By Air or By Sea… The Best Spots to Check Off on Your Nautical Bar and Food Check List for Summer 2018!


Shelter Island and Greenport, NY are well known these days for not just their gorgeous sunsets and pristine beaches, but also for an increasingly growing list of can’t miss spots for the craft cocktail and foodie crowd.

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Photo Credit: Madison Fender Photography

PORT Waterfront Bar & Grill

PORT Waterfront Bar and Grill has once again taken their place among the notable Greenport waterfront in their iconic location next to the Shelter Island North Ferry for their second summer. With a new chef and updated menu and seating layout, PORT is sure to solidify their reputation as a staple of the hotter than hot Greenport restaurant scene.  Signature menu items like the JamesPORT mussels – featuring a local Lenz rosé broth, and a “Food Experts Only” section of the menu – featuring items such as the Crispy Whole Fish Taco, which is served bone-in and head on, sets this spot far apart from the other dockside eateries.

The brainchild of Shelter Island restaurateurs, Keith and Ali Bavaro, whose popular Shelter Island dockside eatery SALT is long-time favorite of Hamptons insiders and Shelter Island locals alike, PORT is a main attraction on the Greenport Waterfront, located adjacent to the numerous – and surprisingly inexpensive –boat slips at Mitchell Marina.  Show your dock receipt to your server and your first drink is on them!

PORT Waterfront Bar and Grill

104 Third Street, Greenport NY 11944

Ram’s Head Inn

Photo Credit: Madison Fender Photography

It’s hard not to feel like a Gatsby or Buchanan when strolling up the grounds to this Grand Dame of Shelter Island. Since 1929, the Ram’s Head Inn has been welcoming vacationers from around the world to this seaside retreat overlooking Coecles Harbor. The current owners, husband and wife James and Linda Eklund, have been at the helm since 1979, keeping this Shelter Island institution primed with craft cocktails, fine farm-table-dining, live music, and chic accommodations. With so many other local hotels and restaurants opening, closing, and changing hands quicker than you can say Labor Day Weekend, the long standing Ram’s Head Inn on Shelter Island has proven to be an exception to the rule and truly offers that authentic, old world East End experience that is coming harder and harder to come by.

The Ram’s Head offers guests 800 feet of private beach, and an expansive fleet of complimentary sailboats, paddle boards, and kayaks.   Stake out a chaise on the beach, relax in the Adirondack chairs on our Great Lawn, or enjoy a sunset cocktail in the beachside gazebo.  Sunday nights offer live Jazz in the lounge all summer long.

For dinner or hotel guests coming by sea, there are 8 complimentary moorings clearly marked “R.H.I.” and a convenient dock located on the causeway for easy access to the hotel and restaurant.  Feel free to land your seaplane on their private beach, just be sure to call ahead and give them fair warning!

Whether you are beaching, dining, or staying, The Ram’s Head Inn is the perfect spot to spend – or end – a summer day with family and friends.

Ram’s Head Inn

108 Ram Island Drive, Shelter Island Heights, NY 11965


Isola Bar & Restaurant

Isola courtesy photo

Located in the heart of Shelter Island Heights Historic District on Shelter Island, New York, Isola isembarking on their second season as Shelter Island’s popular Italian restaurant, lively wine and cocktail bar, and event venue.  Isola’s building as well as location in the historic ‘Heights’ have a storied history as a chic Victorian era summer escape, thriving into the 40’s as a vacation spot for the rich and famous, and finally as the bustling epicenter of the modern social scene on the island.   These days, live music and jazz is offered regularly in Isola’s busy lounge, and their front porch seating is prime location for people watching and cocktail sipping on summer nights.

Isola’s carefully curated menu offers the best of the East End, sourcing menu items from local farms and fisheries such as Shelter Island’s Sylvester Manor, Southold Fish Market, and North Fork Smoked Fish Company. Isola’s kitchen is led by seasoned Chef Seth Nathan, whose seasonally focused New Italian menu boasts fresh local produce, daily seafood specials, signature pasta dishes, and gourmet Neapolitan style brick oven pizza.   

Those coming by sea can dock at Piccozzi’s in Dering Harbor, or take the North Ferry from Greenport to Shelter Island and stroll up the hill to Isola – the perfect summer day excursion! 

Isola Bar & Restaurant

15 Grand Avenue, Shelter Island Heights, NY, 11965


Caci Shelter Island

Photo Credit: Brian Nordstrom

Marking the second location for Caci Restaurants (the first being Caci North Fork in Southold), Caci Shelter Island opened its doors in May 2018 in the popular Shelter Island House hotel. 

One of the first hotels on Shelter Island; the historic Shelter Island House is set on a quiet street just a block off the infamous Sunset Beach. All of the island’s sights, sounds, tastes, water activities, golf, tennis, night-life, restaurants, beaches and history — are all only a short stroll away.  Moor your boat, land your private plane, or charter BLADE to Peconic Bay, spend the day at Crescent beach, and stroll up the hill for lunch, dinner, or snacks and cocktails on their garden set bocce court.

Offering a seasonally inspired menu featuring authentic Northern and Central Italian specialties by Umbrian-born Executive Chef Marco Pellegrini, the cuisine at Caci is inventive and dedicated to all things house-made and authentic.  Seasonal menus feature locally sourced meats, fish, vegetables, which are simply prepared and elegantly served.  Pasta, bread and gelato are meticulously crafted in-house.  Caci Shelter Island will be offering Caci North Fork’s Wine Spectator’s Award of Excellence winning wine list featuring North Fork and Italian wines.   

Caci Shelter Island

11 Stearns Point Rd, Shelter Island Heights, NY 11965


Now get moving on those plans, the summer winds are rollin’ in!

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