A Guide to the Best Bachelorette Party Weekend - Sail in Montauk


You and your best friends are heading to Montauk for a bachelorette weekend of fun-in-the sun. With so many great activities and restaurants to choose from, how could you decide where to spend your three days! Avoid group chat planning confusion and follow our guide for the perfect bachelorette party in Montauk. One of the hottest destinations in the northeast during the summer, you and your gals will have a blast in this seaside town before your friend ties the knot. 

Spend your days sailing in Montauk and ring in the evening sipping a watermelon cocktail while swaying your hips to a live reggae band. From the best breakfast spots to the best bars for dancing, follow our itinerary for a bachelorette weekend your bride will never forget!


Watch the Sunset at the Crows Nest

If you arrive in the afternoon, unpack your bags, hang up your bachelorette decorations, freshen up and head to the Crow’s Nest for sunset. Located on the north side of Lake Montauk, this is one of the trendiest spots in Montauk to watch the sun go down. The main, open-air restaurant is located on top of a grassy hill.


Walk down the hill to a small beach sitting on the lake, but be careful not to slip in those wedges! On this sandy shore you’ll find a beachside bar and gazebos made of driftwood to lounge under, and take Instagram shots of course. Watch the sun fade from blue hues to pink and keep an eye out for the boats peacefully sailing in Montauk.

Start the Day With Pancakes 

Head to Bird on the Roof for a big breakfast to start the day. A longstanding Montauk staple, you can spy this breakfast spot in the middle of town by the large, white seagull painted on it’s roof. Order a stack of pancakes that are light, fluffy yet crunchy in all the right ways along the edge.


If you are looking for something quick instead, go to the Montauk Bake Shoppe and pick up an iced-coffee and one of their infamous croissant jelly donuts. 


Splash in the Waves at Kirk Park Beach

After breakfast, take the short walk that leads to the ocean beach in Montauk. Spend the day tanning with your gals while the crystal clear waters hit the sandy shore.


You can spend the day camped up on the beach and easily walk to nearby stores or restaurants when you need to refresh the beverages or eat something for lunch. If you’re thirsty for a cocktail, go to the Sloppy Tuna located right off the beach. 

Sip a pina colada with your ladies as you overlook the rolling waves of the Atlantic Ocean and the boats sailing through Montauk. 


Dance the Night Away 


Gather your tiaras and bachelorette sashes for a night of dancing with your girlfriends. Start the night at the Gig Shack, a local’s favorite to have a cocktail or Montauk Brewing Summer Ale. The laid-back surfer atmosphere is the perfect spot to get the party started. 

After a drink or two at the Gig Shack, head to The Point or The Memory Motel for a night of dancing at these Montauk bars. These infamous dive bars are the perfect place to let loose and jump to Mr. Brightside.


Sail Montauk on a Sailo Boat Rental

Surprise the bride-to-be with her last sail before the veil. Charter a boat rental to sail Montauk with your ladies. Some of the local charters like Sail Montauk have flotilla parties where up to 15 girls can be split among three private boats. You’ll get a beautiful vantage point sailing Montauk by water as your three boat rentals  sail together through the marina and calm bay. 


The boats can anchor together so you can spend the afternoon sipping rose, tanning and diving in the water with your friends. 


Sway to Reggae at Swallow East 

With a slight sunburn from your day on the boat rental, spend the evening listening to the sweet sounds of live reggae at Swallow East. Hosted on Sunday evenings on the back deck of the restaurant, Swallow East is the place to be on Sunday nights.


The expansive deck sits on a dock and overlooks the boats sailing in Montauk harbor. We hope you enjoy your last evening of celebrations and your time in Montauk!


Take you friends on a dream sail in Montauk on one of our beautiful boat rentals! Choose the perfect charter in Montauk for an amazing bachelorette party weekend!