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Self-Guided Bicycle Tours — Italy

A magic way: Create your own tour

Create your own Self Guided Tour! We have tons of rides and destinations to suggest you. Like a snake that goes through the diversity of Italy this itineary is just an example of what we can offer you. Pick up the section you like better, join your favourite destinations and we'll help you building the tour of your dreams!

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  • Day 1

    Tour begins in Chioggia, Italy

    Highlights: "Little Venice" and the Venetian Lagoon

    Welcome to Chioggia and the Venetian Lagoon! We meet this afternoon at our hotel in the center of Chioggia. We'll fit bicycles and go over route details. Take a walk around the center of Chioggia and admire the canals, bridges and main pedestrian walking street. If you arrive early we can suggest a ride along one of the islands in the lagoon. Mileage (your option)

  • Day 2

    Pedal the Po River Delta

    Highlights: Chioggia, bicycle quiet roads, stay at a working farm

    We leave the Venetian lagoon today towards the Po River Delta. Enjoy cycling on levee roads and birdwatching. Grab some picnic supplies from the local grocery store or stop at a cafe for lunch today. Those who want extra mileage can enjoy a great ride into the delta this afternoon. Our destination tonight is a small country farm bed and breakfast. Distance: 58-101 km (36-63 miles).

  • Day 3

    Ferrara

    Highlights: bicycle along the Po River, bicycle capital of Italy--Ferrara

    It's another day of leisurely riding today as we follow the Po river upstream to the Renaissance city of Ferrara. Entering the city, we'll pass under the 16th century walls, one of the most intact Renaissance walls left in Italy. Other highlights of this UNESCO world heritage site include the many palaces of the Este court from the 14th and 15th century. We'll suggest some great restaurants for dinner on your own this evening. Distance: 64 km (40 miles).

  • Day 4

    Comacchio

    Highlights: Comacchio and its "Trepponti" bridge

    It's another day of leisurely riding today. Our destination is a small lagoon town that at one point was more powerful than Venice in the 700 and 800s. The lagoon town of Comacchio, has a fabulous museum that showcases a Roman boat ant its cargo that was excavated from one of the canals. Built on 13 islands this town is now landlocked but surrounded by the Po River and fresh water wetlands. Enjoy a small float around the canals with a local fisherman before dinner. Distance: 70 km (44 miles).

  • Day 5

    Ravenna

    Highlights: Wetlands, bird viewing and beautiful mosaics, bustling town

    We pedal along the Valley of Comacchio wetlands towards Ravenna. Ravenna was the last capital of the Western Roman Empire and home to more early Christian mosaics than any other city in Western Europe. You can walk to Dante's Tomb and the mosaics of San Vitale, Sant'Apollinare Nuovo and the Mausoleum of Galla Placidia this afternoon, as our hotel is near all the city sights. Distance: 45 km (28 miles).

  • Day 6

    Ravenna to Faenza

    Highlights: Faenza International Ceramics Museum and Renaissance Town Square

    Exiting Ravenna you have the choice to visit another very important Byzantine masterpiece: Sant'Apollinare in Classe. Cross the plains through fruit plantations and arrive to Faenza. Your hotel is a restored convent near the central square of this regional market center and famous ceramics town. Enjoy the bustle in the market square and the main "piazza" which is always full of bicycle riders of all ages. Faenza is world-renowned for its hand decorated ceramics; we recommend a visit to the International Ceramics Museum as well as several of the local artists' studios specialized in this colorful pottery.
    Daily mileage: 51 km (32 miles).

  • Day 7

    Loop ride to Castrocaro and Terra del Sole

    Highlights: Sixteenth century planned Medici Fortress town of Terra del Sole; alternative bicycle ride over Monte Trebbio

    You have two options today. Both include a ride to Terra del Sole, a border town built by the Medici family in 1564 to protect the northern frontier of Tuscany designed with the new Renaissance concept for the "Perfect City". On your way to Terra del Sole you'll pass by our headquarters so we'll plan to show you around, give you morning coffee and cake and send you on your way. Those who want an easy day will ride to Terra del Sole and back to Faenza at the base of the low foothills, giving you time to take it easy in any of the towns today. Those with more energy can climb one of the most famous mountain rides for cyclists in the area, Monte Trebbio.
    Daily Mileage: 38 - 64 km (24 - 40 miles).

