Facing the Atlantic on Long Island’s East End, the Hamptons blend Gilded Age history with sandy dunes and cedar-shingled villages. Southampton claims one of America’s most lauded strands, Coopers Beach, while working harbors and art-filled lanes stretch through Sag Harbor and East Hampton to Montauk’s bluffs and lighthouse. You’ll find windmills, whaling lore, Pollock’s paint-splattered studio, and vineyards tucked among farm fields.

Summer brings beach days and outdoor dining; spring and fall offer quieter roads, oyster season, and migrating birds; winter means cozy fireplaces and museum time between storm-watching walks. Expect seafood shacks and raw bars, wood-fired kitchens, and bakeries as beloved as the beaches. Driving is easiest; the Long Island Rail Road (LIRR) and Hampton Jitney/Jet also reach most village centers.

Fly into New York City (JFK/LGA) or Long Island MacArthur (ISP), then head east. For flights, compare fares on Trip.com and Kiwi.com. From JFK/LGA to Southampton is typically 2–3 hours by car outside rush hour (1–1.5 hours from ISP). LIRR from Manhattan’s Penn Station to Southampton takes about 2.5–3 hours (less on summer express trains).

Southampton

Founded in 1640, Southampton balances manicured hedgerows with dunes and a lively village core. Stroll past boutiques and galleries, then settle into beach rhythm—mornings on the sand, afternoons at museums or wineries, evenings over local fluke or Montauk scallops.

• Top sights: Coopers Beach, Parrish Art Museum (Water Mill), Shinnecock Bay overlooks, Southampton History Museum.
• Taste the region: 75 Main (people-watching and pasta), Sant Ambroeus (Milanese café classics), Tutto il Giorno (coastal Italian), Plaza Café (chef-driven seafood), Claude’s (breakfast done right).
• Nearby gems: Sag Harbor’s harborfront, Wölffer Estate Vineyard (Sagaponack), Channing Daughters Winery (Bridgehampton).
• Fun fact: Coopers Beach regularly ranks among America’s best for its wide, soft sand and view of historic shingled mansions.

Where to stay: Browse beach houses and village cottages on VRBO Southampton or compare inns and hotels on Hotels.com Southampton.

Getting there: From NYC, drive ~2.5 hours, LIRR ~2.5–3 hours, or Hampton Jitney/Jet bus ~2.5–3 hours depending on traffic. For flights into NYC or ISP, check Trip.com and Kiwi.com.

Montauk

At Long Island’s tip, Montauk is salt-sprayed and carefree—surfers at Ditch Plains, sunsets at The Montauket, stars over Camp Hero, and the historic Montauk Point Lighthouse standing watch since 1796. It’s a working-fishing-port-meets-weekend-escape with trails, coves, and convivial seafood spots.

• Top sights: Montauk Point Lighthouse and museum, Camp Hero State Park, Shadmoor State Park bluffs, Hither Hills dune trails.
• Eat & sip: Inlet Seafood (fishermen-owned, sunset views), Duryea’s Lobster Deck (seasonal lobster rolls), Harvest on Fort Pond (Italian-accented family-style), Scarpetta Beach at Gurney’s (shoreline dining), Montauk Brewing Company (tasting room).
• Vibe: By day, beaches and hikes; by night, seafood, bonfires, and music at places like The Surf Lodge (in season).

Where to stay: Find oceanfront condos and cottages on VRBO Montauk or compare hotels and resorts on Hotels.com Montauk.

Getting there: From Southampton, it’s ~32 miles/60–75 minutes by car along Montauk Highway. LIRR Southampton→Montauk is roughly 1–1.5 hours (check schedules). No flight needed between these towns.

Day 1 — Arrive, Settle Into Southampton

Afternoon: Land in NYC or ISP and drive (~2–3 hours from NYC; ~1 hour from ISP) or ride LIRR/Jitney to Southampton. Check in, then shake off the trip with a gentle walk down Job’s Lane and Main Street to window-shop galleries and boutiques.

Evening: Dinner at 75 Main (upbeat scene, rigatoni alla vodka and branzino) or Plaza Café (chef Doug Gulija’s seasonal seafood—try local fluke crudo and Montauk swordfish). Nightcap at Sant Ambroeus for a scoop of pistachio gelato or an espresso before turning in.

Day 2 — Coopers Beach, Parrish Art, Sag Harbor Bites

Morning: Coffee and a breakfast sandwich at Claude’s (Southampton Inn) or pastries at Sant Ambroeus. Head to Coopers Beach for a few hours of surf and soft, groomed sand; arrive early for easier parking (day fees apply) or go by bike.

Afternoon: Tour the Parrish Art Museum in Water Mill—its airy Herzog & de Meuron building houses artists of the East End and changing exhibitions. Late lunch in village: Sip ’n Soda (old-school counter burgers, milkshakes) or Tutto il Giorno (light, bright coastal Italian).

Evening: Drive 15 minutes to Sag Harbor for sunset on the marina boardwalk. Dinner at Lulu Kitchen & Bar (wood-fired octopus, flatbreads) or Le Bilboquet (lobster salad, steak au poivre). Dessert at Grindstone Coffee & Donuts (creative glazes, made fresh daily).

