Same Direction, New Breeze: Sail Inn Gets a Refresh in Montauk

When Montauk resident and New York City restaurateur Colleen Croft first showed interest in purchasing the Sail Inn — one of a handful of similar haunts in the area yet to go upscale — longtime owner George Gallaway told her she’d better hurry; there were several parties circling and poised to make offers.

As Croft puts it, after some “honest” conversation about her modest plans for the property, as well as the limits of her life savings, Gallaway sold it all to her and her son, Luca Guaitolini. The mother-son team closed late last year on the motel and bar in the hot West Lake Drive community for $4.65 million.

After the sale, Gallaway told Croft that she was not the highest bidder. So, how did she pull it off?

“I didn’t want to see it turned into some corporate place,” Croft says over the phone from the site of her new property. “I told (George) I wanted to keep it as much a local place with the same spirit as we can.”

Good news for those worrying the Sail Inn might drift the way of so many other commercial properties in the lakefront area: Sail Inn will remain a bar and motel called the Sail Inn, Croft says.

It probably didn’t hurt that she has supportive friends in the neighborhood, including Brian Gosman of the famed fisheries — or that she has more than a bit of clout herself. Croft is co-owner of New York City power-restaurant Elio’s, and wife of the old-school Italian joint’s eponymous late owner, Elio Guaitolini.

Her Montauk family home is within walking distance of the hotel, she says, and her awareness of local history and admiration for the seafaring life played a role in her acquisition. While Elio’s survived the pandemic (thanks in part to the gratitude of some loyal clients who provided financial help to the waitstaff), she does not own the property where the popular uptown restaurant is located and has been unsuccessful in her bids to buy it.

She has also been worried, at times, that another partner in the restaurant was going to walk away. All of which was additional motivation for her to spend her life savings for her son, Luca, and “his future.”

Croft explains that she has no major plans for the almost 4,500-square-foot bar and motel other than a general “refresh” — updating rooms, the exterior, putting new carpet on the floors and upholstery on the barroom booths, and downsizing the guppy-filled fish tank. For those wondering, she’s keeping the pool table, the original folk art sign and sailboat out front, and the fun, maritime vibes. She will, however, be tinkering with the bar food.

Known among locals in the community for Gallaway’s signature dishes — prime rib, stuffed flounder, ribs, baked clams — the menu at Croft’s version of the Sail Inn appears to be where some distinct changes are afoot. Croft has tapped Guiseppe Lentini, a Bari-born former chef at Elio’s, to be in charge of updating the food options. The hope is that a refreshed Sail Inn menu will be set to sail by the middle of June.

Croft says you can expect Lentini to take advantage of local seafood, which she also personally buys for Elio’s from Gosman’s and delivers to the city each week. Dishes like grilled octopus, ceviche and shrimp couscous will join classic core items like crab cakes, fish and chips, and burgers. Croft says that curious neighbors have been asking her if the menu will be Italian.

Her response is that Lentini has “got some other things up his sleeve,” including some personal specialties, like lasagna, and the meatballs he made famous at Elio’s.

As for the bar itself, Croft has just received a liquor license and is planning to expand on what had been fairly limited offerings. “We’re not going to do anything too wild and exotic, but we will have more wines than we had before.” And she just finished ordering eight dozen martini glasses, so come thirsty!

She was also proud that customers will recognize some of the old faces. “One of the most telling things about our buying the place is that two of the regular bartenders told us, ‘We want to work for you,’” she says.

Her neighbor, Gosman, who’s the owner and operator of the area’s mainstay family business, said that the purchase and renovations are a big undertaking for Croft, but that she had long expressed interest in owning a restaurant property in the community, and “really wants to add her personality to it.”

“I know she wants to keep the charm of the Sail and just add an element of food. She wants to keep the bar feel, the character of the place. A lot of those kinds of places have diminished in the area,” says Gosman. “(George) made the right decision. She has her heart in it.”

Sail Inn is located at 548 West Lake Drive, Montauk. For more info, visit sailinnofmontauk.com.