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7-Nights Boston, Cape Cod & The Islands - Classic Group

New England
7-Nights Boston, Cape Cod & The Islands - Classic Group
New England
Insight Vacations
Vacation Offer ID 1556432
Reference this number when contacting our travel specialist.
Promotions

Special Promotion: Save up to 15% on September 2025 tours or up to 15% on tours departing in the next 4 months

Valid for new bookings deposited March 24, 2025 – May 29, 2025 for travel from September 1 – September 30, 2025 (or) on select tours departing in the next 4 months.

*Promotion may not be combinable with any other offers, promotions, or discounts, and is subject to availability. Other restrictions may apply. 
Overview

Insight Vacations

Boston, Cape Cod & The Islands - Classic Group
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 Plymouth, a coastal town famous for its rich history as the landing site of the Pilgrims in 1620; visit the living history museum at Plimoth Patuxet. 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.


Dining Summary
  • 3 Dinner (D)
  • 7 Breakfast (B)
  • 1 Dinner with Wine (DW)
Choice Highlights
  • Choose between two carefully selected activities
  • Newport: A striking destination for design lovers and motoring enthusiasts alike, this museum reimagines the automobile as a canvas for innovation. Housed in a repurposed missile plant, its collection features over 100 cars, from the sculpted lines of mid-century Cadillacs to performance icons like the Ford GT, Porsche 911 and Corvette Stingray. Each car is selected for its impact on design, engineering and culture.
  • Newport: Established in 1872, this is America’s oldest topiary garden, where horticultural craftsmanship meets imaginative design. Set on seven coastal acres, the collection includes more than 80 sculpted shrubs, from giraffes and elephants to intricate geometric forms. Maintained by generations of gardeners, it remains a living work of art on Rhode Island’s historic shoreline.
Authentic Dining
  • Boston: At 18:00, join your Travel Director for a dinner with wine and an opportunity to mingle with fellow guests.
  • Martha's Vineyard: Indulge in a locally sourced dinner in a private dining space in Bettini Restaurant.
  • Newport: Meet your new friends in the evening for a seafood dinner with wine, where you can share the highlights of your trip while savoring a freshly prepared meal.
Insight Choice
  • Newport: A striking destination for design lovers and motoring enthusiasts alike, this museum reimagines the automobile as a canvas for innovation. Housed in a repurposed missile plant, its collection features over 100 cars, from the sculpted lines of mid-century Cadillacs to performance icons like the Ford GT, Porsche 911 and Corvette Stingray. Each car is selected for its impact on design, engineering and culture.
  • Newport: Established in 1872, this is America’s oldest topiary garden, where horticultural craftsmanship meets imaginative design. Set on seven coastal acres, the collection includes more than 80 sculpted shrubs, from giraffes and elephants to intricate geometric forms. Maintained by generations of gardeners, it remains a living work of art on Rhode Island’s historic shoreline.
Insight Experiences
  • Newport: Meet your captain and jump onboard the Adirondack II, an 80-foot schooner sailing ship and cruise around the coastline. You’ll sail out and pass nearby islands, old historical buildings and homes of the rich and famous, as you learn about the region’s exciting history, including its pirate activity.
  • Newport: Enjoy a visit to one of Newport's renowned landmarks, The Vanderbilt's Breakers Mansion.
Make Travel Matter
  • Plymouth: Led by a Mayflower descendant, enjoy a guided visit to Pilgrim Hall Museum, the oldest continuously operating public museum in the United States. View original 17th-century artefacts and possessions carried on the Mayflower as you explore the personal stories behind early Plymouth Colony. This MAKE TRAVEL MATTER® Experience supports United Nations Sustainable Development Goal 4: Quality Education through inclusive programming, extensive historical resources and its mission to deepen public understanding of America’s colonial beginnings. Your Experiences advances United Nations Sustainable Development Goals 4: Quality Education
Top Rated Highlights
  • Plymouth: Visit detailed reconstructions of a 1600s English village and a Wampanoag homesite. As you walk through the open-air exhibits, see timber-framed houses, dugout canoes and heritage crops, and observe traditional skills in practice. This museum offers a clear, research-based insight into the lives of early colonists and Indigenous communities in what was once Patuxet.
  • Boston: Trace America’s path to independence with your Travel Director as you stroll past Boston’s iconic sites. See Boston Common, the oldest public park in the United States; the red-bricked Granary Burying Ground where Samuel Adams rests; and the evocative Old State House, the spark site of the Boston Massacre.
  • Cape Cod: Experience the natural wonder and human history emphasizing the cultural themes represented on Cape Cod, including the First People--the Wampanoag; European settlement culture; fishing, life-saving, and lighthouses; communication technology of Cape Cod's National Seashore.
  • Nantucket: Walk through historic downtown Nantucket and discover the unique history of the island. Journey through Nantucket’s past and hear about the rise and the fall of the whaling industry, the rise of tourism, and the impacts the island’s economy has had on social and racial development on Nantucket.
  • Martha's Vineyard: After disembarking from your ferry ride, visit the port neighborhood of Oak Bluffs and be transported to a different era. Known for its rainbow-colored, gingerbread-like cottages with Gothic storybook decorations, h

