Out on the East End, Montauk is the last stop on Long Island—a beach town that feels worlds away from New York City—hence its nickname: The End of the World. Yet, it still pulses with an effortlessly cool energy thanks to its trendy, urban refuge scene and a classic coastal allure. Unlike the more buttoned-up Hamptons, Montauk keeps things laid-back, even when it’s buzzing with summer energy: It’s where saltwater-soaked days have the potential to turn into barefoot dance parties, and where bachelorette weekends can be as ultra-luxe or as casual as you wish.
Whether you’re looking for a wine-fueled beachside picnic or a dressed-up dinner followed by DJ sets, Montauk has no shortage of fun new hotspots and must-see classics to add to your bachelorette itinerary. Expect daytime rosé runs to the best East End wineries, sunset Champagne toasts at waterfront restaurants, and nights that will likely last later than planned. Here’s our guide to the ultimate Montauk bachelorette.
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FAQ:
How should my group plan to get around in Montauk?
If you’re journeying from Manhattan (which is around 118 miles from the East End), a trip to Montauk can take up to three hours depending on your choice of transportation. The Long Island Railroad (LIRR) offers multiple departures daily, especially in the summer—though, note that no matter the timing, most of these (oftentimes double decker) trains will be crowded, so arrive early and head to the train for a seat as soon as the track is announced. The three hour Hampton Jitney bus service is another option that offers regular service between NYC and Montauk, with several departures daily from Manhattan and Brooklyn. Its Montauk bus stop is conveniently located at the main roundabout, right next to the beach. And if you’re feeling like you want a more luxurious route there, you can charter a private Jitney to take you and your crew, too.
Once you’re there, it’s easy and typically inexpensive to book rideshare services, whether it be Uber or a taxi. Or, most hotels (and even some Airbnbs) offer bike rentals so you and your group can get around during the day. Of course, if you plan on drinking, it is ill advised to ride your bike under the influence. Since Montauk is far out from most other towns, including the Hamptons, if you plan on day trips, you can either book a party bus service to the wineries (a common pastime for many NYC-vacationing folks) or rent a car so it’s simple to travel around with more freedom.
How many days should I stay in Montauk for a bachelorette trip?
While it will always depend on your group’s schedule, you won’t need more than four nights in Montauk for a proper bachelorette getaway. Some groups I’ve known have booked quick weekend bachelorette getaways to the East End, but more often than not, feel it was a bit too rushed for their liking. To get proper rest and restoration—while having a great time—plan to stay for around four nights. And while it might be more crowded or competitive to score a reservation in advance this way, it’s best to book a stay over the weekend, as many shops and restaurants are closed at some points throughout the week.
When is the best time to go to Montauk for a bachelorette trip?
Late May through mid-September are the best months for ambiance and buzz as well as summer-in-New York weather. Though, consider the summer liveliness as ample reason to plan ahead for getting around—given its removed location, the popular (and fun) spots tend to become more crowded come peak of summer (from June through August). Always make reservations where you can, and book as early as possible, whether it be boat rentals, hotels or Airbnbs, or dining—as early as possible.
Where to eat
For your days out on the East End, fall victim to heaps of beach picnics and last-minute plans of dining on the beach—and in this case, picking up some to-go bites at Joni’s Montauk is a must. For a sit-down outdoor brunch, start one of your days at The Bird, a colorful outpost of trendy yet no frills Daunt’s Albatross Motel, only a few minutes walk to the beach. They also have karaoke on Thursdays, if you want to return for craft cocktails at night, too. For beach bonfires set up by trusted professionals, book with Bontauk—and don’t be shy to let them know your exact preferences of decorations, food, and beverages.
Through the weekend, the fun staple Salivar’s Clam & Chowder House offers live music and waterfront dining. Another classic is Montauket, known as “the hill” by locals; the coastal bar and restaurant has been kicking since the late 1920s. It’s the perfect laid-back scene to enjoy casual drinks with a sunset over Gardiner’s Island, and a pleasant touch of live music (which often becomes great for dancing, too). For an elevated-yet-fun beach dining experience, order at the Navy Beach restaurant, home to cabana-style dining alongside a private stretch with views of Fort Pond Bay. Its casual coastal cuisine has become a favorite amongst visiting yacht-owners (and even a sought-after location for beach wedding venues).
In Bridgehampton, on the outskirts of Montauk, you mustn’t miss a classy lunch at Topping Rose House. Its restaurant, Jean-Gorges, is a prime pick for breakfast or lunch, with ingredients sourced from local farms, orchards, and fishermen—and due to its location, probably best enjoyed when on a longer day trip inclusive of other wineries nearby, such as Wölffer Estate Vineyards. And you can’t not happen upon a lobster roll once you’re in Montauk. For a fun lunch outing, order fresh rolls for the group on the border of Amagansett and Montauk at The Lobster Roll. For a more local and accessible hotspot (via walking or cycling), head to Gosman’s Dock for no shortage of lunch options. Here, you’ll find the freshest of oysters, surf and turf, and lobster rolls to enjoy while sitting alongside the water.
