Embrace the beauty of New England during this 8-Day guided tour. Behold Boston, one of the oldest cities in the U.S. and where much of the country was formed; here, you will traverse part of the red-brick Freedom Trail, where you will see the hall that housed the country’s first-ever town meeting and many more historic sites. Admire the bronzing leaves of Vermont’s lush trees as you travel to Stowe, where the real Von Trapp family of ‘The Sound of Music’ chose to live — and where you will stay. In Montpelier, visit a maple syrup farm where you can taste the sweet golden liquid tapped straight from the trees. Ride a gondola at Loon Mountain Resort into New Hampshire’s White Mountains and see as far as Canada. See Maine’s oldest lighthouse in Portland, then celebrate your trip with a decadent fresh lobster dinner.
New England's Fall Foliage - Classic Group
Deal number: 21500419
INSIGHT VACATIONS
This deal expires 18 Aug 2025
From 20/09/2026 to 24/10/2026
Boston
8-day tour
Price from
$9,325*
per person
Deal number: 21500419
Highlights
3 Dinner (D)7 Breakfast (B)1 Lunch (L)Choose between two carefully selected activitiesStockbridge: Enjoy the warm, colourful scenery as you travel west to Stockbridge for a visit to the Norman Rockwell Museum, home to the largest and most significant collection of original Rockwell art, including enduring favourites from Rockwell’s Saturday Evening Postcovers, together with changing exhibitions of works by American illustrators past and present.Stockbridge: Guided tour of Chesterwood, the former summer home, studio and gardens of America’s foremost 20th century public sculptor. Daniel Chester French is best known for the seated figure of Abraham Lincoln for the Lincoln Memorial. Visitors to Chesterwood will experience the life and work of this prolific and successful artist.From time to time, your Travel Director will delight you with an Insight Flourish, which is a local specialty representing the destination.Hotel and restaurant tips are included - you'll never have to worry about how much to give, nor search for foreign currency. We also include all taxes and porterage charges at hotels.We carry your bags for you and promptly deliver them to your hotel door.Our highly-skilled Travel Director will ensure your journey is seamless, serving as your expert guide, consummate organiser, and friend overseas.Personal radio headsets give you the freedom to wander during visits to famous highlights, without missing any of your Local Expert's fascinating commentary.Stay connected with friends and family with our complimentary coach and hotel Wi-Fi (where available).Boston: Join your Travel Director for dinner and an opportunity to mingle with fellow guests at your hotel.Stowe: At your dinner, taste the creations of artisan brewers with Austrian-style lagers.Shelburne: Connect with Vermont’s agricultural heritage at Bread & Butter Farm, where you’ll meet the owners and explore how regenerative practices are restoring the land and honouring local traditions. Stroll the fields with Chef Tessa, a seventh-generation Vermonter, as she shares stories of seasonal living and sustainable sourcing. Then, gather fresh herbs and blooms before enjoying a wholesome Farm-to-Table lunch, thoughtfully prepared by Tessa and her team at Blossom Whole Food Kitchen.Portland: Enjoy a Maine lobster dinner as you feast on the fresh and local delicacy known for its tender and rich flavour. Raise a glass as you mingle with new friends over this delectable celebration dinner.Stockbridge: Enjoy the warm, colourful scenery as you travel west to Stockbridge for a visit to the Norman Rockwell Museum, home to the largest and most significant collection of original Rockwell art, including enduring favourites from Rockwell’s Saturday Evening Postcovers, together with changing exhibitions of works by American illustrators past and present.Stockbridge: Guided tour of Chesterwood, the former summer home, studio and gardens of America’s foremost 20th century public sculptor. Daniel Chester French is best known for the seated figure of Abraham Lincoln for the Lincoln Memorial. Visitors to Chesterwood will experience the life and work of this prolific and successful artist.North Conway: Learn about regional flora and fauna with a Local Expert during an ecological look at autumn in New England. Your visit directly supports United Nations Sustainable Development Goal 15: Life on Land.