Romance Itinerary
ROMANCE: 14-Day Itinerary
From the rolling hills of western Connecticut to the rugged Maine coast, this trip is full of memorable experiences for couples to enjoy together: dining and nightlife, hiking and biking, and breathtaking views at every turn.
DAYS 1-3: CONNECTICUT
Learn more about visiting Connecticut
Lodging ideas: Graduate New Haven (New Haven), Harbor View Landing–“The Patriot” (Mystic), Litchfield Inn (Litchfield), Madison Beach Hotel (Madison), Mayflower Inn & Spa (Washington), Winvian Farm (Morris), Saybrook Point Inn–Lighthouse Suite (Old Saybrook)
The Litchfield Hills are filled with trails for casual and seasoned hikers alike. Grab coffee and a picnic lunch at The Smithy Market in Preston, then take a romantic walk at the White Memorial Conservation Center or head to Kent Falls State Park for a waterfall hike complete with a covered bridge.
Spend the afternoon on a tasting tour at the Litchfield Distillery, which distills its spirits from locally grown grains and fruit. If you prefer wine, Hopkins Vineyard pours award-winning vintages in a 19th-century barn overlooking Lake Waramaug. Buy a bottle (or two) to accompany your five-course dinner at the French eatery RSVP in West Cornwall.
Next, head to the coast for some seaside romance. Milford’s Silver Sands State Park offers a picturesque boardwalk stroll through a salt marsh and along the shore; you can also explore the 14-acre bird sanctuary on Charles Island. That night, catch a show at New Haven’s Shubert Theatre, which runs a popular Broadway Series. For dinner, Union League Café offers French-inspired ambience, or go casual with “New Haven–style” thin-crust pizza at Frank Pepe’s or Sally’s Apizza, both local landmarks.
Drive up I-95 to the coastal town of Mystic for prime shopping and people-watching. This is also the home of the nation’s largest maritime museum, Mystic Seaport Museum. A cozy dinner for two awaits at The Shipwright’s Daughter, along with superb craft cocktails and succulent oysters.
DAYS 4 & 5: NEWPORT, RHODE ISLAND
Learn more about visiting Rhode Island
Lodging ideas: The Chanler at Cliff Walk, Gardiner House, Hotel Viking
Begin with breakfast at Belle’s Café, a tucked-away local favorite, before heading to Gooseberry Beach, usually less crowded than the popular First and Second beaches. Later, soar above Newport and its yacht-filled harbor with Newport Helicopter Tours, which offers lighthouse, mansion, and other themed tours.
Newport’s dining scene is spectacular, with standouts including Giusto in town and Castle Hill along Ocean Drive. Take inspiration from top local chefs with a gourmet cooking class at Newport Cooks. Before departing Newport, be sure to visit Sachuest Point National Wildlife Refuge or the Norman Bird Sanctuary in nearby Middletown for a peaceful interlude.
DAYS 6 & 7: MARTHA’S VINEYARD, MASSACHUSETTS
Learn more about visiting Massachusetts
Lodging ideas: Nobnocket Boutique Inn, Harbor View Hotel
Even as this island eight miles off Cape Cod has become a favored celebrity haunt, its natural beauty endures. Experience it by kayak with Island Spirit, which offers tours from its Oak Bluffs headquarters.
In Edgartown, Morning Glory Farm draws on its 70 acres of non-GMO fruits and veggies to make to-go soups and sandwiches. Pull together a picnic (complete with fresh flowers) and venture to Aquinnah Headlands Preserve for views of Gay Head Lighthouse, multicolored clay cliffs, and unforgettable sunsets.
