Day 1 – Explore Boston’s Historic Streets and Markets

Once settled, you might make your way through Downtown Crossing to Faneuil Hall, where centuries-old red brick rises beneath a white cupola crowned by a gilded grasshopper weather vane. At neighbouring Quincy Market, granite columns flank the long hall as aromas of warm bread, coffee and chowder drift from the food counters and local stalls. Over dinner at the hotel, you’ll join your Travel Director and meet the fellow guests who will share the next eight days with you.

Day 2 – New England Heritage: Boston to Saratoga Springs

You’ll follow the painted line of Boston’s Freedom Trail across the broad lawns of Boston Common, pause on the Public Garden’s curved iron bridge with the lagoon below and look up at Trinity Church’s warm sandstone and carved arches in Copley Square. For your choice experience in Stockbridge, you might move through the Norman Rockwell Museum from faint pencil studies to richly layered oils, studying the fine details sprawling across the canvases. Or join a guided tour of Chesterwood, where pale plaster studies line the workroom and part of the studio floor rolls outdoors on rails, allowing Daniel Chester French to judge monumental figures in natural light. Beneath its 26-foot walls, you’ll stand in the summer studio of the sculptor who created the seated Lincoln at the Lincoln Memorial. The wooded Berkshires stretch alongside the road to Saratoga Spa State Park. You’ll settle into your hotel among classical colonnades and forest paths, with Saratoga’s mineral springs gently flowing nearby.

Day 3 – Discover Vermont’s Farms, Flavours and Mountains

Across the Vermont border, you’ll browse maple-leaf sweets, golden bottles of syrup and neatly wrapped Vermont cheeses. In Woodstock, you’ll pass Federal-style façades on your way to Billings Farm, where brown Jersey cows fill the working dairy barn. Inside the restored 1890 farmhouse, you move through rooms devoted to butter-making, seasonal work and family life, learning how farmers cared for their animals and land through the changing year. At Morse Farm Maple Sugarworks, you learn how clear sap is boiled down into amber syrup before tasting ‘sugar on snow’. Hot maple syrup thickens over shaved ice into a glossy, chewy ribbon, with a deep maple sweetness on the palate. The Green Mountains surround the Von Trapp Family Lodge in Stowe, where you’ll check into the home established by the musical family after they fled Austria. Over three courses, you taste Alpine flavours and sip German-style lagers brewed on site, savouring their cool malt and gentle bitterness.

Day 4 – Explore Vermont’s Farms and Stowe Village

After a Relaxed Start at the Von Trapp Family Lodge, you’ll follow your guide from Bread & Butter Farm’s cultivated fields into woodland, where orderly growing beds give way to a narrow trail beneath interlacing branches. The route continues through pasture and marshland as you learn how the farm’s plants, animals and people depend on the same working landscape. Afterwards, you’ll sit down to a nourishing lunch prepared by Blossom Whole Food Kitchen. Stowe’s Main Street is yours to explore, with small galleries and artisan boutiques throughout the historic village. Stained glass catches the light beside ceramics, jewellery and paintings by Vermont artists. Later, you’ll explore Stowe at your own pace, wandering through its white-steepled Main Street, small galleries and artisan boutiques.

Day 5 – New Hampshire Heights: Franconia Notch and Beyond

Between the Kinsman and Franconia ranges, you’ll enter Franconia Notch with sheer rock rising beside the road and forested slopes climbing high above it. At Loon Mountain, you step into the gondola (seasonal) and feel the cabin climb as the cable hums overhead. Below, you watch pointed firs and maples merge into sweeps of scarlet, copper and orange while the valley falls farther away. At Loon Peak, you’ll step out 2,733 feet above sea level and scan ridge after ridge, tracing the horizon across New Hampshire towards Maine, Vermont, New York and Canada on a clear day. Later, the Kancamagus Scenic Byway curves beside the Swift River and climbs towards Kancamagus Pass. From the road, you watch water slide over pale granite and track crimson maples among the dark evergreens. For 34.5 miles, you’ll travel without shopfronts or commercial development, surrounded by river, rock and mountain forest towards North Conway.

Day 6 – Follow Forest Trails Through Crawford Notch

With naturalist Chris Lewey beside you, you listen for calls between the trees, scan the canopy and learn how New England’s wildlife adapts to the changing seasons during your MAKE TRAVEL MATTER® Experience. Through Crawford Notch, you’ll travel between steep slopes to Silver Cascade. Water unspools down Mount Jackson in pale ribbons, roaring above Route 302. At Bretton Woods, you look across the valley to Mount Washington, the Northeast’s highest peak, where the 6,288-foot summit may stand clear above the surrounding mountains or disappear into cloud. Later, your Travel Director leads you along the trail to Diana’s Baths. Lucy Brook begins as a murmur through the trees, deepening as you walk until you reach its chain of pools and small falls. You’ll follow the water from one rounded basin to the next, then return to your hotel.

Day 7 – Maine’s Coast: Kennebunkport to Portland

Crossing into Maine, you’ll follow the Kennebunk River towards Kennebunkport, then turn along Ocean Avenue as the Atlantic appears between the pines. You watch waves fold over dark granite and retreat in trails of white foam while lobster boats drift to and from the shore. At Walker’s Point, you pass the summer retreat of former President George H. W. Bush, set at the end of a rocky headland. In Portland, you’ll wander down the Old Port’s brick streets downhill to Commercial Street and the working wharves. Boats rock gently against wooden piers, and ropes creak beside the harbour. That evening, steam rises from your Maine lobster as you crack the scarlet shell, dip the sweet meat into melted butter and share dinner with the travellers who have crossed New England beside you.

Day 8 – Journey South Along Maine’s Rocky Coast

At Fort Williams Park, you’ll approach Portland Head Lighthouse above the dark rocks of the Maine coast, its white tower standing watch over the Atlantic since 1791. From here, follow the shoreline south before returning to Boston. Guests departing today will arrive at Boston Logan International Airport, while those extending their stay will return to the Hyatt Regency Boston.