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California Wine Country 4-Day Weekend



California Wine Country 4-Day Weekend

A Weekend Escape to Sonoma

Newly redesigned Trek Travel biking trip

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.
Introducing ONE, a new type of experience.

Daily Itinerary

View Day-To-Day


Today's Ride:

Healdsburg to Dry Creek Loop
Approximately 30 miles with 500 feet of climbing

Avid Option:

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


Your Trek Travel guides will meet you at the Westin St. Francis Hotel lobby, by the large grandfather clock (335 Powell Street, San Francisco, CA, 94102) at 9:30 AM on the first day of the trip. You'll enjoy a scenic private shuttle across the Golden Gate Bridge from San Francisco to the world-renowned Hanna Winery in Alexander Valley. After a light lunch, a short round of introductions with your fellow travelers and an exclusive wine tasting, get fit to your bike and follow 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, Shed. It is here that the farm culture of Sonoma comes to life and is embodied in their cuisine.


Hotel Healdsburg
Visit Website

Included Meals:

Lunch | Social Hour | Dinner


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 Armstrong Return via Sweetwater Springs
Approximately 42 miles with 1,500 feet of climbing


Today we ride through the Russian River Valley, known for its tantalizing Pinot Noir on our way to Armstrong Woods Park. 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 at a variety of wineries like Gary Farrell, Porter Creek, or Armida and if your legs are up for it, you can tackle the toughest climb of the week, Sweetwater Springs, with grades reaching 20%. There is also a gentler ride back to Healdsburg via Westside Road. Tonight you are on your own for dinner in bustling Healdsburg. Whether it's Italian, French or basic pub fare, Healdsburg has you covered.


Hotel Healdsburg
Visit Website

Included Meals:



Today's Ride:

Chalk Hill Loop
Approximately 37 miles with 900 feet of climbing

Short Option:

Chalk Hill to Jimtown Store 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


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 of Jimtown Store, a Sonoma County Landmark with some of the best sandwiches West of the Mississippi! If you’re feeling up for a challenge after lunch, Pine Flat Road is just around the corner. 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.


Hotel Healdsburg
Visit Website

Included Meals:

Breakfast | Lunch | Social Hour | Dinner


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


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. 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 at the famed Oakville Grocery. You’ll say farewell to your guides at 1:00 PM at the Hotel Healdsburg, before boarding the shuttle to the Westin St. Francis Hotel in San Francisco, arriving at 3:00 PM. Taxi and shuttle services are available to both airports from there. If you plan to fly out of the Bay area on Sunday, please avoid scheduling your flight any earlier than 6:00 PM.

Included Meals:

Breakfast | Lunch

Dates & Pricing

I'm sorry this trip has already happened, check back for future dates.

What is Single Occupancy?

Sometimes it’s more convenient and comfortable to have your own room while on vacation. We understand and that’s why we offer a Single Occupancy option. The additional price guarantees a private room all to yourself.



Hotel Healdsburg

Healdsburg, California

Hotel Healdsburg is Sonoma County’s premier luxury lodging on Healdsburg’s historic Town Plaza. Located in the heart of North Sonoma Wine Country, Hotel Healdsburg is the ideal venue for a romantic weekend, celebration or company meeting. A resort unto itself, the hotel offers a full service spa, pool, country gardens, and the acclaimed Charlie Palmer’s Dry Creek Kitchen.

What's Included

We Include More

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. Learn more

  • Gratuities for all scheduled special events, restaurants, hotels, local guides and transportation during your trip.
  • Private tours
  • Entrance fees to all group events/activities
  • All luggage transfers
  • All transportation during the trip, including private coaches
  • 3 nights of accommodation
  • In every region we travel, we uncover the area’s best, and most delightful accommodations. On our California Wine Long Weekend trip, you will stay in a sleek and sophisticated LEED-certified hotel located in the center of Healdsburg.
  • Daily breakfast, 3 lunches, 2 social hours, 2 dinners, and all snacks and drinks for each day
  • On our California Wine Long Weekend trip, lunch is usually a bounty of seasonal delights, replete with local goodies, while dinner ranges from bistro fare to fine dining. Local Californians dress comfortably and casually for dinner, ranging from shorts and button-down shirts, to jackets and ties. The food in California is typically fresh, local, and light, with hints of French and Italian themes integrated into the dishes.
  • The knowledge, support, and camaraderie of experienced guides
  • Daily route support
  • Paper route guides also available upon request
  • All luggage transfers
  • All transportation during the trip, including private coaches
  • Comprehensive trip literature
  • The use of a Trek Domane SL 7 carbon road bike with Shimano Di2 electronic shifting, or Trek 7.6 FX Hybrid bicycle
  • Trek Electric Assist XM700+ also available in a limited quantity
  • The use of Garmin Touring Plus GPS cycling computer
  • The use of Bontrager bike helmets and other gear and equipment to make your ride comfortable
  • Trek Travel water bottles
  • Coupon valued up to $500 off a new Trek Bicycle. Contact us for details.
  • Trek Travel Bontrager RL jersey and cycling socks

Thank your Guides, by tipping

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.
  • Gratuities for your Trek Travel Guides may be given at your discretion in response to their professionalism and leadership.Industry standard is for each individual guest to tip the guide team 5-10% of the trip price.


