Begin at the northeast corner of Plaza Mayor [1] and perambulate the square counterclockwise, taking in all the sights of interest. Back at the northeast corner, immediately east of the cathedral, cobbled Calle Fernando Hernández (Cristo) leads past a wide staircase.
At the base of the steps is a handsome ocher-colored house—the Mansión de los Conspiradores—with an ornately woodworked balcony. The house is so named because La Rosa Blanca (the secret organization against Spanish colonial rule) met here.
One block east on Cristo brings you to the triangular Plazuela de Segarta and Calle Jesús Menéndez, containing some of the oldest homes in the city, among them the Casa de la Trova, dating to 1777. Off the northeast corner of the plazuela is Calle Juan Manuel Márquez, featuring a trio of houses with wonderfully photogenic elevated galleries.
Turn left on Márquez and walk west one block to Simón Bolívar. To your right, atop the hill, you’ll see the near-derelict Iglesia de la Virgen de la Candelaria de la Popa. It was built in 1726 and is named for the popa (stern) of a ship called the Virgen de la Candelaria that sank off Cartagena. The stern washed ashore near Casilda and a chapel was built. Ascend for the views over the city. (You can continue uphill behind the church to the top of the mountain for unsurpassed views.)
Traveling three blocks farther along Márquez delivers you at Plaza de Tres Cruces, a bare-earth area pinned by three wooden crosses that for several centuries have formed the terminus of [node:61346 link Trinidad annual Easter procession. Note the houses with metal crosses on their exterior walls: They’re way-stops on the procession.
Return along Márquez to Ciro Redondo; turn right. The house at #261 dates to 1754 and was built for Carlos Merlin, a French pirate. Turn left onto Fernando Hernández Echarrí. On your right, at the end of the block, is the Antiguo Convento de San Francisco de Asís. After visiting, turn right onto Piro Guinart and walk one block to Plaza Jigüe, then walk southeast one block to Playa Mayor and turn right onto Simón Bolívar. The cobbled street leads downhill past the Museo Histórico. At Maceo (three blocks), turn right and follow this wide cobbled street for three blocks. Turn right on Lino Pérez, which leads you two blocks downhill to Parque Céspedes at Martí. On the southwest side is the Iglesia de Paula.
Anyone with an interest in art might follow Lino Pérez south five blocks to the former Antigua Cuartel de Dragones (dragoons’ barracks), built in 1844 and now the Academía de Artes Plásticas (Prolongación de Camilo Cienfuegos, tel. 041/99-4350, triart [at] hero [dot] cult [dot] cu, Mon.–Fri. 8 a.m.–5 p.m.). It has seasonal exhibitions of students’ work. Although it’s not normally open to the public, guides are usually happy to show you the various talleres (workshops), from ceramics to computation. It hosts semester-long courses for foreigners.
One block west, the Fábrica de Tabacos (Anastacio Cárdenas, e/ Lino Pérez y Cienfuegos) is closed to the public.
Links:
[1] http://www.moon.com/destinations/cuba/sancti-spiritus-province/trinidad/sights/plaza-mayor