Hampton Bays

Day Trips

Make the most of your day with our curated plans, packed with Hampton Bays's hidden gems and unique experiences!

day 1
Beach Yoga and Village Stroll
morning
:

Greet the day with a refreshing yoga session on the sandy shores of Hampton Bays, listening to the gentle lapping of waves. Practice sun salutations as the sky turns shades of pink and gold. Feel the warm sand under your feet as you find balance and breathe in the salty ocean air.

afternoon
:

Wander into the charming village of Hampton Bays, where boutique shops and local cafes line the quiet streets. Sample freshly baked pastries at a cozy bakery before browsing artisanal crafts. Engage with friendly locals and soak up the laid-back seaside vibe.

evening
:

Return to the beach for a leisurely stroll as the sun dips below the horizon. Watch crimson and lavender hues reflect on the water while you collect seashells along the shoreline. Cap off the night with a bonfire and s’mores under the star-filled sky.

day 2
Local Farmers Market Exploration
morning
:

Start your day at the seasonal Farmers Market in Hampton Bays, where stalls brim with fresh produce and homemade treats. Chat with growers about heirloom tomatoes and locally raised honey. Savor a warm cup of fair-trade coffee as you sample artisanal jams and breads.

afternoon
:

Join a hands-on cooking demo hosted by a local chef, learning to incorporate organic ingredients into your meals. Tour the behind-the-scenes of the market’s bustling kitchen and pick up secret tips for seasonal salads. Gather supplies for a picnic lunch in the nearby park.

evening
:

Pack a blanket and head to Shinnecock Bay for a sunset picnic with your market spoils. Sip on crisp rosé while watching sailboats drift into the marina. Let the gentle evening breeze carry the market aromas as day turns to dusk.

day 3
Sailing on Peconic Bay
morning
:

Climb aboard a classic sailboat at the Hampton Bays Marina and set sail across Peconic Bay. Feel the wind fill the sails as you learn basic navigation skills from an experienced captain. Enjoy the crisp morning air and the sound of water gently lapping against the hull.

afternoon
:

Relax on deck with a gourmet picnic prepared by a local caterer, featuring regional seafood delicacies and seasonal fruit. Drop anchor near a secluded sandbar for a refreshing swim in crystal-clear waters. Take turns steering the boat and snapping photos of the scenic shoreline.

evening
:

Watch the sun melt into the horizon while anchored in a quiet cove, its golden light dancing on the waves. Toast with a bottle of chilled champagne as seabirds call in the distance. Sail back to shore under a sky painted with deep oranges and purples.

day 4
Vineyard Hopping in the Hamptons
morning
:

Embark on a guided tour of the region’s premier vineyards, starting with organic estate growers. Learn about viniculture techniques as you stroll among lush grapevines in the dewy morning light. Sample a crisp Sauvignon Blanc while inhaling the aroma of sun-warmed grapes.

afternoon
:

Travel to a second estate for an exclusive barrel-room tasting, discovering the nuances of oak aging. Enjoy a chef-crafted lunch paired perfectly with local reds and rosés. Stroll through manicured gardens and chat with the winemaker about harvest traditions.

evening
:

Conclude the day at a hilltop vineyard with panoramic bay views, sipping a glass of signature Merlot as the sun sets. Capture stunning photographs of pastel skies over rolling vines. Toast among new friends around a communal fire pit, sharing tasting notes under starlight.

day 5
Wildlife Hike at Shinnecock Hills
morning
:

Set out early on a guided hike through the Shinnecock Hills Nature Preserve, where wildflowers dot rolling dunes. Listen for the calls of migratory birds as you traverse winding trails toward the bay. Spot deer grazing near freshwater marshes at sunrise.

afternoon
:

Break for a packed lunch on a scenic overlook, with panoramic views of the Atlantic and Long Island Sound. Practice nature journaling as local guides point out native flora and fauna. Cross a boardwalk over wetlands and peer through binoculars at osprey nests.

evening
:

Return to the trailhead just as dusk settles, bathing the landscape in a soft glow. Reflect on the day’s discoveries during a sunset meditation session in a secluded meadow. Head back to town for a hearty seafood chowder by a crackling fireplace.