  • Day 8

    Over the Apennines

    Highlights: Bicycle the Apennines and the Mugello.

    We head into the Apennines today, passing first through the medieval village of Brisighella. Take a break and pick up some snacks for climb if you feel like it. If you decide you want to train up and over the mountain, feel free to do so! for those who decide to bicycle, begin climbing (easily at first!) over the Apennines -- remember to look around as you pedal since the scenery changes dramatically as you leave the plains and enter the mountains. Just before we reach the toughest part of our climb there is a very conveniently located train station which allows you a choice in how you reach our destination! Dinner tonight is at the hotel. Distance: 15 - 63km (9 - 39 miles)

  • Day 9

    Florence

    Highlights: Fiesole and its Etruscan ruins, Renaissance Florence, Uffizi Gallery

    There's a small climb this morning to Vetta le Croci, then it's downhill to the old Etruscan city of Fiesole, where you'll enjoy a great view of Florence rising from the valley floor. We recommend waiting until after lunch to ride into town and the rest of the afternoon is yours to explore this capital of Renaissance Italy. Distance: 41 km (26 miles).

  • Day 10

    Florence to Radda in Chianti

    Highlights: The Chianti region

    You'll leave Florence and climb some of the famous Chianti hills as you make your way to Radda in Chianti, your home for the night. Stop in Greve in Chianti for a short visit of the main square and the famous Macelleria Falorni, producer of local salumi. Radda is a delightful gem of a small town and was an important junction for traveler's heading to north and south. Daily distance: 61km (38 miles).

  • Day 11

    Siena

    Highlights: Medieval town of Siena, Piazza del Campo

    Ride the south part of the Chianti Region. The afternoon is yours to explore Siena. Italy's best-preserved medieval city rivaled Florence for dominance in Tuscany during the 1300s. You'll be transported back in time as soon as you enter the city walls. Daily distance: 48-52 km (30-32.5 miles).

  • Day 12

    Ride to San Quirico d'Orcia

    Highlights: UNESCO World Heritage Landscape of Val d'Orcia

    The full beauty of the Tuscan landscape, from the barren, chalk hills of Central Tuscany to the lush green fields of the Orcia Valley, unfolds before you today as you leave Siena and pedal to San Quirico. Daily mileage: 57 km (36 miles).

  • Day 13

    Loop ride

    Highlights: Montalcino, Abbey of Sant'Antimo, Bagno Vignoni

    Pedal through vineyards and wheat fields this morning as you make your way to the Etruscan village and wine town of Montalcino. This fortified town was used as a shelter by Sienese nobles during the 16th Century, but today is even more famous for producing one of Italy's premier red wines, Brunello di Montalcino. Our scenic route takes you to the famous Abbey of Sant'Antimo and then on to Bagno Vignoni, a Medieval spa town. Daily Mileage: 54 km (34 miles).

  • Day 14

    Loop ride to the Abbey of Monte Oliveto Maggiore

    Highlights: Trequanda, Abbey of Monte Oliveto Maggiore

    Our loop route today takes you to Trequanda first and then to the Abbey of Monte Oliveto Maggiore, a Benedictine abbey built in the 13th century and famous for its frescoed cloister and stunning setting. You are back in San Quirico this afternoon in time for a swim or to enjoy the spa center of the hotel. Daily Mileage: 66 km (41 miles).

