Looking for more golden-hour ocean views than celebrity sightings?
Montauk sits at the far eastern edge of Long Island and is often considered the most relaxed town in the Hamptons. Picture windswept beaches, classic seaside towns, and a slower rhythm that feels worlds away from Manhattan.
Our long weekend combined a relaxed three-day Hamptons itinerary with a stay at Hero Beach Club, a boutique property whose breezy, bohemian aesthetic feels inspired by the beach clubs of Tulum.
Arriving in the Hamptons
Although I’m technically from New York, my family lives much closer to Toronto than New York City. Growing up, trips to Lake Ontario and the Finger Lakes defined summer far more than the Hamptons.
This time, however, we decided to approach New York differently.
We flew into Rochester to visit family, then hopped down to NYC before driving east across Long Island toward Montauk.
And because the Hamptons seemed like the perfect setting for a little drama, we rented something memorable for the drive: an Aston Martin DB9.
Some road trips simply call for a convertible.
Where to Stay in Montauk: Hero Beach Club
Hero Beach Club — Hotel Snapshot
Location: Montauk, New York (Eastern Hamptons)
Style: Bohemian coastal boutique hotel
Rooms: 30 guest rooms and suites
Best For: Relaxed Hamptons beach stays and surf culture atmosphere
Standout Feature: Ocean access just steps from the property
Good to Know: Montauk is the most laid-back town in the Hamptons, about a 3-hour drive from NYC
For travelers looking for a more relaxed alternative to the classic Hamptons scene, Hero Beach Club in Montauk offers an easygoing coastal escape.
Driving along Montauk Highway, Hero Beach Club appears almost unexpectedly.
The property began life as a classic 1950s roadside motel called The Oceanside, recognizable for its low-slung roofline and oceanfront location just before entering the town of Montauk.
After a renovation in 2017, the motel reopened as Hero Beach Club, blending mid-century nostalgia with a breezy, modern beach aesthetic.
White-painted exteriors, slatted railings, and rattan swings outside each room give the property a playful coastal personality. The giant yellow smiley face painted on the building only reinforces the point: this place doesn’t take itself too seriously.
And that’s part of the charm.
The Atmosphere at Hero Beach Club
Hero Beach Club is built around a spacious central courtyard known as The Backyard.
Modern sculptures dot the lawn while lounge seating encourages guests to linger between beach walks and afternoon cocktails. The property hosts a rotating schedule of activities, from morning yoga to pottery workshops.
Evenings gather naturally around the outdoor fire pits, where guests toast s’mores and swap travel stories under the stars.
The pool area is equally inviting—white umbrellas, teak loungers, and low-key electronic music drifting through the air. It feels relaxed rather than scene-y, which suits Montauk perfectly.
The Beach Experience
Hero Beach Club sits just steps from the Atlantic.
Guests can borrow umbrellas, beanbag loungers, and beach chairs while the staff happily helps set up a comfortable spot along the sand. Montauk’s waves are also popular with surfers, and the hotel can arrange lessons or rentals for those hoping to try.
For me, the best moments were quieter ones—sitting with a book while the sound of the ocean rolled steadily in the background.
The Suites at Hero Beach Club
We stayed in one of the property’s four suites, located on the second floor with windows on two sides and partial ocean views.
The room embraces a rustic coastal aesthetic: honey-toned wood floors, handmade Balinese decor, and an oversized tiled shower that immediately becomes the focal point of the bathroom.
Like many boutique properties, the layout prioritizes style over traditional hotel functionality. If I were redesigning the suite, I might introduce a Murphy bed and seating area to create more of a living-room feel during the day.
That said, the overall atmosphere works beautifully as a relaxed Hamptons home base.
Early Mornings in Montauk
Montauk mornings have a quiet magic.
On our first sunrise, deer wandered along the dunes while rabbits darted through the grass behind the property. The ocean air still held the cool dampness of the fog that had rolled in overnight.
Even as someone who normally avoids early mornings, it was hard not to appreciate the scene.
A Relaxed 3-Day Hamptons Itinerary
While Hero Beach Club makes it tempting to stay put, the surrounding towns offer plenty to explore.
Here’s how we spent three easy days in the Hamptons.
Day 1: Arrival in Montauk
If you’re driving east from New York City, the journey itself becomes part of the experience.
A classic first stop is LUNCH Lobster Roll in Southampton, where the lobster roll lives up to the name.
From there it’s roughly forty minutes to Montauk. After checking into Hero Beach Club, take a short walk into town for dinner at Alimentari Beach, where Italian dishes pair beautifully with an Aperol Spritz or two.
Day 2: Bridgehampton and Sag Harbor in the Hamptons
Start the morning with coffee and a jelly croissant from Montauk Bake Shoppe, a local institution.
Bridgehampton is one of the most elegant towns in the Hamptons, known for its historic estates, boutique shopping, and refined dining. From Montauk, drive about 45 minutes west to Bridgehampton. Lunch at Topping Rose House, a historic mansion turned luxury hotel with a Jean-Georges restaurant.
Afterward, continue north to Sag Harbor. Sag Harbor has a slightly different character than the rest of the Hamptons, with a historic whaling village feel and a charming harborfront downtown.
Stop for a cocktail at Baron’s Cove, where literary regulars like John Steinbeck once gathered. The Jack Rose—Steinbeck’s favorite cocktail—remains a fitting choice.
Dinner back in Montauk at South Edison is highly recommended. Don’t skip the fried olives.
Day 3: Montauk Point Lighthouse
A visit to Montauk Point Lighthouse offers some of the most dramatic coastal views in the Hamptons.
Built in 1796 under the direction of George Washington, it remains the oldest lighthouse in New York State. Climbing the tower rewards visitors with sweeping views of the Atlantic where Long Island meets the open ocean.
Nearby, lunch at Duryea’s offers oysters, Greek melon salad, and sparkling views across Fort Pond Bay.
Sunset at The Crow’s Nest
For a memorable final evening, head to The Crow’s Nest, a Montauk institution known for its lively outdoor bar and lakefront sunsets.
The restaurant doesn’t take reservations, so arriving early is wise. Even if there’s a wait, cocktails by the fire pit overlooking Lake Montauk make the time pass quickly.
In many ways, the sunset scene here captures Montauk perfectly—relaxed, social, and quietly beautiful.
This may have been our favorite part of the Crow’s Nest experience! The area by the lake has a fire pit, plenty of seating, and a chill vibe.
3 Days in the Hamptons: Final Thoughts
Montauk feels like a different version of the Hamptons—less polished, more coastal, and deeply connected to the ocean.
Between the beachside calm of Hero Beach Club, historic seaside towns like Sag Harbor, and sunsets over the Atlantic, the area offers a refreshing blend of style and simplicity.
And if the giant smiley face painted on the side of Hero Beach Club is any indication, Montauk still believes summer should feel a little bit fun.
FAQ
Is Montauk part of the Hamptons?
Yes. Montauk sits at the eastern tip of Long Island and is considered the most relaxed town in the Hamptons.
Which Hamptons town is best for a weekend trip?
Montauk is ideal for a relaxed beach escape, while towns like Sag Harbor and Bridgehampton offer charming downtown areas and excellent restaurants.
If you enjoy coastal towns with historic charm, you may also love Mackinac Island and the Grand Hotel.
For additional boutique stays with distinct character, see:
- CIVILIAN Hotel in New York
- The Palmetto Hotel in Charleston
- Faena Hotel Miami Beach for a more elevated, design-driven experience
