Amagansett vs Montauk: Which Hamptons Town Is Right for Your Trip?

The East End of Long Island contains multitudes. Drive the same stretch of Route 27 and you’ll pass through towns that feel nothing like each other — some quiet and residential, some buzzy and young, some timeless and some trendy. Two of the most debated are Amagansett and Montauk: neighbors on the map, worlds apart in character.

If you’re trying to decide between the two for a Hamptons trip, here’s the honest breakdown.

The Short Answer

Choose Amagansett if you want a quiet, walkable village with excellent restaurants, boutique shopping, beautiful beaches, and a relaxed pace that works for families, couples, and anyone who wants to actually decompress.

Choose Montauk if you want dramatic ocean scenery, a livelier social scene, world-class surfing, and a more rugged, end-of-the-road energy that feels distinctly different from the rest of the Hamptons.

Both are excellent. They’re just for different kinds of trips.

Amagansett

Tucked between East Hampton and Montauk, Amagansett is the Hamptons village most people overlook — and that regulars never want to share. It has the refinement of East Hampton without the pretension, the beach access of Montauk without the crowds, and a Main Street small enough to know by heart within an hour of arriving.

The vibe: Relaxed, unpretentious, genuinely local. Summer brings weekenders but never overwhelms. September and October are magical — the village empties out, the light turns gold, and the restaurants are still fully open.

Best beaches: Indian Wells Beach is one of the best family beaches on the East End — calm water, soft sand, less crowded than the Montauk alternatives. Atlantic Avenue Beach is the other anchor, ideal for long walks in any season.

Food: Better than it has any right to be for a village this size. Il Buco al Mare brings the spirit of the downtown New York original to a beautifully minimalist setting. Carissa’s The Bakery is worth the trip on its own. Coche Comedor does excellent Mexican and mezcal cocktails. Meeting House is the go-to for a proper dinner. See our full Amagansett travel guide for the complete restaurant breakdown.

Shopping: Ulla Johnson, Love Adorned, Amber Waves Farm Store. Some of the best independent retail in the Hamptons, concentrated in a walkable stretch.

Best for: Families, couples, anyone who wants a proper East End experience without the scene.

Where to Stay in Amagansett

The Roundtree is the standout property in Amagansett and one of the most charming boutique hotels in the Hamptons. Set on two acres of historic farmland on Main Street — just a 10-minute walk or electric beach buggy ride from Atlantic Avenue Beach — the property is made up of a renovated 100-year-old barn, standalone cottages, and beautifully appointed rooms. It’s a member of Small Luxury Hotels of the World and participates in the World of Hyatt loyalty program. Rates include continental breakfast delivered to your room, afternoon tea, and evening s’mores by the firepit. Beach chairs, umbrellas, boogie boards, and parking permits for East Hampton beaches are all included. For families, the three-bedroom cottage is the pick — cathedral ceilings, an open floor plan, and room for up to six guests. For couples, the studio cottage with a gas fireplace and private garden is hard to beat.

Montauk

Montauk sits at the very tip of Long Island’s South Fork, where the land runs out and the Atlantic takes over. It’s the end of the road — literally — and that geography shapes everything about it. The landscape is more dramatic than the rest of the Hamptons: bluffs, crashing surf, a lighthouse that’s been standing since 1796. The vibe is correspondingly more rugged.

Montauk has changed significantly over the past decade. It used to be a scrappy surf town with modest motels and excellent fishing. It still has those things, but it now also has a hotel scene that can legitimately compete with anywhere in the Hamptons, a restaurant scene that’s arrived, and a summer social energy that draws a younger, more scene-oriented crowd than Amagansett or East Hampton.

The vibe: More energetic, more social, more outdoor-focused. Ditch Plains Beach brings surfers and a beach bar culture. The lighthouse and bluffs bring hikers. The nightlife is more active than anywhere else on the East End.

Best beaches: Ditch Plains is the surf beach — dramatic, beautiful, with food trucks and a consistent swell. For calmer water, Gin Beach on the bay side is the pick for families with young kids.

Food: The restaurant scene has grown up. Gosman’s Dock is the classic seafood institution on the harbor. The Surf Lodge has a great waterfront setting and live music. Montauk’s downtown stretch on Main Street has expanded with solid options across every price point.

Best for: Surfers, outdoor enthusiasts, couples who want a livelier scene, anyone who wants to feel like they’ve actually reached the end of something.

Where to Stay in Montauk

Gurney’s Montauk Resort & Seawater Spa is the benchmark luxury property in Montauk — 158 rooms on 2,000 feet of private beach on Old Montauk Highway, with the only seawater spa on the East End. It’s the most full-service resort in the area, operates year-round, and has the best oceanfront setting of any hotel in Montauk. The fire pits in winter are worth a trip on their own. It’s the right choice if you want a proper resort experience with everything handled.

Marram is the design-forward alternative — smaller, more intimate, and pitched at travelers who want barefoot luxury without the full resort footprint. Oceanfront, minimal, well-executed. The in-house café Mostrador Marram has one of the best pastry programs in the Hamptons. It’s walkable to downtown Montauk, which makes it the most flexible base in town. Best for couples.

Hero Beach Club is the value pick — across from Kirk Park Beach, with a wellness-forward programming approach (daily yoga, fitness classes), complimentary bikes, and a relaxed, social vibe. Not on the beach itself but close enough, and consistently one of the most reviewed hotels in Montauk for good reason.

Amagansett vs Montauk: Side by Side

Amagansett Montauk

**Vibe** |Quiet, village, walkable |Lively, rugged, end-of-road

**Best for** |Families, couples, foodies |Surfers, outdoor lovers, scene

**Beaches** |Indian Wells, Atlantic Ave |Ditch Plains, Gin Beach

**Nightlife** |Low-key |More active

**Top hotel** |The Roundtree |Gurney’s / Marram

**Off-season** |Excellent |Beautiful but quieter

**Drive from NYC**|~2.5 hours |~2.5–3 hours

Can You Do Both?

Yes — and it’s worth it. Amagansett and Montauk are only about 10 miles apart. A long weekend split between the two is entirely feasible: base yourself at The Roundtree in Amagansett for the village experience, and drive out to Montauk for a day at Ditch Plains and dinner on the water. Or reverse it — stay at Gurney’s and make the easy drive west for lunch at Il Buco al Mare and afternoon shopping in Amagansett.

FAQ

Is Amagansett in the Hamptons?

Yes. Amagansett is part of the Town of East Hampton, which encompasses the core Hamptons villages. It sits between East Hampton and Montauk on Route 27.

Is Montauk part of the Hamptons?

Technically yes — Montauk is part of the Town of East Hampton — though it has a distinct identity that sets it apart from the traditional Hamptons village experience.

Which is better for families, Amagansett or Montauk?

Amagansett edges it for families. Indian Wells Beach is calmer and less crowded than Montauk’s surf beaches, the village is completely walkable, and The Roundtree is one of the most family-accommodating boutique hotels on the East End.

Which is better for couples?

Both work well, but for different reasons. Amagansett at The Roundtree is quieter and more intimate. Montauk at Marram or Gurney’s has more energy and a stronger social scene. It depends on what kind of romantic getaway you’re after.

When is the best time to visit Amagansett or Montauk?

September is the best month on the East End — warm water, empty beaches, full restaurants, and a fraction of the summer crowds. Late May and early June are also excellent. July and August are peak season: beautiful but busy and expensive.

Also see:

Amagansett Travel Guide — restaurants, beaches, shopping, and how to spend a perfect weekend.