Tucked against the bay, Sag Harbor is the definition of small-town charm. The nautical village boasts a centuries-old main street filled with quirky boutiques, restaurants and galleries, and all manner of water sports fill the harbor. Here’s everything you need to do from morning till night.
How to Have the Best Day Ever in Sag Harbor
9 a.m.: Have Coffee in the Garden
Order yourself a latte from the coffee cart and enjoy Estia’s Little Kitchen’s backyard oasis while waiting for a table at the always-packed restaurant. The tiny spot dishes up some of the best breakfasts in the Hamptons. (Get the El Burro: avocado toast with tomato, grilled onion, melted Swiss and two poached eggs.)
10:30 a.m.: Lace Up Your Hiking Boots
After eating every last bite of breakfast, it’s time to get in touch with nature. Head to Long Pond Greenbelt Trail for a bit of quiet relaxation. This easy hike is just over three miles long, and within a few minutes you’ll be surrounded by woodland tranquility.
12 p.m.: Finally Learn to Sail (or Brush Up on Your Skills)
Make this the year you finally cross “learn to sail” off your Hamptons bucket list. Breakwater Yacht Club offers private and group lessons for adults.
2 p.m.: Save Room for Dessert
After a few hours in the sun, you’re bound to be ravenous. Between the salads (kale and wheat berry), burgers (including veggie and turkey options) and sides (like the smoked Gouda fries), LT Burger has something for everyone in your squad. Just remember to save room for one of the decadent milkshakes.
4 p.m.: Stroll and Shop
There’s plenty to browse around the hubs of Main and Division streets. Pop into the cozy Berry & Co.; you’ll find it hard to leave the well-stocked book and tea store without something new. Afterward, check out the other unique shops nearby: Wharf Shop, Sag Harbor Variety Store and Matta.
6 p.m.: Catch a Show
Grab tickets for the 299-seat Bay Street Theater. Depending on the day, choose from musicals, stand-up comedy acts and family-friendly performances. Or head to Pierson High School, where the Sag Harbor Cinema Arts Center plays movies on Sundays while working to rebuild the iconic one-screen cinema that was damaged in a fire in 2016.
8:30 p.m.: Make It a Pizza Night
We wouldn’t send you home hungry, would we? On Main Street, Sag Pizza sells Northern Italian–style pizza by the slice ($3.75 to $4.50). Snag a seat on the patio for a wood-fired pie (like one with shishitos, sausage, mushrooms and farm eggs). Follow up the pizza with a cone from Big Olaf before you hit the road.