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 colourful neighbourhood of Back Bay and the lively North End, otherwise known as Boston’s Little Italy.Weston: Step back into history with a visit to the Vermont Country Store where you'll find a nostalgic assortment of products ranging from local cheeses to whiskey pecan pie.Woodstock: Visit the quintessential Vermont village of Woodstock. Then explore the Rockefeller's renowned Billings Farm and Museum, a captivating working dairy farm which also serves as a museum showcasing Vermont's rural past.Montpelier: Travel to Morse Farm Maple Sugarworks, where maple syrup is "tapped" from the trees. Taste a Vermont tradition, the unusually named "sugar on snow’" which is maple syrup drizzled over packed snow. This tasty treat is traditionally served with a doughnut and pickle.Franconia Notch State Park: Take a scenic ride on the Gondola SkyRide at Loon Mountain Resort (weather permitting). On a clear day, you'll have superb panoramic views of New Hampshire, Maine, Vermont, New York and Canada.Kancamagus Highway: Later, journey through the dazzling crimson and orange hues of the famed Kancamagus Scenic Byway to North Conway. This spectacular section of Route 112 is unspoiled by industry and boasts 34.5 miles (55 kilometres) of untouched natural beauty.Bretton Woods: More spectacular fall foliage awaits as you journey through Crawford Notch, a scenic pass through the White Mountains. Stop for pictures at the Silver Cascade Waterfall and Bretton Woods, which offers stunning views of Mount Washington, the tallest peak in the northeast at 6,288 feet (1,917 metres).North Conway: Enjoy a scenic hike to Diana's Baths, which features a small series of captivating cascading waterfalls. This historic site is within the White Mountain National Forest and easy paced.Enjoy the comfort of Insight's luxurious, air-conditioned, 40-seat coach with double the standard legroom and onboard washroom. Our customized luxury coaches are sanitized before the start of your tour and are maintained to very high standards. Physical distancing measures have been implemented on our customized luxury coaches.Experience enhanced hygiene protocols to align with the latest guidance following COVID-19. All Travel Directors and Drivers have completed training in enhanced well-being and hygiene protocols.Hand sanitizer is freely available on board for you to use throughout the day.We only work with establishments we are confident will consistently adhere to our high well-being standards, which include hotels, restaurants and sight-seeing venues.
3 Dinner (D)7 Breakfast (B)1 Lunch (L)Choose between two carefully selected activitiesStockbridge: Enjoy the warm, colourful scenery as you travel west to Stockbridge for a visit to the Norman Rockwell Museum, home to the largest and most significant collection of original Rockwell art, including enduring favourites from Rockwell’s Saturday Evening Postcovers, together with changing exhibitions of works by American illustrators past and present.Stockbridge: Guided tour of Chesterwood, the former summer home, studio and gardens of America’s foremost 20th century public sculptor. Daniel Chester French is best known for the seated figure of Abraham Lincoln for the Lincoln Memorial. Visitors to Chesterwood will experience the life and work of this prolific and successful artist.From time to time, your Travel Director will delight you with an Insight Flourish, which is a local specialty representing the destination.Hotel and restaurant tips are included - you'll never have to worry about how much to give, nor search for foreign currency. We also include all taxes and porterage charges at hotels.We carry your bags for you and promptly deliver them to your hotel door.Our highly-skilled Travel Director will ensure your journey is seamless, serving as your expert guide, consummate organiser, and friend overseas.Personal radio headsets give you the freedom to wander during visits to famous highlights, without missing any of your Local Expert's fascinating commentary.Stay connected with friends and family with our complimentary coach and hotel Wi-Fi (where available).Boston: Join your Travel Director for dinner and an opportunity to mingle with fellow guests at your hotel.Stowe: At your dinner, taste the creations of artisan brewers with Austrian-style lagers.Shelburne: Connect with Vermont’s agricultural heritage at Bread & Butter Farm, where you’ll meet the owners and explore how regenerative practices are restoring the land