Sailor's Travels | Shelter Island


Last week, I was out on Shelter Island for a sailing training camp. It was a (short) two years since my last time out there... highlighting that all occasions have been for sailing purposes. As much as I wish to frequent the Hamptons getaway with the plan to eat and lay on a beach, there is still no complaints here. Since I was there for a little less than a week, we stayed at a open and bright AirBnB. The location was prime considering I was able to get my pre-Sailing run in along Crescent Beach around the sunrise. We were also next to Shelter Island House, which made the best dining option after a long day on the water (and the need to spend half the night stretching, followed by Law & Order). 

If I'm being 100% honest, Shelter Island isn't my favorite of the bunch. It becomes quite repetitive after more than a few days and is even more pricey than your standard Hamptons eateries. Though there are several cons, the pros are also pretty strong. The number one is 100% the nature and scenery of the island. One day during the training camp, we sailed around the island... (side note: don't think my legs have recovered yet)... in which, I was truly able to see how beautiful and essentially, untouched the island is still. The other HUGE pro is the coffee. If you don't follow me on Snapchat and see my never-ending caffeine intake nor have read my several coffee centered posts, you'd know that coffee plus me equals smiley face. With that, Stars Cafe's iced coffee is *no words* and is 100% one of the reasons I was able to survive 6 days of training. 

With the simple break down of the island, here are my recommendations on where to stay, to eat, and to wander/do.




Crescent Beach: the Hamptons hot spot home to Sunset Beach. #yachtsonyachtsonyachts 

Biking Around the Island: Since it is a small island, biking is 100% the easiest way to get from point A to point B. Either rent a bike or bring your own. The next step up? Vespa. 

Sailing: I hope this one is obvious. 



SALT Waterfront Bar & Grill: This is my all-time favorite restaurant on the island. Tucked away on the South End, their wide range menu is perfect for whatever your dining preferences are. I was partial to the coconut rice and veggie sushi. 

Shelter Island House: Considering it was next door to my homebase, their summer salad and delectable pasta made it in the weekly rounds. 

Marie Eiffel Market: I can't say enough good things about this market. Whilst the prices are on the steeper side, I personally think it is worth it. Either pick from the delicious array of freshly prepared foods (my personal go-to was the veggie burger and fries), or pick up something for the beach. 

Sunset Beach: For those who want to be seen on a Saturday night. 

Stars Cafe: Iced coffee heaven. I'm also fully convinced that the staff thinks I'm a hardcore caffeine addict. 



Sunset Beach Hotel: See above. (-: 

The Dreamcatcher: Here is the AirBNB, that I stayed at. I highly recommend it for anyone looking for a fair amount of space. The owners were lovely and did a beautiful job renovated the loft.