7 Must-Do Activities on Your Hamptons Sailing Charter

A sailing charter Hamptons offers an unforgettable experience filled with scenic beauty, coastal charm, and exciting activities. Whether you're an adventure seeker or someone who enjoys a relaxing day on the water, there’s something for everyone. From exploring hidden coves to savoring fresh seafood, here are seven must-do activities to make the most of your sailing charter Hamptons.

1. Explore Shelter Island’s Hidden Coves

Shelter Island, nestled between the North and South Forks of Long Island, is a peaceful getaway that can only be fully appreciated from the water. When you sail around the island, you’ll discover quiet coves and inlets perfect for anchoring and swimming.

One of the highlights of your sailing charter Hamptons trip is Coecles Harbor, where you can drop anchor and explore the Mashomack Preserve. This natural sanctuary is home to diverse wildlife, including ospreys, deer, and foxes. Paddleboarding or kayaking along the calm waters here adds an extra layer of adventure to your trip. 

2. Swim and Snorkel in Peconic Bay

Peconic Bay, stretching between the North and South Forks, offers some of the clearest waters in the area. The bay’s calm conditions make it an ideal spot for swimming and snorkeling. Put on your gear and dive in to explore the underwater world filled with small fish and crabs. 

For an even better experience, sail towards Robins Island, a privately owned nature preserve. While you can't go ashore, anchoring nearby gives you access to pristine waters that are perfect for a refreshing swim.  

3. Visit Montauk’s Famous Lighthouse

A sailing charter Hamptons wouldn’t be complete without a stop at Montauk Point, home to the historic Montauk Lighthouse. Commissioned by George Washington in 1792, this lighthouse is the oldest in New York State and offers breathtaking views of the Atlantic Ocean.

Sail close to the shore for a unique view of the lighthouse from the water. If you have time, dock at Montauk Harbor and take a short trip to visit the lighthouse in person. The surrounding cliffs and beaches make for great photo opportunities. 

4. Enjoy a Sunset Dinner on Board

One of the best parts of a sailing charter Hamptons is the chance to dine with an incredible view. As the sun sets over the water, enjoy a meal on deck. Many charters offer catering services, or you can bring your selection of fresh seafood, cheese, and wine. 

For a special experience, pick up fresh lobster rolls from one of the local seafood shacks before you set sail. Pair them with crisp white wine or sparkling water, and enjoy the gentle ocean breeze as the sky turns shades of pink and orange. 

5. Go Wine Tasting at a Waterfront Vineyard

The Hamptons is known for its wineries, and some are easily accessible from the water. One of the best spots to visit during your sailing charter Hamptons trip is Wölffer Estate Vineyard in Sag Harbor. While you can’t sail directly to the vineyard, you can dock nearby and take a short ride to their tasting room. 

Here, you can sample locally produced rosé, chardonnay, and merlot while overlooking the rolling vineyards. If you prefer something closer to the shore, head to Corey Creek Tap Room, where you can enjoy a glass of wine in a relaxed, open-air setting. 

6. Try Paddleboarding or Jet Skiing

If you’re looking for a bit more action on your sailing charter Hamptons trip, bring along a paddleboard or rent a jet ski to explore the coastline. The calm waters around Sag Harbor and East Hampton provide the perfect conditions for paddleboarding. If you’re new to the sport, starting in a sheltered bay makes balancing easier. 

For more speed and excitement, jet skiing around Shinnecock Bay or Gardiners Bay is a great option. Many waterfront rental shops offer jet ski rentals, so you can pick one up and ride the waves while your sailboat remains anchored nearby. 

7. Watch for Dolphins and Seals

The waters around the Hamptons are home to a surprising amount of marine life. While sailing, keep an eye out for dolphins playing in the waves. These playful creatures often swim alongside boats, creating an unforgettable sight. 

During cooler months, you might also spot seals sunbathing on the rocks near Montauk. If you’re lucky, you might even see a whale in the distance, especially if you sail farther into the Atlantic. Bringing binoculars will help you spot these amazing animals from a distance.

Essential Tips to Prepare for Your Sailing Charter Trip

Before setting sail, a little preparation goes a long way in ensuring a smooth and enjoyable trip. Here are five short but essential tips to help you get ready for your sailing charter Hamptons trip:

·      Dress for the Weather: The weather on the water can be unpredictable, so wear light, breathable clothing and bring layers. A windbreaker or light sweater is a good idea, especially for evening sails when it gets cooler.

·      Pack Sun Protection: The sun reflects off the water, making sunburn a real risk. Bring sunglasses, a hat, reef-safe sunscreen, and a cover-up to stay protected throughout the day.

·      Choose the Right Footwear: Avoid wearing regular shoes or heels—opt for non-slip, soft-soled shoes or go barefoot on board to prevent slipping and protect the deck.

·      Bring Snacks and Drinks: Even if your sailing charter Hamptons includes food, having extra snacks and drinks ensures you stay hydrated and energized. Pack fresh fruit, nuts, and plenty of water.

·      Check the Itinerary and Weather: Confirm your charter schedule, route, and any planned stops ahead of time. Also, check the weather forecast to prepare for any changes in conditions.

By keeping these tips in mind, you'll be all set for a relaxing and memorable sailing experience in the Hamptons!

Summary

A sailing charter Hamptons is a perfect way to experience the region’s natural beauty, charming coastal towns, and exciting activities. Whether you’re swimming in Peconic Bay, enjoying a sunset dinner on deck, or spotting dolphins in the water, there’s no shortage of memorable moments.

No matter your interests, these seven activities will ensure that your time on the water is both exciting and relaxing. So grab your sailing gear, gather your friends or family, and set sail for an unforgettable Hamptons adventure!