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Guest Choice: Healdsburg, CA

Just north of San Francisco in the heart of Sonoma County lies the delightful city of Healdsburg. Surrounded by three major wine-producing regions, Russian River, Dry Creek, and Alexander Valley, this is truly wine country. This charming city is a treasure for food-lovers and offers stunning views as you bike along the rolling hills of grape vines.

Our newly redesigned California Wine Country 4-Day Weekend trip takes you through these captivating landscapes and lets you unwind in the charming epicenter of Healdsburg. Here you can sip on very good wine at countless wineries and tasting rooms and feast on equally good food at one of the award-winning restaurants. In a city where old-town culture combines with new, award-winning features, Healdsburg will in some way or another win your heart. When you’ve got the time to take in the city on your own, here’s where I would go to get the most out of my visit.

Ride past vineyards on Trek Travel's California Wine Country bike tour

Where To Go to Wander: Downtown Healdsburg
Just steps away from Hotel Healdsburg, take a stroll through the downtown center surrounding the town plaza. Each block is lined with charming shops, tasting rooms, galleries and outstanding restaurants. In true Wisconsinite-fashion, I search out specialty cheese shops to indulge in new bites of local flavors. Stop by the Cheese Shop of Healdsburg for local artisan cheeses and accoutrements and take your snacks and a blanket to the plaza for a relaxing afternoon picnic. Stop for a pick-me-up with the perfect cup of coffee at Flying Goat Coffee, or for a lovely cup of tea, chai, or hot chocolate. If you have Saturday morning available, be sure to visit the Farmers’ Market one block west of the Plaza to enjoy the the local food community.

Where To Go for Baked Goodss: Downtown Bakery & Creamery
Stopping in to this family run bakery is a must while visiting Healdsburg. Owner Kathleen opened this bakery in 1987 with her friends, all former colleagues at the award-winning and renowned Chez Panisse. Today Kathleen and her children run the bakery, serving up the best baked goods in the area. Using the best local and organic ingredients they can find, the quality of their creations is impeccable. Satisfy your post-biking sweet tooth with one (or two) of the famed sticky buns, or peel apart one of their fresh, buttery croissants. Don’t miss out on trying the cinnamon and sugar-dusted donut muffin that is raved about by locals and visitors.

Where To Go to Dine: Bravas Bar de Tapas
Healdsburg is considered the gourmet center of Sonoma County, and there is no shortage for where you can grab a really great bite to eat just a walk away from your hotel. Enjoy Bravas Bar de Tapas, awarded with “One of the top 20 tapas restaurants in the US” by Travel + Leisure and a “Top 100 Bay Area Restaurant” by the San Francisco Chronicle for the past three years. This tapas bar serves up traditional Spanish and modern tapas-style dining. Owners Mark and Terri Stark are James Beard nominees and own a few restaurants in Sonoma County, this one being their newest, and well-recognized already. They have created a relaxing and fun space to share plates and sip on a cocktail from their impressive drink menu. Sit out on the patio under romantic strings of lights and share the paella with a group of friends or try a selection of smaller plates. This restaurant is a top-choice for locals and visitors, so be aware of busy weekend nights. I’d recommend calling ahead to reserve a table, 707-433-7700. Read more culinary favorites by our Trip Design Manager Meagan Coates from her trip to California Wine Country, including Charlie Palmer’s Dry Creek Kitchen and h2’s Spoon Bar.

Visit Healdsburg SHED on Trek Travel's California Wine Country Luxury Cycling Vacation

Where to go for a snack and shopping: SHED
Winner of a 2014 James Beard Award for restaurant design, SHED is a community gathering space designed to bring us closer to the way we grow, prepare, and share our food. Part market, part café, part farm, this culmination is a delightful stop for fresh flavors and local shopping. Earlier this year we had the honor of interviewing owner Cindy Daniel to learn more about her creation of SHED. The offerings start with a large menu selection including beverages made at their fermentation or coffee bar and a café serving up combinations of fresh, local ingredients. While you’re there pick up artisan-made goods in their packed “pantry” that you won’t be able to resist perusing. Try a refreshing kombucha or shrub at their fermentation bar or a sandwich or salad from the café, grab a seat on the terrace and enjoy.

