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    Join us on an 8-day cycling tour of Tuscany’s picture-perfect landscape covered with olive tree groves, vineyards, and medieval hilltop towns. This trip will test your legs and your willpower as you climb Tuscany’s hills, eagerly chasing the next panoramic view. Prepare to chow down on some of Italy’s finest food (and wine!). Pedal through the heart of UNESCO World Heritage sites, and experience life as a local as you travel through small villages.

    Ride like a titan during the day and in the evening you’ll be treated like royalty with fine dining and luxury accommodations. In other words, prepare yourself to fully embrace la bella vita on this once in a lifetime tour of Tuscany.


    June 5-12, 2018

    - or -

    September 12-19, 2018

    The trip begins in the Castellina in Chianti, a charming town nestled into the vine-draped hills between Florence and Siena. You’ll unpack your bags for four nights at our hotel located in the heart of Tuscany and cycle the surrounding Chianti region getting a quintessential taste of Italy. The Chianti region is brimming with hills, but they are a welcome challenge as an unforgettable view always awaits you at the peak of every summit. Plan to finish your days by the pool, or with a glass of the local specialty (Chianti!) while taking in the sweeping sights of the very hills you just conquered on your bike.

    On Day four of the trip the landscape will shift as you make your way to the next hotel, or should we say, your castle on the hill. Literally. You’ll spend your final two nights sleeping like royalty at Castello di Velona. From the castle you will be cycling through the heart of UNESCO World Heritage site Val d'Orcia. After each day’s loop ride you can look forward to relaxing at the luxury spa to treat your muscles to some rest before the unforgettable rides through Val d'Orcia stunning (and hilly) landscape.

    Not only are you in for exceptional riding but each day on tour you will get a true taste of Italy when we dive deep into local culture. Tuscany is known for many specialties often thought of as quintessential Italy. You’ll enjoy these regional treats including a tasting of Chianti’s finest wine, a guided tour of the historic and architectural jewel of Siena, and visits to a local artisan’s ceramic studio. This 8-day trip will cover most of Tuscany’s finest terrain, unforgettable cuisine, and warm culture that define la bella vita, or the good life.

    Trip Price: $4,999

    Also, check out our Head Wrangler's blog post about how this trip came to be!



    Day 1:

    Ride Details:

    • Distance: 30.3 km (18.8 mi)
    • Elevation Gain: +624 m (+2048 ft)

    Warm Up Spin Welcome to Tuscany! Today we will get everyone settled into their rooms and take care of bike fit before heading out for a short spin. We will take our bikes out for their first ride on roads that are home to the famous Giro d’Italia, Italy’s most famous and grueling multi-stage cycling races. The panoramic views on this warm-up loop will wet your appetite for the jaw-dropping scenery to come over the next seven days of riding. This evening you can take it easy at the hotel, go for a dip in the pool if you’d like, and we will meet for dinner at the hotel’s onsite restaurant.


    • Riding on the roads of the 2016 Giro d'Italia Time Trial stage.
    • Riding by open panoramic views.
    • Views of Panzano in the distance on the way back.

    Day 2:

    Ride Details:

    • Distance: 76.2 km (47.4 mi)
    • Elevation Gain: +1578 m (+5178 ft)

    Chianti Loop Immerse yourself in the region as you pedal through Tuscany’s famous Chianti Classico region. Today you will pass by the trademark Black Rooster – the quintessential symbol for this famous wine, and enjoy a morning coffee in Gaiole, the home and starting point of the L'Eroica - a 209 km ride famous for cyclists participating on vintage bikes while covering lots of gravelly terrain. You’ll get a lay of the land as we climb the highest peak in Chianti: Monteluco, and pedal past Castello di Brolio, the castle where the Chianti wine recipe was made official. This evening we will head into Castellina for a tasting of local wines, olive oils, and balsamic vinegar followed by dinner at Taverna Squarcialupi.


    • Riding in the heart of Chianti Classico vineyards
    • Black Rooster statues of Radda and Gaiole, town of the Eroica
    • Monteluco, highest peak of Chianti · Castello di Brolio (home of the Chianti wine official recipe)
    • Coffee stop at the Eroica Cafè.

      Day 3:

      Ride Details:

      • Distance: 120.5 km (76.1 mi)
      • Elevation Gain: +2096 m (+7042 ft)

      Volterra Loop Buckle up Dude Girls and guys, today we’ll push our limits on the longest ride of the trip. Today’s mileage and elevation gains will not go unrewarded as we will pass some of the most architecturally stunning towns in the region and gain a real appreciation for this region’s rich history – and delicious food! You will have a great view of San Gimignano’s famous medieval towers as we pedal towards one of the most ancient of all Etruscan cities, Volterra. You might almost forget how steep the climb is into this magical medieval town as you take in the city built on a plateau enclosed by volcanic walls. After a tough ride today, plan to take it easy this evening and watch the sunset from the hotel pool, or while enjoying a glass of Chianti at the outdoor patio before we enjoy a special dinner prepared by the hotel restaurant.


