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California Wine Country Self-Guided Bike Tour

A Weekend Escape to Sonoma

On our California wine country self-guided bike tour, saturate your senses in one of the world’s premier cycling regions, which provides an uncommon blend of panoramic views, flavorful wines, and elegant country living along quiet back roads. Experience four exquisite days of active travel, amidst the undisputed elegance of California wine country. Traverse the less traveled Dry Creek, Alexander, and Russian River Valleys, luxurious havens for wine enthusiasts the world over. Savor days filled with inspiring bicycle rides at your own pace, bountiful dining options, and expertly crafted wine, and settle into the lavish comforts of charming wine country retreats. Escape for a self-guided weekend bike trip in this sublime paradise, and we bet you’ll never want to leave. Book your trip with confidence »

 Experience Trek Travel's One Collection where you stay in one luxurious hotel during your trip

One world-class hotel your entire stay See more One Collection trips

$1899 Per Person
4 Days & 3 Nights
Rider Type: ?
3 - Active Non-riders Welcome
From $1899 per person View All Details
Trip Wows
Discover the varied and vineyard-lined terrain of Sonoma County's big three appellations: Russian River, Dry Creek, and Alexander Valley
Savor the delights of Northern California cuisine, inspired by fresh, local ingredients
Enjoy varied and unique tasting rooms, each boasting a different ambiance
Visit California's famous Redwood Forest at your own pace
Watch the Experience
A very well-conceived trip with fun routes, excellent food, and interesting side tours. We felt Trek was fully behind us whilst enjoying the freedom of self-guidance. And the Trek bikes inspired confidence!
-John, Trek Travel Guest

Dates & Prices

The Earlier You Book, The Greater The Rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price and date are guaranteed.
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Single Occupancy
Available for 2021 and 2022. Our trip on your schedule. Simply choose your own travel dates and we will handle the rest. Price based upon double occupancy and may vary based on dates and hotel availability. Contact us at 866-464-8735 to get started.
Don't see your ideal travel date? 
Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. Choose your trip date, get your group together and we will do the rest. Private trip pricing is as follows:
2020 - June 1, 2021 Departures:
  • 6+ Guests    Price as advertised*
  • 4-5 Guests +$500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
  • 1 Guest        Call us for pricing*

2021 Departures After June 1, 2021:
  • 10+ Guests Price as advertised*
  • 8-9 Guests +$500 per person to trip price*
  • 6-7 Guests +$1,000 per person to trip price*
  • 4-5 Guests +$1,500 per person to trip price*
  • 2-3 Guests +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*

Traveling with a small group? Consider semi-private trips.
For groups of up to six people, semi-private trips offer unique flexibility within a larger Trek Travel guided trip. Learn more »

*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Looking for a date that you don’t see?
Look no further. Simply tell us your preferred travel dates and we’ll work together to deliver the same great trip on your custom schedule.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

Your Trek Travel guide will meet you at 11:00 AM at the Harmon Guest House on the first day of your California wine country self-guided bike tour and walk you over to a local café for a light lunch and overview of the week ahead. After lunch, your guide will give you a personalized bike fitting to ensure your comfort on your Trek bike for the trip. Then it's off on your first adventure, cycling the tranquil byways through the Alexander and Dry Creek Valleys. If you're up for a challenge, tackle Rockpile Road, a beautiful detour through the Lake Sonoma Recreation Area with views of Lake Sonoma. You'll pass many distinctive wineries in the Dry Creek Valley, home to more than 50 wineries, and one of the top zinfandel producing regions. Taste wines from the barrel at Zichichi, or a cool, crisp, biodynamic Sauvignon Blanc in Quivira's solar-powered tasting room. Tonight, celebrate this fantastic self-guided bike tour in California with one of the farm-to-table options in the the foody town of Healdsburg!

Today's Ride:

Healdsburg to Dry Creek Loop
Approximately 35 miles with 1,400 feet of climbing

Avid Option:

Healdsburg to Dry Creek Loop with Rockpile Road
Approximately 46 miles with 2,700 feet of climbing


Harmon Guest House

Included Meals:


This morning offers a great opportunity for a walk over to our guide favorite, Flying Goat Coffee. Sit and enjoy a macchiato and watch the square come alive before strolling back to the hotel for our ride start. Today you'll ride through the Russian River Valley, known for its tantalizing Pinot Noir on your way to the Pacific Ocean. You will follow the Russian River to its outlet and to a great café in the town of Jenner. Lunch is on your own today in the town of Jenner, Guerneville, or stop off at Korbel's on-site gourmet deli. You may even choose to cleanse the palate with a little bubbly! You'll have the opportunity to sample at a variety of wineries like Gary Farrell, Porter Creek, or Armida. Tonight, dinner is at your leisure at one of the many famed restaurants in bustling Healdsburg. Whether it's Italian, French, or basic pub fare, Healdsburg has you covered.

