Executive team building retreats rarely look like this: two days on full carbon road bikes from San Francisco to Pebble Beach, with a boutique inn, curated dining and a private guide, for small groups who want the comfortable version of a big ride. The route covers about 130 miles of California coastline, with a support van and driver alongside the whole way.
This middle tier upgrades the bikes, the lodging and the food. It is the most popular of the three packages for this ride, and it works well for leadership groups, partners celebrating a milestone, or friends marking a retirement with a ride they will talk about for years.
What's Included
- A full carbon endurance road bike for every rider, at the level of
Executive team building retreats rarely look like this: two days on full carbon road bikes from San Francisco to Pebble Beach, with a boutique inn, curated dining and a private guide, for small groups who want the comfortable version of a big ride. The route covers about 130 miles of California coastline, with a support van and driver alongside the whole way.
This middle tier upgrades the bikes, the lodging and the food. It is the most popular of the three packages for this ride, and it works well for leadership groups, partners celebrating a milestone, or friends marking a retirement with a ride they will talk about for years.
What's Included
- A full carbon endurance road bike for every rider, at the level of a Roubaix or Domane SL
- An expert local guide on the bike with the group, either the owner or a senior guide
- A support van and driver with upgraded provisions
- One night at a four-star boutique hotel or upscale inn, double occupancy
- Curated dining: a farm-to-table dinner and a local breakfast, plus all meals on the route
- Ride photos taken by the guide, delivered digitally
- GPS files, cue sheets and a souvenir ride map
- Your preferred pedal system and bike transport back to San Francisco
The Route at a Glance
Day one is the longer day, about 75 miles with roughly 3,200 feet of climbing. The group leaves the shop after coffee, pastries and a bike fit, rides through the park and onto the coast, and takes the car-free Devil's Slide Trail above the ocean. Lunch is a picnic near Pigeon Point Lighthouse, and the afternoon follows the bluffs at Wilder Ranch and West Cliff Drive into the overnight stop.
Day two runs about 55 miles with roughly 2,000 feet of climbing. The group passes strawberry fields and Moss Landing, follows a car-free trail past Fort Ord Dunes and Cannery Row, then rides the 17-Mile Drive past the Lone Cypress and Bird Rock. Lunch is at The Lodge at Pebble Beach, and the ride finishes at Pebble Beach.
Why This Tier
Carbon frames are lighter and smoother on long days, and the boutique hotel and planned dinner turn the overnight into part of the reward. As corporate retreat team building activities go, this format gives a small group two full days together with no laptops and a shared finish line. The team also provides personal recommendations for where to stay in San Francisco the night before and on the peninsula the night after, based on your budget and preferences; those two nights are not included in the price.
Rider Fit and Support
The ride is designed for experienced riders. Anyone who prefers help on the climbs can switch to a pedal-assist e-bike, and the van is always nearby with water, snacks, spare parts and a seat if someone needs a break. Groups of two to eight riders keep the ride personal and easy to coordinate, which makes it one of the stronger company offsite ideas for a small leadership team.
Upgrades on This Package
Add-ons include a pro carbon bike with electronic shifting, an e-bike swap, a single room at the hotel, a post-ride sports massage, a van ride home for riders and gear, and a professional photo package from the guide's full-frame camera.
Good to Know
Pricing is per rider with double occupancy, and a minimum of two riders is needed to run the ride. Your pedal system is installed before departure, and every rider gets a fit check at the shop before the group rolls out. The guide is either the owner, who has spent about two decades riding and designing tours, or a senior guide. Past riders rate the team 5.0 stars across more than 1,300 reviews, and the shop has been locally owned for more than a decade.
A Day on the Road
Expect a steady, social pace with regroups at viewpoints, a van that leapfrogs ahead with water and snacks, and meals that are already planned. After the boutique hotel and the farm-to-table dinner, day two starts with a local breakfast and ends with lunch at the famous lodge before the finish.
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.
