American Seasons
It's a bold statement for a city mag to give the stellar-cellar nod to a restaurant located a couple of hours (and several modes of transportation) from downtown. But for those willing to roll with the car-ferry-taxi shuffle, the reward is Orla Murphy-LaScola's gem of a wine list at American Seasons, packed with off-the-beaten-vine vintages from the States. Even jaded sommeliers—stuck tending to creaky libraries of 'important' quaffs from Burgundy and Bordeaux—scratch their heads in amazement at theeccentric yet impeccable collection of small-production wines. 80 Centre St., Nantucket Island, MA 2554, americanseasons.com.
Finale
Finale has the whoopie down to a sweet science: Two palm-size triple-chocolate cookies sandwich a white-chocolate cream-cheese filling. The local dessert chain, which also bakes bite-size whoopies, has late-night hours and multiple locations, letting you take care of those cake-and-cream cravings at (almost) any time. 1 Columbus Ave., Cambridge, MA 2138, finaledesserts.com.
Penang
This refreshing addition to Chinatown has lots of blond wood, modern lighting, and great food. Start with the Penang Poh Piah (steamed spring roll) or Crispy Pork Intestines (you might enjoy this one more if you order in Malaysian). Vegetarian entrees—especially the bean curd—are terrific, as are the varied seafood selections. Late hours are a plus. 685-691 Washington St., Boston, MA .
Barefoot Books
Kids? Reading? Ha. Pass the remote. Fortunately this Porter Square independent publisher and bookshop still emphasizes literacy and creative storytelling, matching up unequaled illustrations with cross-cultural tales to create award-winning titles such as The Gigantic Turnip and the celebrated My Daddy Is a Pretzel. In-store craft sessions, sing-alongs, and community store hours further the case for imagination—no batteries required. 1771 Massachusetts Ave., Cambridge, MA barefootbooks.com.
Tennesse's
By the time the meaty ribs and chicken served up here come off the smoker, they've been slow-cooked for as much as 14 hours over apple, hickory, and cherry woods. Add the tangy homemade sauces, and you can see why Tennessee's is running out of room on the wall of its strip-mall locale for the list of barbecue cookoffs it's already won. Well, here's one more. 341 Cochituate Rd., Framingham, MA tennesseesbbq.com.
Petrushka at ArtsEmerson
Master puppeteer Basil Twist's adaptation of Stravinsky's ballet about a tragic love triangle among a clown, a ballerina, and a Moor managed to convey humanity and grace in the movement of Japanese-style marionettes. One compact hour long, it begged for repeat viewings from both kids and adults. Unique productions like this during ArtsEmerson's inaugural season have proven that this organization should be central to Boston arts for years to come. 559 Washington St., Boston, MA 2139, artsemerson.org.
Colonnade Hotel
Here's the setting: bright blue sky, bright blue water, handsome poolside staff, a full bar and lunch menu, and a 360-degree view of Boston's skyline. On weekdays, 40 bucks buys 12 suntastic hours more than 100 feet above the sweltering sidewalk (towels and an outdoor shower included). Cheapos can spend $20 for a late-afternoon poolside outing, but there's no guarantee of scoring a seat. 120 Huntington Ave., Boston, MA 2116, colonnadehotel.com.
Alchemy
Alchemy: A magical process of transmuting base metals into gold; the quest for the elixir of life. While falling a little short of offering immortality, this restaurant and bar does routinely deliver decadent night life—and damn good risotto fritters. The two-story modernized French bistro bustles after hours as patrons sip key lime pie martinis, cognacs, imported beer, or pinot noir from an affordable wine list. 71 Main St., Edgartown, MA 2539, .
Pine Cobble Trail
If Williamstown is the pro-totype for a picture-perfect country hamlet, its Pine Cobble Trail is the picture-perfect country hike. The wooded 4-mile ramble tops out at 2,100 feet and offers uninterrupted views of Williamstown, North Adams, and the taller and more touristy Mount Greylock. The moderate climb, steep at times, can be completed in two hours, but why rush? Come in September, and the surrounding hills will be ablaze with orange and gold foliage. Pine Cobble Road, Williamstown. Pine Cobble Road, Williamstown, MA 2167, .
Cisco
Nantucket is filled with righteous beaches, but there's something extra-special about Cisco and its shifting moods. On calm afternoons, surfers ride rolling waves for hours, then nap in soft, white sand. On windy mornings, thrill-seekers get adrenaline rushes by battling serious South Shore breakers. And on sunny island days, locals lunch and soak in some rays while being watched over by lifeguards, but not trampled on by tourists. Off Hummock Pond Road, Nantucket, MA 2554, .
The Wauwinet
What's almost as unbearable as the slow ferry to Nantucket? The July and August crowds. Get away from it all at the Relais & Châteaux-recognized Wauwinet, perched among the dunes on the island's sleepy eastern tip. Sunbathe on the resort's private beaches, sip sparkling rose at Topper's, or indulge in a basalt-stone massage at the spa. And if you suddenly desire civilization, there's a shuttle to town that runs daily on the hour. 120 Wauwinet Rd., Nantucket, MA wauwinet.com.
Cisco Brewers
With a brewery, distillery, and winery all surrounding one chill courtyard, this is the perfect place to while away a few afternoon hours on the Grey Lady. Sip a Summer of Lager, slurp oysters (if you're lucky enough to catch the occasional raw bar), and play cornhole, all set to live tunes played by local musicians. Bonus: It's located off the new Hummock Pond Road bike path, so you can safely coast there and back to town. 5 Bartlett Farm Rd., Nantucket, MA ciscobrewers.com.
The Jesuit Urban Center, South End
True, many happy couples found their love in the Ralph Lauren paint department of Homo Depot—er, Home Depot. But Sunday morning Mass at the Jesuit Urban Center spawns more blessed pairings. The Urban Center's liturgy is both classic and contemporary; its mixed congregation is mostly gay; its AIDS and HIV support programs are some of the in town; and its coffee hour is a great place to get phone numbers. 775 Harrison Ave., Boston, MA .
Jillian's
Among up-scale pool halls, the original Jillian's gets bonus points for being there first. But what sets it apart from the competition is all the stuff beneath the third-floor pool tables: hundreds of high-tech video games on the second floor and a decent restaurant/mental amusement park called the Atlas Grill at street level. Which means there's lots of things to do on a Friday night while you wait hours for a pool table. 145 Ipswich St., Boston, MA .
Boston Bowl
If Chuck E. Cheese is for country mice, this place is definitely for city mice. A longtime (since 1959) magnet for neighborhood families, it boasts 44 bowling lanes (30 ten-pin, 14 candlepin), 12 billiard tables, 80 video games, a free indoor playground, and tasty pizza. It's also open 24 hours a day, seven days a week, so it draws its share of singles, too. 820 Morrissey Boulevard, Dorchester, MA .