Morning: Arrive in Boston and settle into your hotel before strolling the historic Freedom Trail, where you’ll encounter key Revolutionary sites such as Boston Common and Paul Revere’s House.
Afternoon: Enjoy a scenic Boston Harbor cruise offering views of the skyline and the iconic Statue of Freedom, then wander the bustling Quincy Market for local snacks.
Evening: Dine in the lively North End, sampling authentic Italian cuisine, and finish the night with a walk along the waterfront at Harborwalk.
Find HotelsMorning: Drive to Portland and start with the iconic Portland Head Light at Cape Elizabeth, capturing sunrise over the Atlantic.
Afternoon: Explore the charming cobblestone streets of the Old Port, browsing boutiques, galleries, and enjoying fresh lobster rolls at a waterfront eatery.
Evening: Savor a farm‑to‑table dinner in the historic Old Port district and stroll along the scenic Eastern Promenade as the sun sets.
Find HotelsMorning: Enter Acadia National Park and hike to the summit of Cadillac Mountain for panoramic views of the Atlantic and surrounding islands.
Afternoon: Picnic at Jordan Pond, then wander the elegant stone bridge and enjoy the famed popovers at Jordan Pond House.
Evening: Drive the historic Park Loop Road at dusk, spotting wildlife and capturing the sunset over the rugged coastline.
Find HotelsMorning: Cross into Vermont and explore the vibrant Church Street Marketplace**, a pedestrian‑only thoroughfare filled with shops, street performers, and cafés.
Afternoon: Take a short ferry ride on Lake Champlain to enjoy lakeside views of the Adirondacks and visit the historic Ethan Allen Homestead.
Evening: Dine at a farm‑focused restaurant overlooking the lake, then unwind with a craft beer at a local brewery.
Find HotelsMorning: Arrive in Newport and wander the breathtaking Cliff Walk**, a coastal path that weaves past dramatic ocean bluffs and opulent mansions.
Afternoon: Tour the grand The Breakers, the former summer residence of the Vanderbilt family, and explore the historic downtown waterfront.
Evening: Enjoy a sunset dinner at a seaside restaurant in the historic Bowen’s Wharf area, reflecting on your New England adventure.
Find HotelsIf you have extra time, add a day in the White Mountains of New Hampshire for hiking or a scenic drive on the Kancamagus Highway. To shorten the trip, skip the ferry on Lake Champlain and combine Days 4 and 5, focusing on Burlington’s downtown and a quick drive to Newport. Adjust the itinerary based on your travel pace and seasonal weather for the best New England experience.