KATIE KENNEDY

Baron’s Cove and Sag Harbor
📍 Sag Harbor, NY

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There’s something undeniably charming about a quick afternoon escape to Sag Harbor. On our most recent visit to the Hamptons, we squeezed in brunch at Baron’s Cove, a stroll through downtown, and just enough time to peek into a few boutiques—each moment reminding me why I adore this corner of the East End. Everything about Sag Harbor feels timeless—from the boats bobbing in the marina to the antique signs that hang above shop doors. It’s a destination that doesn’t shout but gently charms, especially when you only have a few hours and still manage to soak up so much.

Brunch at Baron’s Cove

Baron’s Cove is a Sag Harbor institution—and for good reason. With roots tracing back to the 1950s, it’s played host to creative greats like Truman Capote and Jackson Pollock. Tucked just off the marina, the inn blends historic character with polished modern touches. The interiors are the very definition of quiet luxury: all crisp linens, nautical stripes, warm wood accents, and an inviting palette of soft blues and creams. The patio dining area of the restaurant offers a perfect vantage point to watch boats drift by as you sip your coffee (or in our case, a well-earned brunch cocktail). I ordered the avocado toast and couldn’t a Bellini to celebrate the weekend. The service was attentive but never rushed, creating an experience that encourages you to linger. And linger we did, soaking in the atmosphere and wishing we’d booked a room for the night.

Stroll Through Downtown

After brunch, we wandered into downtown Sag Harbor, one of my favorite stretches on the East End. There’s a kind of cinematic charm to the way the town is preserved—it feels less like a destination and more like stepping into a novel. We popped into a few boutiques, admired the window displays at Sylvester & Co. Modern General, and paused more than once to take in the quaint colonial houses lining the side streets. The details stand out here: American flags fluttering in the breeze, and sidewalks dappled with shade. Though our visit was brief, it left me itching to return—especially to visit the Sag Harbor Whaling & Historical Museum and dinner at the American Hotel. At the museum in particular, the building alone is stunning, and I have a feeling the exhibits inside would offer even deeper insight into this coastal town’s fascinating maritime past.

For a sunny afternoon like this, I leaned into the East Coast summer uniform: classic, breezy, and functional for a day with baby in tow. I wore a seersucker maxi dress from Tuckernuck that balanced comfort with effortless style. My look felt fresh and unfussy, which is exactly the vibe Sag Harbor inspires. Whether you’re heading out for brunch, popping into galleries, or just admiring historic homes, a simple yet thoughtful outfit always feels right at home here.

Love from the Hamptons,
Katie

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England.

Canoe Place Inn Brunch
📍 Hampton Bays, NY

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A summer visit to Hampton Bays wouldn’t be complete without a stop at the Canoe Place Inn. This historic property has been beautifully reimagined—equal parts timeless and coastal cool. Whether you’re staying overnight or just popping in for a meal, there’s a quiet luxury to the space that makes you want to slow down and savor the experience. Every detail from our brunch, down to the linen napkins and fresh flowers on each table, felt intentional without being fussy.

The outdoor patio itself strikes a perfect balance between laid-back and elevated, and the soft hum of conversation create a space that feels both relaxed and thoughtfully designed. There’s a coastal softness to the aesthetic, with neutral tones, natural textures, and just enough polish to remind you you’re somewhere special. The brunch menu leans into refined comfort food: think Brioche French Toast with fresh berries, warmly spiced Shakshuka, and a few rounds of Spicy Bloody Marys that hit just the right note. I ordered the Corn Flake Crusted Fried Chicken with a side of Succotash, which was crisp, flavorful, and generously portioned.

One of the highlights was how relaxed it all felt: no rush, no overdone decor, no trying-too-hard vibe. It was just good food in a beautiful setting, which is exactly what we look for when planning slow weekends out east. After brunch, wander through the hotel’s garden paths and take a peek at the library-style lounge and tucked-away bar areas. There’s a distinct sense of place here—modern but rooted in the inn’s long history—and it somehow manages to feel both new and nostalgic. I could see this being the perfect spot for a fall getaway, too. Cozy, candlelit dinners indoors as the weather shifts and the summer crowds start to thin.

If you’re planning a trip to the Hamptons and want something beyond the usual scene, Canoe Place Inn is absolutely worth a visit. Whether you’re just there for brunch, a long lunch, or checking in for a weekend retreat, it feels like a breath of fresh air—beautifully restored and thoughtfully run. And if you’re someone who appreciates the little things, you’ll feel right at home here. I would love to plot a return in the Fall. Maybe for dinner this time—or a slow Sunday morning with a good book and iced cappuccino.

Love from the Hamptons,
Katie

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England.