Start your first morning with a leisurely coffee and pastry at Bumble & Bee Bakery, then walk across to the shoreline for a peaceful stroll along Main Beach to stretch after travel and soak in the Atlantic light. Afterward, explore the charming village center-browse artisanal goods at Guild Hall's gift shop and pick up maps and recommendations from the friendly staff at East Hampton Village Visitor Center to plan the rest of your stay.
Head inland for a relaxed afternoon exploring the historic streets: browse contemporary exhibitions at Guild Hall Museum, then enjoy a light lunch and people-watching on the patio at The 1770 House. Afterward, take a scenic drive to the nearby wetlands for a short walk along the boardwalk at Mulford Farm, where farm buildings and coastal meadows introduce you to the East End's rural heritage before settling into your accommodations for the evening.
For a relaxed first-night dinner, stroll to One North Lunch for a seasonally focused seafood meal and inventive cocktails on their cozy terrace, then continue to The Stephen Talkhouse in nearby Amagansett for live music and a lively local scene. If you prefer something quieter, enjoy a nightcap and harbor views at The Maidstone Hotel Bar before returning to your accommodations to rest up for tomorrow's coastal drive toward Montauk.
Wake early for a quiet, restorative beach walk at Main Beach at Montauk, then grab a hearty seaside breakfast of lobster-rolls or eggs benedict at The Clam Bar at Napeague before hitting the road. Continue with a scenic coastal drive east along Montauk Highway, stopping to explore tide pools and dramatic bluffs at Camp Hero State Park for short hikes and sweeping ocean views en route to Montauk village.
After a morning at Camp Hero State Park, continue east with a relaxed lunch and waterfront views at Lunch of Love in Montauk, then wander the quirky shops and galleries along Montauk Village Main Street for local art and surf culture finds. In the late afternoon, take a short hike up to the bluffs at Montauk Point State Park to visit the dramatic shoreline and capture sunset-friendly light before checking into your Montauk lodgings.
Wind down your day with a cozy dinner at Harvest on Fort Pond, where waterfront tables and seasonal seafood dishes create a relaxed Montauk atmosphere. After dinner, wander the charming docks around Gosman's Dock for crisp sea air and sunset reflections, then finish with craft cocktails and live acoustic music at The Surf Lodge Bar to soak up the East End's evening vibes before returning to your lodging.
Begin with a sunrise stroll and birdwatching along the dunes at Shadmoor State Park, then warm up with coffee and a savory breakfast sandwich at Java Surf Cafe near the village. Afterward, head to Skippers Cove for a short guided kayak tour around the inlet-look for seals and marsh birds-and finish the morning with a visit to the charming Montauk Farmers Market (seasonal) to sample local cheeses, honey, and baked goods before lunch.
Enjoy a leisurely seafood-forward lunch at Gosman's Dock, then stroll the piers to watch local fishing boats unload and browse the art stalls and boutiques clustered nearby. In the afternoon, take a short drive to explore the historic buildings and tidal wetlands around Federation of Churches Marina, followed by a calm, interpretive walk on the trails at Shagwong Dunes Preserve to spot shorebirds and take in panoramic harbor views before heading toward the lighthouse for sunset preparations.
As daylight fades, enjoy a maritime dinner at The Dock House Restaurant, where waterfront seating and fresh-caught fish set a relaxed tone, then wander the nearby boardwalk to watch lights blink on across the harbor. After dinner, head to Montauk Brewing Company for a flight of local ales and live music (check the schedule), or take a quiet, starlit stroll to Hither Hills Overlook to listen to the surf and close the day with peaceful ocean views.
Set out after a relaxed East End breakfast for a coastal drive on Meadow Lane, pausing to wander the dunes and shoreline at Coopers Beach before turning inland toward the vineyards. Spend the rest of the morning with a tasting and vineyard walk at Wölffer Estate Vineyard, followed by a hands-on tour and artisanal cheese pairing at Channing Daughters Winery to learn about local varietals and terroir while enjoying panoramic vineyard views.
After a morning among the vines, take a leisurely drive down the Southampton coastline to explore the charming hamlet of Bridgehampton-stop for a late lunch of seasonal plates and local oysters at American Hotel's sunny veranda, then browse antiques and local art along Jobs Lane. In the late afternoon, visit Pindar Vineyards Tasting Room for a guided tasting of East End reds and rosés, followed by a short walk through the adjacent orchard paths to watch golden light fall over the fields before returning to your base.
