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California Wine Country Long Weekend Bike Tour

A Weekend Escape to Sonoma

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 remote Dry Creek Valley, a luxurious haven for wine enthusiasts the world over. Savor days filled with leisurely bicycle rides, bountiful picnics, and expertly crafted wine, and settle into the lavish comforts of charming Wine Country retreats. Escape for a weekend bike trip in this sublime paradise and we bet you’ll never want to leave. Book your trip with confidence »

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$2799 Per Person
4 Days & 3 Nights
Rider Type: ?
2 - Recreational Non-riders Welcome
From $2799 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 the local and fresh ingredients
Enjoy varied and unique tasting rooms, each boasting a different ambiance
Pedal to the coast
Watch the Experience
We really enjoyed cycling through the Napa Valleys. Obviously a great place for wine enthusiasts but also superb for those like us who want to cycle in beautiful - and sometimes challenging - places. Quiet country roads, grapes as far as the eye can see, beautiful sunshine.
-Liz, 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 from: +$1000
Oct 7 – Oct 10 
Guaranteed Limited Availability
$2799 / Person, Double Occupancy Book this date
Oct 14 – Oct 17 
$2799 / Person, Double Occupancy Book this date
Oct 21 – Oct 24 
$2799 / Person, Double Occupancy Book this date
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Please contact us to join our exclusive waitlist for first notice about new dates.
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 guides will meet you at the Harmon Guest House on the first day of the trip. After introductions and the bike fit, you will cycle to Alexander Valley Vineyard for a light lunch and an exclusive wine tasting and decide to continue along 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 we will celebrate a great adventure ahead with a farm-to-table feast at a local favorite restaurant, Chalkboard. It is here that the farm culture of Sonoma comes to life and is embodied in their cuisine.

Today's Ride:

Healdsburg to Dry Creek Loop
Approximately 38 miles with 1,785 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:

Lunch | Social Hour | Dinner

Today we ride through the Russian River Valley, known for its tantalizing Pinot Noir on our way to Armstrong Woods Park. Avid riders can push their legs by tackling the toughest climb of the week, Sweetwater Springs, with grades reaching 20%. There is also a gentler ride to Armstrong Woods Park via Westside Road. Once you’ve arrived stop and admire the majestic towering redwoods and enjoy a hike to visit the oldest (1,400 years old), or the tallest (310 feet high) trees in the park. Lunch is on your own today in the town of Guerneville, or stop off at Korbel's on-site gourmet deli. You may even choose to cleanse the palate with a little bubbly! Then, choose a shuttle back to our hotel, or venture into Healdsburg for some shopping and a tasting at one of the many winery rooms on the square. If you decide to ride back you’ll have the opportunity to sample wines at a variety of wineries like Gary Farrell, Porter Creek, or Armida. Tonight you are on your own for dinner 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:

Hotel Healdsburg to Armstrong Return
Approximately 40 miles with 800 feet of climbing

Short Option:

Hotel Healdsburg to Armstrong
Approximately 20 miles with 400 feet of climbing

Avid Option:

Hotel Healdsburg to Sweetwater Springs – Armstrong With Westside Rd. Return
Approximately 42 miles with 1,500 feet of climbing


Harmon Guest House

Included Meals:


Today you’ll follow the tranquil 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 almost taste the wine. Through the quiet stretch of Chalk Hill and the Alexander Valley, you’ll pass many unique and distinctive wineries that will prove tempting for a visit on our way to our lunch stop. There's opportunity for a challenge if you're 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 our 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 you'll gather with your fellow travelers for one last Californian meal at Charlie Palmer's Dry Creek Kitchen.

Today's Ride:

Chalk Hill Loop
Approximately 37 miles with 900 feet of climbing

Short Option:

Chalk Hill to Jimtown with Shuttle
29 miles with 800 feet of climbing

Avid Option:

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


Harmon Guest House

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

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 the guide favorite, Flying Goat. If you choose to ride, hurry out to Healdsburg’s town square for a little last minute shopping, or wine tasting before having lunch from the famed Oakville Grocery. You’ll say farewell to your guides at 1:00 PM at the Harmon Guest House, before boarding the shuttle to the Santa Rosa Aiport, arriving by 1:45 PM.

Today's Ride:

Hotel Healdsburg Yoakim Bridge Loop
Approximately 20 miles with 400 feet of climbing

Short Option:

Hotel Healdsburg Lambert Bridge Short Loop
Approximately 11 miles with 200 feet of climbing

Included Meals:

Breakfast | Lunch


hotel image

Harmon Guest House

Healdsburg, California

New hotel for 2021! Located in the heart of North Sonoma Wine Country, Harmon Guest House is the ideal venue for a romantic weekend, celebration or company meeting. 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.

