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Cyclist enjoys the view of Montepulciano

Picture-perfect Tuscany with charm

The enchanting landscapes between Brunello and Chianti

8 Days / 7 Nights
Athletic
334  kg
CO₂-Emissions get compensated
Cyclist enjoys the view of Montepulciano

The tour title says it all. On this cycling tour, you’ll encounter something truly spectacular. The breathtaking landscape unfolds like a painting before you. You’ll pedal past towering cypress avenues, through golden fields of wheat, and along world-famous vineyards. Don’t resist the temptation to sample the exquisite wines produced here. Brunello di Montalcino and Chianti Classico are among Italy’s finest! Culturally, the region is equally rich. While Siena and Florence are world-renowned, you’ll also stay in beautiful medieval towns like Passignano, the sophisticated Montepulciano, charming Montalcino, and picturesque Radda. Let yourself be enchanted by the picture-perfect Tuscany!

Italy is always an inviting destination, with countless regions just waiting to be explored. A cycling tour in Italy is particularly rewarding; it offers the chance to truly immerse yourself in the land and its people as you journey through stunning landscapes and captivating landmarks.

The architecture and history of Florence captivate every visitor – let yourself be enchanted! Cycle through the Val di Chiana towards the idyllic Lake Trasimeno, where you'll spend the night in Passignano. The characteristic hills of Tuscany will guide you towards Montepulciano, known for its medieval charm and exceptional red wine. Your next destination, Montalcino, also produces a fine wine, the world-renowned Brunello.

Picturesque cypress trees, elegant villas, and landscapes bathed in golden light will accompany you on your way to Siena, where the tower of the Palazzo del Publicco welcomes you. After exploring this Tuscan city, you'll cycle through Vagliagli and along a Strada Bianca to Radda in Chianti. Indulge in an abundance of Italian cuisine, as the final stage back to Florence is already on the agenda.

  • The view of Florence from the Ponte Vecchio: Wandering through the historic streets reveals the masterpieces of artists like Michelangelo, Botticelli, and Leonardo da Vinci. The majestic Santa Maria del Fiore Cathedral, with its iconic Brunelleschi dome, majestically towers over the city and is a must-see for anyone visiting Florence. The Ponte Vecchio, Florence’s oldest bridge, charms with its quaint shops and picturesque views of the Arno River.
  • A glass of wine against the backdrop of Lake Trasimeno: Surrounded by gentle hills, ancient olive groves, and picturesque villages, the region around Italy’s fourth-largest lake exudes a tranquil and relaxing atmosphere. Take a ferry to the lake’s three islands – Isola Maggiore, Isola Minore, and Isola del Polvese – each offering pristine natural beauty and captivating historical sights.
  • Siena, one of Tuscany’s most enchanting cities, delights with its beautifully preserved medieval architecture and unique charm. The city is renowned for its stunning Piazza del Campo, shaped like a shell and home to the renowned Palio, a historic horse race. The slender towers, especially the Torre del Mangia, offer breathtaking views over the city’s picturesque red rooftops.

In Tuscany, the blend of invigorating physical activity and leisurely relaxation in your charming hotels creates a perfect escape. With the region's picturesque hills, each day brings new ascents and rewarding challenges. As the sun sets, you'll recount the stunning vineyard vistas while indulging in exquisite wines and savoring the delightful flavors of Italian cuisine.

Itinerary at a glance

You'll cycle through a truly dreamlike landscape. Breathtaking views will captivate you as much as the beautiful town centers and culinary delights. Savor the specialties and fine wines in the heart of Italy's wine country!

Stroll through the charming city and marvel at world-renowned art history.

In the morning, take the train to Arezzo, where a brief stroll through the magnificent old town is a delightful experience. Then, cycle along scenic paths through the Val di Chiana valley. Soon, the charming town of Cortona will come into view, but continue pedaling through olive groves and over gentle hills to Lake Trasimeno. The lakeside bike path will lead you directly to the historic town of Passignano.

Cycle along the scenic lakeshore to the historic town of Castiglione, where you'll enjoy a stunning view of Lake Trasimeno before leaving Umbria and entering the captivating rolling hills of Tuscany. Glide through the renowned vineyards of Vino Nobile di Montepulciano as you approach the majestic hilltop town of Montepulciano. In the evening, lose yourself in the medieval allure of its winding streets and savor the panoramic vistas of the beautiful countryside.

Cycle along a cypress-lined serpentine road towards the charming fortified village of Montechiello. The white gravel roads, or "Strade Bianche," will lead you to the Renaissance town of Pienza, also renowned as a film location for Hollywood's "Gladiator." The picture-perfect landscape of the Val d'Orcia will accompany you on your journey to Montalcino, where one of Italy's most famous red wines, Brunello, is passionately crafted. Be sure to savor this exquisite wine in one of the many local wine bars.

