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Custom California Wine Country Luxury

Napa, Sonoma and the Russian River Valley

Saturate your senses in one of the world’s premier cycling regions. Is there anything more elegant than a week spent drinking in the breathtaking views and outstanding wine in Napa and Sonoma counties? Add luxurious accommodations and unparalleled adventures, and you’ve got an uncommon blend of indulgence and experience. Sun-drenched vineyards flank us on every side as we pedal through the famed centuries-old Armstrong Redwoods and build an appetite for the farm-to-table fresh food to come. We’ll visit local wineries, savor their favorite varietals, and saturate ourselves in the culinary culture of a foodie’s heaven, Yountville. This isn’t just a wine tour. Nor is it a bike tour. It’s a voyage for your senses from top to bottom. Immerse yourself in the wine, food, and finer side of life of California Wine Country.
$3499 Per Person
6 Days & 5 Nights
Rider Type: ?
2 - Recreational Non-riders Welcome
Hotel Style: ?
From $3499 per person View All Details
Trip Wows
Savor fresh and unique blends discover local and seasonal delights that Bay Area cuisine is known for
Stay in Sonoma's finest - we’ve booked your stay in Healdsburg’s premiere luxury hotel, Hotel Healdsburg
Visit Summit Lake Vineyard to enjoy lunch, a glass of wine and an insider's look at the family-owned vineyard
Explore the ultimate foodie town, Yountville. You won't go hungry in the Culinary Capital of Napa.
Watch the Experience
The itinerary was extremely well thought out. Our vacation was classified as "recreational" but a couple of us wanted something more challenging. No problem - Dan and Jake were happy to arrange. Every day included enjoyable coffee, lunch and/or wine tasting stops. The welcome dinner on the first night and the farewell dinner and cocktails on the last evening were truly excellent.

Dates & Prices

Early Booking Savings Ends January 15th

Book today for the best savings of the year and the widest availability of dates. Not sure where or when you want to travel?
We don’t charge a fee for changing dates or destinations up to 90 days prior to your trip start.
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Single Occupancy from: +$1200
Jul 19 – Jul 24 
$3499 / 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.

Your Trek Travel guides will meet you at the Westin St. Francis Hotel lobby, by the large grandfather clock at 9:30 AM on the first day of the trip. We'll take a scenic private shuttle to Trattore Farms for picnic lunch and wine tasting. After a bike fitting, you’ll start your ride and follow the tranquil byways through Alexander and Dry Creek Valleys on your way to our first hotel: Hotel Healdsburg. Here, connect with locals, expert travelers, farm hands, and vineyard owners alike, all surrounded by an incredible downtown square. If you’re up for a challenge this afternoon, tackle Rockpile Road, a beautiful detour through the Lake Sonoma Recreation Area with views of Lake Sonoma. Along the way you’ll pass many distinctive wineries in the Dry Creek Valley and one of the top zinfandel producing regions. Tonight you'll celebrate a an exquisite meal at Hotel Healdsburg's very own Dry Creek Kitchen part of renowned chef Charlie Palmer's group of classic restaurants.

Today's Ride:

Alexander Valley Loop
Approximately 27 miles with 570 feet of climbing

Avid Option:

Alexander Valley Loop with Lake Sonoma Return
Approximately 36 miles with 1725 feet of climbing


Hotel Healdsburg

Included Meals:

Lunch | Social Hour | Dinner

Today you’ll enjoy the rustic simplicity of tranquil byways over Chalk Hill and through the Alexander Valley. You’ll head south, circumnavigating Healdsburg, beneath a horizon of endless vineyards. Along this stretch of road you'll see the grapes, smell the fermentation, and almost taste the wine. You’ll pass many unique and distinctive wineries that will tempt you for a visit on our way to the suggested 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 a challenging climb that's rewarded with views of the surrounding valleys. If it's not for you, take a shorter option to town and enjoy our charming accommodations. Or, wandering the town plaza of Healdsburg is a must, with its small-town charm and historic appeal. Or simply enjoy an afternoon glass of wine at the hotel. Tonight you'll gather with your fellow travelers for an incredible Californian farm-to-table feast at our local favorite restaurant, Chalkboard. It is here that the farm culture of Sonoma comes to life and is embodied in fresh, local savory foods that make this area second-to-none.

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 3100 feet of climbing


Hotel Healdsburg

Included Meals:

Breakfast | Social Hour | Dinner

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 we ride through the Russian River Valley, known for its tantalizing Pinot Noir on our way to Armstrong State Natural Reserve. 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 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


Hotel Healdsburg

Included Meals:


Today, you'll make your way out of Healdsburg to Yountville, a charming town well known by foodies for Thomas Keller’s French Laundry, along with a host of incredible high-end foodie establishments. Begin your day with a ride through the beautiful Alexander and Knights' Valleys, home to some of the finest Sauvignon Blanc, Cabernet Sauvignon, Malbec, and Merlot due to the high heat of summer and grapes ripening to their fullest potency. You'll soon crest the hill marking the transition into Napa Valley, before descending into the spa town of Calistoga where you can enjoy lunch on your own with the help of your guides. Choose to hop in the van for a quick ride to our brand-new hotel for 2018, the North Block Hotel, where you can sit under a cabana by the pool or book a massage at the renowned North Block Spa (please pre-book in advance by calling 707 944 8080) or complete your ride down the famed Silverado Trail, home to some of the finest wineries in Napa Valley. Rejoin your newfound friends tonight for dinner at James Beard Award nominee chef Richard Reddington’s Italian-inspired restaurant Redd Wood.