A fun dinner before a night out, 668 The Gig Shack offers a relaxed atmosphere with top-tier dining options. Locals simply call it “The Shack”—head here for its eclectic, colorful design and surf atmosphere, just off the strip of Montauk’s Main Street. For your chicest night on the town, the cutting edge Maverick’s Montauk is a sleek and delicious option best reserved for an indulgent sunset dinner. Ideal for splurging on the tastiest pasta, seafood picks (hello, catches of the day), and an extensive wine menu, it is also home to unique and moody coastal views, next to floor-to-ceiling windows overlooking Fort Pond. Watch the sunset and indulge in the raw bar Duryea’s (locally well-known, and maker of the $100 lobster salad). It’s an ultra-buzzy location that is open for walk-ins only—so plan for some ample wait-time upon your arrival.
Where to stay
For a truly high-end, glitzy, and all-around fun stay, the Montauk Yacht Club is where to be for your bachelorette celebration. It’s certainly tempting to stay on the property—where a dining reservation at the on-site Ocean Club is no-brainer, and the property boasts a private beach, a padel court, two updated pools, free-to-book electric e-boat for sunset cruises, and a boutique. But thanks to its convenient location, it’s easy to venture out on the available bike rentals when riding to the town center, or Montauk Village, for beach days, shops, and dining hotspots. Head to The Cabana for a morning of ultra-luxe spa pampering on the onsite (and large) yacht docked on the property.
Solé East was pretty much made for bachelorette parties—with poolside food and drink service as well as live DJ sets and entertainment on the weekends. The property boasts none other than coastal elegance in its chic, simple, yet beachy designs—all evoking a natural St. Tropez-type beat throughout. It’s just a mile from the town’s buzzy downtown village and a five-minute walk to the beach. Of course, for your once-in-a-lifetime bachelorette, a stay at the original Gurney’s Montauk is a fantastic option for those willing to splurge on a classic gem. Known as the epitome of summer vacationing, the property guarantees your group access to excellent seaside food and drink programs, a destination spa, and—of course, fabulous people watching. The vibe is energetic and celebratory, enhanced by the DJ spinning tunes every weekend during the summer. Also offering a relaxed-turned-live atmosphere is The Firepit, an all-outdoor lounge venue with ocean views during the day and a party scene at night (best enjoyed after a visit to its Seawater Spa).
If you’re looking for a more low-key and cozy stay, without the pressure of a hotel booking, there are heaps of Montauk Airbnbs to choose from (just be sure to confirm with the host ahead of time that bachelorette groups are permitted). This modern Montauk bungalow is playfully and tastefully designed: It can fit up to six guests with four beds and two bathrooms—and it’s only an 11-minute walk to Lake Montauk. The home offers an indoor fireplace for cozying up, a washer and dryer, a fully stocked kitchen, a spacious backyard with a patio, BBQ grill, bikes, and a gated pool with daybeds for lounging. Or, book your bachelorette getaway at this two-cottage lakeside property, coined “Sea Roost,” which can fit six guests with three beds and bathrooms. Walking distance from the crashing waves at Hither Hills beach, you can indulge in this property’s coastal charm and elegance, all while having heaps of fun in the private eight-person hot tub, at-home movie theater, and outdoor shower.
Where to play
Montauk is truly one of New York’s best summer playgrounds—and one that offers a plethora of places to play despite its far-removed location. And if you’re planning a Montauk bachelorette, it’s probably true that you’ll be on the lookout for some time out on the water. To begin your search: Montauk Uihlein’s Marina offers all sorts of rentals, and are generally best for group jet-ski excursions. Most fun—and also classic—bookings are with sun sailing catamaran, Mon Tiki Fleets. Here, you can enjoy some lite bites, and perhaps be accompanied by a band while you sail into and around the sunset. Or, book at global boat rental service, GetmyBoat or Boatsetter. Viking Fleet offers sunset cruises, or take advantage of its fast ferry service for a day trip to Block Island, where you can dine and picnic at Fin Beach on Block Island Sound.
Best for dining and playing, head to Montauk Yacht Club’s onsite restaurant and bar, The Ocean Club. Most convenient as hotel guests, it’s still one of the best spots to go to for an upscale dining experience and a genuinely fun scene that feels right out of St. Barts. Here, enjoy poolside cocktails, live music, and a fabulous meal from the raw bar and Braai menu—a traditional South African grilling method. And even if you and your group are staying elsewhere, you can—and should—book a day pass for pool access, with a Water Club fee of $100 per day per person (plus tax).
Best indulged with a party bus or transportation rental, don’t miss a day trip to the East End’s most beloved wineries, including Wolffer Estate Vineyard, Bedell Cellars, Suhru & Lieb Vineyards, and Channing Daughters. There are heaps of bus rental services out there that you can even ask your hotel concierge about, but to help start your search, Tapped Enterprises offers both winery tours and specialized bachelorette day trips to and from Montauk. And for more wholesome play, indulge in Montauk’s nature: Take a drive to Point Lighthouse for incredible trails and sweeping coastal views. Look out to the Atlantic from the diverse landscapes of the gorgeous Camp Hero State Park, where the stretch of coastal cliffs embodies the feeling of being at Land’s End. Or, picnic in the sand dunes (also known as the “Walking Dunes”) of the surf-lover paradise, Hither Hills State Park.
