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California Wine Country Explorer

Calistoga to Healdsburg

Our signature California Wine Country vacation provides a full-bodied blend of panoramic views, flavorful wines, quaint towns, and scenic cycling along twisting byways past vineyards, farms and countryside. California wine country is known internationally for its weather and soil that produces some of the world's most delicious wine. We'll show you some of the lesser-known treasures of this region including the quietly emerging craft spirits and cider brewing scene. We'll pedal the gently undulating terrain that traverses vineyard after vineyard, stopping to sample exclusive wines, fresh California cuisine, and contemporary accommodations. Relax at the completely renovated Indian Springs Resort--a Spanish Mission Revival oasis with a chic, bohemian touch--and the incredibly hip and modern H2 Hotel. You can be as leisurely or as focused as you want, but make no mistake, Trek Travel has crafted this vintage wine tour with you and your travel partners in mind.

Trek Travel Bike Tour Luxury Upgrade Icon Upgrade to California Wine Country Luxury
$2399 Per Person
6 Days & 5 Nights
Rider Type: ?
2 - Recreational Non-riders Welcome
Hotel Style: ?
From $2399 per person View All Details
Trip Wows
Visit one of California's sacred treasures, the Redwood Forest
Experience Healdsburg's brand-new Alley 6 Craft Distillery for an exclusive private tour and spirit tasting
Discover the varied and vineyard-lined terrain of Sonoma County's big three appellations: Russian River, Dry Creek Valley, and Alexander Valley
Enjoy creatively crafted yet approachable cuisine at the lively and vibrant Spoonbar. From plate to place, everything about Spoonbar is a rich alchemy of art and craft
Watch the Experience
Touring by bikes is perhaps the best way to experience the landscape of a region. Sonoma and Napa are beautiful with great wineries, vineyards and art houses along the routes.

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: +$950
Single Occupancy from: +$950
Jun 30 – Jul 5 
Guaranteed Limited Availability
$2999 / Person, Double Occupancy Book this date
Jul 7 – Jul 12 
Guaranteed Limited Availability
$2999 / Person, Double Occupancy Book this date
Jul 14 – Jul 19 
$2999 / Person, Double Occupancy Book this date
Jul 21 – Jul 26 
$2999 / Person, Double Occupancy Book this date
Mar 15 – Mar 20 
$2399 / Person, Double Occupancy Book this date
Mar 22 – Mar 27 
$2399 / Person, Double Occupancy Book this date
Mar 29 – Apr 3 
$2399 / Person, Double Occupancy Book this date
Apr 5 – Apr 10 
$2399 / Person, Double Occupancy Book this date
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. All you need to do is pick any open trip date, get your group together and we will do the rest. Private trip pricing is as follows:
  • 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 +$2,500 per person to trip price*
*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.

After a scenic private shuttle across the Golden Gate Bridge from San Francisco to the charming town of St. Helena, you'll meet your guides at the Clif Family Winery Tasting Room, a local cycling hotspot owned by the Clif family (of Clif Bar fame). Sample the signature Clif Family Wines, and tantalize your taste buds with a bite from their gourmet, on-site food truck. After a short round of introductions to your fellow travelers and a bike fit, you’re free to start riding through the Napa Valley into Calistoga, where you'll enjoy two nights at the newly renovated, chic, bohemian hideaway, Indian Springs Resort and Spa. On your way, pass by the world-famous Culinary Institute of America at Greystone, the historic Charles Krug Winery and beautiful Markham Vineyards. This evening we’ll gather for drinks and dinner at Sam's Social Club. Offering rustic American cuisine prepared with the freshest seasonal ingredients, you'll find a new twist on classic dishes. Paired with artisan cocktails, local wine, or a craft beer that's brewed on site, you won't second guess why the NY Times hailed it, "the tastiest food in Napa Valley."

Today's Ride:

Clif Family Winery to Calistoga
Approximately 11 miles with 560 feet of climbing

Today's Activity:

Private Shuttle from San Francisco to Calistoga, Wine Tasting at Clif Family Winery


Indian Springs Resort and Spa

Included Meals:

Social Hour | Dinner

Options abound today as you leave the Napa Valley and pedal into the pristine Pope and Chiles Valleys. You’ll ride switchbacks through high canyon walls and hillsides covered with scrub brush as you make your way along the shores of Lake Hennessey. Enjoy the peace and tranquility of wine country over a gourmet Trek Travel picnic and private tour of Summit Lake Vineyards, residing high above the Napa Valley on Howell Mountain. Owners Bob & Sue Brakesman made their dream a reality on a small plot of land over 40 years ago. Today, Bob’s daughter, Heather shares her passion for this lifestyle with every Trek Travel guest that passes down their gravel driveway. Spend the afternoon discovering Calistoga on foot or relaxing at the incredible Indian Springs Resort and Spa. Have a soak in their very own Olympic-sized mineral pool, built in 1913. Or, take to their spa and enjoy a signature mud bath of volcanic ash which is unique to the region. The Indian Springs property is blessed with rare resources such as the geysers and a volcanic ash deposit which have inspired a long tradition of healing and renewal. (Please make any spa reservations at Indian Springs Resort & Spa before your trip for any time after 4:00 PM today.) This evening, dine on your own at a suggested bistro or any other in town.

