Skip to main content
Testarossa Winery wine cave

Sip and Cycle Adventure

Urban pathway turns scenic mountain trail with rewards of savory food and fantastic wine.


Rent bikes from Bicycle Express in downtown San Jose and go for a 10-mile spin along the Los Gatos Creek Trail – the best location to catch the trail is on Auzerias Avenue. End your journey in Los Gatos with a visit to Manresa Bread, offering a seasonal selection of hand-made breads and pastries. Then spend some time exploring the many boutique shops along Santa Cruz Avenue.

Tip: Expect a line at Manresa Bread. It’s worth the wait.

Los Gatos Creek Trail biker
Los Gatos Creek Trail


After exploring Los Gatos, make your way to The Bywater for a bite to eat and sample Chef David Kinch’s New Orleans inspired restaurant with menu items including gumbo, red beans and rice and po boys. Continue your bike ride from downtown Los Gatos up the mountain to Testarossa Winery and imbibe a glass of wine or elect for a tasting and sample delicious pinot niors and chardonnays. The historic Novitiate property offers a spectacular ambiance for enjoying wine.

Testarossa Wine Cave with special event set up
Testarossa Winery


Once, you’ve had your fill at Testarossa, ride back to San Jose along the Los Gatos Creek Trail for a sunset ride and return your bikes to Bicycle Express. Unwind at the hotel and freshen up before heading to dinner at Enoteca La Storia in San Jose’s Little Italy for fresh made pastas by Saporito Pasta Company and pizzas made with 72-hour aged dough for a crisp crust with a bit of tang. Too tired to hop on your bike? Call Tommy Johns Wine & Brew Tour and they can specialize a wine or beer tour without all the cycling!

Little Italy Sign
Little Italy