7 Best Day Trips From San Jose California - Just A Short Drive Away

Day Trips From San Jose California

Who’s ready for a road trip? There are so many day trips from San Jose California that make the perfect mini getaway. From exploring award-winning wineries to relaxing on beaches, you’ll fall even more in love with the Bay Area as you explore its hidden gems.

Weekend getaways from San Jose are the perfect way to discover the beauty of Northern California. Get your bags packed and your favorite road trip snacks ready. It’s time to explore the best day trips from San Jose California!

 

1) Explore Wineries With The Morgan Hill Wine Trolley

The best way to start a day trip from San Jose off right is to make your first stop at one of South Santa Clara County’s hidden gems. Morgan Hill offers spectacular views of the Santa Cruz Mountains and is in very close proximity to downtown San Jose.

Our weekend wine-tasting tours take you on an unforgettable journey aboard a traditional San Francisco cable car. Whether you want a Super Saturday or Sunday Funday, your friendly tour guide will make it magical as you venture through the rolling landscapes of South Santa Clara County to several charming wineries.

Of course, we also offer private wine tours for groups that want an exclusive vineyard experience!

Contact us today to book your wine-tasting getaway!

 

2) Go With The Flow At Santa Cruz

If you’re looking for great weekend trips from San Jose, then Santa Cruz is the perfect spot! Just 45 minutes from San Jose, the city is a local favorite that includes the famous Santa Cruz Beach Boardwalk.

You’ll have a fantastic time enjoying fun attractions like:

  • Arcades

  • Vintage rides

  • Restaurants

  • Boardwalk food and shops

  • Seabright Beach

With so much family fun in store, Santa Cruz is one of the top weekend getaways from San Jose. Near Santa Cruz, you can also visit Pacific Grove. This coastal town is just an hour’s drive from Santa Cruz and is home to the award-winning Monterey Bay Aquarium.

Pro tip: Plan your trip to avoid peak traffic hours. Early hours or late evenings are better to get the smoothest ride along Highway 17.

 

3) Visit National Parks

California is home to so many great national parks that make for an amazing weekend trip. There’s year-round fun for the whole family as they enjoy hiking through trails, photography, camping, birdwatching, and being one with nature.

Stunning views of mountains, lakes, and rivers await, along with beautiful wildlife habitats lie just a few hours from San Jose. You can also find plenty of hiking trails ranging from beginner to advanced. Whether you’re looking for a summer adventure or a winter weekend getaway in the mountains, you’ll find year-round options.

Top picks near the San Jose area include:

  • Pinnacles National Park

  • Yosemite National Park

  • Sequoia National Park

  • Point Reyes National Seashore

Pro tip: You can plan your road trip with other local attractions. For example, visit Lake Tahoe, relax by the water, and then explore Tahoe National Forest to round off your adventure.

 

4) Relax At Half Moon Bay

This charming coastal town south of San Francisco is best known for its charming beaches and scenic coastal trails. Spend the day relaxing on the sands of Half Moon Bay State Beach, then take a walk along the Coastal Trail and engage in the beautiful surrounding area of the Pacific Ocean!

This town makes a great weekend getaway with its coastal atmosphere, quaint B&Bs, and variety of small, quiet beaches. Get your feet wet in the ocean and enjoy hours of relaxation in this picturesque town on the California coast.

 

5) Gaze At The Golden Gate Bridge In San Francisco

San Francisco is one of the most visited cities in the United States and is filled with many activities and sights to make for a fun day trip. However, you simply can’t miss your opportunity to gaze upon the Golden Gate Bridge.

Once you’re finished seeing the historic bridge, learn something new at the California Academy of Sciences and stroll through the Japanese Tea Garden in Golden Gate Park!

 

6) A Snorkeling Adventure Awaits You At Lake Tahoe

This freshwater lake invites you to snorkel and visit the local marine life. When you’re done making friends with the turtles, take a breather as you take a guided boat tour.

Along with aquatic adventures, the lake is a perfect area to go hiking and appreciate wildlife.

San Jose is around four hours from the Lake Tahoe area. It’s most popular during the summer thanks to the amazing weather, but it makes a great trip any time of year.

 

7) Explore Silicon Valley

Silicon Valley is one of the most famous parts of California, home to big-name corporations like Apple and Google. It’s also the perfect place to learn all about technology at the Computer History Museum and The Tech Interactive Museum.

Technology isn’t the only highlight, of course. The Valley is also a great place to shop, dine, and appreciate views of the Santa Cruz Mountains. Whether you’re a tech enthusiast or simply looking for a memorable experience, Silicon Valley has something for everyone.

Just 18 minutes from San Jose, Silicon Valley is one of the most popular destinations in the San Jose area. Plan your visit to this dynamic region and engage in the cutting-edge world of technology and the unique charm of Silicon Valley. It’s also a convenient destination for senior residents from the best Morgan Hill assisted living facilities, offering accessible attractions and engaging experiences suitable for all ages.

 

Experience The Best Day Trip From San Jose

With these San Jose day trips, you have a wide array of diverse experiences. From relaxing at the beachside to taking in picturesque scenery, you have plenty of options for the best weekend getaway from San Jose.