Today's Ride:

Healdsburg to Jenner Return
Approximately 60 miles with 2,900 feet of climbing

Avid Option :

Healdsburg to Bodega Bay Return
Approximately 81 miles with 4,200 feet of climbing


Harmon Guest House

Included Meals:


Today you'll follow the quiet byways over Chalk Hill and through the Alexander Valley, enjoying its rustic simplicity. You'll head south, circumnavigating Healdsburg, always within view of its endless vineyards. Along this stretch of road, you can see the grapes, smell the fermentation, and practically taste the wine. You'll pass many unique and distinctive wineries that will prove tempting for a visit. There's the opportunity for a challenge if you are feeling up to it; Pine Flat Road is calling your name. This 11-mile climb entertains local cyclists and pros alike with views of the surrounding valleys. Take a shorter option to town if you'd rather spend time enjoying your charming accommodations. If you haven't already, wandering the town plaza of Healdsburg is a must. Or simply enjoy an afternoon glass of wine at the hotel. If you choose not to ride today, you are free to meander the picturesque streets of Healdsburg, visit the spa, play a round of golf, or visit the endless wineries in the area. Tonight, an array of specialties are at your fingertips in town. Armed with a list of recommended restaurants, choose the one that best suits your tastes for dinner.

Today's Ride:

Dry Creek Alexander Valley Loop
Approximately 39 miles with 1,800 feet of climbing

Avid Option:

Chalk Hill with Pine Flat Road
60 miles with 3,100 feet of climbing

Today's Activity:

Wine Tasting at Alexander Valley Vineyards


Harmon Guest House

Included Meals:


Take a final morning spin through the charming Dry Creek Valley to loosen up your legs or enjoy a peaceful morning in Healdsburg, relaxing at the hotel. Or feel free to take a stroll for a coffee at a guide favorite, Flying Goat. To close out your self-guided California bike tour, your guide will meet you at 11:00 AM at the hotel to collect your bike and gear and offer a shuttle to the Sonoma County Airport if you are flying out today.

Today's Ride:

West Dry Creek to Yoakum Bridge with Return
Approximately 22 miles with 840 feet of climbing

Short Option:

West Dry Creek to Lambert Bridge
Approximately 14 miles with 470 feet of climbing

Included Meals:



hotel image

Harmon Guest House

Healdsburg, California

Located in the heart of North Sonoma wine country, Harmon Guest House is the ideal venue for a romantic weekend or celebration. Rise above it all on The Rooftop terrace and indulge in views of Fitch Mountain, the Sonoma hills, and downtown Healdsburg. Gather around the firepit and sip a glass of wine at sunset. With its location in the heart of downtown, you'll be steps away from local shops, cafes and bakeries, and several tasting rooms.
hotel image

Alternate property | h2hotel

Healdsburg, California

Located just off the plaza in downtown Healdsburg, h2hotel is rooted in nature and fluid by design. Built to LEED Gold Green Building Certification, all aspects in form and function at h2 take an eco-friendly view. With its location centrally located in wine country, you'll be surrounded by a variety of wineries in Northern California’s finest regional wine appellations, including Alexander Valley, Dry Creek Valley, and Russian River Valley.

What's Included

For us, the details matter most

Every moment of a Trek Travel self-guided bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.


Trek Domane SL 7 Disc

It isn’t the cycling vacation of a lifetime unless you have the industry’s best bike to match. In 2019, we upgraded our fleet to feature the award-winning Domane SL 7 with Shimano Ultegra Disc brakes. Because when you combine the lightweight stability and comfort of the Domane with the superior safety and stopping power of disc brakes, you get a match made in cycling heaven. And the best part? It’s included in the trip price. Ride confidently, comfortably and longer in the most beautiful destinations around the world with the new Domane SL 7. Learn More


Trek Electric-Assist Verve+

With its Low-Step frame design, hopping on and off the Trek Verve+ is super easy. The front suspension will take the edge off any bumps in the road and the Bosch system will keep you smiling from ear to ear. The integrated battery keeps this bike looking sleek as you pedal through amazing terrain. Learn More


  • Three nights of accommodation at one handpicked hotel
  • Daily breakfast
  • Day 1 lunch with the guide
  • Daily lunch and dinner recommendations
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+
  • Up to three daily route options on riding days
  • Trek Travel water bottles to keep
  • Each bike is equipped with a flat pack, frame pump, phone mount, front and rear lights
  • Bontrager helmet (optional if you do not bring your own)
  • Bontrager saddle (we suggest you bring your own for the most comfortable fit)
  • Shimano clipless pedals or flat pedals (optional if you do not bring your own)
  • All luggage transfers during your trip
  • A bike lock, all necessary chargers and a floor pump
  • Bike fit on the first day to help you find your optimal position for comfort, with recreational or avid set-up along with saddle preference
  • Ride With GPS app on your phone to navigate and get all the information you need on your self-guided adventure
  • Optional daily phone or video call with the guide to prep you for the next day’s adventure
  • Support on the ground in case of emergency


