Cool Day Trips from San Jose

San Jose is so cool…’How cool is it?’….It's so cool that it’s situated within a very short distance from several other very cool iconic and worldly destinations. This guide is all about popular regions you can visit very quickly from San Jose. From nearest to furthest, the list below outlines some general info and a few pro tips about places like Santa Cruz, San Francisco, Oakland, Half Moon Bay and Wine Country, 

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Santa Cruz - SJ’s Favorite Getaway 

Only about 30-40 minute drive from San Jose and Santa Cruz has beaches, the famous Boardwalk, redwood mountain escapes, and a few shopping corridors including Downtown, Swift Street and 41st. Bottomline is that Santa Cruz is hella cool. Pro tip, the Pacific Cookie Company factory, Pacific Wave Surf Shop, and The Boardroom are all a must go. 

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Morgan Hill

From South San Jose, Morgan Hill is only about a 10-minute drive further south. If you take 101, you can exit at any location in Morgan Hill. If you take Monterey Rd, you’ll drive right thru Downtown Morgan Hill. By way of Santa Theresa you’ll enjoy a two lane country road with rolling foothills and live oak trees. Morgan Hill is cool with lots of restaurants in the downtown area, while in the west mountains you can find waterfalls at the Uvas Canyon County Park. 

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San Mateo

Northbound up the Peninsula about 30 minutes or so, between SF and SJ is San Mateo. With bustling downtown districts for the cities of San Mateo, Redwood City, San Carlos and Burlingame, these regions are both historic and lovely, but also loaded with delicious restaurants. The El Camino Real connects all of these cities and it too is filled with excitement. 

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Gilroy

Only about 30-minutes north of San Jose, Gilroy is a fun city to visit. Gilroy has a very large outlet shopping mall, a cool amusement park for younger kids, several wineries like Hecker Pass Winery, hella good pizza at Pinocchio's, and Mt Madonna park with twin redwoods. The downtown area is historic and has many places to eat and drink. Perfect for a day trip, Gilroy has small town feel with new school vibes. 

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Livermore

Roughly a 30-40 minute drive Northeast of San Jose, past Fremont, the rolling hills open up to Livermore and the Tri-Valley which is home to dozens of wonderful wineries, several golf courses and a fun little downtown strip. Its neighboring city Pleasanton has a similar story. 

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San Francisco

Depending in which part of SF you want to explore, and how you choose to travel to the city, it takes anywhere from 45-1.5 hours to get to San Francisco from San Jose. Highways 280 and 101 connect SJ to SF for drivers, while San Jose’s first BART station in North SJ and the Cal Train Diridon Station in DTSJ are available for public use. The Royal Road, also known as the El Camino Real also connects from Downtown SJ to the Embarcadero in San Francisco. Pro sports teams, worldly icons, major arts groups, and ’the city’ vibes are all worth the trip. But places like Harris Steakhouse, Tommy's Joynt, The Great American Music Hall, and SF's oldest restaurant Tadich Grill are all places to check out.  

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Half Moon Bay

It takes about 45-60 minutes to travel to Half Moon Bay from SJ. With a couple different routes over the mountains to the coastal town, most people make the trip to see the big pumpkins during autumn, or to simply enjoy their cute Downtown restaurants and shops like the San Benito House. Besides the brew that dons the city’s name, HMB is also home to the enormous waves known as The Mavericks. 

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Felton

Deep in the Santa Cruz mountains, about 45-60 minutes away from San Jose is the cool town of Felton. Felton has a live music hall and a number of delicious restaurants. Another 15 minutes or so deeper into the woods past Felton is Boulder Creek’s killer mountain community and town. Both towns are beautifully surrounded with redwoods and fresh air, while being overly naturally quiet and complete opposite of what the city life brings in SJ. Felton and Boulder Creek are both hella cool, especially with a place like The Cowboy and finding Marianne's Ice Cream at the quick stop. 

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Oakland

45-60 minutes North on Hwy 880 is Oakland. Known as The Town, Oakland is a large Bay Area city with rich history and culture. Connected to Berkeley and Alameda, the East Bay’s crown jewel has Jack London Square, The Fox Theatre and one-half of the Bay Bridge. It’s not hard to find good food or fun bars in Oakland and surrounding areas. Plus with BART, you can travel quickly and tipsy to SF or SJ. 

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Capitola

Roughly an hour from San Jose is Capitola. Taking the same route as traveling to Santa Cruz from SJ, Capitola is further south down the coast off Hwy 1. The village at Capitola is what it’s all about. From the nice sit-down restaurants on the beach, to good’ol Pizza My Heart slanging slices of pie and t-shirts for a few bucks, the oceanside block of Capitola Village is a really cool spot. Pro Tip, arrive early, and if you’re only going to chill at the beach, consider a stop at Gayle’s on your way. Also the Shadowbrook’s inclinator and Checker Taxi are a must see.

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Monterey

In about an hour (give-or-take a few minutes) with little traffic, Monterey is a relaxing destination. Of course Monterey has the world famous aquarium and cannery row area, but their Downtown and connecting Pacific Grove have great restaurants and shops too. Depending on the tide, there are fun tide pools to explore at your own risk. Pro tip, on your way back to SJ, you must stop at Pezinni Farms for some world class artichokes and goodies.

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Pebble Beach

Not much further than Monterey, about another 15-minutes or so, you’ll find Pebble Beach and the 17-Mile drive. Known around the world as a mecca for golf and the finer things in life, Pebble Beach and Carmel can be either ultra relaxing destinations or full of action and adventure. Beyond golf and coastal mansions, Pebble Beach is also home to one of the world’s most exclusive car shows. 

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Sonoma & Napa

Wine country is all over the greater Bay Area. Even though San Jose and the Santa Clara County is the oldest wine growing region in Northern California, starting in Almaden Valley and What a wonderful drive to the North Bay Area, and ideally taken over the Golden Gate Bridge, but it will take a couple hours. Pro tip, if you’re wine tasting, pack snacks, water, etc. before leaving SJ. The wine country has little options for nourishment outside of restaurants, and the wineries primarily don’t either. 

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Yes…these are all cool destinations reachable very easily from San Jose and the South Bay Area. In most cases, taking a road trip to any of these cities is very straight forward and perfect for a 1-day trip or quick overnighter. In all cases, please drive safely and responsibly, and feel free to turn up ‘Do you know the way to San Jose’ when you begin your journey back to SJ. 

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