About Guest Choice:
You will often hear us say, “It’s your day, you decide,” because our smaller group size allows the flexibility for you to decide how your day unfolds. In addition to multiple daily ride options and shuttle flexibility, this also means that we offer ‘guest choice’ nights designed for you to indulge at a local restaurant of your choosing, or explore the local sites. Whether you want to order take-out while relaxing by the hotel pool or get dressed up for a fancy dinner in town, guest choice nights let you craft your own perfect evening.

Intern Chronicles: Part 2, the next step

Although interning for Trek Travel has been remarkable, I can’t contain my excitement about moving on.

During the last four years I have lived the dream. I’ve learned from world-class educators. I’ve sailed across the breathtaking Pacific Ocean and skied 30+ days per winter in the magnificent Colorado Rockies. I’ve spent summers enjoying the lakes and bikes paths of Madison, WI. Like I said…living the dream. But when a new opportunity came knocking, I had only one question: when can I start?

Before you worry, I’ll still be around. In fact, I think a better word to describe my move is ‘up’. Last month, I had the opportunity to play hooky for a week and head to Solvang, California for Trek Travel’s 2014 New Guide Training. For ten days, we potential new guides worked tirelessly to learn the ropes. Although my family thought it was a glorified excuse to escape winter and ride bikes in the sunshine, I can assure you this was not the case. We spent far more time learning how to fix, load, clean, and fit the Trek Domane than we did riding it. We went back to drive school and learned how to safely maneuver a fully loaded van and trailer unit. Despite their humility, ask any Trek Travel guide and they are likely to brag about their ability to back a trainer into a parking stall without any hesitation. We spent hours in the hotel conference room, learning as much as we could absorb. We heard from Tania about Trek Travel’s values, spoke with Meagan about trip design, sat in on a sales meeting with Emily, and talked to Tim about expenses on our newly minted credit cards. We learned enough acronyms to make anyone’s head spin. Finally, after we had covered the ‘basics’, it was time for the real test. We met with vendors, drove routes, grocery shopped, prepped bikes, delivered safety talks, crafted picnic lunches, and provided support from the van and the saddle. From start to finish, we guided a mock trip…and that makes it sound simple.

Because of the veterans who made it happen, not a single minute of the week felt like work. They imparted their knowledge, shared their secrets, and patiently answered our questions. They are the rock stars we hope to become. My 2014 co-guides and I come from a broad spectrum of backgrounds and experiences, but during those late nights and early morning we bonded over our enthusiasm for what is the next chapter in each of our lives. The creativity and collaboration, ingenuity and zest, determination and dedication that we bring into our new careers is infectious. With the leadership and guidance of those who came before us, we are ready to put all this talk into action.

This June, college diploma in hand, I will finally get to join my co-guides in the field. I couldn’t ask for better companions with whom to share this adventure. Although the learning never ends, the fun is just beginning. I’m ready to take on the world. The question is: are you?

Intern Chronicles: Part 1, working for Trek Travel

How did a 21-year-old college senior end up with a four-year summer internship at the world’s best cycling vacation company on her résumé? At 17-years-old I was a washed up soccer player, bored summer lifeguard, outdoor enthusiast and recent high school graduate. Over the years multiple broken legs have forced me take up a low-impact fitness alternative and as a decent athlete native to the cycling industry mecca of Madison, WI, cycling was the easy choice. I quickly took to the bicycle and after a few hours in the mailroom each week I had found my place at Trek Travel as well. The people, the mission, the product—it was all such a perfect fit. I was hooked.

