California Wine Country - 4 Night - Relaxed

For a cycling vacation that strikes the perfect balance between satisfying rides and relaxation, our California wine country bicycle tours hit the mark.  Ride at your own pace, desired level of difficulty and distance while some the most celebrated vineyards and coastlines in the U.S. serve as your daily backdrop.  Our relaxed tour routes limit daily mileage in order to free your time for more wine tasting, food-sampling, spa-going, and sightseeing in historic towns.  If you crave more mileage, or more challenge, we can suggest modifications to help you have the experience you want on your California Wine Country bicycle tour!

All breakfasts are included.  Lunches and dinners are yours to choose along the route, and in the lovely towns you will be staying in.  The Napa Valley is home to numerous Michelin Star and other highly-celebrated restaurants, and boasts an overall culinary culture that is fantastic. See full itinerary below.


Dates: Your pick! We offer tours in California Wine Country as early as March and as late as October and into November.
Length: 5 days, 4 nights
Service: Supported, Private, “Self Guided” tour. For more about how our Self Guided tours work CLICK HERE.
Type of riding: Rolling terrain with some climbs.
Bikes suggested: Road bikes or hybrids
Average daily riding: 20 miles
Start city: San Francisco
Finish city: San Francisco
Suggested transport: Fly to San Francisco (SFO) from anywhere.

We work with only local guides, cooperating with those that have a love for cycling, and a desire to show guests the beauty of the land they call home. On our self guided tours we do not bring in guides from other destination to work with you. Having the local perspective only enhances your experience, providing insider knowledge and opportunities that only a local resident can offer.

From greeting guests when they arrive, to personally handling luggage transfers, to curating excursions, to problem-solving (e.g., flat tires and other unforeseen issues) our concierges assist guests daily. They also set you up on your rental bikes, and can help with routing and simple questions. Need help finding a good lunch spot? Is it raining too hard or you’re too tired to continue? The concierge is a phone call away and are there to help you! Each tour group works with a single, dedicated concierge who can be called upon for in-person assistance at any time.

Road Bikes: Our rental road bikes are a racing style with drop handlebars.

  • Giant DefyType – Carbon Road Bikes
  • Sizes – XS, S, M, ML, L,and XL
  • Components – Mixture of Shimano 105 and Ultegra with either triple or compact double cranksets. Many have road-disc brakes.




Hybrid Bikes: Our rental hybrid bikes are a relaxed style with flat handlebars.

  • Giant EscapeType – Aluminum Hybrid Bikes
  • Sizes – XS, S, M, L, and XL
  • Components – Mixture of Shimano road and mountain components with either triple cranksets.



During the registration process you will be asked for specifics to have the correct sized bike waiting for you. We can supply any number styles of pedals – SPD, SPD-r, flat, Speedplay, Look, etc.


  • All hotel accommodations – mostly 3 and 4 star but ask for custom accommodation requests.
  • An OBT cycling jersey!
  • Detailed route notes, maps, and tourist information. This includes standard cue sheet, and GPS courses to upload to your own GPS device.
  • Luggage transfers from hotel to hotel.
  • Meals as explained in the tour itinerary pages. Usually this means all breakfasts, no lunches, and some dinners.
  • Access to your personal guide/concierge (See Guides/Concierge tab).



  • Transportation to start location and from finish location.
  • Bikes, but we have rental bikes available.
  • Travel and Health Insurance.
  • Admission to sightseeing venues, unless explicitly mentioned as included.

Available to rent for $150 per unit per tour. These easy to use GPS units provide an excellent worry-free routing method that you can depend on throughout your tour.

If you choose to rent we will have the until ready for use with the routes pre-loaded onto the unit. All you have to do is start the daily route at the beginning of your riding day, and follow the highlighted line! We will also provide instructions that you can reference when needed. As a backup and supplement to the GPS, we will also provide a local map as well as routing instructions.

garmin edge touring screens

Tour Cost Per Person:

  • Double Occupancy: US$1,895
  • Single Occupancy: US$2,495 (for single room occupancy on multiple person tours)
  • Solo Tour: Please contact us

Bike Rental Per Person:

  • Road Bike: US$225
  • Hybrid: US$145

What’s Next? Registering for your tour!