Today's Ride:

Calistoga to Summit Lake Vineyard
Approximately 37 miles with 3,400 feet of climbing

Short Option:

Calistoga to Pope Chiles Valley Country Store with shuttle
Approximately 30 miles with 1,700 feet of climbing

Avid Option:

Calistoga to Summit Lakes Vineyard Loop
Approximately 54 miles with 3,800 feet of climbing


Indian Springs Resort and Spa

Included Meals:

Breakfast | Lunch

Today we’ll cycle north from Napa Valley into Sonoma County. Enjoy a morning climb to cross the county line or opt to take a shuttle over the hills and save your energy for the eucalyptus-lined country roads of the Knights and Alexander Valleys. Take a break from pedaling and stop to taste a crisp Sauvignon Blanc at Hanna Winery or a robust Zinfandel at Soda Rock. Lunch is on your own in the quaint and inviting town of Healdsburg, your home for the next 3 nights. Spend the afternoon by the pool or indulging in an afternoon nap. Or wander the town plaza and the many boutiques and galleries nearby, stopping for a cappuccino at the guide favorite, Flying Goat Coffee. Tasting rooms abound in town, making it convenient for you to stroll around and discover a new favorite wine. Tonight, choose to dine on your own from one of the numerous exquisite Healdsburg restaurants.

Today's Ride:

Calistoga to Healdsburg
Approximately 29 miles with 1,400 feet of climbing

Avid Option:

Calistoga to Healdsburg with Pine Flats Hill Climb
Approximately 52 miles with 4,800 feet of climbing



Included Meals:


Today you’ll follow the tranquil byways through the Alexander and Dry Creek Valleys. If you’re up for it, challenge yourself on 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. Pause at your leisure to indulge your palate at local favorites such as SIMI Winery, taste from the barrel at Zichichi, or refresh with a cool, crisp, biodynamic Sauvignon Blanc in Quivira’s solar-powered tasting room on our way to lunch at the Dry Creek General Store. Established in 1881, the store is a local hot spot for delicious handcrafted lunch specials, and is loaded with unique gifts. After lunch, back in Healdsburg, experiment with a different taste of Sonoma: a Trek Travel-exclusive tasting at Alley 6 Craft Distillery. This is a true, small batch, grain-to-glass operation, nestled a few quiet blocks away from the lively town square. Maybe take a bottle of their signature Rye Whiskey home to share with friends. Tonight's dinner is yours to choose at one of the many bustling restaurants.

Today's Ride:

Healdsburg to Dry Creek Loop with Sonoma Lake Return
Approximately 41 miles with 1,920 feet of climbing

Avid Option:

Healdsburg to Dry Creek Loop with Rockpile Road
Approximately 46 miles with 2,500 feet of climbing



Included Meals:


Today you’ll cycle through the Russian River Valley, with its tantalizing Pinot Noir grapes and ever-present vineyards. Pedal past scenic views of Mount St. Helena, the Mayacamas mountain range, and the Russian River on your way to the towering redwoods of Armstrong Woods State Reserve. Cruise through the winding park roads and see the oldest tree in the park at 1,400 years old, or the tallest tree at 310 feet high. Enjoy a quick bite before continuing on to the west. Fourteen miles later, feast your eyes on the mighty Pacific Ocean from the coastal town of Jenner. The mist might be eerie and thick but no matter what, you can’t miss the tell-tale scent of the sea. Take our shuttle back to the hotel or choose to challenge yourself with the return ride back to Healdsburg. If you do ride back, you can visit some of the area’s famed wineries on the way like Korbel, Arista, or Porter Creek. This evening, a fantastic week culminates with some real fun. First, enjoy a social hour with your guides and fellow guests at H2 before tonight's meal. Then, head back to the lively and vibrant Spoonbar to enjoy a beautiful presentation of delicious, creatively-composed local Sonoma County fare. Everything about Spoonbar is a rich alchemy of art and craft, from the place to the plate. Tonight, it’s yours to indulge in.