  • Day 15

    Bicycle Southern Tuscany

    Highlights: Pienza and the UNESCO World Heritage Landscape of Val d'Orcia

    Pack your bags and head to Valiano di Montepulciano today, your home for the next 2 nights. Luggage will be transferred directly to the hotel while your ride takes you to one of the first planned Renaissance towns, Pienza. With the help of a number of prominent architects Pope Pius II turned his small hometown into a piece of art in the 16th century. Dinner is included tonight. Daily Mileage: 39 - 48 km (24 - 30 miles)

    You might want to ride all the way to Cortona today to jump ahead to day 18, making it a 60 km (37miles) day

  • Day 16

    Loop Ride to Lake Trasimeno

    Highlights: Trasimeno Lake and Chiusi

    Ride along the shores of Lake Trasimeno today. Along the ride you'll pass close to the tiny Lago di Chiusi before reaching the fortified village of Castiglione sul lago. If you have the time you might want to take a boat ride on Lake Trasimeno to Isola Maggiore. After a stroll on the passeggiata and lunch on your own, continue back to Borgo Tre Rose. Enjoy dinner in the hotel restaurant tonight. Daily Mileage: 35 - 59 km (22 - 37 miles)

  • Day 17

    Cortona

    Highlights: Cortona, Etruscan Museum, gelato

    Your ride today will take you to the Etruscan town of Cortona. You'll pass along the Val di Chiana, famous for the chianina steak bistecca di chianina before reaching the imposing town of Cortona on the top of the hill with its defensive Etruscan, Roman and Medieval walls surrounding the historic town. Enjoy the afternoon in Cortona. A must-see is the recently restored Etruscan Museum or the Museo Diocesano with Fra Angelico paintings. Our favorite gelateria is in the square in front of the museum. Daily Mileage: 22 km (14 miles)

  • Day 18

    Cortona to Perugia

    Highlights: the castle of the Knights of Malta, the well-known artistic centre of Italy: Perugia

    You will leave Cortona today cycling through the picturesque landscapes that have made Tuscany famous and along the shores of Lake Trasimeno, known for Hannibal's defeat of the Roman army in 217 B.C. after crossing the Alps with elephants! You'll go through the hilltop town of Magione with its castle, owned by the Sovereign Military Order of Malta, founded about nine centuries ago in Jerusalem with the aim of protecting the Holy Land. Our destination today is Perugia, the capital of the Umbria region. Daily Mileage: 69 km (43 miles)

  • Day 19

    Assisi

    Highlights: Wine in Torgiano. Assisi, the town of Saint Francis

    Your ride today takes you first to Torgiano, famous throughout Italy for its wines. Take time to explore the comprehensive olive oil museum and the wine culture museum, the famous tower and the narrow alley ways. Leave Torgiano to enter the Umbrian Basin and arrive to Assisi. You'll want to explore the church of Saint Francis, the second most important pilgrimage destination in Italy after St. Peter's in Rome. If you arrive early you might enjoy an extra ride to the hermitage just outside the village where Francis often retreated for meditation. Daily Mileage: approx 44-61km (28-38 miles).

  • Day 20

    Loop ride to Deruta

    Highlights: Ceramics in Deruta

    Your ride today takes you to Deruta where you can enjoy scores of ceramic studios. Deruta is one of the most important ceramics towns in all of Italy. The route back to Assisi takes you through the hamlet of Brufa. Distance: 60 km (37 miles).

  • Day 21

    Bicycle from Assisi to Bevagna

    Highlights: Roman ruins in Spello, medieval wall and Renaissance buildings

    You leave Assisi behind you this morning and head south to Spello, a puzzle made of Roman, Medieval and Renaissance pieces. 13th century town walls connect Roman gateways dating to the 1st century BC and AD. Take time to explore and you'll find the 13th century town hall dominating the Renaissance town square. From Spello you pedal to Foligno another Roman town but with fewer Roman ruins. Enjoy lunch in the square and then head across the Umbria valley to Bevagna. Bevagna is the picture of a well-preserved Medieval village. It, too, dates from Roman times and is centered on the 13th century square and town hall. Unlike most Medieval towns, Bevagna is located on the flat of the Umbrian Basin. Mileage: 35 km (22 miles)

