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West Coast

California Wine Custom 3-Day Weekend



California Wine Custom 3-Day Weekend

Russian River, Alexander Valley, and Dry Creek Vineyards

The bluebird days and vineyard-lined roads welcome cyclists of all abilities to California’s Wine Country Weekend.

Sonoma County - filled with unique wineries, quiet country roads, and world-class cuisine - has transformed Healdsburg into a vacationer’s delight.The locals’ desire for fresh and sustainable-farmed produce - which helps the food burst with flavor - is found in all the restaurants. Discover the varied and vineyard-lined terrain of Sonoma County’s big three appellations: Russian River, Dry Creek, and Alexander Valley. Visit one of the California’s sacred treasures, the Redwood Forest. Share the passion and joy of superb food and exquisite wine with all who live in Sonoma Valley.

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Build Your Own Adventure


Today's Ride:

Quivira Estate to Healdsburg
Approximately 21 miles with 300 feet of climbing

Short Option:

Quivira Estate to Healdsburg Direct
Approximately 14 miles with 1,000 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. After a private shuttle (2 hours), you’ll arrive at our trip start, a winery on the outskirts of Healdsburg. Healdsburg, well-known for its chic boutiques, unique tasting rooms, and exquisite cuisine, is also heralded as the epicenter of California’s three major wine growing regions—the Russian RiverValley, the Dry CreekValley, and the Alexander Valley. You and your new traveling companions will gather for a wine tasting and a picnic lunch, replete with local specialties and tastes for all palates. After a short round of introductions, your Trek Travel guides will discuss the rules of bike safety and specific cycling tips for riding throughout the Wine Country.They’ll spend some time familiarizing you with the Trek bicycle you’ll be riding and making sure that you and your bike are the perfect fit. Once you’ve been filled in on the details of the day, take a pre-bike stroll to explore the winery, or get on your bike and start the ride toward the AlexanderValley.Tonight you’ll gather with your newfound friends for a social hour to boast of our “secret” wine discoveries, before enjoying a glorious dinner at one of Healdsburg’s highly acclaimed restaurants.



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Today's Ride:

Healdsburg to Armstrong Woods Return
Approximately 48 miles with 1,000 feet of climbing

Short Option:

Healdsburg to Armstrong Woods
Approximately 26 miles with 500 feet of climbing

Avid Option:

Healdsburg to Armstrong with Sweetwater Return
Approximately 44 miles with 2,400 feet of climbing


Today you’ll cycle through the famous Russian River Valley, noted for its tantalizing Pinot Noir wines. Heading along quiet, shaded Westside Road, you are always within view of endless vineyards. Along this stretch of road, you can see the grapes, smell the fermentation, and almost taste the wine.This ride also offers you superb views of Mt. St. Helena and the Mayacamas mountain range. For the more adventuresome, you can choose to tackle the toughest climb of the week, Sweetwater Springs, and challenging grades, reaching 20%. Or choose a gentle ride into Guerneville, where you’ll stop midday for a lavish picnic, underneath the towering redwoods of Armstrong Woods Park. Enjoy a hike and visit the oldest tree in the park at 1,400 years of age, or gaze upon the tallest tree, 310 feet high. In the afternoon, enjoy a shuttle back to our hotel to spend time at our luxurious accommodations, or venture into Healdsburg’s town plaza for some last-minute shopping. If you decide to ride back, you’ll have the opportunity to sample some of the region’s favorites at a variety of wineries. Stop in at Gary Farrell, Arista, or C. Donatiello, or wait until you return to Healdsburg and enjoy a tasting at one of the numerous tasting rooms. For our final evening together, you’ll dine at one of Healdsburg’s unique restaurants.


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Today's Ride:

Yoakim Bridge Loop
Approximately 20 miles with 50 feet of climbing

Short Option:

Lambert Bridge Loop
Approximately 11 miles with 80 feet of climbing


Take a final morning spin to loosen up your legs in the Dry Creek Valley, or enjoy a peaceful morning at the hotel, lounging by the pool or reading the paper with a fresh glass of juice in the courtyard. Or, stroll the town square for some last-minute shopping. Enjoy a lunch of your choice in downtown Healdsburg. You’ll say farewell to your guides at 1:00 PM at the h2hotel. You’ll then shuttle to the Westin St.Francis Hotel in San Francisco, arriving at 3:00 PM. Taxi and shuttle services are available to both airports. If you plan to fly out of the Bay area on Sunday, please avoid scheduling your flight any earlier than 6:00 PM.


Dates & Pricing

This trip is available as a custom trip only, please refer to our custom trip page for more details.

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.


Stay at the H2 Hotel on Trek Travel's California Wine bike trip

H2 Hotel

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.

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
  • 2 nights of accommodation
  • In every region we travel, we uncover the area’s best, and most delightful accommodations. On our Custom California Wine Country trip, you will stay in a sleek and sophisticated LEED-certified hotel located in the center of Healdsburg.
  • On our Custom California Wine Country 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
  • The use of Garmin Touring Plus GPS cycling computer
  • Paper route guides also available upon request
  • Comprehensive trip literature
  • The use of a Trek Domane 5.9 carbon road bike with Shimano Di2 electronic shifting, or Trek Domane 5.9 Women’s Specific Design carbon road bike with Shimano Di2 electronic shifting (limited selection), 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

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 7.5-10% 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 | 700

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. California Wine Country Long Weekend 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. Fog, wind, and cool temperatures are characteristic of the coastline, so please be sure to bring warmer clothing and rain gear as well.

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 in boutiques around 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

For an additional fee you may request to upgrade to the brand new 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.

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.

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. We’ll then shuttle 2 hours to the Quivira Estate Winery. Here you’ll enjoy a picnic lunch and wine tasting before the first ride of the weekend. Be sure to have your cycling gear, including shoes and pedals, packed in a small bag, separate and apart from your luggage. After lunch, we will fit you to your bike and begin our day’s ride through Sonoma.

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, h2 Hotel (707 431 2202), and leave a message with your expected arrival time and contact details. The Sonoma County Airport Express shuttle (800 327 2024) services the Sonoma County Airport from SFO for around $30/person. A Taxi from Sonoma County Airport to our first hotel is approximately a 13-mile taxi ride.

Westin St. Francis Hotel | San Francisco, California

You will say farewell to your guides at 1:00 PM at the h2 Hotel. 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

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, and 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

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Trek Travel Difference

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the all-new, ultra smooth Trek Domane SL 7, to the new Trek Electric-Assist XM700+ and the comfortable Trek 7.6 FX Hybrid, 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.