Mr. Sid
Is there anything out there more wonderfully old-school than Mr. Sid? The parquet floors; the in-house bar, hair salon, and billiards table; the genteel service—it all feels reminiscent of another time. The clothing itself is as current as it gets, however, with sharp styles from the likes of Ermenegildo Zegna, Brioni, and Scott James, plus a collection of high-end footwear. Men who prefer to go bespoke will appreciate the "made-to-measure" program, which offers custom clothing from a selection of the store's designers. 1211 Centre St., Newton Centre, MA mrsid.com.
Surroundings
There was a time when anyone on the South Shore interested in fine furnishings had to make the trek up to Boston. But there's no need now. At this lovely one-stop decor shop, you'll find outstanding American lines like Oly and Hickory Chair, French furnishings made by Grange, and accessories by the Vermont-based Simon Pearce. Overwhelmed? Seek out the in-house designer, Bill Barr, who offers complete interiors service. 81 1/2 Fairhaven Rd., Mattapoisett, MA surroundingshome.com.
Wilson Farm
Since the 19th century, the sprawling barn at Wilson Farm has proffered more than 100 varieties of the grower's own fruit, vegetables, herbs, and flowers; fresh-baked breads and pastries; locally made cheeses; and house-made pastas, soups, salads, and more. It's a one-stop shop in the dead of winter, the height of summer, and any time in between. 10 Pleasant St., Lexington, MA 2421, wilsonfarm.com.
Union Brewhouse
Wood paneling, arcade games, a collection of retro beer cans ... hopping onto a barstool at the Union Brewhouse is like sneaking down to your uncle's basement man cave, circa 1976. Thankfully, the beer selection goes well beyond Bud longnecks at this laid-back spot, which boasts 17 craft beers on tap (including special offerings from the likes of Oskar Blues and Firestone Walker) and more than 100 bottle selections (Belgium's Delirium Tremens and Duvel, among others). 550 Washington St., Weymouth, MA 2188, unionbrewhouse.com.
Fin
The romance started with a rich local-oyster-and-bacon chowder with chive and truffle oil. Then came the scallops with oyster mushrooms, asparagus, pancetta, pea shoots, and chive béarnaise, and then the organic beef special with ramps and shiitakes. By the time the heavenly macademia-nut-and-coconut tart showed up, we knew for certain that this homey new spot from Brewster Fish House alum Martha Kane would be more than just a one-night stand. 800 Main St., Dennis, MA 2638, fincapecod.com.
French Memories
As if life on picturesque Duxbury Harbor wasn't sweet enough, French Memories steps in with a cadre of top-notch carbs to up the ante. On hand are tiny petits fours and crunchy baguettes that would hold their own anywhere along the Seine. But the standouts are the truly irresistible almond croissants. Their crispy, buttery layers and dense, nutty filling condense into one cakelike bite. 459 Washington St., Duxbury, MA frenchmemories.com.
American Seasons
It's dark in here. That's one of the reasons couples come in to snuggle up. The other is what amounts to a cross-country tour of American cuisine. We suggest sticking close to home with local seafood and cornmeal polenta, or venturing into the West for hangar steaks and Humboldt Fog goat cheese. Whatever you choose—from here, there, or everywhere—you'll get thoughtfully prepared, seasonal food that's somehow also very sexy. 80 Centre St., Nantucket, MA americanseasons.com.
Sunset Grill & Tap
Just reading the beer menu at the Sunset is enough to make your head spin. At last count there were 100 brews on tap here, as well as 300-plus bottled beers. The selection ranges from the prosaic (Pilsner Urquell) to the obscure (Stone's Arrogant Bastard Ale) to the unpronounceable (the Gueuze 100% Lambic is said to be the champagne of beers). For connoisseurs, there's usually a cask-conditioned ale, like the popular Middle Ages' Wailing Wench; for the less discerning, there are the always-reliable Bud Light longnecks. 130 Brighton Ave., Allston, MA 2134, allstonsfinest.com.
21 Federal
Much as we enjoy fighting for a bar stool with sunburned tourists and libidinous and over-lubricated college students, we do sometimes crave a slightly more civilized scene. 21 Federal, inside a classic Nantucket 1847 Greek Revival building, features a sophisticated downstairs bar and another cozy one upstairs. In-the-know Nantucketers congregate here for masterfully poured drinks; an award-winning wine list; good-looking, genial bartenders; and a crowd that knows how to have a stylish sort of fun. 21 Federal St., Boston, MA 21federal.com.
Coolidge Corner Theatre
The sad fact is that big corporate multiplexes show big corporate movies. Truly, you are what you screen. Which makes Brookline's Coolidge Corner Theatre an art-house jewel among the plastic giants. This 75-year-old, not-for-profit space boasts a classy schedule of documentary, international, and independent movies. The Coolidge also keeps a hand in the community by hosting readings, live performances, and film festivals. 290 Harvard St., Brookline, MA coolidge.org.
Club Hollywood Boston at Ekco Lounge
Butches and femmes hoist their bottles together here on Saturday nights, when this Chinatown karaoke lounge and dance club becomes the closest thing lesbians have to a downtown clubhouse. Two levels of dance floors offer ample space for the mostly young and urban crowd to get down to electro, house, and hip-hop. Once a month, grrls slip on suits and fedoras (and boys and butches, dresses) for "drag karaoke." 41 Essex St., Boston, MA .
Castle Island
What more could you want in a picnic spot? There's grass for the kids and animals, picnic tables, water surrounding you on all sides and a 2.1-mile exercise loop to work off your lunch. Want to picnic without packing? Swing by Sullivan's, a takeout eatery serving burgers, fries, seafood, and ice cream at the entrance to Castle Island. The kicker? Free entertainment in the form of planes roaring over the area seconds before they land at Logan. William J. Day Boulevard, South Boston, MA mass.gov/dcr/parks/metroboston/castle.htm.
Coolidge Corner Theatre
This Brookline landmark sure knows how to draw 'em in. While other art houses are content dishing out classics, these guys go right for the guts, with events like Annie Sprinkle's Herstory of Porn: Rell to Real, Spike and Mike's Sick and Twisted Animation Festival, the New England Film & Video Festival, and even a summer jazz series. They've got a new lease under negotiation, a new spirit, and a fresh pot of coffee brewing for late-night shows. 299 Harvard St., Brookline, MA .
The Roof at the Ritz-Carlton
Plan ahead if you want to trip the light fantastic at this, the city's chicest summer dinner-cum-dancing destination for those of us who outgrew Landsdowne Street years ago. Seating, especially for groups, is booked weeks, sometimes months, ahead. The good news is your alfresco evening will take place regardless of weather: A huge tent encloses tables, band, and dance floor, keeping well-coifed guests warm and dry. 15 Arlington St., Boston, MA .
Lenox Hotel
Whether you're a movie star craving anonymity or a suburban couple looking to flee the rugrats for a night, the Lenox beckons with European elegance and discretion, meaning the doorman may know your name but he'll make sure nobody else does. Escape into the newly renovated (at a cost of $20 million) Back Bay jewel, with its imported crystal chandeliers, working fireplaces, lush carpeting, Victorian wallpaper, gilt-framed Italian, French, and English prints—and the fabulous Anago restaurant. 710 Boylston St., Boston, MA .