Day Trips From Southampton, NY

Southampton, N.Y., located on Long Island’s picturesque East End, is known for its stunning beaches, rich history, and beautiful landscapes. While Southampton is a popular vacation destination, plenty of exciting day trip opportunities are nearby. Whether you prefer dining at one of Sag Harbor’s great lunch spots or walking the beach in Montauk, day trips within The Hamptons offer endless leisure opportunities.

Sag Harbor, just a short drive from Southampton, is a charming village known for its rich maritime history and stunning waterfront views. This historic village is home to cobblestone streets, beautiful architecture, and cultural landmarks like the Sag Harbor Whaling & Historical Museum. Visitors can wander through the town’s boutiques and enjoy fantastic food at local spots like The American Hotel, Barrell House, or Sag Harbor Bakery. It’s the perfect destination for those wanting to experience the quaint charm of an old whaling village.

Just a short drive from Southampton, Montauk is a must-visit for anyone exploring the East End of Long Island. Montauk is known for its rugged coastline, lighthouse, and scenic beaches, and it is perfect for those who want to enjoy the outdoors. Visitors can explore Montauk Point State Park, hike to the famous Montauk Point Lighthouse, or spend the day at one of its popular beaches. Montauk also offers charming seafood restaurants and boutique shops for those looking to unwind after a day of exploring.

Just a short drive from Southampton, East Hampton is iconic for its boutique shopping, art galleries, and brunch spots. You can spend the day browsing local stores or enjoying the views of the pristine beaches like Main Beach or beautiful historic sites such as the Old Hook Mill, one of the last remaining windmills in the area. For art lovers, the Guild Hall Museum is a must-see, offering exhibitions that highlight local artists and culture. East Hampton provides a perfect blend of relaxation and culture, making it one of the best day trips from Southampton.

Bridgehampton is an excellent day trip destination from Southampton for anyone interested in horseback riding and equestrian-themed activities. The area is renowned for its equestrian culture, with beautiful horse farms and riding trails that offer a unique way to explore the region. You can visit one of the nearby horse farms for a guided horseback ride through the scenic countryside, or if you prefer watching from the sidelines, enjoy the excitement of the Hamptons Classic, an annual equestrian event in Bridgehampton. Afterward, you can relax at a nearby café or explore the quaint shops in town to round out your visit.

For wine enthusiasts, the Hamptons Wine Trail is one of the most popular day trips from Southampton, NY. The region boasts numerous vineyards and wineries, where visitors can enjoy tastings of award-winning wines while taking in stunning vineyard views. From elegant wineries like Wolffer Estate Vineyard to the laid-back ambiance of Duck Walk Vineyards, there’s something for everyone. A tour along the wine trail offers delicious wines and a scenic journey through the heart of the Hamptons countryside.

Amagansett offers a more intimate, laid-back vibe compared to other Hamptons towns. The town has a small but vibrant downtown area with boutiques, cafes, and casual dining spots. Amagansett is home to some beautiful beaches, including Indian Wells Beach, perfect for swimming and relaxing. If you enjoy history, visit the Amagansett Life-Saving Station Museum to learn about the town's maritime past. The serene atmosphere and peaceful beaches make Amagansett one of the best day trips from Southampton.

The North Fork of Long Island, located just across the Peconic River from Southampton, is a serene and scenic destination for a day trip. Known for its rural charm, the North Fork is home to apple orchards, wineries, and picturesque small towns like Greenport. Visitors can stroll along Greenport's waterfront, dine at one of its many seafood restaurants, or take a ferry ride to Shelter Island. The area offers a quiet escape from the bustle of Southampton, providing a perfect blend of nature and culture.

For those who prefer to stay closer to home, exploring the South Fork’s local vineyards and farms offers a more relaxed day trip option. Stroll through the scenic landscapes and sample fresh, locally grown produce or artisan products. Southampton’s close-knit community is home to several farms that offer pick-your-own experiences, fresh vegetables, and homemade goods. For a day of relaxation and fresh air, visiting these local farms provides a taste of the region’s agricultural charm.

Water Mill offers some of the best farm-to-table dining in the Hamptons, with local restaurants serving dishes made from fresh ingredients grown nearby. The town also has several art galleries and historic landmarks to explore. A visit to the Water Mill Museum provides insight into the area's history, while the surrounding farms and gardens offer a serene setting for a relaxing day outdoors. Water Mill is perfect for those who prefer a quiet day surrounded by nature, with plenty of opportunities to take in the beauty of rural Hamptons life.

Just a short ferry ride from the North Fork or the South Fork, Shelter Island offers a peaceful, picturesque escape. The island features beautiful nature preserves, pristine beaches, and charming hamlets. For nature lovers, the Mashomack Preserve offers hiking trails through diverse habitats, while the island’s beaches are perfect for sunbathing or a relaxing swim. Shelter Island is an idyllic retreat for those seeking a tranquil day trip with plenty of outdoor activities and serene views.

Looking to find the perfect home near Southampton, NY, or any of these beautiful day trip destinations? Harald Grant specializes in helping clients discover properties that meet their needs, whether you’re looking for a vacation home or a full-time residence. Reach out to Harald Grant today and begin your journey toward finding your ideal real estate investment in the Southampton area.