Private Group Experiences
No two trolley events are the same — and that’s exactly the point.
Our five-star rated private experiences are built around your group, with flexible routes, custom stops, and plenty of ways to enjoy everything South County has to offer, from wineries and restaurants to farms, scenic backroads, and hidden local favorites. Tell us what you’re celebrating and we’ll help create a trolley experience that feels effortless, fun, and completely your own.
Private Group Experiences
Private Group Experience
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.
Private Karaoke Trolley Party
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!
Need More Information?
We are here to help! Please reach out to our customer service team with any and all questions at (855) 324-3377 or cheers@mhwinetrolley.com.