With hundreds of miles of breathtaking beachfronts, charming New-England style villages, centuries-old historic sites including a fairytale castle where you can spend the night, Long Island is an ideal destination to celebrate love. Whether you're looking for an unrivalled setting to pop the question or a dreamy honeymoon escape, Long Island offers the perfect trip for every romantic occasion, in every season. Listed below are some of the region’s swoon-worthy accommodations and experiences, perfect for a romantic getaway, or the ultimate galentine’s day.

Feel Like Royalty with a Gilded Age Romance


Enjoy the beauty and serenity of Long Island’s Gold Coast region where New York’s elite built their mansions, castles, estates, and gardens high upon the North Shore bluffs during the 1920s “Gold Coast” era. Immortalized in F. Scott Fitzgerald’s “The Great Gatsby”, these former homes are known for their sophistication and opulence. Feel like royalty this Valentine’s Day by perusing the great rooms that once played host to foreign diplomats, Hollywood royalty, and socialites. Stay overnight at the breathtakingly beautiful historic mansion Oheka Castle and find luxury at the Garden City Hotel.  

Walk the grounds and take a step back in time to a period of splendor with a mansion tour at Sands Point Preserve, the elegant estate at Old Westbury Gardens, or the historic estate of Coe Hall at Planting Fields.

Best Offers: Enjoy a romantic four course dinner at The Mansion at Glen Cove, spend Valentine’s evening in the romance of Oheka Castle, romance your valentine at the Fox Hollow Inn, or dine at the Red Salt Room at the Garden City Hotel.

Wine and Dine on the East End

Jedediah hawkins

Experience a picturesque winter weekend getaway with the girls for a sip and stay galentine’s day when you visit Long Island’s award-winning wine region, the North Fork. Cozy up inside an elaborate winter igloo and enjoy bungalow-style dining with a view at vineyards like RGNY in Riverhead and Macari Vineyards in Mattituck.

Stay overnight at the nearby Jedediah Hawkins Inn in Riverhead or the Shoals in Southold

Best Offers: Sound View Month of Love: Whether it’s a weekend with your best gals and a few bottles of bubbly or a romantic escape with your partner, enjoy a discounted two-night stay at the Sound View and receive a bottle of prosecco and a special gift upon arrival. And don’t miss a special Valentine’s Day dinner at the on-site restaurant, the Halyard. Share a special weekend with the Menhaden Sipping on Love Package with Macari Vineyards where you can receive a handpicked bottle of wine and chocolate.

The Hampton Maid is reopening in February with a renovated dining room and their Valentine’s getaway package includes an option to take a chef-led cooking class along with accommodations and a three-course dinner at the onsite restaurant. Also, celebrate love at the Bridgehampton Inn with their romantic getaway for two package.

Romance on the Waterfront


As an island with hundreds of miles of coastline and dozens of restaurants and hotel-laden harborside villages, there is no shortage of incredible waterfront romance experiences across Long Island. Explore the endless options for beachfront B&Bs that offer unrivaled views like Danford’s in Port Jefferson that’s nestled right in the Long Island sound or Baron’s Cove in Sag Harbor.

Best Offers: The Allegria Hotel is right on Long Beach’s boardwalk with a Valentine’s Day package that includes champagne and chocolate covered strawberries. Love is in the air with the Aqua by American Beech romance package that can be added on to any overnight stay: the rosé package and the red package. For a luxurious overnight stay just a walk away from the water, the Bellport Inn has Winter Wonder specials and two packages to choose from during the month of February prepared by their private chef, Jen O’Gorman of Rogue Kitchen.

Relax and Rejuvenate at a Luxurious Spa

gurneys spa

Long Island’s diverse range of hotel spas across the region make for a great romantic getaway filled with massages, facials, bodywork treatments, manicures, pedicures, and more. Escape to a spa for a Valentine’s Day rejuvenating, bliss-inducing spa weekend where heated pools and massages are sure to provide the self-care you crave. Don’t miss Gurney’s Montauk Resort & Seawater Spa, home to North America’s only ocean-fed seawater pool and indulge at Baker House 1650 where their amenities like their dry sauna and soaking jacuzzi tub provide for a Hamptons oasis.

