Inspired by Livy Duncan’s latest collection
Windswept beaches, lobster rolls, sandy hair at dinner… Montauk has a way of making summer feel a little more carefree. Located at the very tip of Long Island, the coastal town is less polished than the rest of the Hamptons, and that’s exactly why people love it. It trades manicured hedges and country clubs for surf beaches, waterfront bars, and a laid-back energy that feels barefoot, social, and effortlessly cool.
That easy, sun-faded energy is exactly what inspired Livy Duncan’s latest collection—lightweight pieces, washed color, and silhouettes made for salt air and late dinners outside. Here’s our perfect itinerary for a weekend in Montauk.
Looking for the right hotel in Montauk? These are our go-to picks:
For something classic, book Marram. It’s quiet, design-forward, and directly on the beach.
If you want the full resort setup, Gurney's Montauk Resort & Seawater Spa has a private beach, oceanfront pool, and the famous seawater spa.
For something more low-key, Hero Beach Club is a relaxed, boutique spot a few blocks from the beach.
If you want more of a scene, stay at The Surf Lodge for its waterfront setting, built-in nightlife, and buzzy atmosphere.
Day 1: Beach afternoon & sunset drinks
Getting there: the drive from New York City runs about 2.5 to 3 hours. Leave early or late to avoid rush hour (we love a Thursday morning trip).
Arrive in Montauk and head straight to lunch at John’s Drive-In for lobster rolls and fries. It’s casual, old-school, and makes for a perfect weekend kickoff.
Afterward, spend the afternoon at Ditch Plains Beach, the classic Montauk surf beach just outside the main town area.
For sunset drinks, head to Crow’s Nest. The lawn overlooking the water is the whole point. Arrive early, order a spicy margarita, and plan to stay through golden hour.
For dinner, stay at Crow’s Nest or book Mavericks Montauk. It’s right on the water, with a great raw bar and signature cocktails.
Day 2: Shopping and a Night Out
Start the morning at Left Hand Coffee for iced coffee and breakfast sandwiches, then spend some time walking through town. Stop into Wyld Blue for home goods and beachy clothing, Blue & Cream for elevated basics and denim, and Earthtones for vintage-inspired jewelry and gifts.
For lunch, head to Duryea’s Montauk. It’s one of the most iconic spots in Montauk, known for its lobster Cobb salad and rosé-heavy lunches. Book ahead and request a table by the water.
Spend the afternoon at Montauk Point Lighthouse or back at the beach, depending on your mood.
For dinner and drinks, head to the ever-stylish Surf Lodge. Its waterfront deck, summer concert series, and celebrity crowd have made it one of the most coveted summertime spots not just in the Hamptons, but anywhere. The move is to book a table for dinner, then stay once the live music starts and the crowd spills onto the deck.
Day 3: On the water & spa afternoon
Start slow with breakfast at Joni’s. The smoothies and breakfast burritos are worth the wait.
Spend the day on the water. Charter a small boat, rent paddleboards, or head to Gin Beach, which sits on the bay side rather than the open ocean. The water is calmer, warmer, and better for swimming than the surf beaches, especially if you want a slower beach day.
If you’re in the mood for a fun lunch, head to Navy Beach. The outdoor tables sit right on the sand, and the menu hits all the sweet spots, from truffle mac and cheese to lobster sushi rolls.
Spend a few hours at Gurney's Montauk Resort. The seawater pool is the main draw—people come specifically for the floating, restorative feeling after a long beach day. Book in advance.
For dinner, head to La Fondita. It’s casual, unpretentious, and the fish tacos and margaritas are legendary.
If you want something quieter and a little more romantic, book Muse at the End instead. The seafood is excellent, and the sunset views are hard to beat.
