What to Wear and Do in the Hamptons: A 2025 Montauk Summer Travel Guide

Montauk’s Calling. Are You Packed Yet?

There’s summer—and then there’s Montauk in the summer. Whether you’re planning a stylish weekend out East or spontaneous getaway, this one’s for you. From daytime padel matches and golden hour beach clubs to shopping hidden gems and devouring the freshest lobster rolls, this is your complete Hamptons travel and style guide.

Spoiler: we stayed at the effortlessly cool Montauk Beach House, and yes—outfit planning was part of the fun.

Getting to Montauk

Getting there is part of the adventure. Most visitors fly into JFK, LaGuardia (LGA), or Long Island MacArthur (ISP)and make their way out to Montauk by car or LIRR (Long Island Rail Road). If you’re already in the Hamptons, Montauk is the final stop—and worth every mile for a true coastal escape.

What to Wear in the Hamptons

1. Beach Club Looks That Turn Heads

Pack flowy linen sets, elevated swimwear, and a statement cover-up for Gurney’s, Montauk Yacht Club, or Surf Lodge. Think: Dissh, a DeMellier woven bag, and oversized sunglasses.

2. Lobster Roll Lunch Style

Go breezy and effortless for Lunch (yes, the iconic one from The Affair), Duryea’s, or Clam Bar. A crisp Polo Ralph Lauren sundress and leather sandals will never steer you wrong.

3. Padel Game Ready

Courtside chic is in. An earth-toned athleisure set, statement sunglasses, and a sporty bun complete the look. Bonus points for a visor or silk scarf.

4. Shopping + Strolling

A fitted bodysuit and wide-leg denim, or a two-piece set with low block heels, will take you from Amagansett boutiques to in-town pop-ups in style.

5. After-Dark Dancing

When the sun goes down, it’s time for something sleek. Think silky minis, metallic accents, or a bold linen two-piece paired with a structured clutch and a spritz of your go-to scent.

What to Do in Montauk (Beyond the Beach)

Sunsets & Views

Montauket – The ultimate golden hour drink spot with mudslides and an iconic view.
Crow’s Nest – Dinner and drinks with cozy coastal charm.
Montauk Point Lighthouse – For a scenic drive and seal sightings.

Beach & Bonfires

Marram – Ideal for a luxe beach day or evening bonfire.
Ditch Plains – Local-favorite surf spot with bluffs you can climb.
Montauk Beach House – Your home base with poolside lounging and beachy energy.

Food & Drinks

Bagatelle at Gosman’s Dock – High-energy dinner with waterfront vibes.
Mary Lou’s Montauk – Dinner that turns into dancing.
Bird on the Roof – A charming breakfast/brunch must.
Joni’s – Casual and healthy, perfect for a mid-day bite.
Hampton Coffee Co. – Easy grab-and-go caffeine fix.
Left Hand Coffee – Arguably the best cup in Montauk.

Nightlife & Dancing

Mary Lou’s – A full dinner-to-dance floor experience.
Gospel at Ruschmeyers – High-energy house music scene.
Surf Lodge – Iconic Montauk vibes, often with live music.
Montauk Yacht Club – DJs, dancing, and stylish crowds.
The Point – Local dive bar energy for a casual night out.

Shopping & Strolling

Amagansett boutiques
Local pop-ups in Montauk
Vintage finds and artisan jewelry all around town

Hidden Gems & Bonus Recs

East Lake Drive – Scenic coastal road with a sushi spot at the end.
Montauk Beach Club – Another great spot for daytime lounging or a drink.
Padel – Yes, it’s the sport of the summer. Reserve a court and bring your best game.

Dining & Reservations Guide

Here’s a quick reference list for spots worth booking in advance:

Bagatelle (Gosman’s Dock) – Dinner with a buzz
Mary Lou’s Montauk – Main room for group dining + dancing
Crow’s Nest – Sunset dinners
Surf Lodge / Gospel – Depending on the night’s energy
Bird on the Roof / Joni’s – Breakfast & brunch staples

Final Tips Before You Go

Pack a mini steamer, your favorite SPF, and a roomy weekender
Book reservations in advance, especially for dinner or beach clubs
Save time (and suitcase stress) by planning outfits by day/activity
Want help with packing? Check out our Travel Packing Service for curated looks that take you from sand to sprit

Montauk is more than just a beach town—it’s a vibe. Come with your best energy, a flexible plan, and outfits that make you feel like you. The rest will fall right into place.