Day 3 — NYC Day Trip: Sky Deck + Harbor Views

Morning: Early Hampton Jitney/Jet or LIRR into Manhattan (about 2.5–3 hours; one-way typically $39–$50 by bus or ~$25–$35 by train). Head to Hudson Yards for a thrilling city intro with timed-entry tickets to:

NYC Edge Observation Deck at Hudson Yards Admission Ticket

Soar 1,100 feet up to the highest outdoor sky deck in the Western Hemisphere. Glass floors, angled walls, and full-throttle skyline views make this a photogenic, adrenaline-tinged start.

Afternoon: Quick Midtown lunch—think a classic New York slice, a deli sandwich, or tacos at a food hall—then head to the West Side piers for a fast-paced harbor circuit:

Starship Landmark 90 Minute Sightseeing Cruise

Glide past the Statue of Liberty, Ellis Island, and under the city’s storied bridges. Multiple departures let you keep the day relaxed.

Evening: Grab an early bite near Penn Station—ramen, a classic burger, or Mediterranean bowls—then catch your return bus/train to Southampton. Back at the hotel, unwind with a quiet stroll under the village elms.

Day 4 — Transfer to Montauk via Amagansett

Morning: Coffee at The Golden Pear Café, then check out and drive east to Montauk (about 60–75 minutes). Break in Amagansett for a late breakfast at Carissa’s (flaky kouign-amann, excellent sourdough) or a classic lobster roll at “Lunch” (The Lobster Roll; seasonal).

Afternoon: Stretch your legs at Hither Hills State Park—easy trails over dunes and scrub with ocean views. If you prefer a loungey afternoon, snag a beach pass and post up by the surf.

Evening: Sample Montauk styles at Montauk Brewing Company’s tasting room, then dinner at Harvest on Fort Pond (family-style pasta, local fish, famous duck wings). Nightcap by the water at The Montauket for a sunset you’ll remember.

Day 5 — Lighthouse Day: Shadmoor, Camp Hero, Montauk Point

Morning: Espresso and a breakfast burrito at Left Hand Coffee. Hit Ditch Plains Beach—watch surfers or book a lesson; food-truck snacks like Ditch Witch tacos keep energy up.

Afternoon: Hike Shadmoor’s bluff-top loop for sweeping Atlantic views, then continue to Camp Hero’s WWII-era bunkers and dramatic cliffs. Finish at Montauk Point Lighthouse for the museum and lookout (hours vary seasonally; typically open year-round with modified winter hours).

Evening: Dinner at Inlet Seafood (owned by six local fishermen; the sushi and day-boat specials are spot on). If you’ve got steam, stop by The Surf Lodge or Ruschmeyer’s (in season) for live music and a breezy patio scene.

Day 6 — On the Water: Paddle, Bay Lunch, Easy Ride

Morning: Stand-up paddle or kayak in the calmer waters of Fort Pond Bay or Lake Montauk; rentals and lessons are readily available in town. Alternatively, book a half-day fishing charter for fluke, bass, or blues—this is a working port for a reason.

Afternoon: Lunch at Duryea’s Lobster Deck (buttery lobster rolls, Greek salads, rosé; seasonal) or Navy Beach (feet-in-the-sand vibe; seasonal). Off-season, opt for cozy bowls of clam chowder and a wedge salad back in town.

Evening: Freshen up and head to Scarpetta Beach at Gurney’s for handmade pastas and crudo with the surf as your soundtrack. Wind down star-gazing on the beach or with a scoop at John’s Drive-In (house-made ice cream since the 1960s).

Day 7 — Slow Morning, Farm Stand Fare, Departure

Morning: Brunch at Anthony’s Pancake & Waffle House (old-school comfort) or a healthy spread at Joni’s. Swing by local farm stands on your way west—Round Swamp (Bridgehampton/East Hampton) or Milk Pail (Water Mill)—for pies, cider, and picnic provisions.

Afternoon: Aim for an afternoon flight from NYC or ISP. From Montauk, allow ~3 hours to JFK/LGA (more in peak summer). Search fares on Trip.com and Kiwi.com; if driving, pad the schedule for Hamptons traffic.

Practical Notes and Seasonal Tips

• Getting around: A car is most flexible. LIRR and local taxis/rideshares cover the main villages; bikes are great for short hops. Between Southampton and Montauk: ~60–75 minutes by car; LIRR ~1–1.5 hours.
• Parking & beach passes: Many beach lots require paid daily passes; arrive early or go car-free via bike/ride share.
• Reservations: Summer weekends book up—reserve restaurants and tastings (e.g., Wölffer Estate) in advance. Off-season hours can be limited; always check the day-of.
• Wineries & culture: Consider Wölffer Estate flights at sunset, Channing Daughters for experimental blends, LongHouse Reserve (sculpture garden; seasonal), and the Pollock-Krasner House (Apr–Oct; appointments off-season).

Where to search stays quickly, by base: VRBO Southampton | Hotels.com Southampton • VRBO Montauk | Hotels.com Montauk

From Southampton’s polished village greens to Montauk’s bluff walks and seafood sunsets, this Hamptons itinerary layers beach time, art and wine, and small-town strolls. The NYC day trip adds skyline thrills before you return to the sea breeze. Expect to leave with sand in your shoes and plans to come back for another season.