Click MAP to locate destinations preceded by yellow numbers.

Begin your day at Columbus Ave. and Montgomery St., where old faces new: the old Transamerica Building (4 Columbus), originally the Fugazi Bank Building designed by Charles Paff in 1907, faces the new Transamerica Building (600 Montgomery), designed by William Pereira & Assoc. in 1972. Nearby is the former Bank of Italy building (550 Montgomery), designed in 1908 by Shea and Lofquist, with its ornate white marble interior.

As you walk through the Jackson Square Historic District, be sure to stop in at William Stout Architectural Books (804 Montgomery; 415-391-6757), a rare treat for architecture bibliophiles. En route to North Beach, note the Columbus Tower (Columbus at Kearny), designed in 1905 by Salfield & Kohlberg and now owned by Francis Ford Coppola. And don’t miss the 1860 St. Francis Church (610 Vallejo St.) and Beat poet Lawrence Ferlinghetti's City Lights (253 Columbus Ave.), America's first paperback bookstore.

Walk a block over to Stockton St., Chinatown's main food shopping strip. Architectural highlights include the Chinatown Library (1135 Powell), three buildings by Julia Morgan — the Gum Moon Residence (940 Washington St.), built in 1912; the 1932 former Chinatown YWCA (940-950 Powell); and the 1908 Donaldina Cameron House (920 Sacramento St.) — the Chinese Six Companies (843 Stockton) from 1908, and the Charles Rogers’ 1925 Nam Kue School (765 Sacramento). Portsmouth Square (750 Kearny St.), created in 1971 by Clement Chen/Warnecke & Assoc., was the plaza of the Spanish colonial port town Yerba Buena, renamed San Francisco in 1847. At California and Grant, two pagoda-like buildings designed in 1908 by Ross and Burgren — the Sing Chong Building and the Sing Fat Building — stand in marked contrast to the 1853 gothic revival Old St. Mary's, built by Chinese laborers. Sculptor Beniamino Bufano’s serene stainless steel and rose granite statue of Sun Yat Sen graces St. Mary’s Square.

Transamerica Tower

Old St. Mary's

Chinatown YWCA