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Bicycle Tours — Italy

Bike Across Tuscany - Guided

Among the dreamed destinations in the historic Grand Tour of Europe, Tuscany still today evokes romance, art, culture, wine, cuisine and quintessential scenery. Pedal through art cities, medieval villages, scenic vineyards and olive groves on this 8-day bike tour through the heart of Italy. We’ll traverse the region from north to south, hitting UNESCO World Heritage Sites, Renaissance and medieval towns like Lucca, Vinci, San Gimignano and Siena. Staying in local three-star hotels in smaller and charming towns, you will delight in Tuscan delicacies and the famous red Chianti wine. Our tour ends in the Tuscan capital, the majestic and inspiring Florence. Through it all, you will relish in the camaraderie of your cycling companions while our top-notch guides help make this a most memorable experience.

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  • Day 1

    Arrive in Lucca

    Highlights: Test ride on Renaissance walls

    Meet in Renaissance Lucca, a short train or bus ride from Florence or Pisa airports. We’ll fit bicycles and enjoy a memorable 4 km test ride around the most well-preserved fortified walls in Italy. If you arrive early, make sure to stroll through the city center, visiting the amphitheater (originally built by the Romans and transformed over the ages), the unique Torre Guinigi (with a tree growing on top of the medieval tower), and the marble-faced majestic Duomo. A welcome dinner tonight in a local trattoria starts off our tour together.
    Daily distance: 4 km (or more!)
    Meals: Dinner

  • Day 2

    Bike to Pisa

    Highlights: The Leaning Tower and “Square of Miracles”

    A roundtrip ride to Pisa following the nearby river takes us into the center of this fascinating city to visit the impressive medieval "Square of Miracles", which was built to represent everything a human would need: the Romanesque Baptistery, the Cathedral, the "'civic" bell tower (which began to lean and now is the most famous building here!), and, at life's end, the Monumental Cemetery. We’ll explore Pisa before a delightful return ride to Lucca.
    Daily distance: 55 km (34 miles), 300 m climbing (985 ft)
    Meals: breakfast

  • Day 3

    Ride to Vinci

    Highlights: Leonardo’s birthplace

    Leave Lucca for the small village of Vinci, birthplace and home to the world-famous genius Leonardo da Vinci. A highlight here is a visit to the small town centre, including the town's museum with wooden models of many of Leonardo’s inventions (many of which were never built in his lifetime). Not only a painter, Da Vinci was also an engineer, creating hydraulic machines, war machines and several other fascinating artifacts (like the bicycle!) that show how ahead of his time he was.
    Daily distance: 65 km (41 miles), 600 m climbing (1970 ft)
    Meals: breakfast

  • Day 4

    Ride through Classic Tuscany

    Highlights: Picture Perfect Tuscany

    We’ll leave the province of Florence to enter its historic rival's territory: Siena, on the way passing through the charming ceramics town of Montelupo Fiorentino. A climb takes us up to a delightful ridge road which we’ll follow to our destination. We are in quintessential Tuscany here, with cypress trees, olive groves and vineyards spread out across the surrounding landscape. This evening’s destination, Colle di Val d’Elsa, is a classic walled medieval Tuscan town on a hill, still full of charm and history. You’ll enjoy exploring its cobblestoned streets and alleyways.
    Daily distance: 68 km (42 miles), 1000 m climbing (3280 ft)
    Meals: breakfast

  • Day 5

    Ride to San Gimignano

    Highlights: Optional loop ride

    An optional loop ride to the nearby town of towers--San Gimignano. Once home to dozens of tower-homes, the twelve or so that have remained are still striking to the eye as we approach. Enjoy a stroll through the center of this compact, walled medieval town and perhaps a taste of its signature wine, vernaccia. We'll point out a few of our favorite osterie, or local restaurants, before we return to our own medieval town of Colle di Val d'Elsa.
    Daily distance: 36 km (22.5 miles), 530 m climbing (1740 ft)
    Meals: breakfast

  • Day 6

    Bike to Siena

    Highlights: Postcard Tuscany landscapes

    We continue pedaling south to reach Siena, considered by many to be the most striking Tuscan city (even more so than the Renaissance capital, Florence). After cycling through classic Tuscan scenery and plenty of rolling hills, we’ll settle into our hotel and then enjoy some of the famous sights – like the Romanesque-Gothic Cathedral and the unique shell-shaped Piazza del Campo, which twice a year becomes a tightly-packed horse race field for the annual "Palio". You’ll want to explore the countless alleys and tight streets that bring surprises at every turn. If you prefer to take a break from the bike today, transfer by public bus directly to Siena.
    Daily distance: 45 km (28 miles), 775 m climbing (2540 ft)
    Meals: breakfast

  • Day 7

    Siena and Florence

    Highlights: Rest day - exploring Siena and Florence

    After a few morning hours exploring the marvelous alleys and piazzas of Siena, we will transfer to its historic rival city and today’s Tuscan capital, the mighty Florence. An informal walking tour in the city centre will take us through some of the landmark sights, such as the Piazza Santa Croce, the Palazzo della Signoria, and the stately and jaw-dropping Duomo. You can spend more time exploring on your own, or even visit some of the world-famous museums nearby.
    Meals: breakfast

  • Day 8

    Tour ends in Florence

    Highlights: Farewell!

    We say goodbye this morning. For those wishing to continue their time in Tuscany, Florence provides a great base for further exploration, as well as the perfect place to close your dream Italian holiday. If your travels end today, we will provide suggestions for arriving to the nearby Florence airport.
    Breakfast at the hotel this morning

Includes High quality hybrid touring bike, 7 nights lodging in 3-star or equivalent hotels and inns, with breakfast and tax; a welcome dinner with local wine; GPS navigation tracks provided via Ride With GPS (which you can upload to your personal navigation device); Bilingual English-Italian cycling guide, support vehicle and local driver on most days; Pre-tour travel and sales assistance available (our pre-travel documentation will help you prepare your arrival and departure travel logistics, as well as prepare for your participation on tour).
Countries Italy
Begin/End Lucca / Florence
Arrive/Depart Pisa Galileo Galilei Airport (PSA) or Florence Airport (FLR) / Florence Airport (FLR), Leonardo da Vinci International Airport in Rome (FCO), or Pisa Galileo Galilei Airport (PSA).
Total Distance 275 km (170 miles)
Daily Distance 52 km (33 miles)
Rating 201 to 301
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Notes This is a great tour for active people (who regularly run, bike, or work out) without much bicycle touring experience. Also great for intermediate to advanced cyclists who want a fun vacation, enjoying some hills every day. You will ride 35-68 km per day, on rolling to hilly terrain, with a few steeper or longer climbs. We will cycle on paved backroads with little traffic (on some shorter stretches we share the roads with cars), as well as on hard-packed gravel roads with very little traffic. Experienced cyclists who want longer, optional rides at the end of the programmed ride will have these available.
Terms Terms & Conditions
Dates Prices Single Supplement
Dates 2019 Dates:

July 6 - 13

Aug 3 - 10

Aug 24 - 31

Aug 31 - Sep 7

Sept 7 - 14

Sep 14 - 21

Oct 5 - 12

Oct 12 - 19

Oct 19 - 26


Bike Upgrade Options:


  • Titanium bike € 60 pp
  • E-bike (pedal-assist) € 145 pp
  • GPS Device Hire* € 45 per unit
  • (pending availability)
  • For a detailed description and photos of our bicycle options, please click here
  • Prices €1275 Single Supplement €225
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