Let’s start with the people. At Trek Travel we like to use the word ‘rock star’…a lot. But after many years of working alongside best in class employees I can honestly say that every person on the Trek Travel team is truly a rock star. That first summer I asked hundreds of questions each day. To be honest, I probably still do. Maybe I’d broken the postage machine, jammed the printer, or couldn’t navigate the online database. Pretty small problems in the grand scheme of things, but no matter what I threw their way it was always met with unwavering patience and a true desire to help.

Over time I’ve watched as this same attitude is applied day in and day out with guests. Four summers in a small office has given me opportunities I could not have imagined, the most unique of which is the ability to work with many different departments. Not ironically, this same benefit extends to guests as well. Each and every employee, from sales and customer service consultants to trip design and logistics specialists, work together seamlessly to provide guests with solutions to all their problems and answers to all their questions. Always with unwavering patience and a deep desire to help make yours the best vacation possible. There really is no better way to describe everyone who works at Trek Travel than ‘rock stars’, and there is no better place that I could have worked during the ‘best years of my life’.


If a date is marked as Private, it is reserved for a private group.

Looking to travel with a small group or looking for a custom date?
Call our trip consultants at 866-464-8735

What is the Difference?

Ultimate Luxury:

Savor some of the most spectacular, 5-star properties in the world. Exuding luxury and elegance, these one-of-a-kind accommodations offer the chance to rejuvenate at award-winning spas, dine at Michelin-starred restaurants, and more.


Enjoy luxurious accommodations handpicked for a refined experience. From signature spa treatments to delicious local cuisine, you’ll be more than provided for; you’ll be pampered.


These handpicked hotels provide relaxation and fun in a casual and comfortable environment. Delicious cuisine and great service mix perfectly for a memorable stay.


On select cycling vacations, you’ll stay at a mix of Explorer and Luxury hotels. Rest assured, no matter which hotel level you’re at, our trip designers carefully select every accommodation.

Activity Level

Level 1:

Road: 1-3 hours of riding. Up to 25 mi (40 km). Up to 1,000 ft (300 m).

Gravel: 1-3 hours of riding. Up to 20 mi (35 km). Up to 1,000 ft (300 m).

Hiking: 1-3 hours of hiking. Up to 5 mi (8 km). Up to 1,000 ft (300 m).

Level 2:

Road: 2-4 hours of riding. 20-35 mi (35-60 km). Up to 2,500 ft (750 m).

Gravel: 2-4 hours of riding. 15-30 mi (25-45 km). Up to 2,000 ft (300 m).

Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 m).

Level 3:

Road: 3-5 hours of riding. 25-55 mi (40-85 km). Up to 4,500 ft (1,500 m).

Gravel: 3-5 hours of riding. 20-40 mi (35-60 km). Up to 3,000 ft (900 m).

Hiking: 3-5 hours of hiking. 6-10 mi (9-16 km). Up to 2,000 ft (600 m).

Level 4:

Road: 4+ hours of riding. 40-70 mi (60-110 km). Up to 8,000 ft (2,400 m).

Gravel: 4+ hours of riding. 30-50 mi (45-80 km). Up to 4,000 ft (1,200 m).

Hiking: 4+ hours of hiking. 7-15 mi (11-24 km). Up to 4,000 ft (1,200 m).

What are your trip styles?

Classic - Reserve:

Savor the finer things as you relax in luxurious 5-star accommodations and wine, dine, and ride in some of the most unforgettable destinations around the world.

Classic - Signature:

Explore beautiful destinations by bike, enjoy extra inclusions, savor delicious local cuisine, and enjoy the perfect mix of accommodations.

Classic - Discover:

Enjoy a casual cycling vacation with fantastic routes and comfortable accommodations.

Ride Camp:

Train like the pros in some of their favorite riding destinations.

Pro Race:

See the pros in action at the biggest cycling events of the year.

Cross Country:

Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.


Enjoy a bike tour on your schedule with just your chosen travel companions.

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