Visit Fort Williams Park in Cape Elizabeth to see Portland Head Light standing above Maine’s rocky coast. Take in views of the lighthouse and its Atlantic setting from the surrounding park grounds.

First lit in 1791, Portland Head Light is Maine’s oldest lighthouse and remains a symbol of the state’s maritime heritage. Its position at the entrance to Portland Harbor makes clear why coastal navigation mattered to generations of sailors approaching this stretch of shore.

Insight Vacations

• 3 Dinner (D)
• 7 Breakfast (B)
• 1 Lunch (L)

• 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.

• Business class coach with extended leg room
• Top-rated dining, from farm-to-table to local restaurants
• Premium regional accommodation

Meet your Travel Director and fellow travellers over an included dinner at your Boston hotel. The hosted gathering offers a relaxed introduction to the people sharing your New England journey.

Conversation over dinner sets the scene for a region shaped by revolutionary history, rural traditions and coastal foodways. This is a social experience rather than a guided city visit, with time to get acquainted before exploring farther afield.

Explore Boston with your Travel Director, following part of the red-brick Freedom Trail through a city central to the American Revolution. See Boston Common, Boston Public Garden, Trinity Church and Copley Square while learning how colonial Boston helped shape the United States.

The sightseeing also takes in historically significant landmarks and contrasting neighbourhoods, from the elegant streets of Back Bay to the lively North End. Together, they reveal a city where revolutionary sites remain part of everyday urban life.

Choose to visit the Norman Rockwell Museum in Stockbridge, Massachusetts, home to a major collection of the illustrator’s original work. View images that made Rockwell a familiar presence in American homes, including art associated with his long career creating covers for The Saturday Evening Post.

Changing exhibitions broaden the view to other American illustrators. This included Insight Choice offers a close look at how popular art portrayed everyday life, humour and national ideals; travellers select it instead of the Chesterwood tour.

Choose a guided tour of Chesterwood, the former summer home and studio of sculptor Daniel Chester French in Stockbridge. Explore the setting where he lived and worked, including the grounds that helped make this Berkshire property a creative retreat.

French is best known for the seated Abraham Lincoln figure at the Lincoln Memorial. This included Insight Choice connects the artist’s working life with one of America’s most recognisable monuments; travellers select it instead of the Norman Rockwell Museum visit.

Step inside the Vermont Country Store in Weston, a family-run emporium known for heritage goods and household curiosities. Browse shelves of nostalgic sweets, local cheeses and maple products while discovering the kinds of practical wares and treats that have long belonged in a New England country store.

The visit is a window into Vermont’s tradition of small-scale craftsmanship, with regional flavours alongside familiar products from earlier generations. It is a purposeful stop to explore a distinctive local institution, not simply a break for shopping.

Visit Woodstock, a Vermont village known for its historic streetscape, and explore Billings Farm Museum, a working dairy farm that interprets the region’s rural past. See how farming remains part of the landscape beyond the village’s Federal-era buildings.

Farm exhibits illuminate 19th-century agricultural life and the development of dairy practices in Vermont. The pairing brings together the village’s architectural heritage and the working land around it, offering a grounded picture of how New England communities grew and sustained themselves.

Visit Morse Farm Maple Sugarworks near Montpelier to learn how sap collected from maple trees becomes Vermont syrup. Discover the steps behind a product closely tied to the state’s forests, farms and seasonal traditions.

Taste sugar on snow, a traditional treat made by pouring warm maple syrup over packed snow until it thickens. Its sweet flavour is traditionally set against a doughnut and pickle. The tasting turns a familiar pantry staple into an experience rooted in Vermont’s sugaring heritage.

Tour von Trapp Brewing in Stowe and learn how the family behind The Sound of Music brought Austrian-style lager traditions to Vermont’s Green Mountains. Hear the story of the von Trapps’ life in the region and the brewery founded by Johannes von Trapp.

Sit down to a three-course dinner with locally brewed lager, pairing Alpine-inspired flavours with a distinctly Vermont setting. The experience connects the family’s Austrian heritage with the place they made their home.

Meet the owners at Bread & Butter Farm in Shelburne and explore how regenerative practices support the land. Walk the fields with Chef Tessa, a seventh-generation Vermonter, as she shares insights into seasonal growing and sustainable sourcing.

Gather fresh herbs and blooms before enjoying a farm-to-table lunch prepared by Blossom Whole Food Kitchen. Meeting the people behind the meal makes Vermont’s agricultural heritage tangible, from the soil and seasonal harvest to the food served at the table.

Ride the Gondola SkyRide at Loon Mountain Resort for an elevated view of New Hampshire’s White Mountains. The ascent opens up a broad perspective on forested slopes whose autumn colours can range from gold to deep red.

On clear days, the panorama can extend toward Maine, Vermont, New York and Canada. This is a seasonal, weather-dependent experience, with visibility shaped by the conditions; its appeal lies in seeing the scale of the mountain landscape from above.

Travel the Kancamagus Scenic Byway, a 34.5-mile stretch of Route 112 through New Hampshire’s White Mountain National Forest. Take in the forested ridges and changing autumn canopy along a road celebrated for its largely undeveloped mountain scenery.

Known locally as the Kanc, the route links the Lincoln and Conway areas without the commercial development found along many highways. Its crimson, orange and gold foliage makes the journey itself a focused scenic experience rather than an ordinary transfer.

Explore New England’s autumn ecology with a naturalist guide in the North Conway area. Learn about regional flora and fauna and look more closely at the habitats that support wildlife in and around the White Mountains.

The guided experience adds ecological context to the seasonal colours, showing how forest life extends beyond the foliage visible from the road. This MAKE TRAVEL MATTER® experience is designed to deepen understanding of local nature and supports a focus on protecting life on land.

Explore the scenery of Crawford Notch, a mountain pass framed by steep slopes and autumn woodland. Stop to photograph Silver Cascade, where water descends over rock beside the mountain road, and take in the landscape around Bretton Woods.

From the Bretton Woods area, look toward Mount Washington, the Northeast’s highest peak at 6,288 feet. The combination of waterfall, mountain pass and distant summit offers several distinct perspectives on the White Mountains’ rugged terrain.

Walk with your Travel Director to Diana’s Baths, a series of small waterfalls near North Conway in the White Mountain National Forest. The easy-paced hike leads through woodland to smooth rock and cascading water.

The site’s name recalls a former sawmill operation, while its present-day appeal lies in the quiet meeting of stream and forest. Pause beside the falls to appreciate a more intimate White Mountains landscape than the region’s broad summit panoramas.

Discover Kennebunkport’s coastal setting and travel along Ocean Drive for views of the Maine shoreline. The route reveals the area’s mix of seaside scenery and established summer homes, including the coastal setting associated with former President George H. W. Bush.

Kennebunkport’s long history as a summer destination gives the drive a character distinct from the inland mountain experiences on this tour. Look out across the water and rocky coast for a sense of Maine’s Atlantic landscape.

Savour a Maine lobster dinner in Portland with your fellow travellers. The hosted celebration centres on a local seafood tradition, with lobster prized for its tender meat and rich flavour.

Maine’s working waterfront and cold Atlantic waters give this meal a strong sense of place. Sharing dinner offers a chance to reflect on New England’s landscapes and communities together, while enjoying a dish closely identified with the state’s coastal food culture.