and honouring local traditions. Stroll the fields with Chef Tessa, a seventh-generation Vermonter, as she shares stories of seasonal living and sustainable sourcing. Then, gather fresh herbs and blooms before enjoying a wholesome Farm-to-Table lunch, thoughtfully prepared by Tessa and her team at Blossom Whole Food Kitchen.Portland: Enjoy a Maine lobster dinner as you feast on the fresh and local delicacy known for its tender and rich flavour. Raise a glass as you mingle with new friends over this delectable celebration dinner.Stockbridge: Enjoy the warm, colourful scenery as you travel west to Stockbridge for a visit to the Norman Rockwell Museum, home to the largest and most significant collection of original Rockwell art, including enduring favourites from Rockwell’s Saturday Evening Postcovers, together with changing exhibitions of works by American illustrators past and present.Stockbridge: Guided tour of Chesterwood, the former summer home, studio and gardens of America’s foremost 20th century public sculptor. Daniel Chester French is best known for the seated figure of Abraham Lincoln for the Lincoln Memorial. Visitors to Chesterwood will experience the life and work of this prolific and successful artist.North Conway: Learn about regional flora and fauna with a Local Expert during an ecological look at autumn in New England. Your visit directly supports United Nations Sustainable Development Goal 15: Life on Land.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 colourful neighbourhood of Back Bay and the lively North End, otherwise known as Boston’s Little Italy.Weston: Step back into history with a visit to the Vermont Country Store where you'll find a nostalgic assortment of products ranging from local cheeses to whiskey pecan pie.Woodstock: Visit the quintessential Vermont village of Woodstock. Then explore the Rockefeller's renowned Billings Farm and Museum, a captivating working dairy farm which also serves as a museum showcasing Vermont's rural past.Montpelier: Travel to Morse Farm Maple Sugarworks, where maple syrup is "tapped" from the trees. Taste a Vermont tradition, the unusually named "sugar on snow’" which is maple syrup drizzled over packed snow. This tasty treat is traditionally served with a doughnut and pickle.Franconia Notch State Park: Take a scenic ride on the Gondola SkyRide at Loon Mountain Resort (weather permitting). On a clear day, you'll have superb panoramic views of New Hampshire, Maine, Vermont, New York and Canada.Kancamagus Highway: Later, journey through the dazzling crimson and orange hues of the famed Kancamagus Scenic Byway to North Conway. This spectacular section of Route 112 is unspoiled by industry and boasts 34.5 miles (55 kilometres) of untouched natural beauty.Bretton Woods: More spectacular fall foliage awaits as you journey through Crawford Notch, a scenic pass through the White Mountains. Stop for pictures at the Silver Cascade Waterfall and Bretton Woods, which offers stunning views of Mount Washington, the tallest peak in the northeast at 6,288 feet (1,917 metres).North Conway: Enjoy a scenic hike to Diana's Baths, which features a small series of captivating cascading waterfalls. This historic site is within the White Mountain National Forest and easy paced.Enjoy the comfort of Insight's luxurious, air-conditioned, 40-seat coach with double the standard legroom and onboard washroom. Our customized luxury coaches are sanitized before the start of your tour and are maintained to very high standards. Physical distancing measures have been implemented on our customized luxury coaches.Experience enhanced hygiene protocols to align with the latest guidance following COVID-19. All Travel Directors and Drivers have completed training in enhanced well-being and hygiene protocols.Hand sanitizer is freely available on board for you to use throughout the day.We only work with establishments we are confident will consistently adhere to our high well-being standards, which include hotels, restaurants and sight-seeing venues.
Day 1
Affectionately known as Beantown, this revolutionary city is one of the oldest in the United States. After settling in, perhaps take a stroll to Downtown Crossing or historic Faneuil Hall. For those looking to shop, Quincy Market offers big brands and local products, set indoors and surrounding the columns of a regal 19th-century building. Join your Travel Director for dinner and an opportunity to mingle with fellow guests at your hotel.
