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. At 18:00, join your Travel Director for a Welcome Dinner with wine and an opportunity to mingle with fellow guests at your hotel.

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.

Journey through the bronze fall foliage of Vermont. Visit the Vermont Country Store for a unique shopping experience - you'll step back into history with their nostalgic assortment of products. Followed by a stop in the quintessential Vermont village of Woodstock with its picturesque, covered bridge. Explore the Rockefellers' renowned Billings Farm and Museum, a captivating working dairy and farm life museum. End your day in the northern Vermont town of Stowe, home to the breathtaking alpine setting that attracted the real Von Trapp family of "The Sound of Music." Enjoy Austrian-style lagers over at Von Trapp Brewing Bierhall.

Enjoy Vermont’s beautiful scenery ablaze with fall’s golden red colors. Stop by Morse Farm Maple Sugarworks, where maple syrup is 'tapped' from the trees. Taste a Vermont tradition, the unusually named ‘sugar on snow,’ a combination of maple syrup and packed snow. This tasty treat is traditionally served with a doughnut and pickle. Visit the women-owned and operated Bread and Butter Farm and Blossom Wholesome Foods Kitchen for an introduction to the farm, a hands-on activity and a farm-to-table lunch. Next, travel to Lake Champlain Chocolates for a taste of their award-winning ice cream crafted with local ingredients, before returning to the enchanting town of Stowe for an afternoon at leisure.

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.

In the morning, join a MAKE TRAVEL MATTER® Experience as you enjoy an insightful talk by a woman naturalist expert on the North Woods' 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 meters). Your Travel Director will guide you on a scenic hike to Diana's Baths which features a series of small cascading waterfalls.

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 travelers.

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 at 12:30 pm.