'A legend': Respected restaurateur of Island Gypsy and Hogfish Harry’s dies at 71

Diana Biederman
Naples Daily News

He was a Naples restaurant legend, someone who paid great attention to detail and ushered in a new era of downtown dining nearly 30 years ago.

Jerry Alajajian — who helped create destination dining in Naples — died March 8. He was 71.

Alajajian owned Hogfish Harry’s in Naples and Island Gypsy on Isles of Capri, yet he made his mark decades ago.

While his name didn’t quite roll off the tongue among the many thousands of patrons at his restaurants, longtime residents of the community hold him dear to their hearts.

“I could go on with so many stories about Jerry," said Ann Hall, editor and publisher of Isles of Capri’s e-newsletter The Coconuttele.

Jerry Alajajian at the grand opening of his Island Gypsy Café and Marina Bar.

"I can best sum up what we saw in him with these words: He was a kind, caring, and generous man who loved his family, his friends, and his customers deeply.”

She added: “Jerry paid so much attention to detail, making sure the chairs were comfortable and deciding the kinds of food that would be appealing to a broad spectrum of appetites.”

Restaurant news:Who's new, what's coming, chef moves u0026 deals in Naples, Bonita Springs

The early years:Capri Connection: Island Gypsy Café and Marina Bar celebrates birthday

A legacy of creating destination restaurants

Prior to Island Gypsy's opening in 2011, Alajajian served as opening general manager at the first-ever Tommy Bahama Restaurant and Bar on Third Street South in the mid-1990s and was tasked with helping open several of the chain’s subsequent locations.

Upon leaving Tommy Bahama to strike out on his own, Alajajian opened Handsome Harry’s Third Street Bistro where The Continental now stands, and whose name honored his father.

He acquired 7th Avenue Social in 2018. The restaurant was noted as a late-night hangout for servers and chefs working downtown and made quite a bit of news with its Anthony Bourdain mural painted on the building soon after the chef’s suicide. It closed in 2020 because of the pandemic.

Barry Larkin worked for Alajajian as that restaurant’s bartender. He took over the space, renaming it Seventh South Craft Food + Drink.

“Jerry was an amazing person, friend and mentor. Naples has lost a legend. He will be missed by so many,” Larkin said in an email.

Alajajian opened a North Naples sister Island Gypsy outpost in October 2020 but changed the name to Hogfish Harry’s, which scored a great review by JLB.

Alajajian 'set the bar high'

Mike Cochran was Alajajian’s good friend. They last saw each other at Island Gypsy at lunch, hours before Alajajian passed away.

Cochran's 2012 wedding to wife Gail happened at Island Gypsy. His dog Gypsy Sue was named in honor of the restaurant that donates a delicious buffet and plays host to the pup’s annual fundraising birthday party benefiting Humane Society Naples.

Gypsy Sue, the guest of honor, at Island Gypsy's fundraiser for Humane Society Naples

When driving past the open-air Island Gypsy on Capri Boulevard on March 11, Cochran said he turned to Gail and said, “Jerry's got a smile on his face because he took nothing and turned it into a really cool place and a cool island."

"He had one way of doing things: you do it right and you do it right every time," Cochran continued. "He set the bar high. I watched him talk to his boys Steve, Joe and Nick that way and they picked up the baton. They're running with it just like dad.”

Alajajian put “a lot more into pot than he ever took out,” he added. Alajajian also credited Cochran with Island Gypsy becoming the area’s most dog-friendly restaurant.

Reporter’s point of view about Island Gypsy

My first visit: Christmas Eve 2014. We had purchased a fixer-upper within walking distance and had no working kitchen just yet.

That night, we marveled at the fun golf cart parade passing through the restaurant’s parking lot.

The good food. The chill vibe.

The carrot cake weighing as much as a newborn.

Island Gypsy's carrot cake is a massive slice, drizzled with caramel and encrusted with walnuts.

In 2015, when we officially moved to Isles of Capri, it became our go-to when friends and family from out of town visited. Our debut in the Isles' annual boat parade started with a pizza party for captains and crew at Island Gypsy. The Gypsy retains its place as the official line-up spot for participants.

In 2017 following Hurricane Irma, ours was among the last neighborhoods in Naples to have power restored. When walking to the re-opened Gypsy, we noticed a new coat of blue paint and lights under the bar, our favorite place to sit. We were told it helps repel mosquitos and other biting bugs. Placebo effect or not, it seemed to work.

When inheriting a dilapidated golf cart in 2018 from neighbors who were moving, our test drive was to Island Gypsy.

I never met Mr. Alajajian but remain awestruck that he created a consistently good restaurant that unofficially serves as our community's landmark. When scrolling my phone's 3,000 photos for this story, a whopping 15% were taken there over the course of more than 50 visits, all heartfelt reminders of fun and delicious memories with family, friends and neighbors. From JLB's POV, when readers ask for my top five Naples restaurants, it’s always on the list.

The minute my in-laws arrive, our first family dinner is always Island Gypsy.

My husband’s last visit to the Gypsy was March 3 for Friday’s locally-famous weekly prime rib special and yes, he took our dog.

Care to share your favorite Island Gypsy memory? Connect via diana.biederman@naplesnews.com.