Rail and Sea Itinerary
RAIL & SEA: 14-Day Itinerary
See New England in a whole new way when you step aboard historic schooners and classic trains, carrying you everywhere from the picturesque Atlantic coast to the tallest peak in the Northeast.
DAYS 1 & 2: MASSACHUSETTS NORTH SHORE
Lodging ideas: Beauport Hotel (Gloucester), Briar Barn Inn (Rowley); Ocean House Hotel at Bass Rocks (Gloucester)
The Salem Ferry connects Boston and Salem. Book the ferry’s “Real Pirates Passage” to visit the Real Pirates Museum and see the world’s only verified pirate treasure. For more in-town attractions, the Salem Trolley Tour includes the House of the Seven Gables and the Salem Witch Museum.
Northeast of Salem lies Gloucester, a famous fishing port on scenic Cape Ann. Discover its seafaring heritage at Maritime Gloucester, a working waterfront, museum, and aquarium. Relax at Pavilion Beach, right downtown, and take a sunset sail on the replica fishing schooner Thomas E. Lannon.
Start the next day in Newburyport and explore Plum Island, a barrier island that’s home to the Parker River National Wildlife Refuge. Grab lunch in Newburyport’s quaint downtown, filled with cobblestone streets and plenty of shops and restaurants. Returning to Boston, you can either drive or take the commuter rail to North Station.
DAYS 3 & 4: BOSTON & PROVINCETOWN, MASSACHUSETTS
Lodging ideas: Boston Marriott Copley Place, Omni Boston Hotel at the Seaport, Onyx Boston Downtown, Seaglass Inn & Spa (Provincetown), The Westin Boston Seaport District, Yotel Boston
Stroll the waterfront on the Boston Harborwalk, where highlights include the North End (a.k.a. “Little Italy”) and the Seaport. To get out on the water, book a two-hour Boston Harbor Islands Lighthouse Tour—but make time before or after to visit the Boston Tea Party Ships & Museum, too.
On day two, head to Provincetown via a 90-minute ferry with Boston Harbor City Cruises or Bay State Cruise Company. “P-town” has art, shopping, and dining galore, plus the Pilgrim Monument and Provincetown Museum. For on-the-water thrills, go whale-watching with Captain John Boats or Dolphin Fleet.
Back in Boston, head north to Maine by car or aboard Amtrak’s Downeaster, which departs daily from North Station.
DAYS 5 & 6: SOUTHERN MAINE COAST
Lodging ideas: The Nonantum Resort (Kennebunkport), The Wanderer Cottages (Kennebunk), White Barn Inn (Kennebunkport)
Get to know Kennebunkport on the Intown Trolley Company’s one-hour trolley tour, which goes past sites such as President George H.W. Bush’s “Summer White House.” Afterward, get a taste of Maine’s legendary seafood at Mabel’s Lobster Claw.
More seaside fun awaits just to the north, in Portland. Check out Portland Head Light, the oldest lighthouse in Maine; stroll the Old Port, a trove of 19th-century architecture; and sample the city’s many eateries, from The Holy Donut to Eventide Oyster Co. For a nature adventure, take a guided trip with NaviTour to see coastal wildlife or head out on an Odyssey Whale Watch excursion.
DAYS 7 & 8: NEW HAMPSHIRE LAKES & MOUNTAINS
Lodging ideas: Eastern Slope Inn (North Conway), The Inn at Mill Falls (Meredith), New London Inn (New London), North Conway Grand Hotel (North Conway), Wolfeboro Inn (Wolfeboro)
Discover New Hampshire’s largest lake, Winnipesaukee, during a narrated tour on the M/S Mount Washington, or hop aboard the M/V Sophie C., a “floating post office” that delivers mail to island residents. The New Hampshire Boat Museum offers history and the chance to ride in a 28-foot mahogany replica of a 1928 motorboat. End your day at The Dive, a floating bar and restaurant that moves from one lake hot spot to the next.
Next, travel into the White Mountains for a thrilling trip on the Mount Washington Cog Railway, which climbs to the summit of the Northeast’s highest peak. Train fans can also book a ride on the Conway Scenic Railroad, known for its vintage passenger cars and sweeping views of the Mount Washington area.
DAYS 9 & 10: BURLINGTON, VERMONT
Lodging ideas: Courtyard Burlington Harbor, Hilton Burlington, Hotel Vermont (Burlington), North Hero House (North Hero)
Train travel is a popular way to reach Burlington, with Amtrak running daily service from New York City aboard the Ethan Allen Express. After arriving, wander the 100-plus shops and restaurants of Church Street Marketplace and explore the lakeshore on a rented bike from Local Motion. For dinner, choose from a meal aboard the cruise ship Spirit of Ethan Allen or the Champlain Valley Dinner Train, which serves gourmet cuisine amid classic Vermont landscapes.
Day two is for lake adventure. The beautiful Island Line Trail links cyclists to the Champlain Islands, a prime biking spot whose attractions include 480-million-year-old fossils at the Goodsell Ridge Preserve. Alternatively, head to Kill Kare State Park for picnicking, swimming, and boat rentals. From there, a ferry can take you to Burton Island State Park, offering hiking trails and bistro dining.
DAYS 11 & 12: CONNECTICUT SHORE
Lodging ideas: Hampton Inn & Suites (Mystic), Hilton Mystic (Mystic), The Whaler’s Inn (Mystic)
In Norwalk, board the Maritime Aquarium’s research catamaran, R/V Spirit of the Sound, for sightseeing and educational cruises on Long Island Sound, or book the Sheffield Island Lighthouse Tour to get a peek at Norwalk Harbor’s three historic lighthouses and stroll around Sheffield Island. Train aficionados, meanwhile, can detour to Naugatuck’s Railroad Museum of New England and take a ride powered by a vintage diesel locomotive.
The next day, the rail-and-sea adventures continue. Branford is the jumping-off point for the Sea Mist’s narrated tours of the fabled Thimble Islands. In Essex, look for the Essex Steam Train & Riverboat’s 2.5-hour trip through the Connecticut River Valley via steam locomotive and Mississippi-style riverboat. The Cross Sound Ferry in New London has specialty cruises encompassing historic forts, grand estates, and lighthouses. Sailing buffs will love the schooner Argia, which offers day sails and sunset cruises from Mystic—but save enough time onshore to visit Mystic Pizza, the birthplace of Julia Roberts’s film career.
DAYS 13 & 14: NEWPORT, RHODE ISLAND
Lodging ideas: Gardiner House (Newport), The Newport Harbor Hotel & Marina, Newport Harbor Island Resort
Newport is known as the sailing capital of the world, so learn the basics of this sport (or just enjoy the ride) with Newport Sailing School & Tours. Round out your knowledge with a stop at the Newport Sailing Museum & National Sailing Hall of Fame, newly opened in 2022.
For a bird’s-eye view of Narragansett Bay and the storied Newport Mansions, take to the skies with Newport Helicopter Tours and Charters. Or see the sights from the water when you book Rhode Island Bay Cruises’ 90-minute jaunt past 10 lighthouses, 10 islands, and many other points of interest.
End your trip on scenic Block Island, where beaches, hiking trails, lighthouses, and a charming downtown await. Reached from Newport or Narragansett via the Block Island Ferry, it’s ideal for a day trip or—for more time in this little slice of paradise—an overnight stay.
Itinerary created in partnership with Yankee Publishing. DATTCO Coach & Tour is Discover New England’s transportation partner.
