By Kyle Fengler, co-owner of Loaves & Fishes:
When friends visit, I take them through Sag Harbor first. That's where my house is, and it's probably the most enjoyable town to just walk around. The village has kept its old soul with long-standing local businesses and a perfect mix of things to do. You're right there near the water where you can walk down to the pier, and it's the most accessible of all the Hamptons villages.
The dining here reflects the village's character.
Lulu Kitchen does an excellent job for both lunch and dinner, while Sen showcases what happens when you have talented owners who care - Jesse and his brother Tora are good friends I've known for a long time.
Even though I'm not much of a sweet tooth anymore and try to eat healthier, I'd still take any friend to Olaf's for ice cream. I won't have one myself, but watching someone enjoy it there is part of the Sag Harbor experience.
Leonard Frisbee is a great place to go shopping. They're near Sagtown Coffee and Matt who owns it is a good friend of mine. They've got both a boutique for men and for women - nice casual clothing with a focus on comfort. All very stylish, really great stuff.
There's always something happening if you know where to look. The area around the whaling museum and church regularly hosts jazz nights and community events.
For a more casual scene, Kidd Squid brewery offers trivia nights and live music - my house is maybe 30 seconds away, so I can walk over anytime. They're good friends and the kind of local business that makes this village special.
Don't miss the side streets that many visitors overlook. The Il Cappuccino area and Church neighborhood are wonderful, but it's easy to stop at the main drag and not explore further. Those little streets hold some of the village's best character.
Here's the reality: parking is challenging, especially between 9 AM and 4 PM when the village is busiest. Sag Harbor draws people who want to spend several hours walking around, which means spaces fill up fast. The municipal lots work when available, but when they're full, you might end up parking quite far away. I wish I had secret tips, but I can't create parking spaces where there aren't any.
Sag Harbor, NY 11963, USA
This card was written by Kyle Fengler. Kyle represents the new generation of his family's storied Hamptons culinary empire, which includes Loaves and Fishes Food Store, Loaves and Fishes Cookshop, and the Bridgehampton Inn & Restaurant.
A Hamptons native with a Parsons School of Design education, Kyle pivoted from graphic design to hospitality, bringing a designer's eye and mixologist's palate to the family businesses.
Photo by Barry Riela on Unsplash