7-Nights Boston, Cape Cod & The Islands - Small Group from $4,466

Insight Vacations

OFFER ID 1505912

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.

7 nights from $4,466 per person

Itinerary

Click here for Full Itinerary Details

Itinerary Details

Insight Vacations: Boston, Cape Cod & The Islands - Small Group

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.
Accommodations: Hyatt Regency, Boston
Meals: Dinner with Wine

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, 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.
Accommodations: Hyatt Regency, Boston
Meals: Breakfast

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.
Accommodations: Dan'l Webster Inn and Spa, Sandwich
Meals: Breakfast, Dinner with Wine

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.
Accommodations: Dan'l Webster Inn and Spa, Sandwich
Meals: Breakfast

Day 5 - Martha's Vineyard, a Presidential Paradise
Board a ferry this morning to Martha's Vineyard. 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.
Accommodations: Harbor View, Martha's Vineyard
Meals: Breakfast, Dinner with Wine

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 in?uenced 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.
Accommodations: Viking, Newport
Meals: Breakfast

Day 7 - Newport, 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.
Accommodations: Viking, Newport
Meals: Breakfast, Dinner with Wine

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: Breakfast

Featured Destinations

Sandwich

Newport, RI

Martha's Vineyard

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.

Excursions

Boston: Private North End Italian Food Tasting Walking Tour - 3 Hours

Boston: Private Sunset Boston Harbor Cruise with Cocktails and Hors d'oeuvres - 2 Hours

Boston: Private VIP Boston Yacht Experience With Cocktails & Hors d’oeuvres - 2 Hours

Boston: Boston Private Cycle Boat Charter - 4 Hours

Boston: Discover Boston Private Sightseeing Program - 4 Hours

Boston: Private Historic Boston Pub Crawl - 4 Hours

Boston: Freedom Trail Private Walking Tour - 1.5 Hours

Boston: Private Harvard Campus Tour - 1.5 Hours

Vacation Details

Valid Date Ranges

10/10/2025 - 10/17/2025

from $4,466 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 $4,466 per person

Length

7 Nights

Air City

Call for airfares from your city.

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

1505912

Reference this number when contacting our agency so we may better serve you. Also keeping this number handy will allow you to locate this document again quickly.

Request More Info!

OVERVIEW SUPPLIERS DESTINATIONS DEALS

Vacations Search

Between

And

Escorted Tours Only

Land Only Tours