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Shelter Island Activities

Nestled in the heart of the Hamptons, Shelter Island is a beautiful gem. Whether you’re longing for an exciting adventure or a peaceful escape, this island has something for everyone. Sometimes all you need for relaxation is a breathtaking spot away from the stresses of everyday life.

Waterfront Living at the Rams Head Inn

At The Rams Head Inn, the essence of an island vacation lies in embracing nature. Picture it: Stepping onto our scenic property, taking in the snapshot-worthy waterfront views, and exploring the endless potential of our leisure activities.

To sweeten the pot, our waterfront activities are available at no additional charge. You can experience the most Shelter Island has to offer. We’ve curated a selection of experiences for you to make the most of your retreat. Whether you prefer soaking up some sun in the water or enjoying pastimes with our waterfront as your backdrop, we’ve got you covered.

Daily Waterfront Activities on Shelter Island

Think of our waterfront as your playground for beginners and experienced enthusiasts. Simply fill out a liability waiver. No bookings are necessary as we operate our activities on a first-come, first-served basis. With that, you’re ready to dive into aquatic fun.

Through our water-based activities, you can indulge in some exploration. This includes access to the island’s waterways, creeks, and inlets. So, why not grab a complimentary beach towel and make a splash?


Navigate the hidden coves of Shelter Island with one of our kayaks. You can paddle at your own pace for a relaxing time or a more intensive workout. Who knows? You might just stumble across some wondrous marine life while traversing the clear waters.


If you’d rather stay on your feet but still explore the waterways, hop aboard a standup paddleboard. Challenging yet rewarding, paddleboarding is a great way to connect with the natural beauty surrounding The Rams Head Inn.


For more sightseeing, different boating options are on offer. Cruise on a chartered yacht or lead your own exploration with a rented boat. Whichever you prefer, you can sail the sparkling waters of Gardiners Bay or Coecles Harbor. Feel the wind in your hair as you glide across the waters, letting your daily stresses wash away.


When the summer heat hits, there's no better way to cool off than by taking a dip in the refreshing waters of Rams Head Cove, right in front of the inn. Relax on the beach, wade in the shallows, or dive into the deeper sections. It’s up to you.


Our new docking facilities are designed to accommodate professional charter companies and private boaters alike. Here are the key features:

  • Draft and Mooring: The dock has a six-foot draft at dead low tide and offers nine sturdy moorings. Any boat that can navigate through the channel can be accommodated.
  • Docking Assistance: Captain Graham personally assists with launching and mooring for larger vessels. For help tying up, contact us via channel 77.
  • Mooring Fees: Boaters can choose from two mooring fee options: dine-in or overnight stays.

Playtime at the Shelter Island, NY Waterfront

While the water-based activities are undoubtedly a highlight, we also have a variety of land-based fun for the whole family to enjoy. From trivia nights with our other guests to picnic lunches, the options are bountiful.

Pickleball & More

If you’d rather stay on your feet but still explore the waterways, hop aboard a standup paddleboard. Challenging yet rewarding, paddleboarding is a great way to connect with the natural beauty surrounding The Rams Head Inn.

Board Games

When the weather isn't on your side, head indoors and enjoy hours of enjoyment in a classic board game. From bingo and mahjong to chess, we've got games to suit different ages and skill levels.

Hula Hoops

Unlock your inner child with hula hooping. You’ll be surprised at how much fun it can be for the whole family. Not to mention, hula hooping is an energizing way to get in a workout or share some laughs with your loved ones.

Hammocks & Beds

For those moments when you need to unwind, our hammocks and beach beds call to you. You can sink in, take a nap, or cuddle. Relaxation has never looked so tranquil than a laze on a hammock with a gentle breeze alongside 
the water.

Enjoying Year-Round Fun on the Water

Water sports are available from May through October, but the excitement at The Rams Head Inn has no end. Throughout the year, you’ll find many ways to immerse yourself in the coastal charm of Shelter Island.

Safety and Equipment

To ensure the fun never stops, we prioritize your safety. For all water-based experiences, we’ll provide life jackets. This way, you’ll be safe and secure as you explore.

Experience Coastal Charm at Rams Head

For those seeking action-packed adventure or those longing for a tranquil escape, The Rams Head Inn is the key. Relish the best of Shelter Island and make life-long memories with your friends and family. Waterfront activities and joyful pastimes are available to delight visitors of all ages.

Only a few hours and a ferry ride away from New York City, Shelter Island is the perfect scenic holiday spot. So, grab your swimsuit, lace up your sneakers, and get ready to make the most of this truly special island.

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