California Dreamin’


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Includes all lodging, breakfasts and dinners, support van, van shuttle, leaders, tour maps & narratives.

Assembly Point

Saratoga, CA

Timberline van shuttle is included to and from airport prior to and following tour.

Not included: Airline service to San Jose International Airport, Guide Gratuity.

Meeting Time

Airport 3:00 pm, Hotel 3:30 pm

Drop-off Time

6 pm

We have added a touch of Northern California to Timberline’s California Dreamin’ cycling tour and believe we have captured the essence of the true California in this program. This quintessential California experience combines the Santa Cruz Mountains of Silicon Valley, California’s storied Highway 1, as it snakes southward from Santa Cruz hugging the incomparable Pacific shoreline, then adds the opportunity to explore the rolling, verdant valleys to the east that comprise one of the world’s great wine-producing regions and we believe that you will agree that the California Road Trip is a cyclist’s fantasy to its core.

We start our tour in Saratoga, tucked away in the foothills of the Santa Cruz Mountains of California. Saratoga is a lovely community with a small-town feel, great restaurants, wineries and our hotel for the evening, the charming Saratoga Oaks Lodge.

Day 2, we start riding over the Santa Cruz Mountains ending in the surfing mecca of Santa Cruz County. Before we rest today we will climb almost 6000 feet of elevation through the back roads of the Santa Cruz Mountains. Our destination is the surf town of Aptos. The beach, the shopping, the people watching, and so many restaurants!

Next up Day 3, is the Pacific Ocean as we will bike to Carmel Valley along the Pacific coast trail, through the lush strawberry and artichoke fields, ending the day with the thrill of cycling the famous 17-Mile Drive.

Day 4 brings the excitement of Rocky Point and the many arched bridges and spectacular headlands that extend to Big Sur and beyond. We’ll spend our third overnight south of Big Sur at the spectacular Ragged Point Resort overlooking the ocean.

We continue south along the coast through San Simeon and a visit to California royalty at Hearst Castle eventually settling in the lovely Cambria on Day 5.

On Day 6, we’ll leave the coast for our first of several forays into the wine country to the east. We can’t imagine anything greener or more beautiful than the hills that we’ll encounter as we ride to Paso Robles. We’ll explore several of the region’s local vineyards, and a bakery or two, before settling into the beautiful Paso Robles Inn in the heart of town.

It’s back to the ocean on Day 7 as we ride to Morro Bay and then visit exciting San Luis Obispo. We’ll linger in this historic town well into the afternoon before continuing to Pismo Beach, where we’ll spend our next two evenings in the spectacular ocean side setting of the Shelter Cove Lodge.

We’re headed to the Edna Valley on Day 8, not only to visit a few additional vineyards, but more importantly, to enjoy the valley’s rolling, quiet country roads that constitute a not-to-be-missed cycling opportunity. We’ll climb gradually to the Lopez Lake Recreational Area and then return to Pismo Beach. Early afternoon we will van shuttle back to San Jose where our California Dreamin’ Cycling Tour concludes.


Day 1Arrive, assembly, bike fitting, Orientation Dinner
Day 2Saratoga - Corralitos - Monterey Bay - Aptos56
Day 3Aptos - Pebble Beach - 17 mile drive - Carmel Valley47
Day 4Carmel Valley - Ragged Point74
Day 5Ragged Point - San Simeon - Hearst Castle - Cambria24
Day 6Cambria –Paso Robles44
Day 7Paso Robles - San Luis Obispo - Morro Bay - Pismo Beach48
Day 8Pismo Beach - Lopez Lake Recreational Area- Shuttle back to San Jose, CA30

Total Distance: 323 miles

Inn Highlights

California Dreamin’


(Contact Us to Request Dates)