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 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
- 2 Dinner (D)
- 7 Breakfast (B)
- 2 Dinner with Wine (DW)
- 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.
- 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.
- 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 artifacts and possessions carried on the Mayflower as you explore the personal stories behind early Plymouth Colony. Your visit directly supports United Nations Sustainable Development Goal 4: Quality Education.
- 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 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.
- 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.
Additional Offers |
ID: 8439316
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ID: 8439314
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ID: 8439315
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ID: 8439316
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ID: 8439314
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ID: 8439315
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Find the journey right for you with our selection of tour styles. Whether you're looking to see a number of destinations in a single tour, explore a single destination in depth or you want to take the road less traveled, we have the perfect holiday for you.
Discovery Journeys
Discovery Journeys are the ideal style for first-time travelers, showing you the very best your destination has to offer. Each tour will introduce you to multiple countries in one journey.
Regional Journeys
Travel deeper by picking one place that you’ve always longed to visit. Our Regional Journeys are carefully planned to let you explore one region or country in depth, in order to really know its people, traditions and culture.
Country Roads
Step off the beaten track and discover a different side of your destination. Steering clear of the well-trodden tourist trail, our Country Roads program sends you off to hidden retreats and unexpected adventures with lots of local flavor.
Easy Pace
Love full days at leisure while on holiday? Take more time to explore on your own, with a minimum of three nights in each destination and plenty of free time - including more Relaxed Starts - built into the itinerary.
Special Interest Tours
Explore our collection of Special Interest Tours that are themed around particular local festivals, events or cultural interests. These tours include stops at the Chelsea Flower Show in England, Oktoberfest in Germany and more.
Group Travel
Private Custom Groups
We offer the option to customize your own group tour. Our dedicated team of travel experts will create a tailor-made itinerary to suit your needs.
Groups on Set Departures
Pricing Scales to your group size. Our group sizes have no upper limits and our competitive pricing scales according to your group size and your budget.
Our history of traveling sustainably
OVER A DECADE OF POSITIVE IMPACT
There are few things more stylish and elegant than being a responsible tourist. That's why sustainable and responsible tourism is at the heart of what we do. As a premium travel brand, we recognize that it's our duty to set the right example. We work diligently to leave a positive impact on the planet, its people, and its wonderful wildlife. To cement our commitment, we created our 5-year How We Tread Right sustainability strategy and our not-for-profit organization, the TreadRight Foundation.
OUR COMMITMENT
- Sustainability and conservation: We ensure that we’re protecting our invaluable landscapes and natural resources.
- Cultural preservation: We ensure that the true economic benefit of travel is felt by local communities.
- Protection of our world’s wildlife: We advocate for the highest standard of ethical wildlife experiences.
Our 5-year sustainability strategy
HOW WE TREAD RIGHT
Our 5-year How We Tread Right sustainability strategy is based on 11 measurable goals anchored to the United Nations Sustainable Development Goals, which address the issues of climate change, sustainable food production, waste reduction, travel experiences, diversity and inclusion, and wildlife.
By traveling with Insight Vacations, you're supporting a responsible travel company that truly works hard to make a difference.
How you have a positive impact
MAKE TRAVEL MATTER®️ Experiences
Travel is education and experience is the best teacher. Our MAKE TRAVEL MATTER®️ Experiences teach you about the world all while making it better. Whether that's through supporting local economies, preserving age-old traditions, or advancing conservation efforts for native ecosystems. Find out more about how you can be a truly sustainable traveler.
Climate Action
OUR JOURNEY TO NET ZERO
Since the inception of our sustainability strategy, the global community has continued to rally in response to the urgent need for climate action. We're committed to achieve net zero greenhouse gas (GHG) emissions by the year 2050. Our dedication to this goal is outlined in our Climate Action Plan, with science-based targets that address our carbon footprint. We are proud of the fact that, alongside our sister brands, we became the first global tour operator to have near-term, long-term and net zero targets that are validated by the Science Based Target initiative (SBTi). Gain a deeper insight into our Climate Action Plan and how we're meeting our targets.
Our strategic plan
DIVERSITY, EQUITY AND INCLUSION
We believe diversity is the foundation of meaningful travel. We set out with a curious mind, and the desire to meet new people, hear fresh perspectives and experience different cultures. Embracing and empowering diversity, equity and inclusion in all areas of life requires a conscious effort – whether at home, at work, or in our communities.
At the Travel Corporation (TTC), our Diversity, Equity and Inclusion (DEI) journey started many years ago, with the development of our DEI strategy. We’ve formalized goals in the following areas: People & Culture, Product & Experiences, and Marketing & Communications, to ensure we’re upholding our end.
Find the journey right for you with our selection of tour styles. Whether you're looking to see a number of destinations in a single tour, explore a single destination in depth or you want to take the road less traveled, we have the perfect holiday for you.
Discovery Journeys
Discovery Journeys are the ideal style for first-time travelers, showing you the very best your destination has to offer. Each tour will introduce you to multiple countries in one journey.
Regional Journeys
Travel deeper by picking one place that you’ve always longed to visit. Our Regional Journeys are carefully planned to let you explore one region or country in depth, in order to really know its people, traditions and culture.
Country Roads
Step off the beaten track and discover a different side of your destination. Steering clear of the well-trodden tourist trail, our Country Roads program sends you off to hidden retreats and unexpected adventures with lots of local flavor.
