Proposal Paradise

Perfect settings for the big question

A Family Affair

Heron Yacht Charter
When it comes to the big moment, who better to celebrate with than family and friends? And where better than a luxury chartered yacht gliding through the bays from Sag Harbor to Montauk? Initially built for a family’s world travels, the two-masted, seafoam green catamaran Heron has abundant space both above and below decks, perfect for large gatherings. Treat your guests to a fabulous onboard meal or a day of spa treatments in Heron’s airy staterooms. There’s also plenty of opportunity for a private moment, with the yacht anchored off a secluded beach or at your waterfront restaurant of choice. Then rejoin the party onboard with Heron’s all-white decor providing an elegant backdrop for congratulatory photos. (631.875.3611)

Sunset Scene 

The Beacon
There’s nothing better than a delicious meal made magical by a gorgeous sunset. For those who want to mark their momentous occasion with great food and stunning views, The Beacon in Sag Harbor is a great choice. Situated above the Sag Harbor Cove Yacht Club, the summertime-only Beacon looks across Sag Harbor Bay to Shelter Island, offering al fresco diners a kaleidoscopic sky show as the sun sets. The upscale yet comfy restaurant has an adventurous menu inspired by American, Mediterranean and Asian cuisines. Try favorite dishes like Steamed Mussels “Beacon Style” or Halibut Baked in Parchment, accompanied by a bottle from the extensive wine list, a craft beer or custom cocktail. Then share a signature Beacon Ice Cream Sandwich and start planning your future together. (8 West Water St., 631-725-7088)

Rustic Romance 

Montauk Lighthouse
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If you want to make your move in a picturesque setting, surrounded by history and nature, look to Long Island’s easternmost spot and the charming Montauk Lighthouse. The oldest lighthouse in New York State, commissioned under President George Washington in 1792, this National Historic Landmark has been part of local history for more than 200 years and still does its job orienting sailors around the tip of the island. Take a tour of the keeper’s house-turned-museum, including a climb up the spiral staircase to the top of the tower, where you’ll be surrounded by breathtaking scenery and the best views in the area. (How’s that for an awesome spot to pose an important query?) Then grab a celebratory snack at the Lighthouse Grill and navigate the trails leading down to the beach for an intensely romantic vista of sun setting over surf. (2000 Montauk Hwy., 631.668.2544)

With a Toast 

Sparkling Pointe Vineyards & Winery
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If you want to add even more sparkle to your proposal than the one radiating from The Ring, consider Sparkling Pointe Vineyards and Winery, which produces wines exclusively in the traditional Méthode Champenoise. Located in Southold on the North Fork, Sparkling Pointe offers table service in its lovely Grand Tasting House and relaxing outdoor terrace, which overlooks 40 beautiful acres of vineyard. With its elegant chandeliers, natural light, and colorful Brazilian artwork, the Tasting House provides an effortlessly romantic setting. Make the most of your special day by taking a tour of the vineyard, crush pad, tank room and cellar, which ends with a full tasting of Sparkling Pointe’s award-winning wines; then make a toast to a bright future together. (39750 County Rd. 48, Southold; 631.765.0200)