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Pisa to Florence by Road Bike

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Homepage > Italy > Pisa to Florence by Road Bike
  • Duration: 6 Nights
  • Difficulty: Level 3
  • Tour Type: Self Guided
  • Availability: Not Available in 2022
  • Location: Pisa
Tour Details

Mount your road bike and head out into Tuscany to visit the birthplace of the Italian Renaissance with our self-guided “Giro of Tuscany” cycling holiday. For certain you shall experience some of the

country’s most beloved landscapes, seen on many a photo. The riding is pretty varied from along hilly ranges and fertile plains as you pedal from famous city to famous city.  Your tour starts off with the architectural wonders of Pisa with its famous leaning tower. You then head south passing by the famous road of wines, where a sip of the local Chianti or Brunello di Montalcino will help motivate you to continue on your journey. The local cuisine will also quell your hunger. You will have a chance to visit many historic towns with preserved castles and cathedrals and world-famous town squares. This trip is a great mixture of landscapes, wine, food and historic attractions.

Starting Location


Price Includes

  • 6 Nights Bed and Breakfast
  • 3/4 star Hotels or Guest Houses
  • Smart phone app including Maps and GPS route
  • Information Pack
  • Luggage transfers

Price Excludes

  • Transport before and after tour
  • Travel Insurance
  • Flights
  • Carbon Road Bike Rental Bike
  • Extra Nights
  • City Taxes
Trip Info

Travel Insurance

It is a requirement of booking this tour with Hooked on Cycling that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.


Day 1Arrival to Pisa

During the course of the day arrive at Pisa. The city is famous all over the world for its magic Piazza Dei Miracoli with the characteristic leaning tower, the bell tower of the city cathedral. Part of the UNESCO World Heritage list since 1987, besides a large number of monuments it also offers a friendly and lively atmosphere of a university city.

Day 2Pisa-Volterra  46 miles 75 km, 810m up.

A nice easy day to start with to get your legs warmed up, you cycle from the city of Pisa along the Arno River until you reach Pontedera which is the home of the wine company Castellani.  For those with a sweet tooth, there is a sweets factory called Amedei.  You then continue to Ghizzano, a pleasant village surrounded by vineyards. Shortly after you will arrive in Volterra, a walled medieval mountaintop town famous for its alabaster works. Immerse yourself in the backdrop and enjoy its local sights, such as the Roman Theatre and the Etruscan museum Guarnacci.

Day 3Volterra-Siena  43 miles 70 km, verticale  1140m up.

Today you cycle along one of the famous long distances routes the via Francigena until you arrive to San Gimignano, where you will experience a legitimate taste of a medieval city. This UNESCO awarded walled town is known for its many towers. Maybe time for lunch before you continue to Colle Val d’Elsa, dubbed as Italy’s Bohemia. This area, named after an old Etruscan hero, is known for being a significant industrial centre with medieval architecture. You continue a little further and reach Monteriggioni with its remarkable Roman abbey (Abbadia a Isola) before your arrival in Siena, easily distinguished by old brick buildings and the crown of Torre del Mangia.

Day 4Siena-Montalcino-Siena 72 miles 115 km, 1730m up.

Today a loop ride from Siena to the region to the south of the city. You will be cycling through lush, green hills to get to the renowned Brunello vineyards. Don’t stop yet, your wine-tasting session happens at Montalcino, just a few miles from the actual presses. After a glass or two and maybe the purchase of a crate of wine you can start cycling your way to Asciano. Get an inspired tranquil moment at Monte Oliveto Abbey, known as the Crete Senesi, home of all things Tuscan. From where you stand, you will see a patchwork of fields with pillars of cypress trees, rolling hills, more vineyards, and hidden villages that seem to hide from the dense forest, you might feel you have gone to heaven!

There is a chance to shorten this route to 43 miles 70km.

Day 5Siena-Radda in Chianti  28 miles 45 km, 970m up.

Today first stop is Castagnoli, where you will admire the Brolio Castle, home to the Ricasoli family but today has a well-managed wine cellar. Then you will reach Meleto Castle, its stern-looking architecture tucked in the elevated, tree-covered hills. Your destination is Radda in Chianti, a classic Chianti village nestled inside the verdant hill region, among remnants of the Etruscan age where you can find the medieval palace of Pretorio

Day 6 Radda in Chianti-Florence  43 miles 70 km, 970m up.

Today you will discover the aptly named Tuscany’s “road of wines”! Indulge yourself in the local wine flavours and take a break stop at Greve’s public square. You’ll recognize it easily being a triangle shape! Your last cycle day will bring you to a small town called Mercatale, a little town surrounded by the hills of Chianti, also famous for its vineyards. A few more miles and Florence is waiting for you! Tuscany’s capital is known for its wealth in culture, architecture and art. This bustling metropolis is considered the birthplace of the Renaissance and you can immediately see hints of artisan decor embellished upon buildings and squares.

Day 7Departure

Depart after breakfast.


How to get there

By Plane
Fly to Pisa with Ryanair or with British airways and then by bus or taxi to your hotel

Book Now

2022 Prices – For complete tour price breakdown please click the book now button and select your holiday tour date. Prices will then be listed.

 Tour Code Prices From (per person) Book Now
PisaFRB (6 Nights)  from £N/A Book Now
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