  • Day 22

    Loop Ride from Bevagna to Montefalco

    Highlights: The Roman Via Flaminia, Trevi, and Montefalco

    Yesterday and today you will parallel the historic Via Flaminia, a Roman road, built in 220 BC by Consul Gaius Faminius. The road allowed Roman soldiers and their families access to the region around Rimini where they settled. With the road came all the Roman settlements and military garrisons in the area. Foligno and Spello were Roman towns while Trevi and Montefalco, our lunch destination, were Medieval towns that developed on nearby hills hundreds of years later. Take time to explore these hill towns as they capture the essence of Italy. A variety of routes allow access to the hills south of Montefalco. Plan on a picnic or restaurant lunch in the village, though as it affords a spectacular view across the entire Umbrian basin where you just spent two days cycling. (And plan to pick up a bottle of Sagrantino in Montefalco, one of Italy's most famous wines, for your dinner tonight.) Mileage: 45 km (28 miles) or more if you wish to venture into the hills south of Montefalco

  • Day 23

    Loop ride to Spoleto

    Highlights: The preserved town of Spoleto, its fortress, the Roman aqueduct

    Your ride will take you to the well-preserved medieval town of Spoleto, famous throughout the world for the Festival dei due Mondi, a three week dance, music and opera festival. Discover the hidden corners of this fabulous town that dates back to Roman times. Don't miss the Cathedral and a walk to the fortress Fortezza Albornoz on top of Colle Sant' Elia. Mileage: 68 km (42.5 miles)

  • Day 24

    Bicycle from Bevagna to Todi

    Highlights: Off the beaten track to the medieval Todi

    You're route today takes you away from the busy heartland of Umbria to the beautiful hilltop town of Todi. Todi's history is one of the region's oldest: three thousand years of continual inhabitance by Umbrians, Etruscans, and Romans. Today its main square "Piazza del Popolo" is often described as the most perfect medieval piazza in Italy. Discover why. Mileage: km 38 (24 miles)

  • Day 25

    Loop ride to Monte Castello di Vibio

    Highlights: the smallest theater in the world

    Your loop ride today takes you to the spectacular site of Monte Castello di Vibio. This eagle's nest of a village dominates the surrounding countryside; enjoy the beautiful views and the smallest theater in the world! The "Teatro della Concordia" in Montecastello reflects French architecture of the 1800s. Alternatively take a rest day and explore Todi. Daily Mileage: 45 km (28 miles)

  • Day 26

    Todi to Orvieto

    Highlights: Orvieto and its Duomo

    A quiet ride along the shoulders of the Tiber Valley takes you to the spectacular Renaissance city of Orvieto. Perched on the remnant of a volcanic plateau, Orvieto is one of the most beautiful cities in Umbria. Its cathedral, a transition style between Romanesque and Gothic architecture, is richly decorated with a variety of colored marble and bright mosaics. Orvieto is also famous for its white wine. Mileage: 47km (29 miles)

  • Day 27

    Loop ride to Civita and Bolsena

    Highlights: "Ghost town" of Civita di Bagnoregio and Bolsena Volcanic Lake

    We suggest a loop ride today to one of several volcanic lakes in this part of Italy, the Lago di Bolsena. Before getting to the lake the ride will take you to the "ghost town" of Civita di Bagnoregio. Take time to explore this tiny village also know as "the dying city", because of the eroding rock below it. Daily distance: 65 km (41 miles)

  • Day 28

    Tour ends in Orvieto

    Highlights:

    After breakfast your cycling experience in Umbria ends. We hope you have enjoyed cycling with us! Orvieto is conveniently located on the main rail line to Florence or to Rome. It is also beautiful enough to warrant a relaxing rest day if you are so inclined.

