Boston, MA - Insomnia’s never been an easy proposition in Boston. You’d think a city of close to 700,000 residents (and one which still has the audacity to refer to itself as “the Hub of the Universe”) might offer some form of condolence for those of us whose biological alarms refuse to cease their infernal racket when that last train pulls out of Park Street at 12:30, but you’re wrong. If New York is the City that Never Sleeps and Los Angeles is the “City of Light,” then Boston is the City of Sensible Lifestyles and Biotech Dreams.

You can call it a genetic disposition. A deeply ingrained Puritan hangover. But it wasn’t always this way. If you can remember the days of after-hours Chinatown joints complete with “cold tea,” you probably weren’t there; but they once were as plentiful on Harrison or Tyler St as road construction or illegal parking (not that we’re, um… speaking from experience or anything.) Bad crab rangoons and $10 cover charges not your idea of a 3 a.m. snack? The cholesterol laden trifecta that was Denny’s International House of Bickford’s could guarantee you a bottomless cup of hyper caffeinated heart palpitations and voyeurism at one point. These days, you’ve got to trek a mighty wind out of the city into the North Shore suburbs just to savor the sound of Belinda Carlisle’s music and sizzling trans fat.

Fortunately, there’s still some holdovers left in the city who realize that an unblinking eye and an empty stomach are not mutually exclusive. They’re not plentiful; but they’re a veritable oasis for those of us for whom a good night’s rest is an afterthought. We’re grateful for them; and even if you’re the proverbial morning person, they still deserve your patronage.

Bova’s Bakery
(134 Salem St, Boston bovabakeryboston.net)

New to the city? Just visiting? While we’d love to tell you that the North End you hear so much about is dead after 7:00 pm (especially on the weekends,) we just can’t lie to you. Especially not when Bova’s has been an all-night staple since 1926. If it’s traditional Italian cannolis and tiramisu you’re in the mood for, you can skip the three hour wait at Mike’s and go to the real source; but frankly, we’d recommend their infamous Sicilian pizzas at 3:00 am at least once in your life—just to see how the other half lives.

Doughboy Donuts & Deli
(220 Dorchester Ave, Boston www.doughboydonutsanddeli.com)

Can’t decide if your inner child is Homer Simpson or Count Dracula? You can feed both on the cheap at Doughboy. What you see is what you get; don’t expect pumpkin spiced anything, and if you’re foolhardy enough to try the Fruity Pebbles glazed donut, make certain you have your dentist’s number handy in the morning. But the carrot cupcakes are more hit than miss, and if you’re there early enough (by 10:00 pm,) the pizza’s some of the best on Dot Ave; at least for the immediate two blocks.

South Street Diner
(178 Kneeland St, Boston www.southstreetdiner.com)

Yes, South Street is one of the few remaining diners in Boston; and they’re all too happy to make that clear to you. And yes, they are considered a Boston landmark; a fact that they’ll beat you over the head with at every conceivable chance. And yes, you can find yourself waiting upwards of an hour to find a booth—no matter what time of day it is (call ahead to reserve.) But is it worth the fuss? Let’s see… Chocolate french toast or steak and eggs alongside a mimosa at 1:00 am? You be the judge.

Victoria’s Diner
(1024 Massachusetts Ave, Boston www.victoriasdiner.com

Unlike South Street, Victoria’s doesn’t have to remind you that they’re one of the oldest diners in Boston. Or that they’re open 24/7; chiefly because they’re not (only on Thursdays, Fridays and Saturdays.) Nor are you likely to see Victoria’s the next time some misguided filmmaker wants to capture the “real” Boston. That’s mainly because they can’t decide if their latest iteration is a greasy spoon, an urban foodie outpost, a hipster bistro or some hybrid of the three. Nor do we care. All we know is that the bourbon pecan pie is enough to make you say “South Street what?” As are the short ribs. As is the hot fudge bourbon milkshake. Come to think of it, so is the...

IHOP
(1850 Soldiers Field Rd, Brighton www.ihop.com)

Frankly, we were a bit hesitant to put IHOP on this list. For one, our heads are still reeling from the marketing blitz last summer when they announced they would now be known as “IHOB.” And then back to IHOP. Or is it? But more importantly… we’ve had bad experiences at IHOPs. Not just bad, but horrifying. We mean something out of a David Goodis novel sort of experience. Not on account of the food, mind you. Or the service. Both are just as you remember them from when you were a kid. Perfectly adequate. And you know exactly what you’re going to get. That damn Rooty Tooty Fresh & Fruity thing. And coffee. Bottomless vats of it. In fact, that what you could go for right now. And you’re going to. Go ahead. I’s open 24 hours. It’s going on the list because you really don’t have a choice. It’s as quintessentially as much an insomniac haunt as a 24 hour laundromat; which come to think of it, some young entrepreneur in Boston could make a fortune off of. But back to the experience. We had made the mistake of referring to it as IHOB one evening when…

For readers with insonmia or other sleeping issues, please visit The Sleep Foundation or contact a health professional.