Today's Ride:

Healdsburg to Armstrong Redwoods Loop
Approximately 42 miles with 1,800 feet of climbing

Short Option:

Healdsburg to Armstrong Redwoods with shuttle
Approximately 17 miles with 600 feet of climbing

Avid Option:

Healdsburg to Armstrong Redwoods Loop with Sweetwater Climb
Approximately 42 miles with 2,500 feet of climbing



Included Meals:

Breakfast | Lunch | Social Hour | Dinner

Take a final morning spin through Dry Creek Valley to loosen your legs or enjoy a peaceful morning in Healdsburg and the chance to do some shopping and wine tasting in the town plaza. Sip a cappuccino at the Dry Creek General Store mid-ride while overlooking lush vineyards before pedaling into Healdsburg. Take some time to freshen up before checking out of the hotel. You'll board a private shuttle at 11:00 AM taking you back to the Westin St. Francis in San Francisco.

Today's Ride:

Healdsburg to Yoakim Bridge Loop
Approximately 21 miles with 160 feet of climbing

Short Option:

Healdsburg to Lambert Bridge Loop
Approximately 11 miles with 104 feet of climbing

Today's Activity:

Private Shuttle to Westin St. Francis, San Francisco

Included Meals:



hotel image

Indian Springs Resort and Spa

Calistoga, California

Located in the heart of the spa town of Calistoga, this cozy bohemian hideaway tucked in the Northern end of Napa Valley celebrates its Spanish history while offering supremely comfortable, modern luxuries that will sweep you off of your feet. After a long day exploring, allow yourself to soak in the mineral thermal pools from the four on-site geysers. A unique experience you'll likely not find anywhere else!
hotel image


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 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 XM700+

It’s lightweight and equipped with an adjustable pedal-assist motor that helps riders of all skill levels stay together, play together and make some great memories together. Included at no additional cost, these bikes will be available on a first-come, first-served basis, so reserve yours when you book today. Learn More

Trek 7.6 FX Hybrid

Trek 7.6 FX Hybrid
is also available on this trip


  • 5 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, 2 lunches and 2 dinners
  • 2 social hours of drinks and hors d'oeuvres
  • Ride a Trek Domane SL 7 disc, Trek's newest Electric-Assist, or a Trek 7.6 FX Hybrid
  • 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
  • Bontrager WaveCel helmets
  • 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)
  • Cinch sack day bag to keep
  • All gratuities for drivers, local experts and hospitality staff
  • All luggage transfers and transportation during your trip
  • A personalized 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 7.6 FX Hybrid bike
  • Trek Electric Assist XM700+ also available in a limited quantity
  • 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?

28 miles
166 miles
1,177 feet
7,060 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. 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 in boutiques around Calistoga and 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 Reserve
  • Indulge in a mud bath at Indian Springs Spa

See itinerary for specific daily ride distances and elevation options. 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. 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

San Francisco International Airport (SFO) or Oakland International Airport (OAK)
12:00 PM
Westin St. Francis Hotel lobby, by the grandfather clock, San Francisco, California

Say Farewell

San Francisco International Airport (SFO) or Oakland International Airport (OAK)
11:00 AM
h2hotel, Healdsburg, California


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. From Healdsburg, you may arrange a short taxi to the Sonoma County Airport shuttle which offers hourly shuttles to SFO for $34 per person, schedule available at www.AirportExpressinc.com.

Your Trek Travel guides will meet you at the Westin St. Francis Hotel lobby, by the grandfather clock (335 Powell Street, San Francisco, CA 94102) at 12:00 PM on the first day of the trip. We’ll shuttle approximately 75 minutes to Clif Family Winery in St. Helena to enjoy wine and explore the unique tasting room. Be sure to have your cycling gear, including shoes and pedals, packed in a small bag separate and apart from your luggage. We will fit you to your bike and begin our first day’s ride to Calistoga.

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, Indian Springs Resort and Spa (707) 942-4913, and leave a message with your expected arrival time and contact details. Evans Airport Service provides express bus service from the San Francisco or Oakland International Airport to the City of Napa ($29 one way). Or, "As You Like It! Wine Country Tours" has a Trek Travel rate from San Francisco. The luxury car service costs approximately $195; see www.asyoulikeitwinecountrytours.com.

View our pre hotel recommendations


You will say farewell to your guides at 11:00 AM at the h2hotel. You’ll then have the day on your own to explore Healdsburg or head to your next trip destination. Trek Travel provides one complimentary shuttle to the Westin St. Francis Hotel in San Francisco arriving at approximately 1:00 PM. Taxi and shuttle services are available to both airports. If you plan to fly out of the Bay area on Friday, please avoid scheduling your flight any earlier than 5:00 PM.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

Warm sunny days (70F-80F) 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 & 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, 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 pre- and 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 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.

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