9 A.M. Head east early to beat the traffic — and make Grindstone Coffee & Donuts (7 Main St.) your very first stop in Sag Harbor. Coffee and a donut are a fine way to start your day, but it’s the specialty coffee drinks (hi, honey lavender latte!) and bacon, egg and cheese on the same ultra buttery brioche dough used in the shop’s donuts that have us gladly waiting in line.
10 A.M. Although you’ll need to book it in advance, don’t skip out on scheduling a relaxing wellness experience — that’s what they call a massage or facial on the South Fork — at Onda Beauty (42 Main St.). The highly sought-after wellness studio uses trusted, eco-conscious beauty brands and products for a treatment that you can feel good about inside and out.
NOON Sushi in the park? Yes, please! Head to Sen Restaurant (23 Main St.), a Sag Harbor institution, for incredibly fresh Japanese food to go. Order the crunchy rice tuna and walk across the street for a leisurely picnic-style lunch in Marine Park, where you can watch the yachts come in and out of the harbor.
2 P.M. If we had to recommend one must-do thing for your day trip to Sag Harbor, it’s spending time walking and shopping the village. The downtown is jam-packed with shops, boutiques and galleries. Some of our very favorites include Satori (93 Main St.), a perfectly curated women’s clothing boutique; Sylvester & Co. (103 Main St.), a modern general store plus coffee bar (don’t sleep on their cookies and peanut butter cups); Flashbacks (69 Main St.), part clothing store, part fun vintage candy and knickknacks; Stella and Ruby (144 Main St.), a gorgeous children’s boutique; and Kites of the Harbor (74 Main St.), which stocks beautiful kites and toys.
5 P.M. This hour of the day can mean only one thing: pre-dinner drinks on the famed front porch of The American Hotel (45 Main St.). If you can’t snag a seat there, head inside to the bar to imbibe in old-world style.
6:30 P.M. Although your dinner destination is just a short stroll away, you’ll truly feel transported at French restaurant Le Bilboquet (1 Long Wharf). Reservations are taken for indoor seating only, but the wait to sit dockside is well worth it. You’ll thank us once you watch that sunset from your table. As for the menu, don’t even think about leaving this restaurant without ordering the Le Poulet Cajun. This signature dish is divine.
Looking to stay the night? Baron’s Cove (31 W. Water St.) is a full resort hotel with nautical Hamptons vibes. The harbor-facing hotel is also perfectly situated within walking distance to the village. Win-win.