Downtown San Jose, San Jose
Downtown San Jose has a lot to offer from historic sites such as the adobes to various multinational corporations like Adobe. San Pedro Square is the most popular concentration of bars and restaurants, while the majority of the fancy hotels are just 1/2 mile to the south around the convention center. The San Jose Sharks play at the HP Pavilion and San Jose State University has the usual array of NCAA Division 1 sports, on the east side of downtown. Making it easy to get around downtown are the ample parking (free on weekends and evenings!), numerous pedestrian-only areas, and very nice public transportation.
I have stayed at a few hotels downtown including the historic Sainte Claire and the modern Marriott. I have also eaten at numerous downtown restaurants like Original Joe's and the Tied house, but I prefer some of the surrounding areas like Little Saigon and Japantown. Nightlife downtown is hit or miss in my opinion, mostly trendy nightclubs with just a few good casual bars interspersed.
With so many wineries in California, I often overlook the one closest to my house - just about five blocks away.
J. Lohr is a pretty big producer of California wines, which are made here in San Jose from grapes from various regions, including Napa and Paso Robles and sold all over the US. They have some good wines, so don't fear that this is just a tourist stop; several of their wines have earned significant recognition. They have several different lines of wines, including some expensive ones that are out of my price range and probably won't get a chance to try.
So, if you are in the city and don't have the time or interest to travel away to go wine tasting, take advantage of J. Lohr, just minutes from downtown and the airport hotels.
And on the other side of The Alameda, next to the Towne Theater, there is a new wine bar called Wine Affairs that you should go to if you want to hang out and try some more! www.thewineaffairs.com
California Trolley and Railroad Corporation
The California Trolley and Railroad Corporation operates historical streetcars on the grounds of Kelly Park and inside the History San José park at 635 Phelan Avenue, San José, CA. Tracks run through the park and along Senter Road with stops at the Happy Hollow Park & Zoo and the Japanese Friendship Garden. Hours of operation are generally Saturdays and Sundays between 11 am and 4 pm (fair weather only) and service does not run on a set schedule. Trolley rides are by donation and entrance to the park is free or subject to special event day fees.
Typically only one trolley will be in operation. The 1912 "California Car" #124, built by the American Car Company in St. Louis, Missouri for the San Jose Railroad or the 1922 Birney Safety Car #143, built by the St. Louis Car Co.
The Trolley Barn is often open for visitors most weekends from 11 am to 4 pm. Inside there are interactive displays, numerous restored vehicles such as the 1927 Kleiber Oil Truck, 1863 San Francisco Horse Drawn Street Car #7, "Little Buttercup" a 1899 Baldwin Locomotive Works steam engine and a 1916 Detroit Electric Touring Car. Also on display outside on the park grounds is a 1921 Port Huron Traction Engine and Southern Pacific Railroad's 0-6-0 steam locomotive #1215 built by the Baldwin Locomotive Works in 1913.