November 14, 2026
Napa
Cycle & Sip
We do the homework so you can focus on the ride.
The Day
We’ll confess, this is a day for hedonists. Cruise vineyard roads, linger over great coffee, enjoy a homemade lunch, sip good wine, and take the day at your own pace.
Duration
7:30am–5:30pm
Ride Style
Self-paced + supported
Food + Drink
Coffee · lunch · wine
Bike Rental
Optional
Route Options
Two ways to ride Napa.
Choose your route on ride day.
A relaxed ride through Napa Valley.
Cruise 21 mostly flat miles through Napa Valley, passing world-renowned wineries along the way. You’ll get back to Monticello earlier, leaving plenty of time to lounge on the lawn or visit another nearby winery at your leisure.
Ride Support
Your pace, with support when you need it.
We’ll equip every rider with the route and navigation tools to ride confidently at their own pace. Four Field Trip guides are out on the route supporting setup, food and hydration, navigation, and basic mechanical issues. We keep tabs on everyone’s progress, circle back if someone is overdue, and can suggest extra miles if you’re flying.
Riders should be comfortable completing their route independently. There is no SAG pickup. If you’re bringing your own bike, bring any bike-specific tubes, parts, or tools you may need.
The Schedule
From San Francisco
to Napa and back.
From pickup to drop-off, we handle the details so you can enjoy the ride.
Scroll or use arrows
Friday · 7am–6pm
Bike drop-off
Drop your bike at 1227 Willard Street and we’ll get it to Napa. Renters can skip this.
Saturday · 7:30am
Leave San Francisco
Board the bus at Stanyan × Haight.
9:00am
Arrive in Napa
Meet your guides, grab water and snacks, and get ready to ride.
11:00am
Coffee stop
Take a break around mile 10 before continuing the ride.
12:00pm
Valley riders return
Picnic lunch, wine tasting, and time to hang at Monticello.
2:30pm
Mount Veeder returns
Long-route riders arrive back for lunch and wine tasting.
4:00pm
Head home
Bus departs Napa for San Francisco.
5:30pm
Back in the city
Arrive in San Francisco and meet your bike at 1227 Willard.
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Along the Way
A Taste of Napa
Two distinctly Napa stops, both included in your ride.
Oakville Grocery
Set at the crossroads of Oakville and surrounded by vineyards, this historic market has been in operation for over 100 years. They know their way around a cappuccino too. We’ll stop for a drink and a chance to regroup around mile 10.
Monticello Vineyards
Monticello is tucked into a quieter corner of Napa, away from the main road and surrounded by vineyards. Three generations of the Corley family have farmed and made wine here since 1970. We’ll finish the ride on the lawn with lunch and a tasting.
Book Your Spot
Ready to Ride?
Everything you need for a great day riding in Napa. Choose how you'll get there and whether you need a bike.
Route planning and navigation, support from four ride guides, coffee, ride snacks, picnic lunch, wine tasting, and 10% off bottles at Monticello.
Meet us in Napa or hop on the round-trip bus from San Francisco (+$50).
Bring your own bike or rent one through us (+$100).
Choose your route on ride day. No need to commit when you book.
We'll send all the details, including meeting times, navigation, bike logistics, and rental sizing if needed.
Tickets start at $200 per person. Select your transportation and bike options when booking.
FAQs
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This is your ride, and we want you to take it at your pace. Guides are out on the route to help with directions, flats, or anything else, but nobody’s herding you into a tight pack. Hammer up front or cruise at the back. No one gets left behind.
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Road bike rental: $100, includes pedals and a helmet. If you choose this option at checkout, you’ll receive a follow-up email asking you to share your bike size and whether you’d like to rent acoustic or electric.
You’ll meet your bike at Monticello Saturday morning.
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If you’re unable to finish, you’ll arrange an Uber back to Monticello. We’ll take care of getting your bike back to the vineyard so you can rejoin the group there.
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We’ll have basic tools, bike pumps, and extra tubes on hand in the support van. If your bike requires a specific tube size, tire, tool, or other mechanical item, bring it with you and we can keep it in the van during the ride. We’ll be able to help with common issues, but we won’t have every bike-specific part or tool.
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Open the event link. No Ride with GPS account yet? Create a free one. It takes a minute. Click "+ Join Event," sign the waiver, and add your emergency contact info. When you're ready to ride, pick your route and hit "Save" to download it for offline use, then tap "Navigate" for turn-by-turn directions. We'll walk through this again at the start of the ride.
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Cycling clothes and shoes, layers for the morning fog, your phone, and an ID (there's a wine tasting). No cash needed: food, drinks, and the tasting are covered. Renting a bike? It comes with pedals and a helmet, so skip those.
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Yes! Everyone rolls out together, and both routes share the first 21 miles. The long route splits off from there, and everyone meets back up at Monticello before heading back to San Francisco.
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Not at all. Plenty of riders come solo, and the day has built-in ways to meet people: finding your pace group, grabbing coffee mid-ride, sharing a picnic blanket at lunch. Most solo riders leave with a few new riding buddies.
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Snacks, water, electrolytes, and sunscreen are waiting for you at Monticello before you head out. Everyone stops at Oakville Grocer for coffee around mile 10. Come back to a picnic lunch and a wine tasting: the payoff for the climb.
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Drop your bike at 1227 Willard Street on Friday, 7am to 6pm. We'll get it to Napa and have it ready for you Saturday morning. Pick it up at 1227 Willard once you arrive back in the city on Saturday.
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You’ll have roughly two hours to enjoy Napa before the long-route riders return. We’ll have lawn games set up at Monticello if you’d like to grab a bottle of wine and hang out at the vineyard. If you’d rather keep exploring, you’re welcome to bike or Uber to nearby wineries, or spend more time in Yountville checking out its restaurants, bakeries, and shops. Just be back at Monticello before the group departs for San Francisco.
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November in Napa usually means cool mornings and mild afternoons. If Field Trip determines the weather or roads are unsafe, we’ll cancel the event and issue a full refund.
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Cancel by phone or email at least 14 days before the ride and receive a 75% refund. Cancellations within 14 days of the event are non-refundable. Registrations are transferable, if you can find a backup! If Field Trip cancels the event, you’ll receive a full refund.
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We’ll send everything you need before ride day, including bike drop-off details, route access through Ride with GPS, the rider waiver and emergency contact form, and final day-of logistics. If you’re renting a bike, we’ll also follow up to request sizing information.