As twilight settles, drive toward the waterfront village of North Sea for an easygoing dinner at The North Fork Table & Inn (satellite pop-up) or another seasonal bistro featuring local shellfish and crisp East End rosé; linger on their patio to watch the sky soften over the marsh. Afterward, stop for cocktails and a jazz set at Gurney's Montauk (lounge)-or a cozy hotel bar in Southampton-before a quiet moonlit walk along the harbor at Shinnecock Canal Park to close the day with gentle water views and the scent of salt air.
Begin with a slow, historic stroll through the maritime streets of Sag Harbor Whaling Museum, then warm up over a buttery croissant and coffee at Le Bilboquet while watching locals arrive for the day. Afterward, browse curated antiques and coastal decor along Main Street-don't miss the charming book selection at John Jermain Memorial Library and the galleries clustered near Washington Street for one-of-a-kind finds and illustrator prints.
After a morning of museums and Main Street browsing, wander the waterfront and hunt for unique finds at Bay Street Boutique, then pop into the charming artisanal shop Heart of Sag Harbor for locally made candles and ceramics. Continue with a late-afternoon visit to Town Dock Park for harbor views, followed by a tasting flight and small-plate pairing at the cozy Hurricane Coffee Roasters & Tasting Room to relax before your evening plans.
For a memorable evening, dine on elevated comfort food and locally sourced seafood at The American Hotel Restaurant where dimmed lanterns and a historic dining room set a warm tone, then stroll the waterfront to soak up harbor lights. After dinner, catch an intimate performance or film screening at Bay Street Theater, or enjoy inventive craft cocktails and a cozy fireside vibe at The Union Hall Bar to round out the night with laid-back East End charm.
Start your morning with a hearty seafood-forward brunch at Dock House Cafe in Sag Harbor, sampling local smoked fish and clam chowder before heading out. Afterward, pick up a guided charter from Sag Harbor Whale & Nature Tours for a late-morning bay cruise-keep an eye out for seals and osprey, learn about local maritime history from the captain, and enjoy fresh shellfish snacks served onboard as you cruise toward the open sound en route to the afternoon's Montauk activities.
After your bay cruise, drive east for an oyster-focused lunch at The Dock House Restaurant in Montauk, where shucked-to-order bivalves and lemony mignonette pair perfectly with chilled rosé; linger on their deck to watch working boats come and go. In the late afternoon, join a small-group charter from Native Son Charters for a scenic harbor cruise around Gardiners Bay-expect crisp sea air, narrated local history, and prime vantage points for a photo-friendly golden hour before your evening sunset sail.
After your golden-hour harbor cruise, savor a leisurely seafood supper at The Point Bar & Grill in Sag Harbor, where the raw bar and pan-seared scallops pair perfectly with waterfront views. Later, board an intimate sunset sail from Gardiner's Bay Charters for a twilight cruise past glinting buoys and quiet coves-bring a lightweight blanket, sip a local rosé available onboard, and listen for the captain's stories about lighthouse lore as stars begin to appear.
Begin the day with a tranquil birding and shoreline hike at Mashomack Preserve, following the Red and White trails to salt marsh overlooks where you can spot herons, egrets, and wintering waterfowl before the crowds arrive. After the loop, cycle or drive into Shelter Island Village for a cozy brunch at The Chequit's Garden Cafe (or a local diner alternative) and then rent a kayak from Shelter Island Kayak to paddle the calm coves of West Neck Bay, looking for seals and exploring hidden inlets along the way.
After a morning of paddling and trails, drive to the eastern side of the island for an easy afternoon exploring Sylvester Manor Educational Farm-join a guided garden tour to learn about heirloom crops and the farm's restoration projects, then sample seasonal produce at their farmstand. Continue with a gentle coastal walk along the bluffs at Buskie's Beach, watch for migrating waterfowl from the shoreline, and finish with a relaxed late-afternoon tea or light bites at Pridwin Hotel's veranda while the light softens over Gardiners Bay.