  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+, available in a limited quantity
  • Trek Travel water bottles to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, or flat pedals (optional if you do not bring your own)
  • Bontrager helmet (optional if you do not bring your own)
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights
  • Each bike is equipped with a flat pack, frame pump and phone mount
  • A bike lock, all necessary chargers, and a floor pump
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip.
  • For the most comfortable ride, you may choose to bring your own pedals, saddle, and helmet on the trip. Your guides will install your gear on the first day during your bike fit.


Gratuities for your Trek Travel guide are not included in your trip price. We recommend tipping 7.5-10% of your trip price, preferably in the local currency. Please tip your guide at your discretion, based on their level of professionalism, guest care, and service.
  • Airfare and transportation to and from the trip meeting/departing locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • While we provide daily breakfast and one lunch, the other meals are not included. On self-guided trips, Trek Travel provides restaurant recommendations and invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3 - Active?

34 miles
136 miles
1,425 feet
5,700 feet
The terrain is generally rolling, with a few flat stretches on quiet, but sometimes narrow, roads. For those seeking more challenging rides, the hills to the east or west of the valley are sure to please even the most avid cyclist. Our California Wine Country Self-Guided Bike Tour is best suited for our Type 3 Riders. Type 2 riders with secure bike handling and comfort riding all miles unsupported might consider this trip with the assistance of our electric bike option–you still get a workout but can climb alongside even the strongest rider. Type 4 riders will enjoy the extra mileage the avid route options offer.
There are a variety of non-riding options on this self-guided trip for riders who want to take the afternoon off or travel companions who want to spend little or no time in the saddle. Some of these options may need to be scheduled before your trip–please contact one of our Trip Consultants for more information. Except as specified in the itinerary, expenses and transportation to these activities are not included in the trip price. Some non-riding options on this trip are:
  • Shop the chic boutiques on the plaza in Healdsburg
  • Take a winery tour or indulge in wine tasting in a wide variety of wineries or tasting rooms in town
  • Walk and explore the Armstrong Redwoods State Park
  • Enjoy a spectacular spa experience at Hotel Healdsburg

See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel seeks to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

Averages and totals are calculated from our "Today’s Ride" options.

Travel Details

How to Get There

Charles M. Schulz-Sonoma County Airport (STS)
11:00 AM
Harmon Guest House

Say Farewell

Charles M. Schulz-Sonoma County Airport (STS)
11:00 AM
Harmon Guest House


We recommend flying into Charles M. Schulz-Sonoma County Airport (STS) in Santa Rosa, approximately 10 miles from downtown Healdsburg. Delta, United, and Alaska Airlines serve STS. From just outside the baggage claim, you can take a taxi to the meeting location. Taxi rides from the airport to downtown will cost approximately $40.

Your Trek Travel guide will meet you at the Harmon Guest House at 11:00 AM on the first day of your self-guided California wine country bike tour and walk you over to a local café for a light lunch and overview of the week ahead. Please have your riding gear readily accessible to avoid having to unpack your luggage.

View our pre hotel recommendations


Your guide will meet you at the Harmon Guest House at 11:00 AM to collect your bike and equipment and to offer a shuttle to the Charles M. Schulz-Sonoma County Airport (STS) by 11:30 AM where you can fly out or catch the the Sonoma County Airport Express shuttle (800-327-2024) from Sonoma County Airport to SFO for around $30/person. Please do not schedule flights out before 1:00 PM.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

In Healdsburg, the summers are long, warm, arid, and mostly clear and the winters are short, cold, wet, and partly cloudy. Because of the coastal influence and nearby mountains, there are many micro-climates and weather can be very variable. For this reason, we suggest dressing in layers and always bringing extra clothing for the cooler morning and hotter midday differentials. A rain shell is also a good idea. Packing List

Before and After Your Trip


Before & After: Healdsburg, California

Just about an hour north of the hustle of San Francisco, in the heart of Sonoma County wine country, you'll find Healdsburg. Here, natural beauty unites with world-renowned California artists and artisans to inspire the senses. From sleepy agrarian roots, Healdsburg has become known for its abundance of world-class wineries and tasting rooms, the very best in farm-to-table dining, and picture-perfect countryside of lush valleys and redwood forests that cradle Lake Sonoma and the Russian River. This is the perfect town to get to to get away from it all.

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the ultra-smooth Trek Domane SL 7 to the Trek Electric-Assist Verve+, you deserve the best ride on your vacation. Plus, we offer a range upgrade options to take you the extra mile.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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