I'll be honest with you: There is not much exciting about San Jose, it is a functional city and a logistics hub, and certainly nothing like Quito or Lima or Havana or any other Latin American capital. That said, for most travellers one or two days is sufficient to check out the city and experience some of its attractions and offerings.
The city is laid out on a grid, like most Spanish colonial towns, with narrow streets (many of these are one way only) and colonial architecture. It feels like a gritty downtown, especially some blocks near the bus stations, but that's only on the surface. Once we started walking there and interacting with people, it felt friendly and warm. Street vendors are perfect to buy fruit and groceries from, or inquire about that interesting wooden Jesus doll in a cart full of toys.
Start off at the Central Park (Parque Central) with some icecream and people watching. Right next to the park is the Catedral Metropolitana, the main cathedral in San Jose. Teatro Popular Melico Salazar is a large Baroque style theatre few blocks to the east and has a full schedule of shows. You'll also notice a number of beautiful old buildings flanking the side streets. Keep walking east on Avenida 2 to the Teatro Nacional which is more or less in the central part of the city.
Your options are to stop for a snack, head into the little Chinatown, or turn to a smaller street one block south and go all the way east to the beautiful Iglesia de la Soledad which is built in classical and neoclassical styles. Check out the stained glass windows. Behind the church is a smaller market.
Criscross smaller street in a north-easterly direction to arrive at the leafy national monument park. Lots of students hang out here and it’s a good place to catch some shade, perhaps a large glass of juice. Near the park is a train station, a quick detour for train geeks like me, although I have to say there’s nothing special there. Rail system in Costa Rica is extremely limited.
After relaxing at the park, head west to the Morazan park and Edificio Metálico, or the metal building, that was built in Belgium and assembled here.
If you are around on a Thursday, check out Parque Morazan. It’s a spot for jugglers and drummers to gather and jam together, reminded me of Montreal’s tam tams. During most other days you’ll see young skateboarders. Free event in a public park!