      • Sweeping descent out of Castellina
      • Busy city in Poggibonsi
      • Views of San Gimignano climbing up
      • Change of landscape/open stunning views over Volterra
      • Visit Volterra / Lunch with a view
      • Historic center of Colle Val d'Elsa

        Day 4:

        Ride Details:

        • Distance: 35.7 Km (22.2 mi)
        • Elevation Gain: +632 m (+2073 ft)

        Panzano Loop (Rest day) Today we dive deep into Italy and get a taste of small-town Italian culture while cycling through a number of villages and hill-top towns. You will visit one of Italy’s most famous butcher shops in the charming town of Panzano and watch daily Italian life pass you by over an al fresco lunch in the town of Radda. This evening we’ll take a guided tour of Siena and enjoy a roof-top pizza dinner while looking out over Siena’s stunning skyline.


        • Visit the old little town and famous butchershop
        • Town of Radda and lunch at Bar Dante
        • Relax at the hotel
        • Walking tour guide of Siena
        • Pizza at Il Pomodorino

          Day 5:

          Ride Details:

          • Distance: 99.6 km (61.9 miles)
          • Elevation Gain: +1544 m (+5066 ft)

          Chianti to Val d’Orcia Today we will bid farewell to Chianti and enjoy a shift in landscape as you cycle past charming villages and cypress-lined roads making your way to Val d'Orcia, a region known for its world-famous Brunello wines and stunning landscapes. Prepare yourself to arrive at your home for the rest of the trip. Our hotel, Castello di Velona, a restored castle sitting in the middle of the Val d’Orcia, is literally fit for kings and queens. Enjoy the wide array of offerings from the spa, or take a dip in the outdoor pool overlooking the Val d’orcia before we dine at the hotel’s gourmet restaurant. Words simply cannot describe this place, come see it for yourself!


          • Ciao Chianti!
          • Views on Siena from the distance
          • Stunning Crete Senesi (clay soil) rolling hills
          • Lunch at Abbazia di Monte Oliveto Maggiore
          • Long and gradual descent into Buonconvento
          • Montalcino and views of the Brunello vineyards
          • Descent into our new Hotel/Castle

            Day 6:

            Ride Details:

            • Distance: 82.3 km (43.3 miles)
            • Elevation Gain: +1675 m (+4527 ft)

            Val d'Orcia Loop Today you’ll be riding through the heart of UNESCO World Heritage site, Val d’Orcia. This place is literally the stuff movies are made of - you might recognize it from ‘little known films’ such as the Gladiator or English Patient. As you cycle along cypress-lined roads and admire lush rolling hills in the background you will be making your way towards towns that are so charming you might never want to leave. You’ll be soaked in living history as you enjoy a coffee while overlooking at Roman baths in Borgo Vigoni, cycle through Pienza (home of the famous Pecorino cheese!) and enjoy a breath-taking descent into San Quirico. This evening we will send you off to explore Montalcino - an enchanting town with too many delicious dining options to choose from, but we’ll give you a few suggestions so you may enjoy dinner in a restaurant of your choice this evening.


            • Bango Vignoni, old Roman thermal bath pool 
            • Riding in the heart of Val d'Orcia (Unesco World Heritage Site)
            • Climb into Pienza, the ideal Renaissance town of Pope Pius II and home of famous Pecorino cheese
            • Breath-taking rolling hills into San Quirico
            • Climb back up to Montalcino

              Day 7:

              Ride Details:

              • Distance: 77 km (47.8mi)
              • Elevation Gain: +2094 m (+6869 ft)

              Monte Amiata Loop For our final day of riding you will climb the wonderful and wild Monte Amiata followed by a descent into the medieval town of Pitigliano. While you’ll gradually climb, and climb… and climb today, you will be transported you into a forested, fairy-tale like realm. The rewarding summit will give you sweeping views of this stunning region. If you squint really hard you might even be able to see Castello di Velona! This evening we’ll enjoy our final dinner together in Montalcino.


              • Big Climbing Day up to Monte Amiata
              • Beautiful forested road and medieval stonewall towns
              • Stunning view from the summit
              • Long sweeping descent into Castel del Piano

                DAY 8:

                Abby St. Antimo We will finish the trip with a guided tour of Abbey St. Antimo, a former Benedictine monastery in Montalcino. Having been in existence since the 700s, This stunning monastery, boasts great stories and impressive architecture. We’ll learn about the fascinating history of this beautiful example of Romanesque architecture and taste some of the wine produced on the grounds. This trip is for riders looking to push their limits on some of Italy’s most stunning roads. A feast for both your eyes and your stomach, prepare to ride hard and dine on some of the region’s most delicious dishes and taste Tuscany’s world-famous wines. This tour will tickle all your senses and after eight days of cycling through through rolling hills blanketed with vineyards and eating unforgettable meals, you might find yourself asking: What if I just stayed?


                Also, check out our Head Wrangler's blog post about how this trip came to be!