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Claire Jeffers

Claire Jeffers is a freelance writer living in Portland, Maine. Follow her on Twitter: @claireeats

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Posted: November 17, 2014

For strong drinks on a stately boat, hit happy hour at DiMillo’s. It’s a Portland institution

Written by: Claire Jeffers
Shellacked and stately, the DiMillo’s interior can accommodate a crowd. Claire Jeffers photo

Shellacked and stately, the DiMillo’s interior can accommodate a crowd. Claire Jeffers photo

At night, zigzagging through Long Wharf in Portland, which is basically a giant parking lot, you can only really make out lights – bright lights – so you walk toward them. On first inspection, it’s not entirely clear that you’re walking on to a 701-ton boat – better known as Portland’s only floating restaurant, DiMillo’s – but after a series of ramps and automatic doors, you’re spit out into an expansive reception area – liberally shellacked and stately, in a way only a yacht from the early 1940s can be.

DiMillo’s is more like a floating fortress. In the summertime, it has the ability to seat up to 600, which includes three outside decks, two dining rooms and the bar area.

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On a recent night, bartender Adam “Couch” Sousa explained what it’s like at DiMillo’s on the weekend. “I’m all octopus arms,” he says, describing the hulking crowd as “loyal” and “older,” but is quick to say that even as a young guy who likes microbreweries, he’ll still come to DiMillo’s on his nights off.

The bar is long, rectangular and boasts two counters that face each other, which has a distinctly playful effect – it’s hard not to people-watch.

Sousa is gregarious but tempered, and it would be remiss not to mention his uncanny resemblance to actor Seth Rogen. Don’t ask him if he’s heard that before because the answer is yes. “Channing Tatum?” He’ll joke, anticipating your question, “Brad Pitt? Matt McConaughey?”

A DiMillo’s bartender for three years, Sousa is at ease – chatting with regulars, listening to stories, laughing generously – and he’s prompt to greet you, set your place, and if your drink is running low, he’ll notice that, too.

The “pumpkin pie” martini. Claire Jeffers photo

The “pumpkin pie” martini. Claire Jeffers photo

There’s a tacky frozen margarita machine at either end of the bar. While mostly kept around for summer guests, the machines are still churning out bright red and orange slush well into November. Sousa complies with what seems to be a barrage of orders.

“Don’t get me wrong,” he says, “I like making them because people like them, but there’s something about these things that doesn’t make you feel like you’re working that hard.”

For specialty drinks, Sousa recommends DiMillo’s “New Old Fashioned,” made with Bulleit Rye, muddled orange and cherry, sweet vermouth and ginger liqueur for $10. There’s also DiMillo’s “Jumbo Bloody Mary,” which is garnished with a jumbo shrimp for $11, and five other specialty cocktails.

Recently, the “Pumpkin Pie” martini was featured for $10. Other than a creamy hint at Thanksgiving’s most popular pie, this cocktail was a bust and not worth the novelty. The ingredients – Absolut Vanilla, pumpkin puree and a graham cracker rim – are clearly listed, so there will be no one else to blame but yourself for ordering such a travesty.

DiMillo’s at Long Wharf. Claire Jeffers photo

DiMillo’s at Long Wharf. Claire Jeffers photo

From 4 to 7 p.m. Monday to Friday, all alcohol at DiMillo’s is $1 off, which includes all cocktails, martinis, wine and DiMillo’s special list of scotch and vodka. There’s also a list of 11 appetizers marked down significantly during this time, including Buffalo Gulf Shrimp ($6), Ricotta Meatballs ($5), Truffled Potatoes ($4) and mussels ($6).

When asked what makes DiMillo’s different from other bars (other than the fact that it floats), Sousa snaps a grin and says, “Smiling faces, quick wit and strong drinks.”


WHERE: 25 Long Wharf, Portland
PHONE: 207-772-2216
HOURS: 11 a.m. to 9 p.m. seven days a week
SPECIALS: Happy hour 4-7 p.m. Monday-Friday offers $1 off all alcohol and discounted appetizers.
AMENITIES: Padded swivel bar chairs, dim lighting, front desk/concierge, large/clean bathrooms, and various boat features.
PARKING: Hourly parking lot, although parking is free while dining or drinking at DiMillo’s (don’t forget to bring in your parking ticket to have it stamped).
BOTTOM LINE: DiMillo’s is a Portland institution. A floating restaurant since 1982, this 701-ton yacht can seat up to 600 in the summertime. The bar scene in the winter is more mellow but the place can still get crowded on weekends and Tuesday nights. Expect to find excellent service, a jovial atmosphere and strong drinks.

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