Memorial Day Getaway: Discover the Best of East End Long Island

Explore Charming Towns, Stunning Beaches, and Renowned Wineries for an Unforgettable Holiday

Memorial Day weekend is the perfect opportunity to escape the hustle and bustle of daily life and enjoy a refreshing getaway. Long Island, with its charming towns, stunning beaches, and renowned wineries, offers the ideal destination for a memorable holiday. Here’s a curated itinerary for an unforgettable Memorial Day weekend on Long Island.

Friday: Wine-Filled Weekend in North Fork

Greenporter Hotel

Start your weekend with a leisurely drive to North Fork, where you’ll find the delightful Greenporter Hotel. This charming boutique hotel is perfect for a cozy stay, nestled in the heart of wine country. The Greenporter Hotel offers modern amenities, comfortable rooms, and a friendly atmosphere.

Explore North Fork Wineries

After settling in, begin your wine-filled weekend with a tour of North Fork’s renowned vineyards. Visit top wineries such as:

  • Sparkling Point:  Savor the Exclusivity of Sparkling Pointe Vineyard with an exclusive Greenporter’s Indulgent Tasting Experience
  • Bedell Cellars: Known for its stunning views and award-winning wines, Bedell Cellars offers a serene setting to sample some of the best wines in the region.
  • Kontokosta Winery: Enjoy a wine tasting with breathtaking views of the Long Island Sound at this picturesque, waterfront winery.

Finish your day with a sumptuous dinner at The Frisky Oyster, a local favorite offering delectable seafood and farm-to-table dishes, or the local favorite Claudio’s where you can savor fresh seafood and classic American cuisine in a historic waterfront setting.

Saturday: Fun in the Sun at Montauk

Sunset Montauk

On Saturday, head to Montauk for a day of fun in the sun. Book your stay at Sunset Montauk, where you can enjoy your own private beach. This charming spot offers stunning sunset views, making it the perfect place to relax and unwind.

Beach Activities and Sightseeing

Spend your day basking in the sun, swimming, and exploring the scenic beauty of Montauk. Don’t miss these local attractions:

  • Montauk Point Lighthouse: Visit New York’s oldest lighthouse and enjoy panoramic views of the Atlantic Ocean.
  • Gosman’s Dock: Stroll along the dock, browse quaint shops, and savor fresh seafood at one of the waterfront restaurants.

As the sun sets, return to Sunset Montauk and revel in the breathtaking views while sipping on a refreshing drink.

Sunday: Sun and Surf at Haven Montauk

Haven Montauk

Extend your stay in Montauk with a night at Haven Montauk. This laid-back hotel is perfect for those seeking sun, surf, and relaxation. Haven Montauk offers a vibrant atmosphere, a sparkling pool, and complimentary bikes for exploring the town.

Outdoor Adventures and Relaxation

Kickstart your Sunday with a bike ride around Montauk, discovering its charming streets and hidden gems. Afterward, head to the beach for some sun and surf, or retreat to the hotel’s pool for a relaxing afternoon.

For lunch, visit Joni’s Kitchen, a beloved local spot offering delicious, healthy fare. In the evening, take a stroll through Montauk’s town center, enjoying its unique shops and lively atmosphere.

Monday: Farewell Long Island

On Monday, before heading home, treat yourself to a hearty breakfast at The Montauket, known for its delicious food and stunning ocean views. Take one last walk on the beach, breathe in the salty air, and reflect on a weekend well spent.

Long Island offers a perfect blend of relaxation, adventure, and scenic beauty, making it an ideal Memorial Day getaway destination. From the wine-filled weekends in North Fork to the sun-soaked beaches of Montauk, this itinerary ensures a memorable and rejuvenating holiday.

Pack your bags, grab your sunglasses, and get ready to make the most of your Memorial Day weekend on Long Island!