Current Classic

  • Johnny DiMillo manages the restaurant with his brothers, Steve and Dan, plus a dozen other family members.

  • Tuna tataki is a light and fresh summer starter.

  • Executive chef Melissa Bouchard has worked at DiMillo’s for 20 years.

With respect for the past and thoughtful updates, DiMillo’s on the Water stays the course.

If you’re a longtime local, DiMillo’s may be where you had dinner before your high school prom, or where your grandmother always wanted to go for her birthday. If you’re a visitor, you’ve certainly read about Portland’s only floating restaurant in the guidebooks. And if you’re a newer city resident, you may have bypassed the waterfront landmark, thinking it was too big, too old, too un-hip. But like a classic novel you skipped in college but rediscovered and enjoyed years later, DiMillo’s may surprise you.

For starters, DiMillo’s boasts what is arguably the best view in Portland. From a table on the second-level aft deck (one of three decks on the 206-foot-long former ferry), I take in a sweeping vista that includes cruise ships, Fort Gorges, fishing boats and sailboats underway on the sparkling blue water, and gleaming yachts in their slips at DiMillo’s Marina. Diners inside have a similar view from the tall windows that wrap the exterior.

The main dining room—with an elevated section in the center that adds dimension to the large space—has recently been updated with more modern furnishings and finishes for a stylish yet relaxed look. Gone are the ship’s wheel chandeliers and linen-draped round tables, replaced by sleek glass pendant lights and reclaimed wood tables, the latter made by Maine Heritage Timber in Millinocket. New seating includes high-backed chairs upholstered in gray linen and red leather banquettes for two.

The menu has been updated, too, albeit less dramatically than the decor. “In a big place like this growth is very slow,” says executive chef Melissa Bouchard, who celebrated her twentieth year at DiMillo’s in July, having worked her way up through the kitchen ranks. “Our clientele has certain expectations, so we have to strike a balance.” Tuna tataki and cedar-planked scallops with fig butter now appear alongside traditional favorites such as broiled haddock and the fried Fisherman’s Platter, but some old-fashioned dishes, such as chicken cordon bleu or lobster Newburg, have been dropped. “One thing you don’t see on the menu is that we don’t open up cans,” says Bouchard. “ The majority of what we do here, we do in house.”

Her tuna tataki is bright and fresh, the slices of seared tuna dressed lightly with sesame- ginger vinaigrette and fanned out around precise cubes of perfectly ripe avocado with a tangle of micro cilantro and slices of bright red Fresno pepper. Mussels are plump and buttery, with white wine, a hint of garlic, and tangy, Maine-made Raye’s mustard in the silky sauce. And I’d come back with a friend to sit on that back deck sipping rosé and sharing the calamari bruschetta—a generous portion of crispy squid piled with diced tomato, basil, feta, and a drizzle of balsamic glaze.

From the beginning, DiMillo’s has been a family business. Restaurant managers Steve, Johnny, and Dan DiMillo grew up working for their dad, founder Tony DiMillo, who opened the first DiMillo’s on Fore Street in 1954, moving it to a waterfront location in 1965 and to the repurposed ferry boat in 1982. Today, 15 family members work at the restaurant, including Steve’s children— banquet manager Steve DiMillo, Jr., and Chelsea DiMillo, who is a bar manager along with Lisa Baugher. “Chelsea and Lisa have done at the bar what Chef Melissa did for us in the kitchen—lifted us out of the doldrums,” says Johnny DiMillo. While you won’t find the complex, multi-ingredient drinks common at the city’s newer bars, the cocktail list at DiMillo’s includes choices such as the Tito’s Jam, a refreshing summer sipper made with Tito’s vodka, strawberry puree, simple syrup, lemon juice, and soda water. “At the bar as in the kitchen we have to keep things somewhat streamlined because of our volume,” says Johnny.

With 600 seats, DiMillo’s serves over a quarter-million meals every year—1,200 to 1,400 guests on a summer Saturday night. But Bouchard and her staff still put careful attention into every plate. A bountiful, beautiful bowl of frutti di mare pasta features a zesty tomato sauce with shrimp, lobster, mussels, and hot sausage over squid ink fettuccine; both the seafood and the pasta are perfectly cooked, and the savory scent of the dish causes nearby heads to turn. Also outstanding is a special filet of beef with fried oysters and béarnaise sauce, which food history buffs will recognize as a nod to the old- school “carpetbag steak”—steak stuffed with oysters—still found on some menus in New Orleans. The flavors of Bouchard’s dish are surprisingly compatible, and the combination of textures—tender beef, crispy oysters, silky sauce, and peppery, butter-wilted baby arugula—is sublime.

At 4:30 on a sunny Thursday afternoon, DiMillo’s is already buzzing, with both the bar and the dining room starting to fill. Regulars and first-timers alike are welcomed cheerfully at the front desk—the restaurant’s command central. “We get everybody here, from the rich and famous to someone with just a few bucks in their pocket,” says Bouchard. Like her, many of the restaurant’s staff members have worked at DiMillo’s for decades. “A lot of our regular customers come back to see the employees they’ve had relationships with—some of them for 30 years,” says Johnny DiMillo. “We’re a humble crowd. We love and appreciate our customers, and we are happy they are here.” While other aspects of DiMillo’s have evolved with the times, the commitment to hospitality remains at its heart. And like much else at DiMillo’s, that heart is a big one.


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