Best Offers: East Wind Long Island not only has a luxurious spa with a “Forever Yours Couples Getaway” but a Valentine’s Dinner Dance too! The “Be My Valentine Dinner Dance” is taking place in the Grand Ballroom at East Wind on February 18 and is the perfect way to celebrate Valentine’s Day with a loved one or friends. Gurney’s also has a month of love package this February that includes credit to visit the spa.

Classic Dinner and a Show


From cozy Long Island playhouses in quaint downtown villages to large performing arts centers, the Long Island theatre culture sets the stage for innovative new works and classic theater. What better way to celebrate Valentine’s Day than a classic date of a dinner and show combo. Northport Village is a quaint, thriving picture postcard, waterfront village, settled in the 1600’s – and another ideal setting for romance. Stop by for dinner at Arlo Kitchen and Bar in Northport, then catch a performance at the John W. Engeman Theater in the village.

Another lovely waterfront hamlet is Port Washington in Nassau County. A hidden gem that offers a ton of activities and great eats, you can grab some dinner at Waterzooi in Port Washington and then visit Landmark on Main Street for your evening entertainment before staying overnight at the Fathoms Hotel & Marina. Downtown Huntington is a charming town with something for everyone. Make a reservation at Besito and then stop by the Paramount for a show.  

Best Offers: One mile from Huntington Village and the Paramount in Huntington is the Harbor Rose Bed and Breakfast with rooms that have working fireplaces and a romantic beverage service complete with rose petals and beautiful handmade towel swans.

Chocolate and Unique Galentine’s Day Experiences

disset chocolate

There’s nothing better than the gift of chocolate for your significant other this Valentine’s Day. Order a handcrafted Valentine’s Day box from Disset Chocolate with a collection that offers a medley of delicious chocolates. For a gals night out, the Love Stinks, Let’s Drink Anti Valentines Pop Up is a unique cocktail experience with small tapas options and an interactive visit from naughty cupid (with photo opportunities!)

Best Offers: Get a taste of the ChocoVino event at the Long Island Aquarium in collaboration with Raphael Vineyards. And, take advantage of the Sweetheart Sleepover Package at the adjacent Hyatt Place Long Island/East End.

Swoonworthy Settings for Capturing Romantic Moments

montauk lighthouse

Long Island’s coastlines are a mosaic of beachfronts and historic waterfront villages that offer enough charm to be the set of a romantic comedy or Hallmark Christmas movie.  While Long Islanders may be biased towards their own Main Street scene, a hidden gem nestled on the North Shore worth exploring for date night is Sea Cliff. At only one square mile, Sea Cliff boasts its own beach and 16 neighborhood parks.  Sitting atop a 120-foot bluff, with meandering streets overlooking Hempstead Harbor and Long Island Sound, the waterfront community offers dramatic views of bobbing boats and traditional Victorian houses and antique shops, nestled throughout the cliffside.

On the other end of the Island, you’ll find the off-beat Hamptons Village of Sag Harbor. Originally a whaling port, this historic, Instagrammable downtown is filled with small restaurants, boutiques, and antique shops – many of which are located in restored whaling cottages from the 19th century, often adorned in dandling ivy and other greenery. Watch the rich and famous dock their yachts or grab a photo of the iconic Sag Harbor Cinema, built in 1890 to host vaudeville and burlesque shows.

Experience romance in the Hamptons this Valentine’s Day (minus the crowds!). Stroll the boutique-lined Main Streets of East Hampton or dine at chic restaurants that you’ll actually be able to get into. And for the perfect romantic setting to pop the question, look no further than the Montauk Lighthouse.

Best Offers: No charge for these outdoor locations!