Day 2
Today you’ll discover some of Boston’s most famous sights as you delve into the city’s transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. See Boston Common, Boston Public Garden, Trinity Church and Copley Square. This afternoon, explore Stockbridge with an Insight Choice. Choose to visit the Norman Rockwell Museum, home to the largest and most significant collection of original Rockwell art. Alternatively, choose to take a guided tour of Chesterwood, the former summer home and studio of renowned 20th-century sculptor Daniel Chester French, famous for his work on the Lincoln Memorial. Travel on through the rolling hills of the Berkshires and onto your upstate New York hotel, situated within the Saratoga Spa State Park.
Day 3
Trace the roots of Vermont’s rural traditions as you travel from Saratoga Springs into the heart of New England. In Weston, step inside the Vermont Country Store, a family-run emporium preserving generations of heritage brands and household curiosities. Browse shelves filled with locally made maple syrup, nostalgic sweets and artisanal Vermont cheeses, each reflecting the state’s rich tradition of craftsmanship. Explore Woodstock, a village renowned for its Federal-style architecture and artisanal spirit. At Billings Farm & Museum, gain insight into sustainable dairy farming practices and how 19th-century life shaped the region’s agricultural legacy. Later, at Morse Farm Maple Sugarworks, learn how maple sap is turned into syrup and taste the seasonal delicacy ‘sugar on snow’. Your day concludes at the Von Trapp Family Lodge, home to the famed musical family who made Vermont their refuge after fleeing Austria.
Day 4
Enjoy a Relaxed Start at the iconic Von Trapp Family Lodge, where Austrian heritage meets Vermont’s Green Mountains. Later, connect with the land at Bread & Butter Farm during a guided tour, followed by a nourishing lunch by Blossom Whole Food Kitchen. This afternoon, take time to explore the picturesque town of Stowe, filled with artisan boutiques and local charm. Return to the lodge for a hearty three-course dinner featuring Alpine flavours, thoughtfully paired with German-style lagers brewed onsite at the Von Trapp Brewery.
Day 5
Journey to New Hampshire’s White Mountains and enter striking Franconia Notch. Take a scenic ride on the Gondola SkyRide at Loon Mountain Resort. On a clear day, you'll have superb panoramic views of New Hampshire, Maine, Vermont, New York and Canada. Later, journey through the dazzling crimson and orange hues of the famed Kancamagus Scenic Byway to North Conway. This spectacular section of Route 112 is unspoiled by industry and boasts 34.5 miles of untouched natural beauty.
Day 6
This morning's MAKE TRAVEL MATTER® Experience with naturalist guide Chris Lewey provides an up-close and personal insight into New England's wildlife and ecology. Then, more spectacular fall foliage awaits as you journey through Crawford Notch, an arresting pass through the White Mountains. Stop for pictures at the Silver Cascade Waterfall and Bretton Woods, which offers stunning views of Mount Washington, the tallest peak in the northeast at 6,288 feet (1,917 metres). Your Travel Director will guide you on a scenic hike to Diana's Baths, which features a series of small cascading waterfalls. Return to your hotel where you can enjoy an evening at leisure.
Day 7
Cross from New Hampshire into Maine this morning as you travel along the jagged coastline. Head to Fort Williams Park which is home to the iconic Portland Head Lighthouse that has been in operation since 1791. Then spend the rest of your afternoon at leisure in Portland. In the evening, enjoy a delicious dinner featuring Maine lobster with your fellow travellers.
Day 8
Known for its sandy beaches, Kennebunkport is a year-round coastal destination that houses the rich and famous, even serving as the summer retreat of former President George H.W. Bush. Travel along Ocean Drive with more stunning views of the Maine coastline, before driving back to Boston. Guests departing Boston will arrive at Boston Logan International Airport. Those extending their stay will return to the Hyatt Regency Boston hotel.
Affectionately known as Beantown, this revolutionary city is one of the oldest in the United States. After settling in, perhaps take a stroll to Downtown Crossing or historic Faneuil Hall. For those looking to shop, Quincy Market offers big brands and local products, set indoors and surrounding the columns of a regal 19th-century building. Join your Travel Director for dinner and an opportunity to mingle with fellow guests at your hotel.
