Morgan Hill Wine Trolley

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"

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"

A fresh air farm adventure through the backroads of South County

Hop aboard our iconic open-air cable car for a wholesome ride through South County’s hidden gems. We’ll pick you up at the Morgan Hill Train Depot and head out for a relaxed day visiting local farms, meeting friendly animals, and enjoying a hands-on u-pick experience depending on the season.

Fresh air, local flavor, and farm-to-fun memories await.

Perfect for families, friends, or anyone looking to slow down and enjoy a day in the country.

🎶 The Only Rolling Karaoke in South County - now for kids! 🎤

Looking for a fun family outing that’s anything but ordinary?

Family Karaoke Trolley is a one-of-a-kind sing-along adventure where the fun happens on board.

Hop aboard our luxe El Toro Trolley for a 90-minute rolling karaoke party through South Santa Clara County on select Thursday afternoons this summer. Sing your favorite songs, enjoy the ride, and make memories together as we cruise through Morgan Hill and scenic backroads with music, laughter, and a microphone always ready. Whether you’re belting out Disney classics, pop hits, or family favorites, everyone is invited to take the spotlight.

🚃 Pick-up and drop-off are at the Train Depot in downtown Morgan Hill. [17300 Depot Street, Morgan Hill, CA 95037]
🌲 Our midway stop is at Christmas Hill Park for a stretch and a restroom break.

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.

🎶 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.

✨ All the Swiftie eras, one night on the trolley

Taylor and Travis are saying "I do" — and we're celebrating in full Swiftie fashion. Board the trolley dressed as your favorite Taylor era (Fearless, Red, Reputation, Bejeweled — all welcome) for a cocktail at Willard Hicks, then sing your heart out to Taylor bangers all the way to Tuscan House Vineyards for wine, live DJ and charcuterie.

Gentlemen, this one's for you too. Come repping Travis in his Chiefs gear, a Taylor-approved friendship bracelet stack, or one of his own iconic looks — because every great love story has a leading man. Kelce-coded outfits are strongly encouraged.

Come ready to raise a glass to the greatest love story of our era. Friendship bracelets, cowboy boots, and sequins all welcome. Outfits optional, but best dressed wins bragging rights (and maybe a fun gift.)

The 90s called — they want you on this trolley!

Dust off your scrunchies, lace up your platforms, and dig out your best decade look — because we're throwing it all the way back to the 90s.

Board the trolley for a night of pure nostalgia, starting with a themed cocktail at Willard Hicks before we roll out to Cottage Creek Vineyard for wine and live music by the Crush Band. Come dressed for the decade and stay for the drinks — this is a night you won't forget (again).

Whether you're serving full TLC, fresh off the Fresh Prince set, or just vibing in your best grunge flannel, all 90s looks are welcome. The music will be bumping, the wine will be flowing, and the only thing missing is your old mixtape.

Limited seats. Don't want none unless you got tickets, hun.

Celebrate special milestones with friends, family or work colleagues on board our iconic, open-air cable car trolley (capacity 30) or luxury, fully enclosed El Toro Trolley (capacity 20). Opt for our signature wine-tasting experience or customize your private adventure through south Santa Clara County.

Turn the trolley into your own private karaoke party. 🎤

Our Private Karaoke Trolley experience is a fun, high-energy ride through South County with music, lights, microphones, and plenty of chances to sing along with your group. Whether you’re celebrating a birthday, planning a bachelorette, hosting a team outing, or throwing a kids party, this experience is all about having fun without worrying about the details.

We’ll pick up at your home or chosen location in Morgan Hill, San Martin, or Gilroy, then cruise scenic routes while your group sings, laughs, and enjoys the ride. You control the vibe — from throwback sing-alongs to full concert-level performances.

This is a private experience, so your group gets the whole trolley. Shorter daytime rides for kids parties and family groups are available. Additional time, stops, or custom itineraries can be added with a personalized quote.

Request a quote to check availability and reserve your date!

Reserve our entire luxury trolley for your special celebration!

Gather 20 guests and hop aboard our new white El Toro Trolley and embark on an exclusive and unforgettable wine-tasting adventure through the rolling landscapes of the south Santa Clara County wine country. Your private, inclusive tour starts and ends in charming downtown Morgan Hill and offers a delightful blend of scenic beauty, exceptional wines, and three charming wineries.

After booking with a 50% deposit, you have the option to customize your experience with options (start time, winery stops) and upgrades (home pickup, lunch alternatives).