Easy Pace
Love full days at leisure while on holiday? Take more time to explore on your own, with a minimum of three nights in each destination and plenty of free time - including more Relaxed Starts - built into the itinerary.
Special Interest Tours
Explore our collection of Special Interest Tours that are themed around particular local festivals, events or cultural interests. These tours include stops at the Chelsea Flower Show in England, Oktoberfest in Germany and more.
Group Travel
Private Custom Groups
We offer the option to customize your own group tour. Our dedicated team of travel experts will create a tailor-made itinerary to suit your needs.
Groups on Set Departures
Pricing Scales to your group size. Our group sizes have no upper limits and our competitive pricing scales according to your group size and your budget.
Our history of traveling sustainably
OVER A DECADE OF POSITIVE IMPACT
There are few things more stylish and elegant than being a responsible tourist. That's why sustainable and responsible tourism is at the heart of what we do. As a premium travel brand, we recognize that it's our duty to set the right example. We work diligently to leave a positive impact on the planet, its people, and its wonderful wildlife. To cement our commitment, we created our 5-year How We Tread Right sustainability strategy and our not-for-profit organization, the TreadRight Foundation.
OUR COMMITMENT
- Sustainability and conservation: We ensure that we’re protecting our invaluable landscapes and natural resources.
- Cultural preservation: We ensure that the true economic benefit of travel is felt by local communities.
- Protection of our world’s wildlife: We advocate for the highest standard of ethical wildlife experiences.
Our 5-year sustainability strategy
HOW WE TREAD RIGHT
Our 5-year How We Tread Right sustainability strategy is based on 11 measurable goals anchored to the United Nations Sustainable Development Goals, which address the issues of climate change, sustainable food production, waste reduction, travel experiences, diversity and inclusion, and wildlife.
By traveling with Insight Vacations, you're supporting a responsible travel company that truly works hard to make a difference.
How you have a positive impact
MAKE TRAVEL MATTER®️ Experiences
Travel is education and experience is the best teacher. Our MAKE TRAVEL MATTER®️ Experiences teach you about the world all while making it better. Whether that's through supporting local economies, preserving age-old traditions, or advancing conservation efforts for native ecosystems. Find out more about how you can be a truly sustainable traveler.
Climate Action
OUR JOURNEY TO NET ZERO
Since the inception of our sustainability strategy, the global community has continued to rally in response to the urgent need for climate action. We're committed to achieve net zero greenhouse gas (GHG) emissions by the year 2050. Our dedication to this goal is outlined in our Climate Action Plan, with science-based targets that address our carbon footprint. We are proud of the fact that, alongside our sister brands, we became the first global tour operator to have near-term, long-term and net zero targets that are validated by the Science Based Target initiative (SBTi). Gain a deeper insight into our Climate Action Plan and how we're meeting our targets.
Our strategic plan
DIVERSITY, EQUITY AND INCLUSION
We believe diversity is the foundation of meaningful travel. We set out with a curious mind, and the desire to meet new people, hear fresh perspectives and experience different cultures. Embracing and empowering diversity, equity and inclusion in all areas of life requires a conscious effort – whether at home, at work, or in our communities.
At the Travel Corporation (TTC), our Diversity, Equity and Inclusion (DEI) journey started many years ago, with the development of our DEI strategy. We’ve formalized goals in the following areas: People & Culture, Product & Experiences, and Marketing & Communications, to ensure we’re upholding our end.
About Insight Vacations

PREMIUM TOURS FOR CURIOUS TRAVELERS
Insight Vacations is a premium tour operator that promises a superior experience from start to finish, with an elevated level of detail and attention at every step. Discover more about the Insight Vacations premium travel experience.
PREMIUM EXPERIENCES
Exclusive, crafted experiences that get you up close and personal to every destination. Enjoy Insider Access before and after opening-hours and skip the line access at key sights. Take your pick from one, two or three curated Insight Choice experiences. Plus, Insightful Encounters with Local Experts and Specialists that add even more life, color and storytelling for a truly enlightening experience.
PREMIUM DINING
Whether you’re being welcomed into the workspaces of chefs or taking your seat at top-rated restaurants, you’ll find yourself dining on regional favorites with a seasonal twist. Take your seat for wine-paired meals and enjoy indulging your preferences from a curated choice of restaurants on Dine-Around evenings. Get hands-on with Cooking Demonstrations and enjoy an industry-leading vegetarian offering at every mealtime.
About Insight Vacations

PREMIUM TOURS FOR CURIOUS TRAVELERS
Insight Vacations is a premium tour operator that promises a superior experience from start to finish, with an elevated level of detail and attention at every step. Discover more about the Insight Vacations premium travel experience.
PREMIUM EXPERIENCES
Exclusive, crafted experiences that get you up close and personal to every destination. Enjoy Insider Access before and after opening-hours and skip the line access at key sights. Take your pick from one, two or three curated Insight Choice experiences. Plus, Insightful Encounters with Local Experts and Specialists that add even more life, color and storytelling for a truly enlightening experience.
PREMIUM DINING
Whether you’re being welcomed into the workspaces of chefs or taking your seat at top-rated restaurants, you’ll find yourself dining on regional favorites with a seasonal twist. Take your seat for wine-paired meals and enjoy indulging your preferences from a curated choice of restaurants on Dine-Around evenings. Get hands-on with Cooking Demonstrations and enjoy an industry-leading vegetarian offering at every mealtime.