Day 2
Today you’ll discover some of Boston’s most famous sights as you delve into the city’s transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. See Boston Common, Boston Public Garden, Trinity Church and Copley Square. This afternoon, explore Stockbridge with an Insight Choice. Choose to visit the Norman Rockwell Museum, home to the largest and most significant collection of original Rockwell art. Alternatively, choose to take a guided tour of Chesterwood, the former summer home and studio of renowned 20th-century sculptor Daniel Chester French, famous for his work on the Lincoln Memorial. Travel on through the rolling hills of the Berkshires and onto your upstate New York hotel, situated within the Saratoga Spa State Park.
Day 3
Trace the roots of Vermont’s rural traditions as you travel from Saratoga Springs into the heart of New England. In Weston, step inside the Vermont Country Store, a family-run emporium preserving generations of heritage brands and household curiosities. Browse shelves filled with locally made maple syrup, nostalgic sweets and artisanal Vermont cheeses, each reflecting the state’s rich tradition of craftsmanship. Explore Woodstock, a village renowned for its Federal-style architecture and artisanal spirit. At Billings Farm & Museum, gain insight into sustainable dairy farming practices and how 19th-century life shaped the region’s agricultural legacy. Later, at Morse Farm Maple Sugarworks, learn how maple sap is turned into syrup and taste the seasonal delicacy ‘sugar on snow’. Your day concludes at the Von Trapp Family Lodge, home to the famed musical family who made Vermont their refuge after fleeing Austria.
Day 4
Enjoy a Relaxed Start at the iconic Von Trapp Family Lodge, where Austrian heritage meets Vermont’s Green Mountains. Later, connect with the land at Bread & Butter Farm during a guided tour, followed by a nourishing lunch by Blossom Whole Food Kitchen. This afternoon, take time to explore the picturesque town of Stowe, filled with artisan boutiques and local charm. Return to the lodge for a hearty three-course dinner featuring Alpine flavours, thoughtfully paired with German-style lagers brewed onsite at the Von Trapp Brewery.
Day 5
Journey to New Hampshire’s White Mountains and enter striking Franconia Notch. Take a scenic ride on the Gondola SkyRide at Loon Mountain Resort. On a clear day, you'll have superb panoramic views of New Hampshire, Maine, Vermont, New York and Canada. Later, journey through the dazzling crimson and orange hues of the famed Kancamagus Scenic Byway to North Conway. This spectacular section of Route 112 is unspoiled by industry and boasts 34.5 miles of untouched natural beauty.
Day 6
This morning's MAKE TRAVEL MATTER® Experience with naturalist guide Chris Lewey provides an up-close and personal insight into New England's wildlife and ecology. Then, more spectacular fall foliage awaits as you journey through Crawford Notch, an arresting pass through the White Mountains. Stop for pictures at the Silver Cascade Waterfall and Bretton Woods, which offers stunning views of Mount Washington, the tallest peak in the northeast at 6,288 feet (1,917 metres). Your Travel Director will guide you on a scenic hike to Diana's Baths, which features a series of small cascading waterfalls. Return to your hotel where you can enjoy an evening at leisure.
Day 7
Cross from New Hampshire into Maine this morning as you travel along the jagged coastline. Head to Fort Williams Park which is home to the iconic Portland Head Lighthouse that has been in operation since 1791. Then spend the rest of your afternoon at leisure in Portland. In the evening, enjoy a delicious dinner featuring Maine lobster with your fellow travellers.
Day 8
Known for its sandy beaches, Kennebunkport is a year-round coastal destination that houses the rich and famous, even serving as the summer retreat of former President George H.W. Bush. Travel along Ocean Drive with more stunning views of the Maine coastline, before driving back to Boston. Guests departing Boston will arrive at Boston Logan International Airport. Those extending their stay will return to the Hyatt Regency Boston hotel.
Enquire to book this trip
Deal number: 21500419
New England's Fall Foliage - Classic Group
INSIGHT VACATIONS
From 20/09/2026 to 24/10/2026
Boston
8-day tour
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