By air, San Mateo is conveniently located near San Francisco International Airport (SFO). Oakland (OAK) and San Jose (SJC) are alternative airports, though not preferable.
By rail, use CalTrain (there are 3 CalTrain stations in San Mateo named San Mateo [downtown], Hayward Park, and Hillsdale) or BART from Millbrae.
By car, US-101 and I-280 run through the city. It is also connected to the East Bay via the San Mateo-Hayward Bay Bridge.
The most convenient way is by car. If you're using public transit, check out the trip planner on http://www.511.org.
It is also easy to get around by bike or by walking. Lots of good destinations. There are two downtown shopping areas: the primary downtown is between 2nd and 5th streets, bordered by El Camino Real and the train tracks. The big, new San Mateo Public Library is also downtown. The "other" downtown is south about 15 blocks, at 25th ave on the West side of El Camino Real. Continuing south on El Camino Real is the Hillsdale Mall.
Central Park is located off of El Camino Real between 5th Ave and 9th Ave. Inside the park is a beautiful Japanese Tea Garden. There is also a small train on rails for children that runs for a few hours each weekend day all year round and during the week during the summer.
North of the park, downtown San Mateo runs along 3rd Avenue (spilling somewhat onto 2nd and 4th) between El Camino Real and Caltrain the train tracks; it's one of the more successful urban downtowns left on the Peninsula.
Until recently, San Mateo was home to the only horse racing track on the San Francisco Peninsula, Bay Meadows. It's being redeveloped, although the structure is (as of mid-2010) still visible from the outside. The grounds are also home to the San Mateo County Events Center, where the annual county fair is held and various other events (including the recent Bay Area stops of Maker Faire. Take the Delaware Street exit off of Highway 92 and head south; the Event Center parking lot is directly off Delaware. What part of Bay Meadows remains visible are best viewed on foot from this area.
For fans of the local mid-century modern architecture, San Mateo is home to two Eichler neighborhoods - 19th Avenue park is a very early tract group of Eichlers, and The Highlands is a later neighborhood of custom Eichlers.
Coyote Point is a park located in the North-East corner of San Mateo off of Highway 101 at Peninsula Avenue. A small boat harbor is there as well as a natural history museum. There is also a public shooting range, open weekday evenings.
Poplar Creek golf course, a municipal course, is located there as well. A hiking trail allows easy access to San Francisco Bay.
Crystal Springs Reservoir is located in the watershed area off of Highway 280 on the western edge of San Mateo. Crystal Springs dam is located just south of Crystal Springs off of Skyline Boulevard.
Along with shopping and dining, there is a medium-size movie theater (12 screens, none of them huge) just off B-street between 3rd and 2nd Avenues.
M is for Mystery, 86 East Third Avenue, (650) 401-8077 An excellent mystery bookstore, with knowledgable staff. Holds many readings.
Hillsdale Mall. A large enclosed mall with mid- to high-end shops. Features Macy's, Nordstrom, Sears.
The area of downtown San Mateo around the intersection of 3rd Avenue and B street has a large number of local shops. There are also smaller shopping streets around 25th Avenue and 41st avenue, in both cases just west of El Camino Real.
Thai Satay, 173 E 4th Avenue, (650) 342-3617 Decently priced, with an extensive menu, this Thai restaurant serves authentic dishes that could fulfill any kind of mood you're in. They also allow you to choose your level of spiciness!
As of July 2010, Sinbad has closed; it's possible that they will re-open elsewhere.
Taquería Pancho Villa, 365 South B Street, (650) 343-4123. The line out the door should give a clue to the quality inside. Well-roasted meats, tacos and real Mexican food made to order, and inexpensive. Their horchata is good, but their smoothies are better (and made with fresh fruit.)
Shanghai East, 105 W. 25th Ave, (650) 522-9098. Tasty Chinese food at very affordable prices. Great dumplings and noodles, and the best Mongolian Beef around.
Yumi Yogurt, 3955 S El Camino Real (650) 341-0939. Amazing flavors of soft serve frozen yogurt and a huge topping bar. Also serve hand scooped ice cream.
Little Shanghai, 17 E. 25th Ave, ☎ 650-573-7161, . Cheap, authentic Shanghainese place. Always seems to be filled with local Chinese families getting their fill.$$.
San Mateo has a large number of Japanese restaurants. A few that stand out are:
Santa Ramen 1944 S El Camino Real, 650-344-5918. Has the best ramen on the peninsula. Always has a wait around meal times, sometimes with a line out the door. (Himawari on 2nd Ave is an acceptable substitute if you don't feel like waiting.)
Hotaru "33 E 3rd Avenue, 650-343-1152 . Authentic Japanese with an excellent all-around menu including sushi and cooked favorites. Very busy for weekday lunches, quieter at other times. Good value for lunch; prices go up on the dinner menu.
Shabuway 145 E 3rd Ave, 650-548-2483 . One of only a few Shabu-shabu restaurants on the peninsula.
Many of the restaurants in downtown have full bars - good for a pre- or post-movie drink, but many close relatively early and there is not urban nightlife scene to speak of. There are a few local bars (The Swinging Door on 25th, another on Pacific a few blocks south of Hillsdale) and a small nightclub at the Crowne Plaza Hotel in neighboring Foster City .
Best Western San Mateo, 2940 S Norfolk Street, (650) 341-3300, Fax: (650) 341-9999, .
Residence Inn San Francisco Airport/San Mateo, 2000 Winward Way, (650) 574-4700, Fax: (650) 572-9084, .
San Mateo Marriott San Francisco Airport, 1770 South Amphlett Blvd, (650) 653-6000, Fax: (650) 573-0533, . Located at the corner of two major freeways, great if you're staying in San Mateo to get somewhere else. Nice lobby for hanging out and a 7-11 convenience store just 1 block away for those late night alcohol runs. Interesting pool and exercise room setup as well. Abundant parking, but you have to pay for it (and it's controlled with gates).
Courtyard San Mateo Foster City, 550 Shell Boulevard, Foster City, ☎ 1-650-377-0600, . The newly renovated Courtyard San Mateo Foster City hotel gives you access to the entire Bay Area. Our new state-of-the-art lobby provides greater flexibility and choices for our guests.
Stone Villa Inn San Mateo, 2175 South El Camino Real, San Mateo, CA. 94403, ☎ (650) 458-6556, . Located just south of San Francisco, the newly renovated Stone Villa inn of San Mateo is within walking distance to the San Mateo Event Center,College of San Mateo, Oracle, AT&T Communications, Electronic Arts, Visa USA, Visa International and the San Francisco Airport.
If you're trying to go north to San Francisco, head to the Millbrae BART station nearby.
If you've already visited San Francisco, you can drive east to the East Bay via the San Mateo-Hayward Bay Bridge or further south down US-101 to Silicon Valley.