The Notorious F.I.G.

photo/Figgy DiBenedetto

DiMillo’s on the Water
154 Commercial St., Portland

Thanksgiving Eve, 2009. My then three-year-old son and I were on our final night visiting Portland. We’d spent several days touring the neighborhoods of the city, trying to decide where we wanted to live. We probably looked at a dozen houses in our young family’s price range, all on the peninsula. Remember those days? 

We decided to take ourselves out for fancy dinner to celebrate the upcoming move. I dressed him in a sweet little sweater and corduroys, and I wore a wool blazer. Our server that night let us split the twin lobster special ($29, maybe?) because we were “so cute” — her words, not mine. My son was impressed that the green beans we chose for our side were not “squeaky,” as was his mother. Dinner was especially memorable because it was our first time eating on a floating restaurant!

To this day, whenever we have visitors and/or want fancy dinner out, DiMillo’sis our go-to. There are oversized, comfy padded chairs, large tables for families and several outdoor dining areas. Owned and still operated by the DiMillo family, the decommissioned car ferry turned restaurant has kept her nautical charm — and menu — for over four decades. Things have been updated, but there are still wisps of total ’80s awesomeness all around. 

The menu has your standard seafood restaurant fare: Fried Calamari with Sweet Peppers ($15), Sautéed Mussels ($18), Wedge Salad ($15), and a few more modern items, like Avocado Toast ($12) with everything-bagel seasoning, and Tuna Tartare ($20) with some way-out-of-state ingredients: pineapple, pico de gallo and poppy seeds. Go for the classics, like we do, and you won’t be disappointed. 

Our most recent meal began with Cheesy Garlic Bread with Marinara ($13). It’s floppy Italian bread, with broiled cheese on top, and you dip it in homemade sauce. We also had the Steamers ($19), “freshly dug from New England mud flats” and served with broth and drawn butter. ‘Nuff said, right? 

They still have the Twin Lobster Special (that you’re not supposed to split; it’s $63 these days), and staples like Broiled Haddock ($32) and Fried Clams ($33). But my two favorites are on the sandwich side: the What the Fish ($19) fried haddock on a brioche bun (suggestion: sub American cheese for the Havarti) and the Lobster Club ($31). 

And guess what — you get to choose your own adventure for the sides! Who does that anymore? Mashed potatoes, cheddar polenta, fries, vegetable or coleslaw are offered, and though the polenta and fries are delightful, I sure wish they offered a baked potato (mostly for the side of sour cream that comes in that odd-shaped, cardboard cone thingy). 

The desserts are pretty standard, but tasty, like the Wild Blueberry Cobbler ($12) to which you can add a scoop of vanilla ice cream ($3.50). Or feed your chocoholism with Chocolate Fudge Cake ($11). 

You know the menu already. It’s but a small part of the pleasure of dining at DiMillo’s. Again, it’s a freakin’ giant boat! It has an amazing “Tip of the Ship” outdoor bar overlooking Casco Bay and some giant yachts. There are brass railings, clean carpets, and a big-ass stuffed marlin over an electric fireplace. Also, for all its class, nary a snobby server in sight! Rather, you’ll find everyday folks who seem to have worked there for decades, and actually love doing their job.

A lot has changed since I moved to Portland over 13 years ago, and DiMillo’s soothes my nostalgic soul. Salt-of-the-earth folks dressed to the nines for their fancy dinner out, tipsy attorneys loose lipped at the bar and octogenarians being seated for dinner by 5 p.m. — that’s the Portland I fell in love with. And if the gentrification ever gets too bad, I say, “Anchors aweigh on the S.S. DiMillo, please and thank you!”

DiMillo’s is open Monday through Saturday noon to 9 p.m., and accepts reservations by phone. Dig the 3-D tour of the boat on

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