DAYS 8 & 9: PORTSMOUTH, NEW HAMPSHIRE
Learn more about visiting New Hampshire
Lodging ideas: Hilton Garden Inn Portsmouth, Hotel Thaxter (Portsmouth), Wentworth by the Sea (New Castle)
Cruise beside the Atlantic on Route 1A, past the famous sands of Hampton Beach, on your way to the Seacoast’s northern tip. There you’ll find Portsmouth, a small city with outsize appeal, where you can browse destination shops like Sault and Macro Polo and visit one of New England’s best living history museums, Strawbery Banke. Pick up a bottle of wine at South Street & Vine for an evening sail on the Piscataqua River with the Gundalow Company; depending on the night, there may be musicians aboard or guest speakers discussing local history and ecology.
Back downtown, wander the gardens at Prescott Park, whose summer festival of performances, movies, and special events offers magical outdoor evenings (pay to reserve chairs or a blanket, or bring your own). For more nightlife, check out The Music Hall, a historic gem that welcomes music and comedy headliners, and the always-lively Jimmy’s Jazz & Blues Club.
DAYS 10 & 11: BURLINGTON & STOWE, VERMONT
Learn more about visiting Vermont
Lodging ideas: Blind Tiger (Burlington), Hotel Vermont (Burlington), Talta Lodge (Stowe), Topnotch Resort Stowe), Sterling Ridge Resort (Jeffersonville)
Get a feel for Burlington by renting bikes and exploring the waterfront via the Island Line Trail; along the way, look for the brand-new Moran FRAME, a power plant turned into a showstopping public park that’s ideal for a picnic lunch. Sailing fans can book a private cruise for two with Whistling Man Schooner Co., while creative couples might opt for a glass-blowing class at AO Glass. Just a half hour away are the idyllic Champlain Islands; soak up their scenery by bike or car, and follow a mini wine trail to the Ellison Estate, Snow Farm, and Isle La Motte vineyards for tastings.
That evening, grab a table at a James Beard Award–nominated restaurant such as Hen of the Wood (farm-to-fork) or Honey Road (Turkish small plates) before a show at Vermont Comedy Club or The Flynn.
On day two, discover cozy romance in the mountain town of Stowe. Ride a gondola to the top of Mount Mansfield, then indulge in a couples massage at the AAA Four Diamond Topnotch Resort. For more of the great outdoors, take a 4 Points Vermont mountain biking lesson or simply stretch your legs on the 5.3-mile Stowe Recreation Path—which happens to run past Stowe Cider, so stop in for a taste. End the day with an intimate, upscale dinner at Michael’s on the Hill or Edson Hill.
DAYS 12-14: MAINE COAST
Learn more about visiting Maine
Lodging ideas: AC Hotel Portland (Portland), Bluebird Ocean Point Inn (East Boothbay), Boothbay Harbor Inn (Boothbay Harbor), The Inn at Ocean’s Edge (Lincolnville), The Lincoln Hotel (Biddeford), White Barn Inn (Kennebunkport)
Begin in Boothbay, home of the Coastal Maine Botanical Gardens—New England’s largest—with over 300 acres of native plants. Feel the romance of the Age of Sail on a cruise with Boothbay Harbor Schooners before heading up the coast to Camden. There, you can hike or drive up Mount Battie for panoramic views of Penobscot Bay, then descend back to town for dinner at award-winning Asian eatery Long Grain.
In the morning, embark on a can’t-miss day trip to stunning Acadia National Park. Its Park Loop Road is one of Maine’s best scenic drives; stop along the way for a short, flat hike around Jordan Pond (refuel at nearby Jordan Pond House, famous for its popovers).
End your trip with a food-centric visit to Maine’s biggest city, Portland, where you can take a culinary walking tour of the historic Old Port with Maine Day Ventures, visit Allagash Brewery for a guided tasting, and embark on a wine-and-cheese sunset sail with Wine Wise. For dinner, nationally acclaimed restaurant Twelve specializes in hyperlocal prix fixe dinners and impeccable service.
Got time to spare? Head to Kennebunkport for a lunch of fried clams and ocean views at the Tides Beach Club or take a sunset walk at Ferry Beach State Park in nearby Saco.
Itinerary created in partnership with Yankee Publishing. DATTCO Coach & Tour is Discover New England’s transportation partner.