Today's Ride:

Healdsburg to Calistoga with afternoon shuttle
Approximately 27 miles with 1,500 feet of climbing

Avid Option:

Healdsburg to Yountville
Approximately 48 miles with 2,200 feet of climbing


North Block Hotel

Included Meals:

Breakfast | Dinner

Today’s options are many as you ride out of the Napa and Sonoma Valleys and into less discovered but equally inviting cycling territory—the Pope and Chiles Valleys with its switchbacks, high canyon walls and scrub-brushed hillsides. Enjoy a gourmet Trek Travel picnic lunch with our good friends at Summit Lake Vineyards, a small family-owned winery perched atop Howell Mountain. We've been joining them for lunch and wine for over a decade, and each time we visit, it's a true delight. Heather, the daughter of the bunch, is the vineyard guru serving you some of the most incredible Petite Sirah, Cabernet, and Zinfandel you've ever tasted. Afterward, you can choose to ride or shuttle back to the hotel for a relaxing spa treatment, or to relax by their pool. This evening, you'll dine as a group at one of Thomas Keller's prized restaurants, Ad Hoc. Originally created for showcasing the American comfort food of his childhood, Ad Hoc has become a staple in the "culinary capital" of Napa Valley. Featured as one of Food and Wine magazine’s “25 Places to Try" you'll experience four, family-style courses, changing nightly. It's sure to be a meal you'll never forget.

Today's Ride:

Yountville to Summit Lake Vineyards with shuttle
Approximately 31 miles with 2,700 feet of climbing

Short Option:

Yountville to Pope-Chiles Valley General Store with shuttle
Approximately 24 miles with 1,500 feet of climbing

Avid Option:

Summit Lake Vineyards Loop
Approximately 52 miles with 3,000 feet of climbing


North Block Hotel

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

Take an optional short morning spin along the Ride the Vine Trail to loosen up your legs. If you are not up for a ride, enjoy a peaceful morning at the hotel, strolling over to the famous Bouchon Bakery for a morning snack. Be sure to get there early before the line makes its way out onto the sidewalk! You will say farewell to your guides at 11:00 AM at the North Block Hotel and depart via private shuttle back to San Francisco.

Today's Ride:

Ride the Vine Trail
Approximately 13 miles with 160 feet of climbing

Included Meals:



hotel image

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.
hotel image

North Block Hotel

Yountville, California

Trip Advisor Certificate of Excellence Award This quaint, Mediterranean-inspired property is perfectly suited for a romantic wine country getaway. Home to 20 cozy, elegant rooms , each complete with wonderful beds, espresso machines, and luxurious bathrooms with a separate six-foot bathtub and walk-in shower. Post-ride, enjoy an intimate and upscale spa with personalized treatments; and an outdoor heated swimming pool with private cabanas and a Jacuzzi. Redd Wood, the hotel's restaurant (with James Beard Award nominee and Michelin-starred Chef Richard Reddington at the helm) offers Italian-inspired cuisine. Within brief walking distance of acclaimed restaurants in Yountville and a short drive to wineries, golfing, and boutique shops, this is the ideal home base for your journey in Napa Valley.

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


  • 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, 3 lunches and 4 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 and socks 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 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 and socks 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?

30 miles
179 miles
1,138 feet
6,830 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 all around Sonoma, Yountville and Healdsburg
  • Enjoy winery tours and tasting available at The Hess Collection, Silver Oak, and Porter Creek, to name a few
  • Walk and explore the Armstrong Redwoods State Park
  • Enjoy a relaxing and rejuvenating afternoon at one of the many exceptional spas.

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)
9:30 AM
Westin St. Francis Hotel lobby, by the grandfather clock, San Francisco, California

Say Farewell

San Francisco International Airport (SFO) or Oakland International Airport (OAK)
12:30 PM
Westin St. Francis Hotel, San Francisco, 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.

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. We'll take a scenic private shuttle to Trattore Farms for picnic lunch and wine tasting. 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 to Healdsburg.

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) 431-2800, 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 (STS) in Santa Rosa for around $34/person. Taxi from the Sonoma County Airport (STS) to Hotel Healdsburg is a fifteen minute taxi ride.

View our pre hotel recommendations


You will say farewell to your guides at 11:00 AM at the North Block Hotel. You'll then shuttle to the Westin St. Francis Hotel in San Francisco arriving at approximately 12:30 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 4:00 PM.

View our post hotel recommendations

Planning For Your Trip

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-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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