day 6
Deep Sea Fishing Charter
morning
:

Board a luxury fishing charter before dawn and set off toward the open Atlantic. Feel the engine’s rumble and sea breeze as the sky lightens on the horizon. Learn casting techniques from seasoned anglers while waiting for the first bite.

afternoon
:

Reel in striped bass, bluefish, and fluke as your captain shares tips on local fishing hotspots. Enjoy a fresh catch ceviche demonstration on deck, sampling your own haul with tangy citrus and herbs. Swap fishing stories and laughter as the boat dances on gentle swells.

evening
:

Return to the harbor with your bounty and have it filleted for a take-home seafood feast. Dine at a waterfront restaurant, savoring grilled fish with seasonal sides. Toast to a successful day on the water as lanterns glow on the marina docks.

day 7
Southampton Art and Culture Tour
morning
:

Begin with a visit to a contemporary art gallery showcasing emerging Hamptons artists. Discuss avant-garde pieces with the curator over a cup of imported tea. Admire vibrant canvases that capture coastal light and modern design.

afternoon
:

Head to the Southampton Cultural Center for interactive workshops in pottery and watercolor. Create your own art inspired by the seaside landscape and get personalized feedback from local artists. Explore historical exhibits that trace the area’s rich artistic heritage.

evening
:

Attend an intimate recital at a historic chapel, where classical musicians perform under vaulted ceilings. Let the harmonies of string quartets and piano fill the candlelit space. Conclude the night with a glass of burgundy at a cozy nearby wine bar.

day 8
Quogue Wildlife Kayaking
morning
:

Launch a guided kayak tour through the serene marshes of Quogue Wildlife Refuge. Glide silently under mangrove canopies, watching great blue herons hunt for fish. Feel completely immersed in the coastal ecosystem as crabs scuttle along submerged logs.

afternoon
:

Paddle to a hidden lagoon for a picnic lunch on the shore, complete with fresh garden salads and chilled lemonade. Practice wildlife photography as you observe harbor seals basking on distant rocks. Learn about saltwater conservation efforts from your knowledgeable guide.

evening
:

Return at dusk for bioluminescence spotting in shallow creeks, paddles stirring sparkles in the water. Experience the magic of nighttime nature as fireflies dance overhead. Cap off the excursion with s’mores around a beachside fire pit.

day 9
Beach Horseback Riding
morning
:

Saddle up at a local equestrian ranch for a guided horseback ride along the ocean’s edge. Feel the rhythmic pounding of hooves on wet sand as the tide recedes. Enjoy panoramic views of the surf and dunes with each gallop.

afternoon
:

Disembark for a beachside brunch under a canopy tent, indulging in fresh pastries and fruit bowls. Learn basic grooming techniques and participate in a short riding clinic. Bond with the gentle horses while brushing their manes and feeding them carrots.

evening
:

Return to the stables for a sunset ride, silhouette horses framed by copper skies and foamy waves. Revel in the gentle sea breeze and tranquil beach atmosphere. End the day with live acoustic music at a nearby beachfront tavern.

day 10
Sunset Dinner Cruise
morning
:

Spend your morning at leisure exploring vintage shops and artisan markets in Hampton Bays Village. Discover handcrafted jewelry and seaside keepsakes while sipping iced tea. Chat with local vendors about their inspiration and techniques.

afternoon
:

Relax on a paddleboard rental near Washashore Creek, gliding through calm waters as egrets perch nearby. Stop for a casual lunch at a floating dock cafe, enjoying fish tacos and tropical smoothies. Watch kayakers and sailboats drift by in the warm sun.

evening
:

Embark on a luxurious sunset dinner cruise, where gourmet dishes are served with panoramic bay vistas. Toast with sparkling wine as the sun dips into the horizon, painting the sky in hues of amber and magenta. Dance to live jazz under the moonlit sky, bringing your immersive ten-day journey to a jubilant close.

Discover Hampton Bays

Read more in our Hampton Bays 2025 Travel Guide.

Hampton Bays Travel Guide