It might not be the first thing you'll smell walking down street, but a frappe from Bartley's may be an even better reason to stop in than the tantalizing aroma of frying beef. Between batches of Elvis burgers and sweet-potato fries, Mr. Bartley's turns out one of the most consistent, reliable, straw-pluggingly thick frappes around, beating tony Boston ice cream parlors hands down. 1246 Massachusetts Ave., Cambridge, MA .
Some nights just call for a simple dinner served in a cozy dining room where the service is relaxed and the food is just like mama used to make. That's the essence of an evening at Sage, chef (and North End native) Anthony Susi's American-Italian bistro. No matter that the wait for one of the eight tables is often long: Susi's handmade gnocchi and pastas are heaven-sent, with melt-in-your-mouth textures and impeccable use of fresh seasonal ingredients. 69 Prince St., Boston, MA .
Here's a tavern in the truest—and best—sense of the world: a homey magnet for folks from many walks of life, with good comfort food and plenty of drink. The Washington Square hits all the right marks on all the scales: high on quality and atmosphere, but low on pretense. Hang at the long wooden bar or the communal tables to chat with everyone from pierced college kids to nuclear families, or slide into one of the dark corner booths with your better half for a dinner for two. 714 Washington St., Washington Square, Brookline, MA washingtonsquaretavern.com/.
Kill two birds with one stone: Armani Cafe —at the Prime Viewing Central between Fairfield and Exeter — is not only the best place to see other people, it's the best place to be seen in all your sartorial splendor. Required accouterments: cell phone, beeper, head-to-toe black Eurowear, and the Beemer double-parked nearby so all can see you coming and going. The pricey, trendy, yet tasty fare satiates cravings while you watch the creatures of Newbury stroll by. 214 Newbury St., Boston, MA .
With close to 200 herbs and spices to choose from, Harvest remains the wise shopper's best bet. Planning a romantic dinner? In one stop you'll find the cardamom, tumeric, and cilantro for your seductive Chicken Pasanda, and some Damiana herb to help keep the— uh— mood up. Bulk dispensers allow you to buy as much or as little as you need, and the staff is knowledgeable and friendly. 581 Massachusetts Ave., Cambridge, MA .
It takes a brave soul to sample lobster ice cream, and an even braver one to put it on a menu. But Ben & Bill's is that bold and, after years in the shadow of that other island sweet shop, has emerged as the Vineyard's frosty frontrunner. The servings of handmade ice cream (ginger, pumpkin pie) and gelato (tiramisu, chocolate mandarin) are enormous, but if your sugar cravings still aren't sated, you can bag some candy and truffles to go. 20A Circuit Ave., Oak Bluffs, MA 2557, benandbills.com.
If the smiling waitstaff, bright artwork, and delicious smells drifting from the kitchen don't immediately delight you, just wait for the food to arrive. Casa Portugal's fare will comfort homesick Lisboans and enlighten those unlucky ones who have yet to try classic and tempting combinations like tender pork with squid and clams, steak with fried egg and ham, and blackened chourizo sausages that arrive at the table still sizzling. 1200 Cambridge St., Cambridge, MA 2139, restaurantcasaportugal.com.
Sometimes it feels as if romance has all but vanished. Luckily there's L'Espalier, where Frank McClelland's sumptuous cuisine is guaranteed to set hearts aflutter. Settle into a table at one of the bay windows of this charming townhouse, and unwind together as a parade of champagne, oysters (served with a sensuous dab of pink sorbet), and decadent chocolates comes and goes as if by magic through our stomachs. 30 Gloucester St., Boston, MA lespalier.com/.
This is the most important baked good you'll ever purchase. With that in mind, shop owner Ellen Bartlett has a simple philosophy: Every one of her confections should taste as heavenly as it looks. Flavor options like mocha-Frangelico infusion and strawberry-orange blossom, combined with Bartlett's exquisite floral and graphic designs, make for tiers of absolute joy. 248 Cypress St., Brookline, MA 2445, cakestoremember.biz.
Gleaming, deep-cup Island Creek oysters. Salty-sweet Wellfleets. Fleshy shrimp and crab so tender, they go down in one gulp. This is the ocean's bounty as originally interpreted by way of French brasseries: an icy onslaught of shellfish that is mostly raw (of course), but occasionally cooked (as with the Jonah crab claws). Everything is so fresh, the sauces and mignonettes ought to be superfluous—and yet they're so damn tasty, you can't leave them alone. 129 South St., Boston, MA 2111, winebar.com.
With 112 drafts and 380 total beers to choose from, this just ain't much of a competition. Sure, other places offer great lists: The Publick House has a slate of about 35 beers on tap. But 35 is not 112. And where Lord Hobo—another bar with an admirable lineup—can come off as aggressively hip, friendliness rules the day at this Allston spot. The servers enthusiastically steer you through the menu in search of a pint that'll suit your mood. And that mood, more often than not, is a good one. 130 Brighton Ave., Allston, MA 2134, allstonsfinest.com.
For the past two decades, Barbara Lynch has relied on sommelier Cat Silirie for all things wine—and for good reason. No. 9 Park is one of the city's most rewarding places to order, sample, drink, and think about vintages and varietals—and then there's Menton, where Silirie's staff remembered wines that we'd liked and disliked during a visit the year before. Now if that's not service (and smarts), we don't know what is. 9 Park St., Boston, MA 2108, no9park.com.
The farther southeast you go in Massachusetts, the more Portuguese influence you'll find in the food. No one explores the genre quite as inventively as chef Brian Jenkins at Sintra. Drawing on Mediterranean flavors (as well as the coastal bounty at hand), he turns out punchy, unforgettable dishes like fisherman's stew with fennel, orange, and potatoes in saffron-tomato broth; mussels with chorizo and garlic toast in spicy tomato sauce; and grilled salmon with ratatouille and Sardinian couscous. 906 Washington St., Braintree, MA 2184, sintrarestaurant.com.
Sure, there's what seems like an interminable wait for one of the nine tables. But that's only because all the hipsters who got here before you want to savor every bite of their fashionably late dinners of adobo-rubbed pork and grilled garlic calamari. Our advice: Ask for a blood orange martini and be patient. You'll be very well rewarded. 278 Shawmut Ave., Boston, MA 2118, franklincafe.com.
After 40 years of Best of Boston, it takes a lot to shock us. But if you told us that we would eat a sandwich that doesn't even have meat—Cutty's eggplant spuckie, a ciabatta roll filled with mozzarella, olive-carrot salad, and, of course, roasted eggplant—and that it'd be one of the best sandwiches we've ever eaten, we'd be shocked. Guess what? We were shocked. Also great: the sandwiches that actually have meat (go Saturday for the special pork). 284 Washington St., Brookline, MA cuttyfoods.com.