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7-Nights Boston, Cape Cod & The Islands - Small Group from $5,250

Insight Vacations

OFFER ID 1556433

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: 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.


7 nights from $5,250 per person

Black Friday Promotion: Save Up to 30% on Select “Business Class” Tours

Valid on new bookings deposited November 1, 2024 – December 5, 2024 for travel in 2025.  

*Discount may already be included in the displayed price. Promotion may not be combinable with any other offers, promotions, or discounts, and is subject to availability and airline booking guidelines. Other restrictions may apply.

Itinerary
Click here for Full Itinerary Details
Featured Destinations
Newport, OR
Boston

Vacation Details

Valid Date Ranges
05/08/2026 - 05/15/2026
from $5,250 per person
08/21/2026 - 08/28/2026
from $5,250 per person


* This departure has been designated a guaranteed departure by the operator, meaning that the minimum number of guests has been met, although still subject to weather and other conditions.
Prices Start At
from $5,250 per person
Length
7 Nights
Air City
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Vacation Rating
Deluxe
Remarks
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.

OFFER ID
1556433

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