Think breezy linen, ocean views, and a glass of crisp Chardonnay in hand—but make it modern, chic, and anything but old-fashioned. The Coastal Grandmother aesthetic is all about effortless elegance and a love of life by the water, and these escapes deliver it in style.

We’ve curated eight dreamy destinations, from the serene luxury of The Reform Club in Amagansett, to the iconic charm of White Elephant on Nantucket, to the timeless sophistication of White Barn Inn & Spa in Kennebunkport. And because the setting is only half the story, we’ve styled a head-to-toe look for each stay—pieces that blend relaxed polish with a hint of seaside romance.

Whether it’s strolling a quaint harbor town, dining al fresco under twinkling lights, or curling up with a novel after a day by the shore, these outfits and destinations make every moment feel like a scene from your favorite Nancy Meyers film—modern, chic, and effortlessly coastal.