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California Wine Country


Napa might be more famous, but when it comes to cycling, neighboring Sonoma is the favorite amongst those in the know. Located just 60 minutes North of the Golden Gate Bridge, the charming village of Healdsburg couldn’t seem farther away from the city, and it makes the perfect base for a visiting cyclist. The roads are quiet, the terrain offers everything you could want for a bike trip, and there are so many route options that you’ll always find something new to explore.

For this wine country adventure, we’ll explore the roads around Healdsburg and everyone’s end-of-the-season fitness will be put to the test. It won’t all be work though. The food on this trip promises to be a real highlight with an abundance of dishes inspired by quality, seasonal and local produce, and we’ll be washing it down with a fine selection of big California Cabs as well as  the local Pinots, Chardonnays and Zinfandels.


Included With Trip:

  • All food and beverages**
  • Pinarello Dogma F Disk with SRAM RED eTap AXS
  • Daily Bike Wash
  • Daily post-ride massage from a professional soigneur
  • Custom Castelli × inGamba cycling kit
  • Laundry service for cycling clothing

*Lodging is not included in this trip. We have reserved rooms at h2hotel in Healdsburg for your convenience. 

**Beverages ordered by guests beyond normal amounts and away from group activities will incur additional charges

Trip at a Glance

Start Location:

Healdsburg, CA

Finish Location:

Healdsburg, CA

Days Riding:


Group Size:

8 – 12

Total Distance:


Total Elevation:


Longest Day:

Day 4. Fort Ross. 131km

Biggest Climbing Day:

Day 3. Pine Flat and Chalk Hill. 1,380m


Day by Day Breakdown


West Dry Creek Welcome Ride

Sonoma can be enjoyed in a variety of ways and we’ll kick off the long weekend by pedaling adjacent to some of its best wineries weaving along its most scenic roads. Quickly making our way out to West Dry Creek Road, this strip of fresh tarmac weaves its way north and into quintessential Healdsburg riding. Turning east at Yoakim Bridge, we’ll then see the only climb of the day a gradual ascent to Geyserville and an easy roll back to our abode.


The Grasshoppers are a fixture of Sonoma cycling. A series of mixed terrain rides-slash-races, now in their twentieth year they were well ahead of the trend when they started in the gravel scene. One of Ted’s first experiences with ‘hoppers was a close derivation of this Geysers route. Setting out north along Dry Creek Road, we’ll pass the popular Dry Creek General Store, onto Cloverdale, and then start the true adventure when we begin Geysers Road. The road snakes besides Big Sulphur Creek and Truitt Creek on a road that will see nary a car, before a few switchbacks have us crest Geysers Road and sweep downhill back into the Dry Creek Valley.

Pine Flat and Chalk Hill

Don’t be deceived by the name Pine Flat, a more accurate title name would be Pine Sinuous Mountain Climb Road. This lonely strip of pavement offers a spectacular view its entire way skyward. And because it's an out and back, you’re free to call the climbing good for the day at any point and enjoy the descent to the valley. From there, we can opt for a 0.3 mile detour to the popular lunch spot, the Jimtown Store. Next we’re off to Chalk Hill Road, bursting with equal parts productive viticulture and photo worthy spots, it’s then a short way home from the town of Windsor.

Fort Ross

Anyone who comes home from riding in Sonoma will somewhere have collected “the fish was THIS big!” yarn that was spun somewhere along Fort Ross Road or the subsequent plunge down Meyers Grade. Setting off south along West Dry Creek Road, we’ll soon be dwarfed by towering redwoods pedaling towards the bohemian town of Cazadero. Mirroring the 2012 stage one from Tour of California, when Ted had the pleasure of pulling the peloton along this stretch knowing that the elastic effect was ferocious to those behind. His team went onto win this stage, starting with that magnificent sixty mile leadout. From Cazadero, the road makes its way up thanks to a series of seemingly countless rollers along Fort Ross Road. At last we’ll emerge onto Meyers Grade where the smell of the ocean is met with one of the best descents in California. With options to take a flat route home again through the redwoods or continue south with a short, but abrupt assault of Coleman Valley Road, each route has a friendly final pedal back to Healdsburg.


This is our final morning together and after a leisurely breakfast, it will be time to say goodbye, or at least arrivederci, until we meet again. Transfers to the airport will be arranged by our hard-working crew but if you’re planning on staying a few extra days, let us know if we can help with reservations or a few recommendations.

YOUR Guides

Eros Poli

The Champion

The night before Eros Poli took victory atop Mont Ventoux he couldn’t sleep. It was not like he was dreaming of victory or even had the slightest idea the next day's stage would change his life forever. It was just that it was hot. Unbearably, unsleepably hot in his less-than stellar French hotel. His roommate had taken his mattress off the bed and was sleeping on the small balcony outside their room. And the man who would shortly become known as Monsieur Ventoux was watching football, Italy vs. Brazil in the World Cup final, to be exact. Italy lost. The following morning as Eros dragged his weary, tired legs out of bed and down the stairs, as there was no lift, James Brown came into his head. “I feel good, I knew that I would now,” started to repeat over and over in his head. As it would the rest of the day. He felt good and the rest, as they say, is history.

Sérgio Paulinho

After an impressive pro career that started back in 2003, Sérgio Paulinho joined the inGamba team at the start of 2022 after his retirement. But we've known him for a long time, as not only did he race against our founder João Correia, but he was also a teammate of our star guide Manuel Cardoso back in the day. A two-time national champion in Portugal, Sérgio has also won stages at the Tour de France and Vuelta a España, and in 2004, he won a silver medal in the road race at the Athens Olympics. So it's fair to say the man has pedigree! It isn't the racing victories that impress us most about Sérgio though, it's his personality, his friendly nature on and off the bike, and the fact that he's always ready with a smile. That said, if you find yourself running out of gas on a big climb, it certainly helps to have someone like him beside you!




Pinarello Dogma F


ZIPP Service Course SL




Speedplay (or your own)


Selle Italia


Zipp 303 S Carbon Tubeless


Vittoria Corsa


Elite Custom Race


Elite Corsa Team


Garmin Edge 1030