Shelter Island Travel Guide
August 7, 2019
Shelter Island

The other weekend Matt, Logan and I headed out to Shelter Island for a little getaway. Matt and I visited Greenport about two years ago and took our bikes over on the ferry (about a 5 minute ride) to explore Shelter Island for a few hours and see what it was all about. It was after Labor Day and sadly a lot was already shut down, so we knew we wanted to come back one day and actually stay on the island and see what it was all about.

Shelter Island is a quaint and a pretty quiet place that the locals still say is somewhat of a secret. Nestled between the Hamptons and Greenport (the two access points to the ferry) it is the perfect escape from busy New York City.


We stayed at The Chequit, a boutique bed and breakfast with the most amazing decor (I fell in love with our room). They have a main inn and then a smaller house with rooms directly across the street (which is where we stayed). Our room was on the level of the porch, which was great because we could hang right outside and look into the window while Logan took a nap or was sleeping at night. Breakfast is included in your stay and is homemade (and AMAZING) each morning. It always includes some fresh baked pastries, an egg dish, and homemade granola. We also loved hanging out on the large patio with the twinkle lights and enjoying a glass of wine.

I have mentioned this before, but the bounce seat for Logan is such a life saver when traveling. It collapses flat, but we used it all over the hotel property for him to hang out in with us when our arms got tired (breakfast, on the patio, etc.).


Beach it! – Lots of beach time! The most convenient beach to where we were staying was Crescent Beach, also known as Sunset Beach. Our hotel had beach chairs and an umbrella available which was great since we don’t own them with living in the city. We also rented a paddle board right on the beach and Matt and I took turns going out. If you have kids, Shelter Island is ideal because its situation in the bay makes the water really calm, with virtually no waves.

Rent Bikes/Walk Around – If you don’t have a little one in tow (or they are old enough to sit in a bike seat or have their own bike), I would highly recommend biking around the island. We did this before and it was a lot of fun, but stuck to long walks this time around.

Happy Hour – Grab a drink + listen to live music at Shipwreck (part of SALT). Located right along the marina, you can either grab a drink (and can also order food) at the outdoor bar with live music, or dine on the water at the adjacent restaurant.


Pharmacy – Sounds crazy, but hear me out. This hidden gem is known to have the BEST breakfasts on the island so you better believe Matt and I tried it out! Right next to our hotel, there is a mini old-school diner nestled inside a pharmacy and they are pumping out the yummiest breakfast sandwiches and hash browns in town. No frills, just the real deal, but make sure you go before noon for the hash browns, they stop making them after then!

Pridwin – We came here directly from the beach one day (it is located right on Crescent beach) for a late lunch. We sat outside on their deck and overlooked the water. The food was amazing, honestly one of my favorite meals of the trip! Super fresh and homemade with a lot of TLC. We split the house smoked ricotta and I had the Cobb salad with grilled shrimp and Matt enjoyed a Ceasar salad with grilled shrimp.

Marie Effiel Market – We took a walk here one morning to grab iced coffees and a french pastry. We ate breakfast at our hotel, but heard this place is known for their avocado toasts! Honestly, everything looked so yummy here. It is a grab and go type of spot right on the water. A great pit stop before you head to the beach!

Sunset Beach – 100% come here for the atmosphere. Its definitely a scene, but fun people watching! Plus the decor is extremely well done and you cannot beat the location. The food was fine — but nothing special. Matt and I ordered a few raw bar apps and about 5 minutes after we got them our meals were ready. Nothing had much flavor and everything pretty overpriced for what it is. I would still 100% recommend coming here for a drink and to watch sunset and maybe just one appetizer. Awesome decor and overall vibe and really the only “hot spot” for nightlife on the island.

Isola – Right around the corner from The Chequit, this Italian spot was quite good. The waitstaff was so friendly and the food on the menu hit the spot!

Vine Street Cafe – We heard such great things about this spot so I would recommend giving it a try if you can! Matt attempted to make reservations before our trip, but had no luck. We also weren’t 100% sure how kid friendly it was.

(snapped in Greenport on our way back to the city)

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