There’s something to be said about strength in numbers — humans are meant to live in communities, after all. Yet, sometimes, you have to pour into No. 1 — yourself — so you can show up better for your people. For some, that may mean a Netflix-and-chill-alone kind of day (perhaps with a favorite, snuggly pet). But solo time doesn’t need to be spent in solitude. Around the Hamptons, there are restaurants, shops and activities that welcome a party of one with open arms.
Throughout the next few months, we’re sharing a dream itinerary for solo days around the South Fork. Next up: Southampton.
Southampton’s glistening Main Street and Jobs Lanes carry a Hallmark movie-meets-Laguna Beach vibe. It’s a classic upscale beach town, brimming with luxury shops and galleries galore. But there’s no shortage of mom-and-pops, giving it a small-town appeal. Come summer, the warm air and outdoor seating at cafes and restaurants are ripe for people-watching. It’s a glistening gem any time of the year, for shopping, foodie adventures and gazing out at waterside vistas for days (or hours).
Should you want to break free from hibernation or the heat — without losing the quietness of a cold or rainy day — it’s also possible to fly solo in Southampton. This me-day itinerary will help you reset, refill and recharge in Southampton.
Breakfast at Sip ‘n Soda
The sign says “homemade ice cream,” and you can certainly return for that later (your day, your way). But Sip ‘n Soda has an ample breakfast menu with all the comfort classics. The retro-fit luncheonette with a 1950s diner ambiance serves up short stacks and silver-dollar pancakes, eggs and omelets, cereal, bagels and more. It also has an old-fashioned soda fountain, but first thing in the morning, you may prefer your caffeine in the form of a cup of Joe (though we won’t judge you for ordering a chocolate milk).
40 Hampton Road, 631-283-9752
Choose your mid-morning adventure at Cooper’s Beach or Southampton
Depending on your mood and the weather, head to Cooper’s Beach or the Southampton Arts Center as your food digests. Cooper’s Beach — Dr. Beach’s pick for top beach in the U.S. in 2025 — is a white-sand, high-dune stretch with a hundred-plus-yard shoreline and a skyline of mansions. Southampton Arts Center is a community hub for fine and visual arts. You can book a dance class, peruse a gallery exhibition or enjoy local musical talents.
Cooper’s Beach: 268 Meadow Lane | Southampton Arts Center: 25 Jobs Lane, 631-283-0967
LUNCH | Lobster Roll
The slogan is “where summer begins,” but LUNCH’s Southampton outpost is open year-round, a departure from the iconic roadside institution in Amagansett that’s drawn the likes of the Clintons and Jerry Seinfeld through the years. Warm the soul with the creamiest clam chowder this side of the Parish Art Museum. Lobster specials include a classic roll and a hot “special” with hot claw chunks, meat and generously drizzled butter on a toasted bun.
32 Montauk Highway, 631-293-3460
Shop your heart at on Jobs Lane and/or Main Street
Retail therapy is easy in Southampton, where local shops and luxury retailers coexist. Discover treasures of the plant and gifty kind at Topiare. Find your new statement piece at Twin Hearts Vintage or an Italian Pucci prize at Coco Cabana. Browse Main Street mainstays like Therapy Life & Style, Tenet, Mint Clothing, historic Hildreths, and Alice + Olivia.
Grab dessert before dinner at Tate’s
We promise we won’t tell. Tate’s is a nationwide sensation — the thin, crispy, slightly buttery chocolate chip cookies are loved by people who’ve never set foot on our shores. But TATE’s began as a passion project of Kathleen King, who cut her teeth in baking at 11 and opened her first bakeshop, Kathleen’s Bake Shop, in 1980. She opened Tate’s in 2000, and, while she’s since sold, the quaint cottage still feels like walking into your home for an afterschool snack. But there’s more than chocolate chip cookies (not that there needs to be). Expect cookie pies, cookie ice cream sandwiches and vanilla buttercream pies. If you’re a rules-follower, you can find cappuccinos and other caffeinated beverages in lieu of a dessert food prior to dinner.
43 North Sea Road, 631-283-9830
Pull up a chair at 75 MAIN
For dinner, head back to Main Street to dine at one of Southampton’s most happening restaurants. 75 Main’s well-lit dining room, with light furnishings and plants, puts you in an island state of mind, no matter the temperature. Choose from bar seating or small tables perfect for one, with plenty of grub. The surf ‘n turf menu features apps like crispy buttermilk fried calamari and king crab rolls. Entrées include fresh Crescent Farms seared duck glazed in mango-honey and filet mignon with grilled asparagus.
75 Main Street, 631-283-7575
Catch a new (or vintage) flick at Southampton Playhouse
When the good folks at Southampton Playhouse brought back the much-missed movie theater here, they didn’t just open the doors and call it a day. With an IMAX screen and wonderfully curated selection of both new and classic films, plus a kick-ass café, there’s always something screening here, day and night, to check out.
43 Hill St., Southampton, 631-339-9069
