The Rita Moreno, Gargoyles on the Square
A string of too many unfortunately flavored concoctions had put us off anything other than the classics...and then we met the Rita Moreno. A sexy southwestern cousin of the cosmo, it combines vodka, Rose's lime juice, and fresh lemon with sriracha and cilantro. The resulting creation strikes a perfect tart-sweet balance, then takes the experience to the next level with a spicy kick. 219 Elm St., Somerville, MA 2144, .
Spice
Pittsfield, once derided as the underarm of the Berkshires, has made a turnaround in recent years, thanks in part to its revitalized North Street. The hippest on the block is the much-hyped contemporary American eatery Spice. The place is at its liveliest after the dinner rush, when the band packs up and an energetic young crowd assembles in the roomy backlit bar for sipping and mingling. 297 North St., Pittsfield, MA .
Sconset Café
Hidden away on the eastern end of the island, the Sconset Café isn't fancy and serves no alcohol (has a BYOB setup), but it's got one of the best little menus around. Entrées change often, and depending on the season might include salmon in saffron-tomato fish broth with ;ciabatta or grilled chicken with garlic and scallion mashed potatoes. If you're fortunate, the knockout lemon tart with homemade lime cream will be available. You'd be wise to order it, even if you think you're stuffed. Post Office Sq., Siasconset, MA 2564, sconsetcafe.com.
Figs
Part of the original English (as in Todd English) restaurant empire, Figs in Charlestown still serves delicious thin-crusted pies with simple toppings, innovative salads laced with blue cheese and toasted walnuts, and rich and warming plates of handmade pastas to the upwardly mobile. Rarely can you get such homecooked flavor or feeling in a restaurant. And with such earthly prices, the question really becomes, Why not eat here every night? 67 Main St., Charlestown, MA cheftoddenglish.com.
Winston Flowers & Garden
Winston's Newton store feels more like a mom-and-pop shop than the Boston area florist's biggest location. The mind-boggling array of blooms on offer includes roses, hydrangeas, peonies, calla lilies, and arty, twisted sea grass. And the resourceful, creative staffers will be eager to help you, once you're done staring slack-jawed at the symphony of colors. 11 Florence St., Newton, MA winstonflowers.com.
Bergamot
This warm, elegant Somerville bistro was cleverly designed to suit both neighborhood residents and those who travel for a celebratory meal—a nice balance that can be attributed in part to wine director Kai Gagnon's skill in choosing wines for both crowds. His bottle list is lengthy and varied—a veritable tour through Europe—but there are also nearly two-dozen by-the-glass options for those with commitment issues. Most important? The knowledgeable servers to guide you to the perfect selection. 118 Beacon St., Somerville, MA 2143, bergamotrestaurant.com.
Yankee Lobster Company
The waterfront boasts flashy seafood emporiums mad with pricey cocktails and massive TVs, but we still head down the wharf to this retail arm of a decades-old lobster wholesaler. Sure, the napkins come in dispensers and the stellar view is of the street, but this is the freshest affordable seafood around. Grab a bowl of thick chowder, a basket of fried scallops, or go for lobster (in a bisque or on a roll) for a meal that's big on substance, not on flash. 300 Northern Ave., Boston, MA 2210, yankeelobstercompany.com.
The Comedy Studio
Few comedy clubs these days are actually dedicated to the craft—which makes this Harvard Square studio a rare gem. Not only does it fill seats six nights a week with a variety of acts, it also devotes time to nurturing up-and-coming cutups and runs a sought-after comedian-in-residence program. And because it's located above the Hong Kong, you can get your laughs with a side of greasy-good Peking ravioli and a scorpion bowl. 1238 Massachusetts Ave., Cambridge, MA thecomedystudio.com.
Harvard Book Store
It's not exactly a shock that Harvard is able to reel in big names for its reading series. The pleasant surprise is the sheer variety, from political leaders (Ralph Nader) to literary-world sweethearts (Gary Shteyngart). Listen to discussions on the environment, the economy, or good old-fashioned plot analysis—and even take part in one yourself, with the book circle or the "Philosophy Café" Many events are free, and the ones that aren't seldom cost more than $5. 1256 Massachusetts Ave., Cambridge, MA 2138, harvard.com.
Jerry Remy's
Owned by Mr. Red Sox Nation himself, Jerry Remy's has upped the ante (and the cholesterol count) for Fenway bars. The TVs are mammoth, and the kitchen serves a burger wedged between two pieces of fried dough. Best of all, the barroom is so close to the park that when the windows are open, you can even join a 'Yankees suck' chant while noshing on a tasty RemDawg sandwich. 1265 Boylston St., Boston, MA 2215, jerryremys.com.
Alma Nove
Technically speaking, Alma Nove is a restaurant. But why quibble? There are only so many places where you can sit outside next to a giant fire pit, sip a well-crafted cocktail, and look out over the bay—and this Wahlberg-family-owned spot is one of them. If you just can't miss the Sox game, head inside. The bar is long and armed with two 50-inch TVs. 22 Shipyard Dr., Hingham, MA almanovehingham.com.
The Scarlet Oak Tavern
With its classically elegant dining room and steak-and-seafood-packed menu, the Scarlet Oak plays the part of a swanky suburban establishment. But don't expect the usual tepid filet mignon and gluey mashed potatoes. Every dish, from the spicy tuna tartare and perfectly cooked rib-eye to the oven-fired blue-crab-and-sharp-cheddar dip, is meticulously prepared and delicious. 1217 Main St., Hingham, MA 2043, scarletoaktavern.com.
Giblees
Occupying the better part of a nondescript strip mall on Route 114, Giblees has attire for every manly occasion: golf, work, weekends, and formal affairs—plus a pool table and coffee bar for gents who need a break from the dressing room. Assistance is available but never forced—our inquiry about a birthday bow tie for a super-stylish pal yielded a drawer full of dapper options. 85 Massachusetts 114, Danvers, MA 1923, giblees.com.
Chez Nous
In his newly renovated restaurant, chef Franck Tessier serves extraordinary French cuisine including goat cheese—and—portobello timbale, scallops with saffron risotto, and chicken fricassée. Guests sit in one of three tasteful dining rooms, and pastry chef (and Tessier's wife) Rachel Portnoy makes a hot chocolate mousse and a banana toffee tart that are sweet bliss. 150 Main St., Lee, MA cheznousbistro.com.
The Williamsville Inn
Set in bucolic West Stockbridge, the Williamsville Inn boasts everything a home away from home should: superb service, snowy linens, and cut flowers. Husband-and-wife team Erhard and Kandy Wendt have transformed this once dilapidated 18th-century inn into a modern country guesthouse complete with blond hardwood floors and quaint touches. Erhard also acts as the inn's chief chef, and his German-inspired fare is some of the finest in the county. 286 Great Barrington Rd. (Rte. 41), West Stockbridge, MA williamsvilleinn.com.