    Featured Destinations

    Newport, RI

    Newport, RI

    Newport became important as a resort for wealthy industrialists who built their “summer cottages”, modeled after European palaces, here and elevated Newport to position of “Queen of Summer Resorts.” A tour of the mansions is a must. Newport is also famous as a yachting capital and site of international tennis championships. Colonial Newport boasts a collection of 18th- and 19th-century and pre-Revolutionary buildings. Colonial Downtown is best explored on foot, and much of the town was burned down during British occupation, but enough buildings survived to rival Boston in number of original 18th-century homes. George Washington’s assurances to Newport’s Jewish community of religious liberty encouraged them to build Touro Synagogue in 1763, making it the oldest in the nation. St. Mary’s Church is the oldest Catholic parish in Rhode Island. The Grand Newport Casino and International Tennis Hall of Fame held the first national tennis championship in 1881 and is now Tennis Hall of Fame with a museum on tennis fashions and trophies.
    Destination Guide
    Martha's Vineyard

    Martha's Vineyard

    A summer resort island just off the coast of Massachusetts, Martha's Vineyard floats in the memories of generations of vacation society. Visit the beach front avenue of Oak Bluffs lined with gingerbread-trimmed cottages, and the Flying Horses antique carousel.
    Destination Guide
    Sandwich

    Sandwich

    Sandwich was settled by Europeans in 1637 in Barnstable County, Massachusetts. It is the oldest town on Cape Cod. Sandwich was predominantly a Puritan settlement however a growing number of settlers converted to Quakerism. Beliefs clashed and many Quakers left Sandwich. In 1825 Deming Jarves founded the Boston & Sandwich Glass Factory and recruited workers for his factory. Skilled laborers were imported from Ireland whereupon a majority of them were Catholics. The first Catholic Church was established in Sandwich as well. After the Civil War, the glass factory closed down due to a huge decline. This historic town is rich with beautiful scenery and landmarks. Visitors can take a river cruise down the Cape Cod Canal or bike down the Cape Cod Canal Bike Path. The Shawme-Crowell State Forest is a perfect hiking and camping location for the avid adventurer. Visitors can also immerse in old New England culture.
    Destination Guide
    Boston

    Boston

    The history and bricklaid beauty of Boston is easy to enjoy. Follow the Freedom Trail past Old North Church, Paul Revere Park, Fanieul Hall, the Commons, Old Ironsides and more landmarks of America's birth. Across the Charles River is Cambridge and Harvard. Venture to Marblehead and Salem to the south, or Lexington and Concord to the north. Back in town, have clam chowder at the warf or great Italian food in North End.
    Destination Guide

    View Full Itinerary

    Valid Date Ranges

    May 2026
    05/15/2026 05/22/2026 $4,545 per person
    05/29/2026 06/05/2026 $4,815 per person
    June 2026
    06/12/2026 06/19/2026 $4,815 per person
    06/26/2026 07/03/2026 $4,703 per person
    July 2026
    07/09/2026 07/16/2026 $4,766 per person
    September 2026
    09/04/2026 09/11/2026 $4,658 per person
    09/11/2026 09/18/2026 $4,658 per person
    09/18/2026 09/25/2026 $4,658 per person
    09/25/2026 10/02/2026 $4,658 per person
    October 2026
    10/02/2026 10/09/2026 $4,658 per person
    10/09/2026 10/16/2026 $4,658 per person
    Trip prices are per person, land only, based on double occupancy and reflect applicable discounts. Trip prices and discounts are subject to change. Airfare is additional. Tour prices, dates and itineraries are correct at the time of the website going live, however are subject to confirmation at the time of booking. Other restrictions may apply.

    All fares are quoted in US Dollars.