As dusk falls, enjoy a relaxed seafood-forward dinner at The Chequit's Red Barn Restaurant, where rustic maritime decor and locally sourced dishes set a cozy tone, then take an after-dinner stroll along the village waterfront to watch lights shimmer on Gardiners Bay. Afterwards, join a guided moonlit walk or night-vision wildlife program at Mashomack Preserve's visitor center (seasonal offerings) to listen for owls, spot nocturnal marsh life, and end the day with starry views over the salt marsh.
Begin your day with a restorative coffee and gallery-hopping session in Bridgehampton, starting at The Parrish Art Museum's Bridgehampton satellite to view contemporary Long Island works, then browse rotating exhibitions and artist talks at Guild Hall Annex for local emerging talent. Follow with a late-morning studio tour and ceramics demonstration at Mattituck Millworks Collective (check seasonal hours) and a leisurely brunch at The Baker & The Chef-a neighborhood cafe known for its artisanal pastries and conversations with local creatives.
Spend a creative afternoon exploring contemporary and folk art: start with a focused visit to The LongHouse Reserve to wander its sculpture gardens and seasonal installations, then head to Quogue Gallery for a rotating show of regional painters and photographers. Follow up with a hands-on printmaking workshop or artist talk at Southampton Artists' Cooperative, and finish with a late-afternoon cider and light bites at The Village Idiot while reflecting on the region's artistic influences.
As twilight falls, savor a seasonally driven dinner at The Living Room at The Plaza in Southampton (or a similarly intimate neighborhood bistro) where chef-led tasting menus highlight local seafood and farm produce, then wander to nearby galleries for late openings. After dinner, catch an evening program or artist talk at Southampton Arts Center (check event listings) and finish the night with cocktails and live piano at The Tamed Fox Tavern, soaking in local creative energy and conversation to round out a culturally rich day.
Ease into the day with a restorative morning at Gurney's Montauk (spa)-book a coastal-inspired massage and thermal suite time to melt away travel fatigue, then enjoy a light, healthful breakfast on their terrace with sea-salt air. Afterward, wander the fragrant gardens at Mulford Farm Lavender Walk (seasonal plantings and quiet benches) for a short, meditative stroll before returning to town for a leisurely herbal tea at The Maidstone Hotel Conservatory, setting a calm, pampered tone for the day's spa-focused rhythm.
After a morning of thermal suites and a lavender stroll, head to Topping Rose House Spa for a signature hydrating facial and a restorative salt-scrub treatment, then linger over a light farm-to-table lunch in their conservatory. In the late afternoon, take a gentle harbor-side walk to Hooked on the Harbor for fresh oyster tasting and chilled rosé, followed by a calming private yoga session at East End Yoga Collective to center body and mind before an easy evening.
As twilight settles, enjoy a leisurely dinner at Nick & Toni's, where rustic Mediterranean plates and candlelit tables create a warm, celebratory end to your spa day. After dinner, take a short stroll to East Hampton Point to watch the harbor lights from a bench, then finish with classic cocktails and a cozy fireside chat at Topping Rose House Bar, savoring the calm pace you've cultivated all day.
Before you check out, enjoy a relaxed final morning wandering the historic lanes with a light breakfast and espresso at Topping Rose House Café, then pick up specialty provisions-artisanal jams and local honey-at Beach & Barn Market for the trip home. Afterward, take a peaceful walk through the maritime gardens at Hook Windmill and snap last photos of the village green before a scenic drive past the dunes at Two Mile Hollow Beach en route to your departure.
Spend a relaxed final afternoon savoring local flavors with a leisurely lobster roll and iced tea at The Lobster Roll (Amagansett), then wander the nearby dunes and tide pools at Hither Hills State Park for fresh sea air and last-minute coastal photos. Before you head out, pop into East Hampton Antiques Center to pick up a memorable vintage find, then enjoy a scenic drive along Three Mile Harbor Road to soak in marsh views as you make your way toward departure.
For a relaxed final evening, dine on seasonal, locally sourced dishes at The 1770 House Dining Room, where the historic ambiance and lantern-lit patio make for a cozy farewell to the East End. After dinner, take a short post-meal stroll to Two Mile Hollow Beach Overlook to watch the last of the day's light fade over the dunes, then finish with classic cocktails and warm conversation at The Maidstone Hotel Bar before packing for your departure.