Ease into your Hamptons escape with a late-morning stroll and brunch: head to Topping Rose House in Bridgehampton for farm-forward dishes and seasonal cocktails, followed by a leisurely walk through the nearby Bridgehampton Main Street shops and galleries. After brunch, drive out to Sagaponack Beach for blustery winter coastline views and a brisk walk along the dunes, then warm up with a hot chocolate or espresso at Le Bilboquet back in town before checking into your accommodation.
As the afternoon unfolds, head to Guild Hall in East Hampton for its rotating art exhibitions and occasional artist talks, then wander the adjacent Main Street boutiques and antique shops for unique finds. Follow with a cozy late-afternoon visit to The Stephen Talkhouse in Amagansett for a pre-dinner drink and live music (check the schedule), or if you prefer something quieter, enjoy a warming clam chowder and waterfront view at The Lobster Roll before returning to your hotel to freshen up for evening plans.
As twilight settles, dine by candlelight at Nick & Toni's in East Hampton for its rustic Mediterranean menu and lively local vibe, then take a short drive to Main Beach Park for a moonlit shoreline walk to soak in the crisp winter air. Finish the night with crafted cocktails and cozy seating at The American Hotel bar in Sag Harbor, where you can linger over dessert and plan tomorrow's Montauk adventure.
Start your Montauk morning with a hearty breakfast at John's Pancake House before heading to the dramatic cliffs of Montauk Point State Park for rugged seaside hikes and the iconic Montauk Point Lighthouse vistas, where you can watch waves crash against the rocks. Afterward, warm up with a seafood-forward mid-morning bite and lobster roll at Clam & Chowder House near the harbor, then stroll the working docks to spot fishing boats and local charters preparing for the day.
After your cliffside morning, head into town for a relaxed seafood lunch at Duryea's Lobster Deck, then wander the galleries and surf shops along Montauk Highway to soak up local character. Spend a mellow afternoon exploring Camp Hero State Park's hidden bunkers and scenic trails, finishing with a warming cup of coffee and pastries at Love Lane Kitchen while watching surfers trickle back into the harbor as the light softens.
As the sun dips, settle in for a seafood-forward dinner at The Point Bistro, savoring fresh catch and local wines in a cozy harbor-side setting, then stroll the nearby Montauk Village lanes to pop into a few artisan shops and a gallery before they close. Cap the night with craft cocktails and live acoustic music at The Sloppy Tuna Bar & Grill or, for a quieter end, head to Gosman's Dock to watch the harbor lights shimmer and sip a nightcap while listening to the gentle lap of waves.
Begin with a cozy breakfast at The Golden Pear in East Hampton, savoring seasonal omelets and locally roasted coffee before wandering the charming lanes of Guild Hall's Saturday market for artisan goods and winter florals. Then take a brisk seaside stroll at Coopers Beach to admire the wide, windswept shoreline, followed by a warm-up and pastry tasting at Sweet Maresa where their house-made croissants pair perfectly with a latte.
Spend a leisurely afternoon wandering the charming lanes of Love Lane in Southampton, popping into independent boutiques and cozy bookshops before stopping for a late-lunch of seasonal small plates and oysters at Atlantic on the Lane. Afterward, head to Mashashimuet Park for a peaceful riverside stroll or, if you prefer art, visit the nearby Watermill Center for contemporary exhibitions and winter installations, finishing with a warm spiced cider at The Dock House as the light softens.
As dusk falls, savor a farm-to-table dinner at The Maidstone, where seasonal Long Island produce and a warm dining room set the tone for a cozy winter evening. After dinner, catch a low-key comedy or live music set at The Stephen Talkhouse (check the night's lineup) or drift over to The Parrish Art Museum for a Friday night gallery opening or evening program, then finish with a nightcap at The American Hotel bar to plan tomorrow's Sag Harbor vineyard visits.
Start the day with a historic stroll through Sag Harbor Whaling & Historical Museum, then wander the quaint streets to admire the 19th-century homes and pop into Custom House Maritime Museum for maritime artifacts and local lore. After a light mid-morning tasting, drive out to Wölffer Estate Vineyard for a guided cellar tour and seasonal wine tasting paired with local cheeses, followed by a warm coffee and pastry on their heated terrace to soak in vineyard views before lunch.
After your cellar tour, take a scenic drive to the nearby village of Shelter Island for a calming harbor-side lunch at The Chequit or seasonal small plates at Prisoner Wine Company's tasting room, then stroll the serene paths of Mashomack Preserve to spot wintering birds and salt marsh vistas. Late afternoon, return to the South Fork for a behind-the-scenes tour and barrel tasting at Channing Daughters Winery, followed by a cozy tasting of their eclectic blends paired with artisanal charcuterie as the light softens toward evening.
As evening falls, enjoy a relaxed seafood-forward meal at Lucharito's in Sag Harbor, where rustic plates and a lively bar create a convivial atmosphere perfect for sharing. After dinner, take a short drive to Pindar Vineyards' tasting room for a cozy evening tasting of reserve pours by the fireplace, then finish with a moonlit stroll along the historic wharf at Long Wharf Park to hear the harbor's evening hush and plan tomorrow's departures.
Linger over a slow breakfast at The Palm Inn with freshly baked pastries and locally roasted coffee, then take a gentle post-breakfast walk through the winter gardens at Quogue Wildlife Refuge to spot waterfowl and enjoy quiet salt-marsh views. Before you depart, stop by Hampton Coffee Company for single-origin beans to take home and pop into East End Home for one last browse of locally made goods and cozy textiles-perfect souvenirs to remember your winter escape.
Ease into the afternoon with a leisurely late lunch and waterfront view at The Dock House, savoring seasonal seafood and a warm bowl of chowder while watching the harbor activity. Afterward, take a serene post-lunch stroll through Shinnecock Hills Nature Preserve to admire winter grasses and tidal views, then stop by Lulu Cake Boutique for a take-home pastry and a final coffee before a relaxed drive back to pack and depart.
Wind down your Hamptons escape with an intimate dinner at The 1770 House in East Hampton, where seasonal New American dishes and a candlelit dining room offer a quietly elegant final meal. After dinner, stroll the lantern-lit lanes of Egypt Lane to savor the village ambiance, then toast the trip with a nightcap at Le Bilboquet's cozy bar before returning to pack and prepare for your departure the next morning.