- 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*
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 lunch and a perfectly paired glass of wine. 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.
Alexander Valley Loop
Approximately 27 miles with 570 feet of climbing
Alexander Valley Loop with Lake Sonoma Return
Approximately 36 miles with 1725 feet of climbing
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.
Chalk Hill Loop
Approximately 37 miles with 900 feet of climbing
Chalk Hill to Jimtown Store with Shuttle
29 miles with 800 feet of climbing
Chalk Hill with Pine Flat Road
60 miles with 3100 feet of climbing
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.
Hotel Healdsburg to Armstrong Return
Approximately 40 miles with 800 feet of climbing
Hotel Healdsburg to Armstrong
Approximately 20 miles with 400 feet of climbing
Hotel Healdsburg to Sweetwater Springs – Armstrong With Westside Rd. Return
Approximately 42 miles with 1,500 feet of climbing
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.
Healdsburg to Calistoga with afternoon shuttle
Approximately 27 miles with 1,500 feet of climbing
Healdsburg to Yountville
Approximately 48 miles with 2,200 feet of climbing
North Block Hotel
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.
Yountville to Summit Lake Vineyards with shuttle
Approximately 31 miles with 2,700 feet of climbing
Yountville to Pope-Chiles Valley General Store with shuttle
Approximately 24 miles with 1,500 feet of climbing
Summit Lake Vineyards Loop
Approximately 52 miles with 3,000 feet of climbing
North Block Hotel
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.
Ride the Vine Trail
Approximately 13 miles with 160 feet of climbing
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.
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
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
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. Learn More
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.
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
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
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:
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 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.
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.