Everyone knows Napa and Sonoma. Far fewer people know that one of California’s oldest wine regions sits right at the bottom of Silicon Valley. The Santa Clara Valley wine trail, in the hills around Gilroy and Morgan Hill, is small, friendly, and refreshingly uncrowded — and it makes a perfect low-key weekend, especially for a group. Here’s how to do it.
Why this wine country
The valley has been growing grapes since the 1800s. Today it’s a cluster of mostly small, family-run wineries where the tasting rooms are relaxed and the hillside views run for miles. It’s an easy drive — no fighting Napa traffic — and prices are gentler, too. For a weekend with friends or family, that unhurried pace is exactly the appeal.
A sample two-day itinerary
Saturday
- Morning: Slow start at your home base — coffee outside, no rush.
- Midday: Lunch in historic downtown Gilroy or Morgan Hill, then out to the hills.
- Afternoon: Two or three tasting rooms along the wine trail. Book a designated driver or a local car service so everyone can relax.
- Evening: Back to the estate for a BBQ, the fire pit, and a soak under the stars.
Sunday
- Morning: A short hike at Uvas Canyon or Coyote Lake to balance out Saturday.
- Midday: A final winery or a stop on Gilroy’s “Taco Trail” before heading home.
Tips for a group wine weekend
- Call ahead — many of the smaller wineries prefer reservations for groups.
- Always line up a driver or car service; the trail is spread across country roads.
- Stay together. Splitting one house beats scattering across hotels — you regroup each night in one place.
Where to stay
The wine trail is minutes from GilroyGlamping, which makes an ideal base for a group. You book the whole private estate — a main house plus three geodesic domes that together sleep up to 20 — with a heated jacuzzi, a fire-pit lounge, and a full kitchen for the nights you’d rather stay in. It’s a natural fit for a group getaway or a milestone celebration.
Planning a wine-country weekend for your crew? Check availability and book the estate directly — no booking fees, instant confirmation. And if you’re still mapping out the trip, see our guide to things to do in Gilroy.
