Experience the Best Of Long Island’s Upscale Lifestyle

The eastern end of Long Island is known for mansions, luxury hotels, and exclusive restaurants. You can spend a weekend shopping at high-end boutiques and browsing antique shops. Here are a few more ways to experience the best of Long Island’s upscale lifestyle.

Horseback Riding Along Block Island Sound

Experienced equestrians and novice riders alike won’t want to miss a relaxing horseback ride along Long Island’s majestic white sand beaches. Saddle up at Deep Hollow Ranch in Montauk for your private guided trip and explore the Block Island Sound shoreline.

When you need to rest after your ride, you can check into a room at a luxury hotel or beachfront bungalow. Choose from upscale accommodations appointed with fine linens, heavenly beds, and personal service.

Chauffeured North Fork Wine Tour

Image via Flickr by Joel Shlabotnik

Long Island wineries create a variety of wines to satisfy sophisticated connoisseurs. Travel through Long Island Wine Country along the eastern end of the island to sample robust and fruity reds and dry or zesty whites. Sweet dessert wines and sparkling wines are ready for tasting too. With over 60 wineries open to visitors, you’re sure to find a vintage that suits your taste.

Winemakers showcase their innovative and sustainable methods while you enjoy the beautiful scenery during your winery tour. Pindar Vineyards and Kontokosta Winery are just two of the many places to enjoy a flight of local wine. Leave the car at your hotel and book a stretch limousine for your tour through the North Fork wine trail.

Private Yacht Charter on Long Island Sound

Breathe in the salty air along Long Island Sound. Why not rent a private yacht for the day or enjoy a full weekend on the water? Choose from vessels including classic schooners, sleek modern yachts, and powerboats, captained or bare-boat. Try Metro Yacht Charters of New York or Long Island Boat Rentals. Both companies offer departure points on Long Island, including Oyster Bay, Glen Cove, Port Washington, and Northport. Treat your family and guests to a luxury sunset cruise to Manhattan or Fire Island. Add extra glitz to your nautical tour with live music.

Romantic Dining in The Hamptons

Couples who want to reconnect can have an impromptu meal at one of the casual seafood shacks that dot the area. Two popular shacks to visit are Clam Bar and Lobster Roll in Amagansett. In the evening, savor a candlelit dinner with your sweetheart at a romantic Hamptons eatery.

Watch the sunset as you eat a delicious meal at Bay Kitchen Bar. Enjoy views of the Gardiners Bay marina while you enjoy fresh local seafood like striped bass and sea scallops. Try Pierre’s in Bridgehampton if you prefer Long Island duck a l’orange served alongside seafood favorites and organic free-range chicken.

When you’re ready to pamper yourself and your family, choose the southern end of New York on Long Island as your next vacation destination. Travel just outside New York City to explore the island’s breathtaking shorelines while you relax and enjoy the region’s exquisite food and wine.