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Il Gallo Nero

The Black Rooster marks some of the greatest wines in the world.

It is easy to see why Tuscany remains one of our most popular trips. I moved to Italy some 12 years ago to immerse myself in this magic, and have determined that cycling through this region is the ideal way to learn about the place.

On a bike, we leave other tourists behind and get to experience places as they have remained for thousands of years. The epicenter of Tuscany – flanked by Florence to the North and Siena to the South – for its wine, wild boar, small, winding roads and forested hilltops. In the center of Chianti is the ideal, 9th century one-strip hilltop wonder of cobblestones enotecas and cafés known as Radda in Chianti. Ride up to the entrance of Radda in the morning and you’ll find Fabrizio Ferrucci, owner of Bar Dante making panini for the hungry denizens who flock to his café for local treats. Fabrizio will assure you that while Radda is not perfect, it is pretty close.

Visit Tuscany on a Trek Travel bike trip

Radda is so ideal, in fact, that the two warring city-countries of Florence and Siena have fought over it for centuries. Legend has it that late in the 12th century, these two archenemies finally decided to end their bloody land-feud peaceably. By parliamentary agreement, at the first crow of their respective roosters on the appointed day, one knight from Florence, and one knight from Siena would depart on horseback down the road the connects the two cities. At the precise point the two knights meet on their journey, the line would be drawn to divide the Province of Florence from the Province of Siena.

While Siena chose to fatten and spoil a fine, plump rooster, the Florentines were far more devious. They selected a lean, black rooster and locked it in a windowless dungeon without food or water. When the date arrived, the rooster’s hyper-sensitive retinas led him to crow his heart out, giving the Florentine knight a dramatic head start. He reached all the way to Fonterutoli, a territory of Castellina, before he met the Sienese knight. And so they established the border at Castellina, a mere 19 kilometers from Siena’s walled city.

To this day, the internationally recognized symbol of Chianti is a silhouette of Il Gallo Nero, The Black Rooster. It marks some of the greatest wines in the world, and cyclists wear the jersey with pride. Next time you find yourself in Radda, ask Fabrizio about his story. He just may fill you in on some more history of this remarkable area that we are fortunate to ride our bikes through. The rest of the learning comes from the air flowing in your face while you spin down the winding roads, the same roads the two knights thundered down all those years ago.

By Jacob Young, a guide for Trek Travel

Visit Tuscany on a Trek Travel bike trip

Experience a Trip to Tuscany for yourself»

Culinary Delight

A great meal is about more than the food on your plate. A perfect atmosphere makes any meal taste richer, effortless company makes it more fulfilling, and the right beverage helps it go down easily. A wave of nostalgia always sweeps over us as we sit down to our first meal at home. We crave the flavors and the environments of far away places. Though Healdsburg and Tuscany may top our list, we know that our next vacation will bring new tastes to savor, new friends to laugh with, and new landscapes to adore.

Healdsburg, CA by Meagan Coates

I sat down at my desk after returning from a weeklong bike trip in California’s wine country with a request to write a piece on my favorite North American restaurant and I have found it nearly impossible to pick a clear winner. Napa and Sonoma biking trips with Trek Travel

My first inclination is Charlie Palmer’s Dry Creek Kitchen in Healdsburg—an obvious choice as they receive so many nods in the culinary world with their fresh, local and seasonal food that is perfectly paired with a supremely local wine list and formal but non-stuffy service. Diners enjoy fresh caught fish, local duck and an array of farm-fresh vegetables in a hip and beautiful dining room with expansive ceilings and large windows.

Our Trek Travel groups even have the unique opportunity to dine in the intimate wine library off the hotel lobby after spending a day on the bike and an afternoon at the pool or spa on property. We cap it off with decadent desserts like the chocolate tart with pear sauce or the variety of fresh sorbets served in an old-fashioned soda jerk style container.

california-wine-country-weekend-02-1600x670However, I would be remiss not to mention other Healdsburg haunts like my new favorite—The Shed—located just off the square behind Hotel Healdsburg. Area farmers showcase their handmade products and provide the makings of super hydrating “shrub” drinks at the fermentation bar. I sampled the strawberry, carrot and kumquat but ultimately loved the blood orange best.

