Hard work and commitment to family keep the DiMillos’s diversified business afloat.
Just off the lobby of the floating restaurant that bears his family’s name, Steve DiMillo’s compact office is stuffed with memorabilia: framed photographs; plaques and awards from local organizations; a watercolor of the first restaurant his father, Anthony (Tony) DiMillo, opened in Portland in 1954. Hanging on one wall, directly across from Steve’s mahogany desk, is a tribute to the family from DiMillo’s employees. On another wall is the framed front page from the Portland Press Herald, Saturday, February 21, 1987—“Jubilant DiMillo celebrates,” the headline shouts in large type. Just below are photos of Tony leaving the Cumberland County courthouse after being found innocent of federal tax fraud charges, shooting reporters with a water pistol. “It looks like he’s angry,” says Steve with a laugh. “But my dad had a great sense of humor.”
Tony DiMillo also had a vision and a work ethic that persists in his children and grandchildren today, sustaining his legacy on the Portland waterfront. When he bought Long Wharf in 1978, it was falling into Casco Bay and the city was struggling to get back on its feet. The opening of the Maine Mall had hurt retailers downtown. The State Theatre showed porn films. But the port was popular with boaters, and pleasure craft soon filled the marina Tony built at the end of the pier. Two years later, he purchased a massive old car ferry, refurbished it, and opened DiMillo’s Floating Restaurant in 1982. Now a Portland icon, the restaurant remains the heart of the family enterprise, which also includes the adjacent marina, along with a yacht sales business with locations in Freeport, New York, and Maryland. Steve manages the restaurant with three of his eight siblings—his twin, Stephanie Quattrucci, and brothers Dan and Johnny, while Chris takes care of marina operations and his yacht sales business. Stephanie’s husband, Tony Quattrucci, runs the kitchen with chef Melissa Bouchard and her boyfriend, Fred Breton. DiMillo’s employs a total of twelve DiMillo family members, including both of Steve’s children. Two of Tony DiMillo’s sisters, Justina and Jeannette, recently retired after serving at the front desk of the restaurant since it opened. “It’s a crowd, but it works,” says Steve. “Sometimes it’s hard for us to make a decision, but generally the one with the strongest opinion will persevere and the rest will just relent.” Not having financial worries removes considerable stress, he adds. “Thanks to my dad buying this property, we all make a decent living and we’ve got a great future.”
To ensure that future, Steve is active in a group of pier owners who have worked with the city on zoning changes designed to preserve access for fishermen while increasing economic opportunity. Except for Maine State Pier and Fish Pier, which belong to the City of Portland, all of the property along the waterfront is privately owned. “They all have the same dilemma we have, which is how do you keep your infrastructure in good operational shape if you’re not generating income?” says Steve. In 2010, the group successfully lobbied the Portland Planning Board and the City Council to loosen regulations that had been enacted in the mid-90s following the construction of luxury condominiums on the waterfront. “Lobster fishing is still strong, but the decline in ground fishing has left a lot of these piers with empty berths, empty buildings,” Steve explains.
As an example, he cites the once-vacant brick building on Merrill’s Wharf that now houses The King’s Head pub in part of the ground floor and the Pierce Atwood law firm on its upper floors. “You’ve got to keep the perimeter of the dockage for commercial boats and 55 percent of the ground floor for the marine industry, but now you can use the rest of the ground floor and all those upper floors for other businesses.” Because much of the DiMillo’s property doesn’t have direct water access, the revised rules make it possible for the family to develop some of what is now a large parking lot. “We’re planning to stay in the restaurant, marina, and parking business, but we have some ideas,” says Steve. “We keep saying we’re waiting for the dust to settle, but man, it doesn’t seem to be settling as far as new properties and new hotels.”
The youngest of the nine siblings, Chris DiMillo got his start on the marina side of the family business in 1996. He had waited tables at the restaurant as a teenager, but after college was working in medical sales in Southern California when Tony called. “He said that the marina operation here, which he had always leased out to a management company, was up for renewal—did I want to come back and run it,” Chris remembers. “He said, ‘I can’t be at peace until I know all my family’s taken care of.’”
The marina in Portland has 125 slips, and the business runs year-round, with about 50 people living aboard over the winter, says Chris. In the summer, large boats are a common sight at DiMillo’s, which can accommodate up to eight 100-footers at a time. “Maine has always been a destination for cruising yachts and we have the good fortune of being right downtown, as well as near an airport,” he says. In the late 90s, Chris launched the yacht sales operation, specializing in powerboats ranging from 30 to 66 feet. With 35 employees in five locations, DiMillo’s is the exclusive dealer for Sabre Yachts in Maine, New York, and Maryland, and also sells the luxury brand Monte Carlo Yachts, built in Italy. “It’s an experiment,” Chris says of his involvement with the high-end boats. “New York is where we see the market—Sag Harbor, the Hamptons.” While this aspect of the family business may seem to be in contrast with the unpretentious restaurant, Chris attributes some of his success to the familiarity of the family brand. “I was at a boat show somewhere and
I had a DiMillo’s shirt on and someone said, ‘DiMillo’s—what are you doing here? That’s the restaurant.’ We struck up a conversation, then a relationship, and the fellow bought a new Sabre a year later.”
Although trendier restaurants have turned Portland into a coveted dining destination, DiMillo’s reputation, and prominent location on the waterfront, continues to make it one of the most visited in Maine. “We run a high- volume, simply prepared seafood operation that focuses on quality,” says Steve, praising the talent of chef Bouchard, who has worked at DiMillo’s for more than 20 years, rising through the ranks. The kitchen’s skill with classics such as lobster stew and baked haddock with breadcrumbs keep loyal fans coming back, as does the family’s hands-on involvement. “It looks like this because this is not my business,” Steve says, gesturing to the piles of paper on his office desk. “My business is out there in the kitchen and dining room, talking to people, hosting, bussing, whatever it might be. The customer experience is what keeps us going.” So do strong family ties and a commitment to Portland that’s as deep as the ocean beyond DiMillo’s bow.