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cycling trip California Dreamin' Cycling Tour New Itinerary

Dates: 3/1 - 7

7 days, 6 nights (Sun- Sat)


Assembly Point: San Jose, Ca

(airline service to San Jose, Timberline van shuttle to and from airport prior to and following tour)

Meeting time: 2/28- airport 2:30 pm, hotel 3 pm

Drop off time: 3/7- 6 pm

Tour Cost: $2,750

(includes all lodging, breakfasts and dinners, support van, van shuttle, leaders, tour maps & narratives)

Single Occupancy Lodging Cost: $554

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 1, we start riding over the Santa Cruz Mountains ending in the surfing mecca of Santa Cruz County. Before we finish 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. There we ill visit the locals only award winning restaurant The Sparrow Cafe for a well deserved, relaxing dinner.

Day 2, a special day, we will hike in Pinnacles National Park (the newest National Park).

California RidersNext 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. Early into our ride through the hills east of Cambria, you’ll know why we’ve chosen a spring date for this bike tour. 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. We’ll call it a tour mid-afternoon in Pismo Beach and van shuttle back to San Jose where our California Dreamin' Cycling Tour concludes.


Day 1 Saratoga - Corralitos - Monterey Bay - Aptos 56 miles
Day 2 Aptos - Pebble Beach - 17 mile drive - Carmel Valley 47 miles
Day 3 Carmel Valley - Ragged Point 74 miles
Day 4 Ragged Point - San Simeon - Hearst Castle - Cambria 24 miles
Day 5 Cambria –Paso Robles 44 miles
Day 6 Paso Robles - San Luis Obispo - Morro Bay - Pismo Beach 48 miles
Day 7 Pismo Beach - *Hike in Pinnacles National Park (newest NP)- Shuttle back to San Jose, CA 8 miles

Total cycling mileage: 269 Total hiking mileage: 8

Day 1

Day 2

Day 3

Day 4

Day 5

Day 6

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Routes, mileage and accommodations are subject to change due to safety, road/trail conditions, weather and availability.