Or, just steps away are other amazing restaurants such as Willi’s Seafood, Ravenous, Bistro Ralph, Barndiva and countless others. Savor a craft cocktail at h2’s Spoon Bar (like the cucumber martini!) or just stroll around Healdsburg and you are sure to find something that suits even the most discerning palates. After visiting restaurants in every corner of the world, Healdsburg is definitely the best kept secret for foodie’s looking to travel in North America.

Tuscany, Italy by Kari Kruckow

But close your eyes and take a 6,000-mile journey across the Atlantic. Rolling green hills lined with cypress trees, sun kissed vines, slow food and delicious wines…oh and Roberto. Welcome to Tuscany!

Last week I was able to cycle through this beautiful region and experience its culture. The way Trek Travel invites you to be a local for 6 days on a Trek Bike is amazing. Cycling was the biggest highlight for me on this trip, but food was not far from the top.


Tuscany
I encourage you to grab a little something to munch on…I promise you will get hungry as I tell you about my favorite lunch spot on this trip: da Roberto, Taverna in Montisi.

Roberto made us all feel at home as soon as we rolled in on our bikes. He is a countryside cuciniere (cook), whose only claim is to feed himself and guests honestly. Roberto is a true joy and lives to feed people at his table. His mantra is to wake up every morning happy and build a space of peace, balance and harmony to offer to people that dine at his Taverna, which ties perfectly to the experience that you have cycling through Tuscany.

Aside from the comfort and ambiance, the food prepared was as honest, delicious, and as inspiring as the hilltops that overlook the Tuscan valley. The three-course meal was not a surprise on this Trek Travel trip, being as every meal and break on the bike offered plenty of fuel for the calories burned that day.

Tuscany LuxuryRoberto started off the lunch with a unique bean and carrot salad. It goes without saying, but the beans sourced from a local farmer, the carrots grown in his garden behind the restaurant. Food aside, one of the best “accents” to the menu was Roberto’s story behind each dish, his amicability is contagious with every guest that comes into his “home.” Next was the homemade pasta with a true Italian Ragu sauce, to coin a phrase, “mama, mia!” The lunch ended with three dessert options, my favorite was the panna cotta with berries. It provided just enough guilt and enough fulfillment to encourage the balance of the gorgeous ride that afternoon.

Roberto is proud of his food by identifying flavors by gathering fresh, local ingredients, protecting the value of biodiversity, and visiting farms for fresh cheeses and to certify the quality of his meal.

Roberto’s lunch experience was enriching on all levels and what made for a perfect afternoon was the short bike ride to a beautiful accommodation, which felt like an estate and offered a very relaxing evening.

What can I say, Tuscany is tasteful in so many ways. And it is certainly my favorite culinary delight in Europe.

Why Tania Picks Tuscany…

I have been lucky enough to collectively spend 2 years in Tuscany guiding and researching new trips, and when people ask what my favorite TT trip is, although hard to choose I pick Tuscany.  It really lives up to its reputation. Great wine, food, people, hotels, picturesque cypress lined drives, riding.  For me not one of those items stands out on it’s own.  It’s the blend of all these simple things that make it special; moments like watching the sunset over the Chianti hills, tasting wild boar ragu, watching the old men chat in the parks, the scent of Pecorino cheese wafting out of the stores in Pienza, taking a photo of the loan cypress tree on the top of a hill, tasting Brunello di Montalcino – in Montalcino, riding on some of the smoothest black topped roads through small villages, eating vine ripe tomatoes with just olive oil and salt. I could go on forever.  I would live in Italy again if the opportunity arose but for now I just feel lucky to have spent the time there that I did. If you love to travel and bike – don’t miss Tuscany!

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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.

Luxury:

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.

Explorer

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

Combined

On select cycling vacations, you’ll stay at a mix of hotel levels, from Explorer to Luxury to Ultimate Luxury. Rest assured, no matter which level of hotel 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).

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).

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).

Level 4:

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

Gravel: 3-5 hours of riding. 30-50 mi (45-80 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 - Discovor:

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.

Self-Guided

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