Highlights Itinerary
HIGHLIGHTS: 14-Day Itinerary
Though it begins and ends with two landmarks of American history, this trip has a little bit of everything for travelers: ocean cruises and mountain summits, art museums and shopping meccas, and grand old mansions (not to mention an even grander resort casino).
DAY 1: BOSTON, MASSACHUSETTS
Learn more about visiting Boston
Lodging ideas: Boston Marriott Copley Place, Copley Square Hotel, Hilton Boston Park Plaza, Newbury Guest House, The Revolution Hotel, The Whitney Hotel
Spend the day walking between past and present on the Freedom Trail, a 2.5-mile (4km) path connecting 16 important sites in the founding of the United States. Among the highlights are Faneuil Hall, the USS Constitution, and the Old North Church.
There are lots of reasons to detour along the way. Next to Faneuil Hall is Quincy Market, filled with shops and eateries. Sample local seafood at Boston’s oldest restaurant, Union Oyster House, or visit the North End (Boston’s “Little Italy”) for some pizza and cannoli.
Catch some thrilling basketball at TD Garden, home of the Celtics, or watch the Red Sox play at Fenway Park, the nation’s oldest ballpark.
DAY 2: MASSACHUSETTS NORTH SHORE
Learn more about visiting North of Boston
Lodging ideas: Beauport Hotel (Gloucester), Briar Barn Inn (Rowley); Ocean House Hotel at Bass Rocks (Gloucester)
It’s time to hit the road and explore the North Shore. The Essex Scenic Coastal Byway is a 90-mile route that links 14 seaside towns and cities north of Boston, offering famous attractions and hidden gems along the way. Salem is home to the Peabody Essex Museum as well as the Salem Witch Museum. In Gloucester, visit the Hammond Castle Museum and the Cape Ann Museum.
End the day in Gloucester’s Rocky Neck Cultural District. Its many galleries and studios include the Salted Cod Arthouse, which also offers a casual dining space.
DAYS 3 & 4: PORTLAND, MAINE
Learn more about visiting Portland
Lodging ideas: Aloft Portland, Hilton Garden Inn Portland Waterfront, Nonantum Resort (Kennebunkport)
Portland has built up its culinary reputation with excellent bakeries, breweries, fine dining, international cuisine—and, of course, seafood. Try Eventide Oyster Co. or DiMillo’s on the Water, Maine’s only floating restaurant.
Maine Day Ventures and NaviTour offer a variety of themed tours that immerse you in Portland history, art and architecture, neighborhoods, and more. Portland’s Lucky Catch Cruises and Kennebunkport’s Rugosa Lobster Tours give a close-up look at how Maine’s most famous seafood is harvested.
Less than an hour’s drive south from Portland is York’s Nubble Light, one of the world’s most-photographed lighthouses. To the north, Freeport has outlet shopping and the flagship store of Maine’s L.L. Bean.
DAYS 5 & 6: NEW HAMPSHIRE WHITE MOUNTAINS
Learn more about visiting New Hampshire’s White Mountains
Lodging ideas: Eastern Slope Inn (North Conway), North Conway Grand Hotel, White Mountain Hotel & Resort (North Conway)
Board the MS Mount Washington for a cruise on New Hampshire’s largest lake, Winnipesaukee, with the majestic White Mountains in the distance. Or take a scenic drive on the Kancamagus Highway, which travels 34.5 miles (55km) through the White Mountain National Forest.
In North Conway, enjoy outlet shopping at Settlers Green, take a ride on the Conway Scenic Railroad, and find four-season fun at Cranmore Mountain Resort. Nearby attractions include Rek’ Lis Brewing Co. in Bethlehem, Polly’s Pancake Parlor in Sugar Hill, and the Mount Washington Auto Road, which takes you to the top of the highest peak in the northeastern U.S.
