Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Perfect family and/or artist getaway. Indoor heated pool. Private ocean beach. Outdoor shower. Modern kitchen with dishwasher. Flat screen cable TV. Wi-fi. Built-in 1940. It is a two-bed, one-and-a-half bath, cottage, that sleeps eight with a pull-out sofa. Indoor heated pool with beautiful views from the large deck overlooking the ocean. Completely surrounded by hedges and separate from the rest of the complex, private. New kitchen and all new appliances put in this year.

PLACES TO EAT

Duryea's:
Food served mostly family style & ordered through a counter window (drinks ordered tableside)
Lobster cobb salad & market fish are menu highlights (they had a branzino last time I was there and it was TDF) No reservations - on weekends, get there around 5 and expect a wait for large parties unless you want to just do cold seafood inside at the bar (oysters, shrimp, etc.). Grab some rose and wait for your table on the dock. Weekday evenings and lunch are usually a bit slower but the place is generally always busy.

Scarpetta Beach:
Same as Scarpetta in NYC, traditional Italian food, inside Gurney's hotel.

Crows Nest:
Super chic restaurant at a boutique hotel, one of my favorite places. Mostly Mediterranean inspired, simple menu. No reservations - like Duryeas, on weekends, get there between 5-6 and expect a wait for large parties. They usually cut the waiting list off at a certain point (have waited upwards of 2 hours for dinner here before). Weekday evenings should be more low-key but the closer to the weekend you are the more likely there will be a long wait.
They have a cute bar down the hill in the bag with a small beach and cabanas set up. Go down and have a drink while you wait for your table and watch the sunset (spicy tequila or watermelon drinks are my favorites).

Surf Lodge:
The quintessential Montauk hotspot. Food is ok, this is more of a place to go to be part of the "scene."
On the weekends this turns into a full-on club - insanely difficult doorman, bottle service, outside DJ (until ~9), sweaty inside bar. Sometimes they have live music on Saturday / Sundays for sunset hours.

Montauket:
BEST SUNSET IN MONTAUK. Very casual spot with a divey inside bar and picnic tables outside.

Gosman's:
Casual seafood spot with a bar - a traditional Montauk staple (not sceney).
No reservations, so again, expect a wait unless you show up early or during the week.

Navy Beach:
Beach front, nautical vibe with lots of white and blue. Food is okay but it's another one of those places sceny NYC people tend to talk about.
I think they take reservations.

Showfish:
Seafood restaurant at the other Gurney's property on Star Island. The food is pretty good, traditional. Not really a scene.
I think they take reservations

Joni's:
Great little breakfast spot off the main town road.

Round Swamp Farm:
Montauk outpost of the East Hampton Farmstand (overpriced but love it)

Sel Rose:
Oysters and cocktails.

Harvest On Fort Pond:
Outdoor dining, amazing food.

The Dock:
Montauks best dive bar, super fun, almost tacky vibe, and great food.

Montauk Bake Shoppe:
For jelly croissants.

BEACHES & HIKES

Gurney's:
The best beach is the one by Gurneys. The beach is technically public, but they won't let you park on the Gurney's property unless you have a reservation and you won't be able to use their beach chairs. If you want to have a splurge day, rent a cabana or seating area for an afternoon. Sometimes they have a DJ playing on the weekends. Full-service world-class spa on the property.

Ditch Plains Beach:
Most popular beach for surfing and swimming. Scenic, sort of has a coastal California feel.

Kirk Park Beach:
Closest to town, family-oriented

Hither Hills:
Trails and campgrounds

Montauk Point / Camp Hero:
Scenic lighthouse at the end of the road / gift shop with some trails around. Be careful hiking there are tons of ticks.

SHOPS

Shops in town are mostly of the beachy variety (think Jersey shore hoodies and sweats kind of stuff). In the last ~5 years, they've opened a bunch more stores but mostly womenswear.

Whalebone / Adam Mar has some men's stuff I think and there is this new super hip store called wyld blue that is fun to browse.
Some places in town offer surf lessons or paddle board / kayak rentals (you might also be able to book a reservation through Gurney's)

Deep Hollow Ranch - horse back riding, etc. - never been here but just saw some brand do an influencer activation and it looked cute.