Boston, Cape Cod & The Islands - Small Group
Boston, Cape Cod & The Islands - Small Group
$5253
Boston, Cape Cod & The Islands - Small Group
8 Days Starting and ending in Boston (MA)
Visiting: Boston, Sandwich, Cape Cod, Martha's Vineyard, Nantucket, Newport
Tour operator:
Tour code:
SACAPZN20
Specialist Group:
Family/Kids
Guide Type:
Fully Guided
Group size:
12 - 24
Age range:
5-99
Special diets catered:
Vegetarians
Tour operated in:
EnglishInterests:
Tour 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.
Highlights
Itinerary
Day 1: Boston, The Cradle Of Liberty
Location: Boston
Accommodation Name: Hyatt Regency, Boston
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.
Day 2: Historic Boston
Location: Boston
Accommodation Name: Hyatt Regency, Boston
Meals Included: Breakfast
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.
Day 3: Pilgrim Heritage And On To Sandwich
Location: Boston, Sandwich
Accommodation Name: Dan'l Webster Inn and Spa, Sandwich
Meals Included: Breakfast
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.
Day 4: Explore Cape Cod
Location: Sandwich, Cape Cod, Sandwich
Accommodation Name: Dan'l Webster Inn and Spa, Sandwich
Meals Included: Breakfast
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.
Day 5: Martha's Vineyard, A Presidential Paradise
Location: Sandwich, Martha's Vineyard
Accommodation Name: Harbor View, Martha's Vineyard
Meals Included: Breakfast
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.
Day 6: Nantucket Island
Location: Martha's Vineyard, Nantucket
Accommodation Name: Viking, Newport
Meals Included: Breakfast
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 influenced 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.
Day 7: Newport, The Queen Of Summer Resorts Relaxed Start
Location: Newport
Accommodation Name: Viking, Newport
Meals Included: Breakfast
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.
Day 8: Back To Boston Relaxed Start
Location: Boston
Accommodation Name: Hyatt Regency Boston
Meals Included: Breakfast
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.
What's Included
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Meals
The tour includes 3 dinners with wine, 1 dinner, and 7 breakfasts.
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Guided Tours
Enjoy guided tours of Fenway Park, the John F. Kennedy Presidential Library and Museum, and the Pilgrim Hall Museum.
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Welcome Dinner
Join your Travel Director for a Welcome Dinner with wine on the first day.
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Sea-to-Table Highlight Dinner
Experience a Sea-to-Table Highlight Dinner at Menemsha Room with fresh offerings from local farms, fishing boats, foragers, and markets.
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Celebration Dinner
Enjoy a seafood Celebration Dinner with wine in Newport.
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Accommodation
Stay at the Hyatt Regency Boston and other luxurious hotels throughout the tour.
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Transportation
Board a ferry to Martha's Vineyard and a high-speed catamaran to Nantucket Island.
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Cruise
Cruise around the coastline on the Adirondack II schooner in Newport.
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Transfers
Complimentary transfers to Boston Logan International Airport on the last day.
What's Not Included
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Optional Activities
Optional experiences such as the Sand Dunes of the National Seashore are not included.
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Personal Expenses
Personal expenses such as souvenirs, additional meals, and drinks are not included.
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Travel Insurance
Travel insurance is not included and should be purchased separately.
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Gratuities
Gratuities for guides, drivers, and hotel staff are not included.
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Flights
International and domestic flights to and from Boston are not included.
Mode of Transport
Travel in style with a mix of guided tours, ferry rides to Martha's Vineyard and Nantucket, and a high-speed catamaran. Enjoy a scenic cruise on the Adirondack II schooner in Newport and comfortable coach transfers throughout the tour.
Accommodation
Stay at the Hyatt Regency Boston, conveniently located near Boston's top attractions, and enjoy charming inns and luxurious hotels in Sandwich, Martha's Vineyard, and Newport, each offering unique local experiences and comfort.