What's Included

For us, the details matter most

Every moment of a Trek Travel 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 Domane+ LT

The Domane+ LT combines the best of the race-built Domane endurance bike with a slight pedal-assist perfect for climbing the toughest hills. This bike primarily functions as a road bike, but on tough hills or in strong headwinds, you can get an extra boost by using the electric assist feature. Upgrade to the Domane+ LT on this trip for $500. 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 handpicked hotels
  • Two experienced guides to provide local knowledge, support, and camaraderie
  • Daily route support with both guides and our support van
  • Daily breakfast, three lunches and two dinners
  • Two social hours of drinks and hors d'oeuvres
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+
  • Up to three daily route options on riding days
  • Snacks and drinks for each day's ride
  • Trek Travel Bontrager cycling jersey to keep
  • Trek Travel water bottles to keep
  • Cinch sack day bag to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, flat pack, front and rear Bontrager Flare R lights, a Bontrager saddle, and pedals (Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals)
  • Bontrager WaveCel helmets
  • All gratuities for drivers, local experts, and hospitality staff
  • All luggage transfers and transportation during your trip
  • A personalized digital photobook of your trip
  • Entrance fees for all activities, private tours, and events


  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+, available in a limited quantity
  • Upgrade your bike to a Trek Electric-Assist Domane+ LT carbon road bike with Shimano Di2 electronic shifting
  • Trek Travel Bontrager cycling jersey to keep
  • Trek Travel water bottles to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals
  • Bontrager WaveCel helmet
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights and a flat pack
  • Garmin Edge 1030 GPS computer
  • Cinch sack day bag to keep
  • Upgrade your bike to include carbon wheels (+$200)
  • 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 guides are not included in your trip price. We recommend tipping 7.5-10% of your trip price for the guide team. Local currency is preferred and unless you want to tip separately, guides will divide tips amongst themselves. Please tip your guides at your discretion, based on their level of professionalism, guest care, and service.
  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • On select trips some meals are not included. On these trips, Trek Travel invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 2 - Recreational?

32 miles
127 miles
650 feet
2,600 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. The California Wine Country is best suited for our Type 2 Riders. Our Trek Travel guides can also easily accommodate Type 1 Riders, who seek less mileage or fewer uphills, with a boost in the van. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option–you still get a workout but can climb alongside even the strongest rider. Type 3 Riders will enjoy the extra mileage the avid route options offer.
On most Trek Travel trips, we offer non-riding options 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. Expenses and/or related transportation to these activities may not be 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)
9:30 AM
Harmon Guest House

Say Farewell

Charles M. Schulz-Sonoma County Airport (STS)
1:00 PM
Harmon Guest House


We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into Charles M. Schulz-Sonoma County Airport (STS).

The easiest way to arrive in Healdsburg is to book your flight to the Santa Rosa Airport (STS) and take a taxi for about $30. Car rental agencies from the San Francisco Airport (SFO) are currently only offering vehicle drop off to Santa Rosa. There is also car and limo service available at SFO for approximately $275 to get you to Healdsburg if you prefer.

Your Trek Travel guides will meet you in the lobby of the Harmon guest House at 9:30 AM on the first day of the trip. After a round of introductions, your Trek Travel guides will discuss bike safety and specific cycling tips for riding through the wine country. They’ll spend some time familiarizing you with the Trek bicycle you’ll be riding and we’ll make sure that you and your bike are the perfect fit before cycling to lunch and a tasting.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip start with their names and contact details. If you cannot reach them, please call our hotel, Harmon Guest House (707-431-8220), and leave a message with your expected arrival time and contact details. The Sonoma County Airport Express shuttle (800-327-2024) from SFO to Sonoma County Airport for around $30/person. Taxi from Sonoma County Airport to our first hotel is approximately a 13-mile taxi ride.

View our pre hotel recommendations


You will say goodbye to your guides at the Harmon Guest House at 1:00 PM or have the option to be shuttled by the guide team to the Charles M. Schulz-Sonoma County Airport (STS).

View our post hotel recommendations

Planning For Your Trip

For packing gear, please review our packing list page for more details. Packing List»

Warm sunny days (70F-75F) and cooler evenings, with temperatures at least 15 to 20 degrees cooler. Bring layers for the cooler morning and hotter midday differentials - a rain shell is also a good idea. Packing List

Before and After Your Trip


Before: Napa, California

Soak in the delights of wine country with a stay in Napa. Enjoy a stroll along the Riverfront Promenade as you enjoy local shops and restaurants. Consider spending an evening at the Napa Valley Opera House or visit the Oxbow Public Market to discover local foods and wines. We recommend the following accommodations for your pre-trip hotel:


After: San Francisco, California

Keep in mind that San Francisco is a city best explored via foot and cable car and involves a great deal of hill walking. There are numerous attractions in the San Francisco area - from the Golden Gate Bridge, Chinatown, Fisherman’s Wharf, and Alcatraz to Ghirardelli and Union Square. For a preview and help in planning, try www.OnlyinSanFrancisco.com or one of the many websites available on the city. There are endless options and - whether you pre-plan and book your itinerary, or just arrive with no plans - you’re sure to be charmed by the City on the Bay! We recommend the following accommodations for your post-trip hotel:

Customer Reviews

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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