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

New England
7-Nights Boston, Cape Cod & The Islands - Small Group
New England
Insight Vacations
Vacation Offer ID 1505912
Reference this number when contacting our travel specialist.
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Overview

Insight Vacations

Boston, Cape Cod & The Islands - Small 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 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.


Dining Summary
  • 4 Dinner with Wine (DW)
  • 7 Breakfast (B)
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 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: Visit the Plimoth Patuxet (Puh – tux- it) Museum – which is really more like a living memorial dedicated to the lifestyle of the first English settlers and the Wampanoag Indigenous community. Enjoy a guided journey to the early homesite of the Wompanoag people, a living version of the early English settlement village and a full scale replica of the Mayflower 2 – the ship that made the initial voyage in 1620. By visiting, we’re helping the museum preserve the histories and stories of the early inhabitants and the revitalization of pre-industrial crafts, trades, domestic skills, horticulture, and maritime arts.Your experience advances UN Global Goals 10 & 11: Reduced Inequalities & Sustainable Cities and Communities.
Top Rated Highlights
  • Boston: Explore the great city of Boston, 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. Journeying to other historically significant sights that include the Boston Common, the Old Corner Bookstore and the Bunker Hill Monument in Charlestown. View the colorful neighborhood of Back Bay and the lively North End, otherwise known as Boston’s Little Italy.
  • Plymouth: Visit Pilgrim Hall Museum, the oldest continuously operating public museum in the country and America’s museum of Pilgrim possessions. Meet a direct descendant of the Mayflower party that landed on America's shores in 1620 and hear their family stories.
  • Sandwich: View through the lens of the skilled craftsmen at the Sandwich Glass Museum, where you will learn the techniques of the English and Irish glass-makers developed during the early 19th century.
  • 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.
  • 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, high-peaked roofs, and dainty verandas. You’ll also find the oldest operating platform carousel in America here.
  • 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.

Featured Destinations

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
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
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

October 2025
10/10/2025 10/17/2025 $4,466 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.