A private two-day guided road bike ride from San Francisco down the California coast to Pebble Beach, built as a team building retreat for small groups of experienced riders. Your group rides about 130 miles with about 5,200 feet of climbing, with an expert local guide on the bike and a support van always close behind.
This is the classic tier of the ride: quality bikes, full van support and a comfortable hotel for the night in between. The ride is 100 percent private, so only your group is on the road with the guide, and it suits company team building retreats, milestone birthdays, anniversaries and friends who want a big shared goal.
What's Included
- An aluminum endurance road bike for each rider, with your
A private two-day guided road bike ride from San Francisco down the California coast to Pebble Beach, built as a team building retreat for small groups of experienced riders. Your group rides about 130 miles with about 5,200 feet of climbing, with an expert local guide on the bike and a support van always close behind.
This is the classic tier of the ride: quality bikes, full van support and a comfortable hotel for the night in between. The ride is 100 percent private, so only your group is on the road with the guide, and it suits company team building retreats, milestone birthdays, anniversaries and friends who want a big shared goal.
What's Included
- An aluminum endurance road bike for each rider, with your preferred pedal system installed
- An expert local guide riding with the group, either the owner or a senior guide
- A support van and driver carrying water, snacks and spare parts
- One night in a comfortable three-star hotel, double occupancy
- All meals on the route: lunch and dinner on day one, breakfast and lunch on day two
- Coffee and pastries at the shop before you roll out
- GPS route files and cue sheets, plus bike transport back to San Francisco
Day One: Down the Coast
The first day covers about 75 miles and about 3,200 feet of climbing, with five to seven hours in the saddle. After a bike fit and safety briefing at the shop, the group warms up through the park and heads south. The car-free Devil's Slide Trail offers clifftop ocean views, and a cafe stop halfway gives the van a chance to top up water and snacks. Rolling farmland leads to Pigeon Point Lighthouse, one of the tallest lighthouses on the coast, where a picnic lunch is waiting. In the afternoon the route passes a tiny surf town and the bluffs of Wilder Ranch, where riders keep an eye out for whales in season, before rolling in along West Cliff Drive past Steamer Lane to check in and have dinner.
Day Two: To the Finish
Day two is shorter, about 55 miles and 2,000 feet of climbing over four to five hours. After breakfast the group rides through strawberry fields and artichoke country to Moss Landing, watching for sea otters and shorebirds along the bay. A car-free coastal trail runs past Fort Ord Dunes and Cannery Row. Then the group enters the gates and rides the famous 17-Mile Drive, past the Lone Cypress, Bird Rock and Spanish Bay, with lunch at The Lodge at Pebble Beach. A stroll through a storybook village by the sea, with galleries and a white sand beach comes before the finish at Pebble Beach, where the bikes are loaded for the trip home.
Who It Is For
This is one of the most memorable active team building activities for adults who already ride. It is a real road ride on open roads and coastal trails, so riders should be comfortable with long days in the saddle. Riders who want help on the climbs can swap to a pedal-assist e-bike, and the support van is always nearby if anyone needs a lift. Groups of two to eight riders keep the pace social and the logistics simple.
Upgrades on This Package
Add-ons on this listing include a pro carbon road bike with electronic shifting, a pedal-assist e-bike upgrade, a single room at the overnight hotel, a sports massage at the hotel after day one, a van ride back to San Francisco for riders and their gear, and a pro photo package shot on a full-frame camera with a gallery delivered within two days.
Good to Know Before You Book
Pricing is per rider with double occupancy at the overnight hotel, and a minimum of two riders is needed to run the ride. Hotels in San Francisco the night before and on the peninsula the night after are not part of the package, but the team shares personal recommendations based on your budget and preferences. Pedal systems are installed on your bike before departure, so riders can bring their own shoes and clip in from the first mile. The shop has been locally owned for more than a decade, and past riders rate the team 5.0 stars across more than 1,300 reviews.
What a Ride Day Feels Like
The guide rides with the group and sets a steady, social pace, regrouping at viewpoints and towns. The van leapfrogs ahead with water, snacks and spares, so riders carry very little. Meals are planned along the way, which means nobody has to hunt for lunch in a small coastal town with tired legs.
How to Book
Pick a date and guest count on this page to see the price for your group, then send a request to book. The team confirms the dates, the bikes and the hotel before the ride.
