Island romance need not always involve a tropical locale. The islands of the Northeast, reachable by ferry, car, plane or train, are rich in a passionate trifecta of natural splendor, charming history and the beauty of four seasons. And alluring hotels provide a unique sense of place and ideal starting point for exploration. While summer is prime time for these romantic hotels, don’t think of them as a summer fling — the love affair continues well into shoulder season.
Spring House Hotel – Block Island, Rhode Island
Since 1852, visitors to “the Block” have flocked to the Victorian-style hotel on a hill — you can’t miss its red mansard roof, expansive wraparound porch and sprawling lawn facing the Atlantic Ocean. Thirteen miles off the coast of Rhode Island, natural beauty and classic New England ambiance surround the relaxed island (accessible via ferry) where visitors leisurely bike and fish, but Spring House is the main attraction. Three on-property gardens mean heirloom tomatoes, eggplant and zucchini are likely to pop up on the menu. Simply put, if it’s romantic enough for a Kennedy wedding, it’s good enough for a romantic getaway.
The White Elephant – Nantucket, Massachusetts
Preppy, nautical, elegant — The White Elephant has been synonymous with this mellow Massachusetts island since the 1920s. With 66 rooms right in town on Nantucket Harbor, the grey shingled hotel keeps it quintessentially Nantucket with its mellow plaid furnishings and black and white sailing photos. Sip a Nantucket Mule (a cranberry vodka cocktail) and watch sailboats float by at the hotel’s Brant Point Grill, and book a detoxifying salt polish at the spa. Reserve the top three-bedroom suite for keys to the hotel’s BMW for the duration of your stay (that is, unless you prefer to travel by boat).
Baron's Cove – Sag Harbor, New York
While Hamptons real estate has made more than a few fall in lust, enduring love is found in its unassuming nooks — like the nautical village of Sag Harbor, a year-round enclave with a decidedly artsy vibe. On one of its prime corners opposite the water, the 67-room Baron’s Cove (once a destination for the likes of Jackson Pollock and John Steinbeck) gets flirty with nautical maps and anchor pillows in guest rooms, happy pineapple-print wallpaper in the handsome lounge and its own burgee flags. As for the sexiest spot, it’s a tie between the outdoor fireplace and a table on the deck of the upstairs restaurant.
Gurney's Newport Hotel & Spa – Newport, Rhode Island
Tip: If your summer travel is already booked solid, tony Newport is still a safe bet well after Labor Day — perhaps even lovelier once prime season crowds dissipate. Recently debuted on Goat Island, the 10-acre Newport outpost of Gurney’s is happening year-round. The 257-room resort has all the makings of an ideal waterfront retreat: views of both Narragansett Bay and Newport Harbor, marina, indoor and outdoor pools and four restaurants, plus walkability via a small bridge to downtown’s Thames Street and proximity for exploring the famed Gilded Age “cottages” of the founding families.
Ram's Head Inn – Shelter Island, New York
Birds chirping, wine glasses clinking and bay water gently lapping is what you’ll hear from a perch in a pair of Adirondack chairs on the sprawling lawn of this neatly tucked away, historic 17-room inn. Shelter Island, known as the “un-Hamptons,” sits quaint and quiet on Long Island’s east end (accessible only via ferry from Greenport or Sag Harbor). Ram’s Head’s private beach, tennis court and charming farm-to-table restaurant render leaving the property entirely optional, though you’ll want to explore the island’s 17 miles of shoreline, trails of Mashomack Preserve, antiques shops and gorgeous sunset over Crescent Beach.
The Great George – Prince Edward Island, Canada
On Canada’s East Coast island full of history, The Great George in the capital of Charlottetown encompasses 20 restored historic buildings — guests get a behind-the-scenes take during the hotel’s daily afternoon walking tour before breaking for local PEI brews. Built in 1846, the property has carefully transformed these local colonial landmarks into 54 suites with charming freestanding claw-foot tubs and antiques. Whiles beaches are a short drive, the nearby Charlottetown waterfront and boardwalk are instantly accessible.
The Winnetu Oceanside Resort – Martha's Vineyard, Massachusetts
It’s not just a beach, but the beach — with sunbathers, surfers, sandcastles and large dunes protecting this stretch of three-mile stretch of sand, The Winnetu sits on the Vineyard’s most coveted South Beach. Comprised of the Winnetu Hotel and surrounding Mattakesett Properties’ private home rentals, touches like lawn games, lemonade and s’mores tout the feel of a proper old-fashioned shore getaway, with the Atlantic as the background.
Gurney's Montauk – Montauk, New York
At the eastern tip of Long Island, Gurney’s Montauk is a local icon of the town that gets more popular with each passing Memorial Day. While a cooler-than-thou surfer scene pulses throughout Montauk, Gurney’s gets all the romance points—and it’s not just because of the epic 2,000-foot private beach and 146 rooms with ocean views. A yellow daybed and Gurney’s Punch at the Beach Club is the most coveted spot to watch the brave ones catch waves. Even if the weather doesn’t cooperate, dinner at Italian hotspot Scarpetta and a dip in the seawater indoor pool keep up the good vibes.
Chebeague Inn – Chebeague Island, Maine
A short ferry ride from Portland or Yarmouth, Chebeaugue’s eponymous hotel retains the away-from-it-all feeling of the small island in Casco Bay. Everything about it says Maine: The restored 1920s Greek Revival-style inn features artwork from local crafters and photographers, bikes to borrow to pedal across the three-mile island, and a top restaurant boasting freshly caught lobster. Here, visitors favor games and books over TVs (there are none in-room) and cool ocean breeze swaying through open windows over buttoned-up air conditioning.