A Sunrise and a Sail: Escape to Montauk


I was expecting “Wolf of Wall Street” and I got “On Golden Pond“.

Montauk’s got a bad reputation. It’s widely reported that NYC hipsters and throngs of kids with fake IDs descend on the easternmost village in the Hamptons and trash the place during summer weekends. It’s gotten so bad the locals are fighting back.

But, during the week and off-season, Montauk remains a sleepy coastal village, where people fish. Surf. Veg. Repeat.

Let’s start with the embarrassing part. Despite being a native New Yorker, I’ve not explored Long Island beyond trips to Jones Beach. Feeling that this presented a definite hole in my travel experience, I invited my daughter to accompany me as a reward for a successful sophomore year. We booked a Sunday-Tuesday stay to avoid potential weekend party shenanigans.

The Gold Coast and Wine Country

A successful road trip requires detours. In thinking about Long Island several things came to mind, besides the horrific traffic on the LIE. For example, Gatsby. Over 500 mansions were erected by wealthy industrialists after the turn of the 20th century, earning the North Shore its nickname, the Gold Coast.


We opted for a visit to the Old Westbury Gardens which served as the inspiration for the Buchanans’ home in the Leonardo DiCaprio version of “The Great Gatsby“. Stepping on the grounds and imagining decadent Gilded Age parties was a fun exercise in make-believe. Who wouldn’t want their own croquet court? The estate is meticulously maintained. Picture a meandering path called “The Lilac Walk” and then think about the smell. It was heaven. I was awestruck by the sun porch; its massive glass walls were designed to be lowered into the basement. Put me in a silk gown, drape me on a chintz sofa, and surround me with cut hydrangeas. I’d be a happy, happy kept woman.


Long Island is also home to a number of wineries. We stopped in Sagaponack at the Wölffer Estate, one of only three vineyards in the Hamptons. I was familiar with it because I’d visited the Owera Vineyards in Cazenovia, New York, and the owner had mentioned that they’d used Wölffer for design inspiration. The tasting room was a popular destination for families with young children, surprisingly, on a windy Sunday afternoon. I chose a 4-wine tasting for $15. Unfortunately, none of the wines made my palate sing; fortunately, it meant we left with my wallet still intact. The tasting room was lovely and situated with a terrific view of the vineyards. It must be magnificent in late summer when the vines are laden with ripe fruit.

Exploring Downtown Montauk


As we approached Montauk, I startled my dozing passenger by swerving sharply right, tossing up a gravel plume, and screaming “The Lobster Roll!!!” Montauk landed on my travel radar via Showtime’s “The Affair“. Season 1 was set primarily in the town; the Lobster Roll is the restaurant where Noah Salloway meets his mistress Alison.

I was a bit underwhelmed as we approached the Montauk Beach House. It’s set off a side street populated by establishments with pasts much brighter than their presents. But, opening the lobby’s glass door, we entered a chic little lounge and received a warm welcome from the hotel’s French manager. He led us out into the entertainment area which includes a bar, grill, and plenty of bed-sized, umbrella-shaded, loungers surrounding two heated pools. When the weather warms, the Beach House hosts weekend block parties with guest DJs. The place has a funky, retro feel. Until a massive renovation in 2012 it was a seedy efficiency motel known as the Ronjo.






They kept the giant tiki, painted it bronze, and pitched everything else. Our Moonlight Suite had dark grey walls, furniture from Restoration Hardware, including two queen-sized beds, and a giant, clawfoot tub. In the room. Sounds weird, but it works. The best way for me to describe the style is “decadent practicality”. The staff was friendly, engaging in pleasant conversation with the guests as we sampled the complimentary continental breakfast. We talked a lot about the weather, which has been unseasonably cold.

Although we were initially put off by the downtown location, it was great for walking to several good restaurants, shops and the beach.

We caught a magnificent sunset at Harvest, an upscale Italian restaurant on Fort Pond. Or try the great fish tacos at The Gig Shack. And, if you need a bigger breakfast, Mr. John’s Pancake House has a line out the door and it’s worth the wait.

For shopping, you can hand over all of your money to the ladies in Calypso St. Barth and walk away with the chicest summer styles. Or, toddle round the corner and visit Land Shark Unlimited for spirit jerseys and hoodies with their appropriate Montauk whale logo. For gardeners, be sure to wander around Fort Pond Native Plants, a family owned nursery offering, you guessed it, native plants.

To the Lighthouse


What’s on the activities list for a mother-daughter getaway? There was the obligatory spa mani-pedi. We also schlepped to the top of the iconic Montauk lighthouse and explored its museum, dedicated to the area’s nautical history. I actually went out to the lighthouse twice in the same day. Based on earlier advice I’d received from professional photographer Avery Meyers, I got up predawn to take some people-free photos of the popular tourist attraction, bathed in soft pink light. I’m not a religious person, but I sense a higher power in the early morning hours, listening to birds chirp as I walked home from a party that ran way too late or nursing a newborn. It was a tremendous way to start the day. And driving out there I found another spot from “The Affair” – the Deep Hollow Ranch.


But the best part of our trip was a two-hour sailing lesson on Block Island Sound. I booked it with Sail Montauk, operated by business and life partners, Ali and Darius. The weather was perfect for our lesson with good winds and just the right amount of sun. Darius motored us out of the Montauk harbor and then gave us an intro to basic sailing techniques. He and my daughter hit if off immediately; they’re both huge “Survivor” fans. We each tried our hand at steering the boat by controlling the tiller and I attempted several  tacks. We were sad when the sail ended and it was time for us to drive home because Darius had filled us in on so much weird Montauk history that we wished we had another day to explore. We’ll definitely be returning to learn more about the secrets of Plum Island and the myth of the Montauk Monster. And I’ve got to sample some more lobster rolls. Right now, Gosman’s is #1 but I need to log a few more before I give it the gold.