Includes 3-4 star accomodations with all breakfasts, use of high quality titanium racing or hybrid bicycle; bike delivery and collection; use of GPS with preloaded tracks; detailed route descriptions; map; suggestions for dinners and lunches; luggage transfers
Countries Italy
Begin/End Venezia / Orvieto
Arrive/Depart Venice Marco Polo Airport (VCE) / Rome Fiumicino Airport (FCO)
Total Distance Up to you !
Daily Distance Approx 50 km
Rating 101 to 301
About Tour Ratings »
Notes The best rides in Italy of the level of challenge you choose!
Terms Terms & Conditions
Dates Prices Single Supplement
Dates Tell us about the self guided tour of your dreams and we'll make you a quote!
Electric bikes available
Prices €0.00 Single Supplement Contact us
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  • VENICE TO PARMA: Thank you all for the work you did to organize our adventure. We especially appreciated the extra information on places we visited. The maps and city guides were very helpful. Hotel selections were terrific. We especially liked the central location of the city ones, and the agriturismo near Riolo Terme where the hosts were charming and prepared locally sourced food including delicious fresh pasta. The bikes were great, the bags worked well. Step by step instructions were mostly clear and accurate. We enjoyed the prearranged dinners, the gelato tasting and the balsamic vinegar manufacturing tour, tasting, and lunch. The owner is great and the guide spoke English very well so we understood the complicated process. Lunch was more than light. He cooked cod and fry bread, and had bresaola and rucola salad and prosciutto. Thank you for all.

    Nancy L.
    California, USA
    June 2016

  • TUSCANY: The folks at Bike Plus did a great job. We wanted to do something slightly different then their usual trips. They came up with some great ideas to assist us. They have lots of experience in Italy and they took the time to research some things that really made a difference. I had many favorite experiences... Food, architecture, views, people...

    Dan R.
    Colorado, USA
    May 2016

  • VENICE TO PIENZA: Grazie mille! This was our first cycling tour and we enjoyed it very much. We hope to do more of them.

    Sam T.
    California, USA
    Sept. 2016

  • RAVENNA TO REGGIO EMILIA: Beautiful challenging ride from Faenza to Dozza Great views and lovely lunch in such a cute town Brisighella. Very good route notes. We were very happy and really appreciated the help by email from stefania and Sara But in particular special when we needed it on the ride

    Australia
    September 2018

  • RAVENNA TO FLORENCE: We pretty much used the gps and was very helpful. Having the notes to read through was informative and helpful for the area we were headed the next day! Hotels were great. Favorite experience on this trip? The freedom of self guided. Thank you, great trip!

    Ramona D.
    WA, USA
    September 2016

  • TUSCANY: I can highly recommend Bike Rentals Plus! Our trip through Tuscany was well planned, easy to navigate, through spectacular and low traffic countryside! The bikes were properly geared and well maintained. Thanks for a great trip! The routes provided were fantastic. Bike Rentals Plus covered all their bases via, turn by turn instructions in print, route maps in print, and GPS unit with easy to follow map. Was nice to preview the course the night before with the printed route. Then just follow the GPS during the day. Hotels were great. Great locations. Good breakfast. Nice accommodations!

    Jim H.
    WA, USA
    May 2016

  • TUSCANY: This was our fist bike tour. We are fit, avid cyclists but still had no real idea what touring would be like. The tour that was setup really allowed us to be challenged physically while still being able to see a lot of sites and really experience the Italian sites, sounds and culture. This was the perfect introduction to cycle touring for us and we are really excited to do more touring and introduce cycle touring to our friends and family. Thanks for the amazing work you guys do at setting up these types of tours. The notes were excellent and served as a great reminder of side trips. If we hadn''t had these to trigger our memory we almost rode past a couple of very memorable side trips. Being able to go at our own speed and agenda allowed us to make stops where and when we wanted. Some of our most memorable experiences were just sitting on the side of the road having an impromptu picnic The hotels were very well selected and located in great locations.

    Brendon J.
    Canada
    April 2016