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Leah & Matthew

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Restaurants

We're so excited to share a few of our favorite places to eat around the island with you!

Stars Cafe

17 Grand Avenue, Shelter Island Heights, NY 11965

The best fast casual brunch spot on the island. They have everything from breakfast burritos, omelettes, pastries, to salads, as well as coffee & smoothies. Tons of GF options.

The Islander

63 North Ferry Road, Shelter Island, NY 11964

The Shelter Island diner. Great option for a casual brunch/lunch. Venmo/Cash only.

The Eccentric Bagel

25 West Neck Road, Shelter Island, NY 11964

Delicious bagels on the island. We usually go halves on a cream cheese nova bagel and a bacon egg and cheese. GF bagels available.

Marie Eiffel Market

184 North Ferry Road, Shelter Island, NY 11964

One of the best spots on the island for a casual breakfast or lunch with water views. We recommend the curry chicken salad or one of the hot homemade sandwiches.

Léon 1909

29 West Neck Road, Shelter Island Heights, NY 11965

Leah & Matt's favorite restaurant on the island for dinner. Everything is delicious, especially the burger! Note: If you go, dress in layers. They have a stone hearth oven inside the restaurant so it can get quite toasty depending on the night.

Vine Street Café

41 South Ferry Road, Shelter Island, NY 11964

One of our go-to's on the island for dinner. Highly recommend the tuna tacos!

Isola

15 Grand Avenue, Shelter Island Heights, NY 11965

Classic Italian on the Island.

SALT Waterfront Bar & Grill

63 Menantic Road, Shelter Island, NY 11964

One of our favorite spots to get seafood on the water. We recommend hanging out at their "Shipwreck Bar" after dinner for a cocktail & to hear live music.

The Ram's Head Inn

108 South Ram Island Drive, Shelter Island Heights, NY 11965

Very delicious upscale restaurant on the Island. We like the duck!

The Chequit

23 Grand Avenue, Shelter Island Heights, NY 11965

Bruce & Son

208 Main Street, Greenport, NY 11944

Our favorite brunch spot in Greenport.

Goldberg's Famous Bagels

131 3rd Street, Greenport, NY 11944

There is also a location in Sag Harbor

Crabby Jerry's

111 Main Street, Greenport, NY 11944

One of our favorite spots to jetski for lunch (you can also drive here). It has great waterfront views with even better fresh seafood!

Claudio's Tavern & Grill

111 Main Street, Greenport, NY 11944

Billys by the Bay

2530 Manhanset Avenue, Greenport, NY 11944

A causal restaurant with fresh seafood & live music. We love the food here. A must try is their crabby-mary cocktail!

The Halyard Restaurant

58775 County Road 48, Greenport, NY 11944

A waterfront restaurant on the Long Island Sound at the Sound View. The views alone are worth the drive there & the fresh oysters!

Kontokosta Winery

825 North Road, Greenport, NY 11944

1943 Pizza Bar

Main Street, Greenport, NY 11944

Sen

23 Main Street, Sag Harbor, NY 11963

The best sushi/ asian food.

For all the days along the way
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