Planning a New England tour itinerary is challenging because the region offers such a wide array of rich history, scenic landscapes, and vibrant cultural experiences. Below is a carefully planned tour that is ideal for first-time visitors eager to explore New England’s most iconic destinations and hidden gems. 

Day 1: Arrival in Boston and Welcome Reception

Begin your New England itinerary in the heart of Boston, a city brimming with historical significance. After arriving at Logan International Airport, settle into your downtown hotel. In the evening, join your fellow travelers for a welcoming wine and cheese reception, setting the tone for the journey ahead. Boston’s diverse culinary scene provides plenty of options for an enjoyable dinner on your own.

Day 2: Exploring Historic Boston and the Berkshires

Go on a guided tour of Boston, following the famous Freedom Trail. This journey through the city’s historic sites, including Faneuil Hall and the Old North Church, offers a deep dive into the birthplace of American liberty. After soaking in Boston’s history, venture westward to the Berkshires, a region celebrated for its cultural richness and scenic landscapes. Enjoy a memorable dinner at the historic Red Lion Inn in Stockbridge, surrounded by the quintessential charm of New England.

Highlights: Boston Freedom Trail, Faneuil Hall, Berkshires Hills

Day 3: Touring the Berkshires and Green Mountains

Continue your New England itinerary with a tour of the grand Gilded Age mansions in the Berkshires, often called “Berkshire Cottages.” These opulent homes offer a glimpse into the luxurious lifestyles of America’s elite during the late 19th century. Then, travel through the picturesque Green Mountains of Vermont, stopping at the Bennington Monument. The day concludes with a visit to Hildene, the summer home of Robert Todd Lincoln, before retiring to your Vermont resort.

Highlights: Gilded Age Mansions, Bennington Monument, Hildene

Day 4: Vermont’s Maple Farms and the Trapp Family Lodge

No New England itinerary is complete without experiencing Vermont’s renowned maple syrup. Visit a family-run maple sugar farm to learn about syrup production and enjoy tastings. Spend your afternoon exploring Montpelier, Vermont’s charming state capital. Later, visit the iconic Trapp Family Lodge in Stowe, where you can learn the history of the famous von Trapp family.

Highlights: Vermont Maple Sugar Farm, Montpelier, Trapp Family Lodge

Day 5: White Mountains and Mount Washington Cog Railway

Visit New Hampshire’s majestic White Mountains, which are known for their breathtaking beauty. Tour the historic Omni Mount Washington Hotel, a stunning example of Spanish Renaissance architecture, followed by a luncheon in its grand dining room. The day’s highlight is an exhilarating ride on the Mount Washington Cog Railway, ascending the Northeast’s highest peak and offering unparalleled views.

Highlights: Omni Mount Washington Hotel, Mount Washington Cog Railway

Day 6: Lakes Region and Scenic Drives

Continue your exploration of New Hampshire with a visit to the Lakes Region. Start your day in the idyllic village of Wolfeboro, where you’ll board the M/S Mount Washington for a relaxing cruise on Lake Winnipesaukee, complete with a buffet lunch. Afterward, head to Moulton Farm for a delightful wagon ride and some tasty local treats. Conclude your day with a drive along the Kancamagus Highway, renowned for its scenic landscapes and vibrant autumn colors.

Highlights: Lake Winnipesaukee Cruise, Moulton Farm, Kancamagus Highway

Day 7: Coastal Maine and Lobster Cruise

The second last day of your New England itinerary is about stunning coastlines and delicious seafood. Explore Kennebunkport, a popular summer destination, and view the Bush family’s summer home at Walker’s Point. After some free time in Dock Square, continue to Ogunquit for a fun-filled lobster cruise. Learn about lobstering from a Maine lobsterman and enjoy a traditional lobster dinner to cap off the day.

Highlights: Kennebunkport, Ogunquit, Lobster Cruise

Day 8: York Village and Portsmouth

Conclude your New England adventure with a visit to York Village, home to the iconic Cape Neddick Lighthouse, known as “the Nubble.” Capture photos of this famous landmark before touring the historic town of Portsmouth. Reflect on the cultural experiences and memories made throughout your trip as you prepare for your departure from Boston Logan International Airport.

Highlights: Cape Neddick Lighthouse, Portsmouth

Conclusion

Our comprehensive New England tour itinerary includes the best of the region, blending history, culture, and natural beauty. It contains everything from exploring the vibrant streets of Boston to experiencing the tranquility of Vermont’s maple farms and the excitement of a lobster cruise in Maine, guaranteeing an unforgettable journey through New England.