When celebration is in order (or money simply isn’t an object), Bostonians reserve at Clio (370 Commonwealth Ave., 617/536-7200, 6:30 a.m.–10:30 a.m., 5:30 p.m.–10 p.m. Mon.–Sat.; 5:30 p.m.–10 p.m. Sun., www.cliorestaurant.com , $34–44). With one of the most elegant menus in town, chef Ken Oringer pulls out all the stops on both flavor (butter-basted Maine lobster and California squab with truffles) and adventure (red shrimp sashimi with caviar).
Grab a seat at cheeky Delux Café (100 Chandler St., 617/338-5258, 5 p.m.–1 a.m. daily, $7–13) and prepare for the unexpected. The clientele is a mix of seemingly every kind, as is the decor—which includes an Elvis shrine and a miniature Christmas tree that stays up all year. The menu makes the lowly grilled cheese sandwich into a work of art.
One of the first restaurants to help transform the South End  into a restaurant mecca, Hamersley’s Bistro (553 Tremont St., 617/423-2700, 5:30 p.m.–9:30 p.m. Mon.–Fri.; 5:30 p.m.–10 p.m. Sat.; 11 a.m.–2 p.m. and 5:30 p.m.–9:30 p.m. Sun., www.hamersleysbistro.com , $25–38) evokes a slice of French countryside. The buzzing, airy dining room fills with the smell of roasted chicken with garlic and the sound of conversation and food being enjoyed.
Ask most chefs where they go to unwind after hours and they’ll tell you Franklin Café (278 Shawmut Ave., 617/350-0010, 5:30 p.m.–2 a.m. daily, www.franklincafe.com , $16–19). There they can slip into the wooden booths and sup on rosemary-grilled shrimp and just chill out.
Short of hang gliding, the best view of the city is from the windows of the Top of the Hub (800 Boylston St., 617/536-1775, 11:30 a.m.–1 a.m. Mon.–Sat.; 11 a.m.–midnight Sun, www.topofthehub.net , $27–48), on the top floor of the Prudential Center. Go for the vista rather than the victuals; dinners are mostly perfunctory continental cuisine.
Bumped up against the upscale world of Newbury Street, The Other Side Café (407 Newbury St., 617/536-9477, 11:30 a.m.–1 a.m. Mon.–Wed.; 11:30 a.m.–2 a.m.; Thurs.–Fri.; 10 a.m.–2 a.m. Sat.; 10 a.m.–1 a.m. Sun., www.theothersidecafe.com , $6–10) is a refreshing enclave of funky, alternative café culture and cheap vegetarian sandwiches and salads.
Gelati, sandwiches, and pastries fly from the counter to tables at L’Aroma (85 Newbury St., 617/412-4001, 7 a.m.–7 p.m. Mon.–Fri.; 7:30 a.m.–7 p.m. Sat.; 8 a.m.–7 p.m. Sun., www.laromacafe.com , $6–7).
On the bang-for-your-buck front, don’t miss the eclectically decorated Anchovies (433 Columbus Ave., 617/266-5088, 5 p.m.–11 p.m. Mon.–Sat.; 5:30 p.m.–11 p.m. Sun., $7–14). None of the pasta prices rise much above $10, and pizzas start at $5.
Meaning “crazy way” in Italian, Via Matta (79 Park Plaza, 617/422-0008, 11:30 a.m.–1 a.m. Mon.–Sat.; 11 a.m.–midnight Sun., www.viamattarestaurant.com , $16–38) is one of the hottest restaurants in a culinary ghetto known as Park Square. The loud dining room jumps with a crew of regulars downing perfectly made pasta and simple Italian classics.
One of the hottest new tables in Back Bay is City Table (61 Exeter St., 617/933-4800, 11:30 a.m.–1 a.m. Mon.–Sat.; 11 a.m.–midnight Sun., $24–34), the big-ticket seafood restaurant that takes the whole ocean as its inspiration. Chef Robert Fathman has concocted witty takes like “oysters in bondage” (that is, encrusted in smoked salmon and potato, and daubed with sour cream and caviar).
Now a national chain found in eight states, Legal Sea Foods (26 Park Plaza and other area locations, 617/426-4444, 10:30 a.m.–midnight daily, www.legalseafoods.com , $16–37) still sets the standard for creamy New England clam chowder and other classics like steamed cod and boiled lobster. Its latest menu twist is “ayurvedic” cuisine loaded with fiery South Indian spices.
In most cases, a steakhouse is a steakhouse. But Grill 23 Bar & Grill (161 Berkeley St., 617/542-2255, 11:30 a.m.–2 a.m. Mon.–Fri.; 11 a.m.–2 a.m. Sat.; 11 a.m.–midnight Sun., www.grill23.com , $27–49) moves beyond the usual formulaic clubby decor and menu to include big bouquets of flowers in its airy space and tilapia on its specialty board. The usual suspects (prime rib to lobsters) are there, too—as are desserts like rhubarb cobbler and an epic wine list.
A café with counter service, Flour Bakery (1595 Washington St., 617/267-4300, 7 a.m.–9 p.m. Mon.–Fri.; 8 a.m.–6 p.m. Sat.; 9 a.m.–5 p.m. Sun., www.flourbakery.com , $8–13) does a swift business in both take-out and eat-in. The biggest draw is the baked goods—fruit tarts, sandwiches, and cookies.
At Charlie’s Sandwich Shoppe (429 Columbus Ave., 617/536-7669, noon–10 p.m. Mon.–Sat.; 5 p.m.–10 p.m. Sun., $4–9), you go for the excellent turkey hash and breakfast specials, and stay for the communal tables, loud diner atmosphere, and funny wait staff.
Odds are you won’t find a juicier burger in town than those at Tim’s Tavern (329 Columbus Ave., 617/437-6898, 11 a.m.–11 p.m. Mon.–Sat.; 5 p.m.–10 p.m. Sun., $7–14), and if you do, you certainly won’t find one any cheaper. The people-watching, meanwhile, is equally good: Cops gab with artists, barflies drink with students, and everyone plays tunes on the jukebox.
The eclectic Tremont 647 (647 Tremont St., 617/266-4600, 10:30 a.m.–2 p.m. and 5:30 p.m.–10:30 p.m. Sun.–Thurs.; 10:30 a.m.–3 p.m. and 5:30 p.m.–10:30 p.m. Fri.–Sat., www.tremont647.com , $13–25), with its lively staff and even livelier dining room, has one of the most loyal clienteles in town. They come back for fixings like lamb sirloin with pomegranate glaze and “two stinky cheeses” with black truffle honey.
The multi-floored Tapeo (266 Newbury St., 617/267-4799, 5 p.m.–midnight Mon.–Sat.; noon–10 p.m. Sun., www.tapeo.com , $24–25) is as popular for its al fresco patio as for its tiny plates of tapas (the roast duck with blackberry sauce is a knockout) and citrusy pitchers of sangria.
Picture the quintessential tapas hangout in Spain, and you’ve got Toro (1704 Washington St., 617/536-4000, noon–midnight Mon.–Sat.; 10:30 a.m.–2 p.m. and 4:30 p.m.–midnight Sun., $4–15), a paragon of the genre.