1. The Upper East has long offered refuge from the riffraff (some call it character) that permeates New York. Two hundred years ago, country estates like Gracie Mansion (88th St at East End Ave) lined the river, and wealthy businessmen traveled by boat rather than car. These days, the 1799 mansion is the official mayor’s residence—lived in by everyone but Bloomberg since 1942—and open only on Wednesdays for tours ($4–$7, students free; reservations required—call 311).

2. Head west to Doyle New York (175 E 87th St between Lexington and Third Aves, 212-427-2730), where boom-time extravagances hit the block. The auction house holds exhibitions before every sale: Check out Warhol Factory girl Brigid Berlin’s rhinestone cuffs and Chanel flower pins at “Costume Jewelry,” Saturday 4–Monday 6 (10am–6pm).

3. Locals giving you cashmere envy? Find armloads of it at The Arthritis Thrift Shop (1430 Third Ave between 81st and 82nd Sts, 212-772-8816), a trove for luxe bargains like Ferragamo coats ($145) and Manolo Blahniks ($75). Investment bankers should rummage at the Memorial Sloan-Kettering Cancer Center Thrift Shop (1440 Third Ave between 81st and 82nd Sts, 212-535-1250) to keep up appearances: Fine wool Brioni suits, normally $4,000, go for $350.

4. Get some marble beneath your feet at the Beaux Arts Neue Galerie (1048 Fifth Ave at 86th St, 212-628-6200; $10–$15), a former Vanderbilt home that now houses the most opulent painting in the city, Gustav Klimt’s lustrous gold Adele Bloch-Bauer I.

5. Amble down to Crawford Doyle Booksellers (1082 Madison Ave at 82nd St, 212-288-6300), probably the only store along Madison you can afford. There’s an afternoon’s worth of browsing here, with used auction catalogs on carts outside and clerks eager to talk fiction. And don’t miss Burlington Antique Toys (212-861-9708) in the basement; it’s lined with cases of toy soldiers and oil paintings.

6. For a private club dating back to 1754, The New York Society Library (53 E 79th St between Madison and Park Aves, 212-288-6900) is surprisingly welcoming. Nonmembers can use the reference room to read books from the extensive history and arts collection, or tour the wood-paneled study.

7. To stretch your lunchtime dollar, head east to the popular J.G. Melon (1291 Third Ave at 74th St, 212-744-0585), a dim, tin-ceilinged pub, for a juicy burger ($8.50) and cottage fries ($4.25). Filled with Ivy Leaguers and their lunching mothers, this local fave makes cheap eats socially permissible.

8. Walk down Madison to Ralph Lauren (867 Madison Ave at 72nd St, 212-606-2100), a Waspy fun house hung with oil portraits and crystal chandeliers. Formerly the Rhinelander Mansion, the chateau-style building was commissioned by an eccentric socialite who ran out of money before she could move in. Outside, look for statues of knights on the second-story wall.

9. Long before hedge-funders hoarded Damian Hirsts, Henry Clay Frick bought Rembrandts and Sèvres porcelain. His mansion, with its elegant furniture and burbling fountain, now houses The Frick Collection (1 E 70th St at Fifth Ave, 212-288-0700; $5–$15), which is pay-what-you-wish on Sundays from 11am to 1pm.

10. Lastly, trek east to the Mount Vernon Hotel Museum (421 E 61st St between First and York Aves, 212-838-6878; $7–$8, children under 12 free), a 19th-century carriage house with a front porch and sloping lawn. In the 1820s, genteel society retreated here to dine on turtle stew and swim in the East River. You can tour its parlors, tavern and garden. It may be the only getaway locals—even UESers—can afford.