Dining Summary
- 4 Dinner with Wine (DW)
- 7 Breakfast (B)
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.
Check out our Q&As
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What kind of activities can I choose from in Boston?
In Boston, you can choose between visiting Fenway Park, America's oldest baseball stadium and home of the Boston Red Sox, or touring The John F. Kennedy Presidential Library and Museum dedicated to the memory of the nation's thirty-fifth president.
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What unique experience is offered in Plymouth?
In Plymouth, you will visit the Pilgrim Hall Museum, the oldest continuously operating public museum in the country, and the Plimoth Patuxet Museum, which is dedicated to preserving the histories of the Native and English inhabitants of the region. You will also meet a direct descendant of the Mayflower party and hear their family stories.
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What can I expect during the visit to Martha's Vineyard?
During your visit to Martha's Vineyard, you will board a ferry to the island, explore the port neighborhood of Oak Bluffs known for its rainbow-colored, gingerbread-like cottages, and see the oldest operating platform carousel in America. In the evening, you will enjoy a Sea-to-Table Highlight Dinner at Menemsha Room with fresh offerings from local farms, fishing boats, foragers, and markets.
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What is special about the visit to Newport?
In Newport, you will visit the Breakers, the grandest of Newport's summer cottages and a symbol of the Vanderbilt family's social and financial pre-eminence. You will also sail on the Adirondack II, an 80-foot schooner, and cruise around the coastline, passing nearby islands, historical buildings, and homes of the rich and famous while learning about the region's exciting history, including its pirate activity. In the evening, you will enjoy a Celebration Dinner at La Forge Casino restaurant.
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What historical insights will I gain from the tour in Boston?
In Boston, you will follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. You will visit sights such as Boston Common, the Old Corner Bookstore, and the Bunker Hill Monument in Charlestown. You will also explore the colorful neighborhoods of Back Bay and the historic North End, known as Boston's Little Italy.
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What is the significance of the Sandwich Glass Museum?
At the Sandwich Glass Museum, you will learn about the techniques of English and Irish glassmakers developed during the early 19th century. The museum showcases the skilled craftsmanship and history of glassmaking in the region.
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What can I expect from the Nantucket Island visit?
On Nantucket Island, you will experience the charm of a bygone era with antique cobblestone streets, high-end boutiques, and breathtaking architecture. The island is known for its simple homes dating back to its whaling days, which influenced much of the local culture. You will return to the mainland in the late afternoon to relax at your luxurious hotel.
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Can I join the tour once it has departed?
We regret that no refunds can be made for absences from a tour, including experiences such as missed meals or sightseeing.
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How long has the tour company been trading?
Since 1978.
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What Ethical Travel credentials does the tour company have?
Insight Vacations is a founding member of the TreadRight Foundation, a joint initiative created by the brands within The Travel Corporation (TTC) almost 15 years ago to ensure our impact through tourism is positive. Our ethos to #MakeTravelMatter guides our decision-making at every level of our business.
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Will the accommodation included meet local health and safety regulations?
Yes
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Do you operate a “single share” option and how does it work?
You have two options as a solo traveller. Either choose to be matched with a same sex partner for a room share - at no extra cost. Or choose a room of your own with a reduced or even free private room upgrade on select tours.
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What policies are in place for Covid-19?
Please contact us for latest COVID-19 policies
Reviews of this operator
1 Select your preferred date
Friday - Friday
Oct 10, 2025 - Oct 17, 2025Book with Confidence
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Low Deposit
Insight Vacations requires a minimum deposit of 350 USD per person or the full booking value, whichever is less, with the final balance not due until 90 days before departure.
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Cancellation Policy
We don't charge a cancellation fee, here is a summary of insight vacations charges.
Up to 91 days before tour starts: Forfeit 100% of deposit.
At 90 days before tour starts: Forfeit 50% of booking price.
At 29 days before tour starts: Forfeit 80% of booking price.
At 1 days before tour starts: Forfeit 100% of booking price.
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Terms and Conditions