Questions: First, please feel free to ask us any questions about the tour. We are happy to help clarify any details.

Registration: Once you are ready to register please go to and complete the registration form. EACH tour participant will need to complete the form. At the end of the registration for you will be asked for a US$800 deposit. You can pay the deposit by bank check, wire, or credit card. Once we have all registrations we will secure all of the details of your tour – hotels, bikes, etc.

Final Payment: 60 days prior to your tour we will invoice you for the balance of the tour.

Tour Packet Delivery: Once the balance is paid and approximately 30 days before your tour we will send you a complete tour packet containing all details of your tour – accommodation information, detailed routing, a suggested packing list, maps, tourist guide, and much much more!

For more information on our Terms & Conditions please CLICK HERE.

Daily Itinerary:

Day 1 – San Francisco to Healdsburg – 20 miles
From downtown San Francisco, we will transfer you north through Petaluma to the small hamlet of Graton.  After a full map briefing and equipment check, you will ride the rails-to-trails bike path past scenic vineyards, historic mansions, and an art gallery.  This is a gentle ride with plenty of opportunities to visit wineries along the way.  Even if you don’t plan to taste, many wineries are oases for picnics—grab a bite or simply rest in the shade of an oak tree.

After 20 miles of riding, you will arrive in Healdsburg, the hub of the Alexander Valley and Dry Creek wine regions.  It is a prosperous but relaxed town where you are equally likely to come across Silicon Valley escapees and vineyard workers.  Around the Spanish-style Plaza, you will find smart restaurants, bookstores, antiques stores and a regular farmers market.

Day 2 – In & Around Healdsburg – 20 miles
Today’s 20-mile route takes you outbound along the eastern border of the Dry Creek Valley— classic back roads that snake past small farms and family-run wineries are enjoyed with the Mayacamas Mountains framing the scene.  Many guests collect a picnic lunch at the Dry Creek General Store, to be enjoyed in the gardens of a nearby winery.  Stay again in the town of Healdsburg overnight, where a large handful of great restaurants, a small handful of spas, and a few hot air ballooning companies await.

Day 3 – Healdsburg to Guerneville – 20 miles
Today’s route offers another 20 miles of truly classic wine country riding, starting on rolling terrain in the Dry Creek Valley before proceeding down through the Redwood groves to the Russian River.  Temperatures are a little cooler in this area, as the weather is moderated by the nearby ocean.  Stay overnight in Guerneville, with its quirky and relaxed atmosphere and diverse community that echoes its unique history.  The town went from prime logging country in the early 19th century to a resort town in the early 20th century, to a Beat Generation alternative community by the 1960s.  Summer attractions include beaches, kayaking and a jazz festival that mimic the area’s funky vibe.

Day 4 – In and Around Guerneville – 20 miles
Today would be a good day to do biking, hiking, horseback riding or kayaking.
Three miles north of town, the Armstrong Redwoods State Reserve can be visited to see massive and ancient Redwood groves.  Here you can hike or horseback ride through the redwoods up to the alpine meadows of the Austin Creek State Park.

As an alternative to cycling, consider a kayaking trip down the gently-flowing Russian River.  Expect to meander for miles past ranch land, vineyards and redwood forests before ending at the Pacific Ocean (and don’t be surprised if seals accompany you for part of the way).  Kayaking trips are not included in the base price of the trip, but we are happy to help arrange one for you.

Day 5 – Guerneville to Jenner – 25 miles
Today, you will awaken your legs with a gentle descent alongside the Russian River. Before you reach the Pacific, take a detour along single-lane roads that snake alongside Austin Creek under towering redwoods.  After 25 miles, you will finally reach the Ocean near the seaside town of Jenner.  Here, a large sand spit forms a lagoon that is home to families of seals.  The town of Jenner is a great place for lunch and where your guide will meet you to return you to downtown San Francisco.

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