On the renowned routes of the “Eroica” cycle through golden, shimmering wheat fields. The play of colors across the hills is as captivating as the cypress-lined avenues leading to the grand estates of yesteryears. From a distance, you’ll catch sight of the towering Palazzo Pubblico in your destination, Siena. Glide through the famous Piazza del Campo, where the annual Palio horse race is held.

Enjoy stunning views over the vineyards from a picturesque mountain road. Pause in the charming stone village of Vagliali for a delightful Italian cappuccino before cycling along a white gravel road through vineyards and deciduous forests to Radda. Refuel with a classic plate of pasta for lunch and soak in the ambiance of this village gem. Wine lovers and cycling enthusiasts should not miss the chance to explore Castellina and the heart of Chianti.

Continue on hilly roads towards Florence, winding past grand vineyards, olive groves, and medieval villages until you reach Greve in Chianti. The journey is still accompanied by charming stone houses, cypress avenues, and breathtaking views. As you approach the Tuscan capital, enjoy a long, leisurely descent to the Ponte Vecchio. By now, you’ve likely discovered your favorite Tuscan wine—treat yourself to it one last time as you conclude your journey in beautiful Florence.

Afterwards: individual departure, extension of your trip, or combination with the tours “Venice-Florence” and “Florence-Rome”.

Difficulty Level

Athletic

Cycling will primarily take place on hilly terrain, with several challenging climbs to tackle starting from the second stage. The route follows low-traffic secondary roads and the so-called Strade Bianche, which are nearly traffic-free, well-maintained gravel roads. However, expect heavier traffic when entering and exiting cities.

Prices & Dates

Prices per person in EUR

Sustainably on the go

Offsetting your carbon footprint

334 kg
CO₂-Emissions get compensated
The total value of all emissions per travel and per person is carefully tracked using the CO2 calculator 'Carmacal,' which was specifically developed for tour operators. The individual components that make up this value are shown in the diagram. The overall impact is contributed to by accommodations, luggage transport, on-site catering, and activities, and it is fully offset through our climate protection projects.
Accommodation (70%)
Meals (10%)
Transport (20%)
100%

Our rental bikes

Eurobike Men's Rental Bike with 21 gears
Men's bike 21-speed
Dereilleur gears with freewheel

High-quality men's touring bike with classic diamond frame

Body size approx. 165 cm - 205 cm

56-51 "sloping" cm |
60 cm |
64 cm
Eurobike unisex rental bike with 21 gears
Unisex bike 21/24-speed
Dereilleur gears with freewheel

High-quality unisex touring bike with comfortable low entry

Body size approx. 148 cm - 190 cm

43 cm |
46 cm |
51 cm |
56 cm
Eurobike e-bike rental from KTM
Unisex Electro bike 8-speed
Hub gears

High-quality unisex electric bike with comfortable low entry

Body size approx. 148 cm - 195 cm

46 cm "xs" |
46 cm |
51 cm |
56 cm
Eurobike Rental Bike PLUS
Rental Bike PLUS 20/27-speed
Dereilleur gears with freewheel

Sportier, lighter and more precise premium rental bike with diamond frame

Body size approx. 155 cm - 205 cm

46 cm |
50 cm |
51 cm |
55 cm |
60 cm |
63 cm
Eurobike Gravelbike
Gravel Bike 20-speed
Dereilleur gears with freewheel

Very sporty, roadworthy premium rental bike with diamond frame

Body size approx. 155 cm - 195 cm

49 cm |
55 cm |
57 cm |
59 cm
Services and Information

Further details about this tour

Included

  • Accommodation in hotels with charm
  • Breakfast
  • Welcome briefing (German, English)
  • Luggage transfer
  • EUROBIKE developed route
  • Detailed travel documents 1x per room (German, English, French)
  • 1 train journey Florence - Arezzo incl. your bike
  • App for Navigation and GPS-data
  • Service hotline

Optional

  • Bike rental, including rental bike insurance

Arrival / Parking / Departure

  • Florence train station
  • Florence or Pisa airport
  • Public parking garage, costs approx. EUR 30 per day; public parking spaces, costs approx. EUR 140 per week; public parking spaces at the periphery, costs approx. EUR 20 per week

Things to note

  • Tourist tax, if due, is not included in the price!

Join us in achieving greater sustainability by choosing our digital route book, rather than the printed version. As a small thank you we will give you a discount of EUR 20 per room.

Our Hotels

Relax in our charming accommodations along your cycling tour

Sarah Salzlechner

"We look forward to making your holiday dreams come true"

Sarah Salzlechner
Travel Specialist
One call to vacation bliss
Monday - Thursday: 09:00 AM - 06:00 PM
Friday: 09:00 AM - 05:00 PM
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