals Included:
- Breakfast
Accommodations: Viking, Newport -
Day
7Newport, the Queen of Summer Resorts Relaxed Start
Your day begins with Newport’s famed Ten Mile Drive, a scenic route that hugs the coastline, showcasing public parks, historic landmarks and breathtaking ocean views. Afterwards, explore the grandeur of Newport’s "summer cottages" as you visit the Breakers, the grandest of them all. A symbol of the Vanderbilt family’s wealth and prominence, this opulent mansion offers a glimpse into the lavish lifestyle of America’s Gilded Age elite. Cap off the day with a sunset sail aboard the Adirondack II, gliding along Newport Harbor and Narragansett Bay.
- Meals Included:
- Breakfast
- Dinner with Wine
Accommodations: Viking, Newport -
Day
8Farewell to Boston Relaxed Start
As your tour comes to a close, bid farewell to your fellow travelers and transfer to Logan International Airport for your onward journey. With memories of Boston’s historic charm, the beauty of Cape Cod, and the elegance of Newport, you leave with a deeper appreciation for this unique corner of New England.
- Meals Included:
- Breakfast
More Details
Insight Vacations is informing us of the following additional details regarding their Boston, Cape Cod & The Islands - Classic Group tour:
Travelers Notes
NOTE: This Trip falls under Tour Deposit Level 1. 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.