Shelter Island is about a 3 hour drive from New York City and makes for the perfect weekend getaway – the town is a charming throwback, and the island an absolute haven for sailors and people who enjoy being near or on the water. The town is very chill and there are plenty of activities to fill your day, including kayaking, biking, swimming, hiking, golf, tennis…and boating. Some of our favorite spots on the Island are below…enjoy!
Kelly + Kepina
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Chapter 1: Play. Rent a kayak from Jay at Shelter Island Kayak Tours and paddle around Coecles Harbor. 2 hours is probably enough time to take a spin around the harbor. Hike through the Mashomack Preserve, an absolute gem of a place owned by the Nature Conservatory that consists of over 2,000 acres of fields, marshes, wooded areas, and trails. Depending on the route you take, you could spend anywhere between 2-6 hours exploring this beautiful piece of property. Hit a few tennis balls at one of the public courts on the island, or take a lesson with Moussa at Shelter Island Tennis.
Chapter 2: Sleep. There are a handful of great hotels and B&Bs on the island. The Chequit was recently renovated, is right in town and also has a great restaurant (Red Maple). Shelter Island House and Seven on Shelter are also newly renovated in the last few years and great places for a stay. If you are looking for more of a scene and want to stay on the beach, book a room at Sunset Beach.
If you don’t mind something a little more rustic, the best view in town is Dering Harbor Inn (these are privately owned condos, so every unit is different – some are more updated than others). Another bonus at the Inn is the pool, tennis court, yoga and spin classes all on the property.
Chapter 3: Eat. Having coffee and croissants or breakfast sandwiches at Marie Eiffel is daily routine for us – grab a paper and sit on the back patio for a relaxing start to the day. Marie Eiffel is an upscale market and cafe so pick up meats, cheese, and other delicious food and drink on your way out to stock your kitchen. Stop by SALT for lunch and follow it up with drinks at the The Shipwreck (just a few steps away) for a fun afternoon (usually includes live music). For dinner, Vine Street Cafe is a must!