The perfect long weekend in Shelter Island
the non-fussy Hamptons
I (Madison) and my family (husband and 8 month old son) just spent a few days in Shelter Island, NY. It’s one of our favorite places to go and we usually find ourselves there every year. The Hamptons has gotten SO damn fussy and expensive, while Shelter Island isn’t cheap, it’s way less fussy than other parts of the Hamptons. Also, you can pass through Greenport on the North Fork to get there which was wonderful.
So let us walk you through how we’d spend a few days out there and what we did + a few additional recs.
Day 1: Drive to Greenport, NY on North Fork
Grab lunch Little Creek Oyster Farm and bop around the little town. Little Creek just moved into a larger space so they have a pretty extensive menu. You can get roasted oysters (pesto ones), curds (try the local tuna), and bao bun lobster rolls! It’s such a vibe.
Other Greenport recs:
Bruce & Sons: cutest cafe for breakfast or lunch
Claudio’s: This spot is a party but they have a little seafood shack and restaurant too
Lucharito’s: Simple Mexican spot
Crazy Beans: Cute diner
1943 Pizza Bar: You always need a pizza rec
Kontokosta Winery: Really nice North Fork Winery
IF YOU CAN stop at Briermere Farms on the way there or way back for their famous raspberry pie or any pie!
Hotel: The Pridwin Cottages (Shelter Island)
This hotel is wonderful! From the little cottages to the inn, it’s truly an oasis on Shelter Island. It feels almost like adult summer camp or even a perfect place for kids. There’s a pool, beach access, tennis courts, bikes and so much more. Plus they have a wonderful restaurant on the property that includes daily breakfast or you can join them for lunch and dinner.
Plus they have a wonderful restaurant on the property that includes daily breakfast or you can join them for lunch and dinner.
Alternatively! The Sunset Beach Hotel is iconic on Shelter Island and has hotel rooms. Their whole property feels like a little piece of the South of France in New York.
That night we had dinner at Leon 1906, they specialize in local ingredients + a massive open air wood-fired grill. You can sit and watch the chefs cook while enjoying Montauk red shrimp and scallops, grilled ribeye, and the best brioche of your life!
Day 2:
We spent most of our morning enjoying the benefits of the hotel like the breakfast, gym, and beach access. But we really wanted to try Maria’s Kitchen for breakfast burritos. This spot is no frills with a wonderful outdoor garden. Be sure to grab a fresh green juice too.
As mentioned, a ferry to Sag Harbor is 5-10 minutes and $25 round trip so we highly recommend heading into town for the day to bop around.
Here are some of our Sag Harbor recommendations:
Babes Diner: A newcomer this year, a small 8 seat counter with a diner-like menu for breakfast or lunch. Watch our review!
Sag Harbor Tavern: The iconic Red Hook Tavern Brooklyn burger, it’s fussy but the food is great
Doubles: Specializing in Caribbean roti and double but they make a wonderful BEC on a roti
Carissa’s Bakery: grab a matcha and lunch sandwiches so you can hit the beach - we love their chicken banh mi and roast beef
That night we headed back to Shelter Island to have dinner at Vine Street Cafe. This is one of our favorite places out east. It doesn’t feel as fussy as other parts in the Hamptons and the food is excellent.
What to order: calamari salad, tuna tacos, seafood spaghetti, steak and frites (with au poivre sauce)
Day 3: Shelter Island day
We like to start each morning with some version of a caffeinated beverage and Heights Cafe at the Chequit Hotel was our favorite. They are really building up this hotel and it looks very pretty.
Right down the street you have Stars Cafe or Marie Eiffel’s for breakfast. Marie Eiffel’s is more of a market meets restaurant using local produce while Stars is a bit more straightforward.
After that, we decided to hit the beach. While we could have sat at The Pridwin’s beach, just down the street is the iconic Sunset Beach (you can walk). They usually have a fun activation going on at the hotel since it’s very trendy. If you are beach people, rent some chairs or just go for lunch. The food is expensive but kind of tasty!
That night we had dinner at the Pridwin again because the menu is large and we also have an 8 month old so early bedtimes and dinners can be harder. I will say, there were a lot of kids here and their staff was very accommodating.
However, we needed a sweet treat and Tuck Shop ice cream is the main ice cream shop on the island. It’s not exceptional but it gets the job done.
Overall, this was a perfect 3 day getaway and we love Shelter Island. Let us know in the comments if we missed any must visit spots.
AND here are so me Hamptons recs for your ride home!
The Frisky Oyster and The Halyard are two of the best restaurants in town. Always busy, always packed. Fresh seafood. The Kontokosta Winery is a beautiful building high on the bluffs, but frankly their wines are terrible.