New England Leaf-Peeping Custom Adventure Tour

Arrive in Boston, pick up your rental car, and settle into your centrally located downtown hotel, where valet parking makes for an easy start to your New England adventure. This afternoon, take a guided walk along Boston’s famed Freedom Trail, tracing the red-brick path to all 16 historic landmarks. Hear vivid stories of Revolutionary icons Paul Revere, John Hancock, and the often-overlooked women, African Americans, and immigrants whose contributions shaped the nation. Your guide brings to life Boston’s pivotal role in the Revolution, abolition, and education reform. Afterward, enjoy free time to explore at your own pace—stroll Beacon Hill’s charming streets, dine in the North End, or visit nearby Cambridge, home to Harvard University and MIT.

Drive north toward Bar Harbor, stopping to savor Maine’s coastal character along the way. If time permits, stop in the charming seaside town of Kennebunkport for a taste of classic New England charm. This afternoon, discover Portland on a guided city tour, exploring its lively downtown, vibrant Arts District, and historic Old Port lined with excellent restaurants and waterfront energy. Admire rows of brownstones and elegant Victorian in residential neighborhoods, watch lobstermen at work, and take in sweeping coastal views across Casco Bay. A highlight is iconic Portland Head Light, where dramatic ocean scenery meets rich maritime history. After your tour, continue along the scenic coast to Bar Harbor, gateway to Maine’s rugged island landscapes.

This morning, set out with your private guide and driver for a full-day exploration of Acadia National Park and Mount Desert Island, tailored to your interests and pace. Pause for easy scenic walks at highlights such as Sand Beach, a striking crescent of golden sand tucked between granite headlands, and Thunder Hole, where surf crashes dramatically into a narrow rock inlet. Admire the sheer granite wall at Otter Cliff, stroll the rocky shores of Otter Cove, and enjoy the serene beauty of Jordan Pond, famed for its crystal-clear waters and mountain backdrop. Weather permitting, ascend Cadillac Mountain for sweeping coastal vistas from Acadia’s highest peak. Return to Bar Harbor with the evening free to explore at leisure.

Check out of your hotel and meet your private guide for a flavorful walking tour through historic Bar Harbor. Stroll less than a mile along charming village streets as you sample classic local specialties—buttery lobster rolls, creamy New England clam chowder, fresh oyster tastings, wild blueberry pie, and whoopie pies beloved across Maine—are all possibilities! Between bites, hear stories of Bar Harbor’s maritime heritage, Gilded Age grandeur, and enduring connection to the sea. After your culinary adventure, enjoy a scenic drive inland to North Conway, nestled amid the White Mountains and rich with small-town New England charm.

In spring and summer, other options for this day, such as whale-watching cruises, private catamaran sails, and traditional clambakes, offer another memorable taste of the coast.

Drive west toward Burlington along the legendary Kancamagus Highway, one of New England’s finest fall foliage routes, where mountainsides glow with brilliant reds, golds, and oranges. Passing through White Mountain National Forest, Rocky Gorge, Lower Falls, or Lost River Gorge for waterfalls, easy walks, and remarkable geology. Cross into Vermont and take time to stroll through charming Stowe, a picture-perfect village of steeples, shops, and classic New England charm. This afternoon, saddle up for a private guided horseback ride from Franconia Stables, following forest and meadow trails ablaze with autumn color, with mountain views and possible sightings of deer, moose, and wild turkeys.In spring and summer kayaking or canoeing are options and make a great way to experience the White Mountain region.

There are many ways to experience Burlington, with a menu of memorable adventures. Glide along the shores of Lake Champlain on a guided e-bike ride or take to the water for a scenic cruise with wide-open mountain views. Food lovers may choose a visit to the famous Ben & Jerry's factory for a behind-the-scenes taste of Vermont’s sweetest icon, while history and nature enthusiasts can explore the pastoral beauty of Shelburne Farms. Another tempting option is a guided craft brewery tour through Burlington’s lively downtown, sampling inventive local brews. Whatever you have planned for the day, Burlington’s lakeside charm and creative spirit shine through.

Set out on scenic Route 100, one of Vermont’s most beautiful byways, winding south through rolling hills, vibrant villages, and classic autumn landscapes. Head for Woodstock, stopping for self-guided exploration at Vermont gems such as Quechee Gorge’s dramatic river-carved views and charming towns like Warren. Meet up with your guide for a private organic farm experience in the rolling hills of Vermont. Pop a sweet cherry tomato in your mouth and pick some blueberries or even put your hands in the warm soil and plant a seedling. During the tour, you'll harvest produce for your lunch and learn about sustainable gardening and farming methods before enjoying an outdoor picnic with your fresh-picked ingredients—a delicious hands-on taste of Vermont’s agricultural heart.

This morning, meet your MT Sobek guide for a private exploration of central Vermont's most charming backroads and hidden treasures. Travel through a landscape of green hills, winding country lanes, and postcard-perfect villages, stopping to admire classic covered bridges and scenic state parks. In the Warren and Woodstock region, discover the authentic rhythm of small-town Vermont, where white church steeples, village greens, and historic inns create timeless New England appeal. Enjoy leisurely walks at scenic overlooks and tucked-away local spots known best to insiders, with opportunities to browse artisan shops, sample regional specialties, and soak in the peaceful beauty of the countryside. It is a day rich in quiet discoveries, local flavor, and the unmistakable charm that makes Vermont so beloved.

Today, enjoy a final scenic drive back to Boston, reflecting on the landscapes and experiences of your New England journey. As you travel south, consider taking a stroll in the lively town of Brattleboro, known for its welcoming town square, and excellent local farmers market, perhaps picking up a last Vermont treat for the road. Return your rental car in Boston before boarding your flight home. With memories of coastal villages, mountain drives, farm-fresh flavors, and brilliant fall landscapes, your adventure comes to a rewarding close.