If you’re ready to kickstart your adventure, then come on down to the Morgan Hill Wine Trolley! Experience a delightful wine tour and explore the charming town of Morgan Hill.

To schedule your tour, simply contact us at our website and get ready for a memorable adventure!

Wine Trolley
Duration
4 to 5 hours
Group Size
Up to 30

Classic Cable Car Weekend Wine Tasting Tour

Hop aboard our iconic cable car trolley and embark on a unique and unforgettable wine-tasting adventure through the rolling landscapes of the south Santa Clara County wine country. Our signature wine-tasting tour starts and ends in charming downtown Morgan Hill and offers a delightful blend of scenic beauty, exceptional wines, and three charming wineries.

✨ This is the same experience as our El Toro Trolley Wine Tasting Tour; the only thing different is the Trolley. To see all tour availability, click Book Now and sort by the top tab "Shop by Date"

Duration
4 to 5 hours
Group Size
Up to 20

El Toro Trolley Weekend Wine Tasting Tour

Purchase individual tickets to hop aboard our new white El Toro Trolley and embark on an unforgettable wine-tasting adventure through the rolling landscapes of the south Santa Clara County wine country. Your chic, inclusive tour starts and ends in charming downtown Morgan Hill and offers a delightful blend of scenic beauty, exceptional wines, and three charming wineries.

✨ This is the same experience as our Classic Cable Car Weekend Wine Tour; the only thing different is the Trolley. To see all tour availability, click Book Now and sort by the top tab "Shop by Date"

Duration
1 hour 30 minutes
Group Size
Up to 30

Karaoke Trolley Nights (21+)

🎶 The Only Rolling Karaoke Party in South County 🎤

Looking for a night out that’s different from the usual bar scene?

Karaoke Trolley Night is a 21+ karaoke experience where the party happens on board!

Hop on our luxe El Toro Trolley for a 90-minute rolling karaoke party through South Santa Clara County. Sing your favorite songs, enjoy the ride, and let loose while we cruise scenic backroads with music, lights, and a microphone always ready.

This tour is planned every other Thursday night.

NOTE: This is a public event. To reserve the entire El Toro Trolley for a private karaoke event, reach out to us at cheers@mhwinetrolley.com.

Duration
2:30 to 3 hours
Group Size
Up to 30

It's Gonna Be May: Boy Bands Theme Night (May 1)

This isn’t just a playlist — it’s a full-on throwback experience.

Kick off the night at Willard Hicks with a welcome cocktail, then hop aboard the trolley for a ride packed with wall-to-wall boy band hits, sing-alongs, and the songs you definitely still know every word to.

We’ll head to Miramar Vineyards where you’ll enjoy your choice of wine or beer and a Tri Tip Sando small plate in a relaxed, scenic setting. Then it’s back on the trolley for round two — bigger energy, louder sing-alongs, and a ride home that feels like the grand finale.

Come dressed like your favorite boy band era — or your own version of 90s/00s fits. Think denim on denim, all white, band tees, streetwear, or full pop star energy. Go subtle or go all in, but come ready to be part of the vibe.

Whether you’re front-row concert energy or just here for the nostalgia, this night is for you. No choreography required… but highly encouraged.

Duration
4 to 5 hours
Group Size
Up to 30

Viva Vino: Cinco De Mayo Wine-Tasting Tour (May 3)

🤍 11:30am TOUR ON EL TORO TROLLEY (WITH KARAOKE) IS AVAILABLE 🤍
⭐️12:00pm CABLE CAR TOUR IS SOLD OUT⭐️

Hop aboard our iconic cable car trolley or the nostalgic El Toro Trolley or Viva Vino: A Cinco de Mayo Celebration — a festive twist on our signature wine country experience. We’ll roll out from charming downtown Morgan Hill at 11:30am or 12:00pm and spend the afternoon savoring curated pours at three unique South Santa Clara County wineries, surrounded by vineyard views and sunshine.

Expect vibrant energy, standout wines, and a little extra fiesta flair as we sing (and maybe dance) to salsa, rancheras & latin pop hits on our way through the vines. It’s the perfect blend of celebration and elevated wine country charm — no crowded bars, just scenic stops and unforgettable moments.

We’ll return to downtown around 4:30 or–5:00pm, leaving you perfectly primed to keep the celebration going.

Want to come but don’t drink? Our Zero-Proof Ticket includes selected non-alcoholic beverages in a souvenir tote so you can fully enjoy the tour.

NOTE: We may have tickets available for another weekend wine-tasting tour. Click on 🏠 icon above, then SHOP BY DATE or SHOP BY ACTIVITY link at the top of this window to see all our available tours.

Duration
4:30 to 5 hours
Group Size
Up to 30

Cheers to Mom Wine Tasting Tour (May 9)

Celebrate Mom aboard our iconic cable car trolley on this May 9th Wine Tasting Tour, departing at 12:00 PM from downtown Morgan Hill. Sip champagne, enjoy curated tastings at three local wineries, indulge in a catered hot lunch and charcuterie and cruise wine country with scenic views, and zero planning required.

✨ This is a special event. To see availability for all of our weekend wine tasting tours, and special events, click Book Now and sort by the top tab "Shop by Date"