Exploring Shelter Island, New York by Boat

Welcome to Shelter Island, a charming gem nestled between the North and South Forks of Long Island, New York. Boasting pristine waters and idyllic landscapes, Shelter Island is a haven for boating enthusiasts. If you're planning a trip, here's a curated list of must-visit destinations, including top-notch restaurants and hotels accessible by boat.

Shelter Island Areas & Activities 

Dering Harbor

Picturesque marina with docking facilities.

Shelter Island Yacht Club for socializing and events.

• North Ferry to North Fork - Greenport, Long Island

Coecles Harbor

Serene harbor surrounded by lush landscapes.

Opportunities for kayaking and paddleboarding.

Near Ram Island

Sunset Beach

• Beautiful sandy beach for a relaxing day.
• 
  Sunset views that live up to its name.
• 
  Restaurant  

Shelter Island Heights

Quaint village with Victorian architecture.

Boutiques and art galleries for shopping enthusiasts.

Cafes and restaurants 

Walking distance to North Ferry

Smith Cove

• South Ferry to South Fork - Sag Harbor, Long Island

Beaches

• Shell Beach - Secluded, No Lifeguard, Tranquil facing the South Fork and West Neck Harbor
  
  
• Crescent Beach - Lifeguards, Restrooms, Kayak Rentals facing the Peconic Bay

• Wades Beach - Lifeguards, Restrooms, facing Shelter Island Sound
  
  

Beachfront Dining

• Sunset Beach Restaurant - Offers a delightful dining experience with a beachfront setting. Not only is it a fantastic restaurant, but it also features a fabulous bar, a charming boutique, and a stunning hotel with breathtaking sunset views.
• The Pridwin Hotel & Restaurant -  Historic hotel with a waterfront restaurant serving fresh, local fare. The Pridwin has been an iconic presence since its establishment in 1927 offering a a perfect blend of leisure and sophistication, making it a sought-after destination for those seeking a serene escape on Shelter Island.
• SALT Waterfront Bar & Grill - Indoor-outdoor dining destination on the water with creative eats, cocktails & a kids' menu, sundecks & boat dock. SALT is a welcoming restaurant that prides itself on offering fresh and local cuisine for everyone to enjoy and relax.  

Coffee & Breakfast

• Eccentric Bagel - Experience delight at Eccentric Bagel, where artisan bagels are meticulously crafted from scratch, promising to tantalize your taste buds with delectable flavors and visual appeal.
  
• The Islander - Savor the delectable comfort food at a timeless, family-friendly restaurant. From breakfast to lunch, this restaurant serves its delectable fare every day of the week, all year round. 

• Stars Cafe - Stars Cafe is the ultimate destination on Shelter Island to satisfy your cravings for a cup of freshly-brewed organic coffee, delectable hot-out-of-the oven muffins, cookies, croissants, and other mouthwatering pastries. From warming soups in the winter to refreshing healthy smoothies and iced coffees in the summer, Stars Cafe has something for everyone. 

Dining

• Vine Street Café -  At Vine Street Café, they take pride in creating their dishes from scratch, using only the finest and freshest ingredients available. Their chef, cultivates a variety of herbs and heirloom vegetables that enhance the flavors and support sustainability.  We also collaborate with local farmers, fishermen, purveyors, and winemakers, who contribute their bountiful produce to inspire our seasonal menus.
• The Chequit Restaurant - The Chequit on Shelter Island boasts a variety of dining options to suit every taste. Indulge in elegant coastal cuisine with Asian favorites and Omakase in their upscale dining room, Weakfish. For a more intimate and lively setting, venture downstairs to their Tavern and Terrace, where you can enjoy outdoor dining with stunning harbor and sunset views. Join them for a cozy and vibrant experience in the Tavern, where you'll find a warm and inviting atmosphere.
• Leon 1909 - Léon, a charming dining destination, pays tribute to owner Valerie's paternal grandfather, a lover of romantic European adventures and coastal getaways. The restaurant's ambiance is infused with warm, natural elements and subtle nods to the rustic flavors of French and Italian countryside cuisine. Immerse yourself in the past as you indulge in Léon's Provençal-style menu, inspired by regional ingredients.
• Isola -Isola is a charming dining destination with indoor and outdoor seating, a traditional bar, and a wood-fired brick oven. Located in a beautiful historical building on Grand Avenue in Historic Shelter Island Heights, Isola is conveniently close to the Shelter Island North Ferry.
• Shelter Island Slice - Immerse yourself in the rich Long Island family history at Shelter Island Slice, the ultimate destination for a quick slice or an authentic Italian meal. Indulge in the mouthwatering slices that boast a perfect blend of a crispy crust and delectable toppings.

Hotels

If you are yearning to enjoy the breathtaking views of Shelter Island for more than just a day trip, we highly recommend you do! Take a look at some of these charming coastal accommodations. 

The Ram’s Head Inn 

Perched atop a hillside on an island within an island, The Rams Head Inn is a renowned waterfront destination that exudes elegance and historic charm. With its tranquil ambiance, comfortable country-style accommodations, exceptional dining options, and warm hospitality, every visit to this picturesque venue is truly unforgettable.

Spread across 4.5 acres of beautifully landscaped grounds, The Rams Head Inn offers a private beach with moorings, 17 thoughtfully designed rooms, a farm-to-table restaurant that highlights the best of the sea and land, a cozy bar, and stunning event spaces. This idyllic setting is perfect for any occasion, from dreamy weddings and rejuvenating wellness retreats to memorable family gatherings and blissful long weekends. No matter the time of year, The Rams Head Inn welcomes guests with open arms, providing a wide range of experiences that cater to every individual's preferences.

Chequit Inn

Located on the picturesque Shelter Island, NY, The Chequit presents an array of accommodations, ranging from inviting rooms to luxurious suites. Guests can enjoy dining options available, both indoors and outdoors, while enjoying the breathtaking views over Dering Harbor.

Sunset Beach Hotel

Situated on Shelter Island, Sunset Beach Hotel offers a laid-back retreat where guests can unwind by the water. The hotel blends in with the island's natural beauty, providing a comfortable and straightforward atmosphere. The rooms are designed for relaxation, offering views of the surrounding waters. With a private beachfront, guests can enjoy casual strolls along the sandy shores or partake in various water activities. The on-site restaurant serves up local-inspired dishes, creating a low-key dining experience against the backdrop of the island's sunset. Sunset Beach Hotel on Shelter Island is a simple and inviting getaway, inviting guests to enjoy the easygoing charm of coastal living.

Tips for Boaters:

Navigation:

• Utilize up-to-date navigation charts for safe boating.
• Be aware of local regulations and speed limits.

Docking:

• Check docking availability in advance, especially during peak seasons.
• Some restaurants offer transient slips for patrons.

Weather Awareness:

• Stay informed about weather conditions before setting sail.
• Be prepared for changes in weather, especially on the open water.