DAYS 7 & 8: BURLINGTON, VERMONT
Learn more about visiting Burlington
Lodging ideas: Courtyard by Marriott Burlington Harbor, Hilton Garden Inn Burlington Downtown, Hotel Vermont
The heart of Vermont’s “Queen City” is Church Street Marketplace, a four-block pedestrian mall packed with shopping, dining, and people-watching. A few blocks away is the famous Lake Champlain, which you can explore on a scenic cruise with the Spirit of Ethan Allen or Whistling Man Schooner Co. Check out local nightlife in the South End Arts District or visit top local breweries with City Brew Tours.
Within a short drive is Shelburne Museum, a 45-acre art and history museum, as well as the Upper Green Mountains, where you can visit the Trapp Family Lodge brewery, Cold Hollow Cider, and the Ben and Jerry’s factory. For thrills, ride the Stowe Gondola SkyRide or drive the twisty two-lane Smugglers’ Notch Road.
DAY 9: MASSACHUSETTS BERKSHIRES
Learn more about Massachusetts Berkshires
Lodging ideas: Hotel Downstreet (North Adams), Hotel on North (Pittsfield), The Porches Inn at Mass MoCA (North Adams), The Red Lion Inn (Stockbridge)
Massachusetts is known for its coast and beaches, but it also offers a beautiful mountain getaway in the Berkshires. The hills and valleys of this region are filled with picturesque towns and must-see attractions, such as the Norman Rockwell Museum and the Tanglewood Music Festival. Head to North Adams to visit one of the world’s largest museums of contemporary art, Mass MoCA. At the end of your day, drive to the top of Mount Greylock for views of five New England states.
DAYS 10 & 11: CONNECTICUT COAST
Learn more about visiting Connecticut
Lodging ideas: Foxwoods Resort Casino (Ledyard), Great Wolf Lodge (Ledyard; opening 2025), Inn at Mystic (Mystic), New Haven Hotel (New Haven), The Blake Hotel (New Haven)
In New Haven, Yale University lets you visit its world-class art gallery, natural history museum, and British art center—all for free. Explore New Haven on an Elm City Party Bike tour, and don’t forget to sample New Haven–style pizza at Sally’s Apizza or Frank Pepe’s.
An hour east of New Haven is Foxwoods, the largest resort-casino complex in North America, with seven casinos and four hotels. Go outlet shopping, take a ride on the HighFlyer zipline, try indoor karting at MONZA, and play golf at the award-winning Lake of Isles. And learn about the indigenous tribe that made Foxwoods a reality at the Mashantucket Pequot Museum and Research Center, the nation’s biggest Native American museum.
DAYS 12 & 13: NEWPORT, RHODE ISLAND
Learn more about visiting Newport
Lodging ideas: Forty 1 North, Hotel Viking, Newport Harbor Island Resort
Start by strolling the Cliff Walk, a 3.5-mile (5.6km) path that runs alongside some of Newport’s grandest historic homes, the Newport Mansions. Several properties also offer tours, if you’d like a look inside these Gilded Age gems. The nearby International Tennis Hall of Fame is also worth a visit. Then hit the water with a sailing cruise from local outfitters, such as America’s Cup Charters and Newport Classic Cruises.
Take a guided tour of the city on a trolley cars with Viking Tours of Newport or choose a walking-tour option: Newport History Tours shares stories about the city’s earliest days, while Ghost Tours of Newport combines history with spooky thrills.
DAY 14: PLYMOUTH, MASSACHUSETTS
Learn more about Plymouth
Lodging ideas: Fairfield Inn & Suites Plymouth, Hotel 1620 Plymouth Harbor, John Carver Inn & Spa, Mirbeau Inn & Spa
Stop at the waterfront to snap a photo of Plymouth Rock, then head to Plimoth Patuxet Museums to see a full-scale reproduction of the Mayflower II and learn all about the Pilgrims and the indigenous people of this area. Just a few blocks away, Pilgrim Hall Museum features many artifacts owned by the Pilgrims themselves.
After soaking up some history, go on a whale-watching trip with Captain John Boats, take a cranberry bog tour in the fall, sample local beer at the Mayflower Brewing Co., and enjoy your day of exploring “America’s Hometown.”
Itinerary created in partnership with Yankee Publishing. DATTCO Coach & Tour is Discover New England’s transportation partner.
