Italy – Tuscany Escape Short Bike Tour

Welcome to Siena, the Heart of Tuscany!

Begin your journey in Siena, a UNESCO World Heritage Site famous for its medieval charm and vibrant culture. Settle into your accommodations, perfectly located to access the city’s historic treasures. Relax and soak in the beauty of your surroundings. Spend your afternoon exploring Siena’s iconic landmarks: Wander the cobblestone streets and marvel at Piazza del Campo and the Duomo di Siena; enjoy boutique-lined streets with artisan shops and cafes that capture Tuscany’s essence. In the afternoon, our team will meet you for bike delivery and fitting, ensuring your bike is perfectly adjusted for comfort and performance. No matter the type of bike you are using, we’ll ensure you’re ready for the adventure! We’ll also provide a detailed trip briefing, outlining the itinerary and sharing tips for your rides. This is a great time to ask questions and get local insights into the highlights of the region, from landmarks to local dining spots.

Overnight: Siena

Today’s ride takes you from Siena to the charming hilltop town of Montalcino. Experience the stunning beauty of Tuscany’s rolling hills and the unique landscapes of the “Crete Senesi,” known for their distinctive colors and textures. Montalcino, a charming Tuscan hilltop village, is known for its rich history, stunning landscapes, and the renowned Brunello di Montalcino wine. The town features medieval streets, a 14th-century fortress with panoramic views, and notable landmarks like Palazzo dei Priori and Sant’Antimo Abbey. Enjoy traditional Tuscan cuisine, explore artisan shops, and immerse yourself in local culture – the complete Tuscan experience! The short option is done by taking a 20 min train out of Siena with the bike and starting further into the route, from Monteroni d’Arbia.

Meals: breakfast
Distance Short Option: 36 km / 17 mi +794 m
Distance Long Option: 54 km / 35 mi +1120 m
Highlights: UNESCO countryside, Crete Senesi, Montalcino exploration
Overnight: Montalcino

Today, as part of your self-guided Tuscany bike tour, you’ll leave Montalcino and head toward Pienza, a UNESCO World Heritage Site with deep Etruscan roots. Take in the breathtaking views of the Asso, Ombrone, and Arbia valleys. As you set off, admire the silvery olive orchards, sprawling vineyards, and quaint villages dotting the picturesque landscape. The town’s hilltop location kept it free from conflict for centuries, and its lower slopes are now dominated by productive vineyards and olive groves. Descend through the land that produces Brunello di Montalcino, with over 200 wineries producing more than 330,000 cases annually. Continue through serene countryside to Pienza, known as the “Ideal City of the Renaissance,” offering quaint streets, artisanal shops, and incredible views over the Val d’Orcia. Enjoy the cycling experience as you traverse Tuscany’s stunning landscapes and rich heritage. A relatively short ride, there is still a good amount of climbing. This will leave plenty of time to explore Pienza and save legs for more riding tomorrow!

Meals: breakfast
Distance: 26 km +509 m
Highlights: Montalcino, Brunello wine country, Pienza exploration
Overnight: Pienza

Enjoy breakfast at the hotel on your own, when you want. Today you have two ride options; both options highlight the beauty and charm of Tuscany, offering memorable experiences tailored to your preferred level of self-guided Italy cycling.

Short Option: Bagno Vignoni (33 km) Embark on a loop ride to the charming village of Bagno Vignoni, known for its ancient Roman thermal baths and modern spa facilities. The village’s unique piazza features a thermal pool dating back to Roman times, providing a tranquil and picturesque setting. This gentle ride with rolling hills through the serene Val d’Orcia is perfect for a relaxing exploration of Tuscany’s hidden gems. You may like to just enjoy the relaxing pools and spa and come back by a private shuttle.

Long Option: Montepulciano (51 km) For those seeking a more challenging ride, this loop takes you to the renowned hilltop town of Montepulciano. Famous for its rich Vino Nobile wine and stunning Renaissance architecture, Montepulciano offers a rewarding destination. The rolling road to Montepulciano’s vineyards and back is an enjoyable one, with some steep climbs that will allow you to have grand views on the Tuscany countryside.

Another option today is a cooking class: Traditional Italian Farm to Table Cooking class: You will tour the local farm with our chef/guide and learn how produce and dairy are produced in the region. Using farm raised produce and ingredients, you will learn how to make traditional wood fired pizza and breads. Be sure to come hungry. Once your creation is complete, you will be able to eat the delicious food you have prepared.

Meals: breakfast
Distance Short Option 1: 30 km / 18 mi +458 m
Distance Long Option 2: 56 km / 34 mi +1192 m
Highlights: Bagno Vignoni & baths, Montepulciano & wine, cooking class
Overnight: Pienza

Today is your departure day. Take your time in the morning if you wish and enjoy breakfast at your leisure. Transportation to Florence is available, ask for assistance. Please let us know in advance if you would like to book additional nights in the area, or if you would like to add on another Pure Adventures tour!

Meals: breakfast