Ride with a Winemaker: The Most Unique Way to Discover Napa Valley

Gerardo Capiel
Vine Trail Adventures
3 min readMay 22, 2024
Ted tasting a sample from the barrel while discussing the vineyard’s terroir and varietals

Imagine this. You’re riding through a vineyard with the person who turned its grapes into the wine you’re going to taste from a barrel 30 minutes from now.

It’s magical.

Cycling the varied terroirs of Napa Valley, it’s easy to wonder what distinguishes wines from one vineyard to the next. To quench this and other curiosities, we decided to partner with kindred cycling enthusiast Ted Osborne, who is both founder of Olabisi Winery and a winemaker for a number of Napa Valley wineries and estates.

With routes of 20–40 miles, stops in vineyards and a barrel room, and ending with a sit-down tasting flight in Calistoga, our exclusive Ride With a Winemaker rides are the absolute best way to experience the grape-to-glass journey in the Napa Valley. Riding along with Ted, there’s no better way to learn so much so easily and have so much fun doing it (and getting a bit sweaty). Your adventure awaits.

“What do I love about cycling with guests through wine country? It is so fun to be able to share the real Napa Valley with folks on a bike tour. The questions I get from cyclists are completely different from those on a bus or limo tour. The slower pace and the 360-degree views, bring you close in to the actual farming, the age of the vineyards, the way the rows are mowed, and the vines are trellised. Why is that one vine seemingly cut in half and why did they take all the leaves off of that one?” — Ted Osborne, Founder & Winemaker, Olabisi Winery

THE CYCLING

From Calistoga, we offer several options; flatter routes for more casual cyclists and hillier terrain if you want to climb upwards through some of the incredible north Napa terrain. This isn’t interval training so the pace will be casual and the conversations informative. Think “learn as you pedal.”

THE VINEYARDS

Regardless of the route, you’ll pass vineyards where the fame and renown of the Napa Valley begin. When we stop, you’ll get up close and personal with Napa’s famed Cabernet Sauvignon vines and perhaps some Zin, Pinot Noir and high-altitude Sauvignon Blanc. You’ll see workers pulling leaves or thinning the crop, training vines up the stake, resetting trellis wire, pulling leaves in the fruit zone, or even harvesting.

THE BARREL EXPERIENCE

Tasting out of the barrel is one of the frequent perks of actually being a winemaker like Ted. You’ll get to do it, too. It’s fun, exciting and educational. Get ready to explore and assess wine aromas and flavors before they’re corked.

THE TASTING

The finale of your Ride With a Winemaker outing is a Taste With the Winemaker. We end our ride inside Olabisi Winery, enjoying a selection of roses, whites and reds. Think of it as closing the circle; from the farming activities in the vineyard, to the cellar aging as magic happens in the barrel, and finally, to swirling, nosing and enjoying the vintages.

If you’re interested in one of Napa’s most unique experiences, contact us to discuss Ride With a Winemaker dates and route options.

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Gerardo Capiel
Vine Trail Adventures

Bike Guide, Owner Vine Trail Adventures, Board Member, Former Product Leader, Founder, Puerto Rican