Trip Changes

Our itineraries are an approximation of our trips. Trek Travel strives to offer each and 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.

  • Rider Type | 2
  • Average Daily Mileage | 35
  • Terrain | Hilly
  • Average Daily Elevation | 1,200

On all of our vacations, Trek Travel strives to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. 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. 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. See Itinerary for specific daily ride distance and elevation options.

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.

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. See Included In The Trip Price for more information. 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 one of the hotels
  • Exclusive wine tasting at Hanna Winery

For an additional fee you may request to upgrade to the Trek Emonda SLR with Shimano Di2 Electronic shifting or Bontrager Aeolus carbon wheels for the ultimate riding experience. Contact our trip consultants for more details.

If you’re going we’re going on almost all our trips. Trips with 1 guest booked are guaranteed to run. Select trips like Cross Country, Race and Special Edition trips require a minimum number of guests to run and are not guaranteed until that number is reached. Contact your Trip Consultant for more details.

In the event that a departure has low enrollment, we will notify guests at 60-90 days before departure to give the option to select a different date with more guests booked. Please do not reserve airfare before confirming your Trek Travel trip.

When a trip is booked, a guest confirmation letter is immediately sent out. One week prior to the trip start you will receive an email containing a trip start meeting location reminder and any last minute information that you will need to know before your trip. Once you arrive at your destination Trek Travel staff will brief you on the day-to-day plan for the trip and provide you with daily route guides and a detailed map allowing you to ride with complete confidence and independence.

We understand things happen in life and sometimes you have to cancel or change your bike tour. We want to make it as easy as possible to do so and below you will find our timeline. If you ever have a question, just give us a call, 866 464 8735. Read our cancellation policy.

Please review our packing list page for more details.

Didn't find what you were looking for? Check out our General FAQs section. You will find answers to all the most common questions that don't necessarily pertain to a specific trip.

Meeting & Departing

How to get there

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 San Francisco International Airport (SFO) or Oakland International Airport (OAK).

All major airlines fly into and out of San Francisco International Airport. Taxi and shuttle services are available from both airports to downtown San Francisco. Taxi rates range from $50-75 from San Francisco International Airport to San Francisco; and $50-60 from Oakland International Airport to San Francisco. The Bayporter Express (415 467 1800) and Super Shuttle (415 558 8500) also run between both airports and San Francisco, with rates ranging from $20-30 per person.

Westin St. Francis Hotel lobby, by the large clock | San Francisco, California

Your Trek Travel guides will meet you at the Westin St. Francis Hotel lobby, by the large clock (335 Powell Street, San Francisco, CA, 94102) at 9:30 AM on the first day of the trip. You'll enjoy a scenic private shuttle across the Golden Gate Bridge from San Francisco to the world-renowned Hanna Winery in Alexander Valley. You and your new traveling companions will gather for a picnic lunch, overflowing with local specialties. 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.

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 first hotel, Hotel Healdsburg (707-922-5256), 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.

Hotel Healdsburg | Healdsburg, California

You will say farewell to your guides at 1:00 PM at the Hotel Healdsburg. You'll shuttle to the Westin St. Francis Hotel in San Francisco, arriving at 3:00 PM. Taxi and shuttle services are available. If you plan to fly out on Sunday, please avoid scheduling your flight any earlier than 6:00 PM.

Before & 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. Should you decide to explore before your trip start, you may want to consider giving your legs ample rest time for the cycling ahead! There are numerous attractions in the San Francisco area - from the Golden Gate Bridge, Chinatown, Fisherman’s Wharf, Alcatraz, to Ghirardelli and Union Square. For a preview and help in planning, try 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 pre and post-trip hotel:

The Hotel Monaco

The Hotel Monaco is a French-inspired luxury hotel catering to the savviest of travelers. Located just steps from Union Square and the Theatre District in downtown San Francisco, you’re sure to find entertainment to suit your tastes.

501 Geary Street | 866 622 5284 | | ~$355

Westin St. Francis

Renowned for its legendary service, the historic Westin St. Francis boasts luxurious guest rooms and world-class dining.

335 Powell Street | 415 397 7000 | | ~$297

W San Francisco

A chic, modern hotel set in the heart of downtown San Francisco, W San Francisco was listed on Condé Nast Traveler’s Gold List in 2002.

181 Third Street | 415 777 5300 | | ~$445

* Hotels listed above are local properties we love. We do not have special rates available.

Experience It

Similar Trips

Trek Travel Difference

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the full-carbon, ultra smooth Trek Domane 5.9, to the comfortable Trek 7.6 FX Hybrid–both included in the trip cost, to our numerous upgrade options, you deserve the best ride on your vacation.

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.