Tuscany by Bike: Florence, the Chianti region, Siena and Pisa

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Tuscany Pisa Florence bike trip

As specialists in bike tours in Tuscany, we at Grand Angle have crafted an itinerary that captures the essence of this iconic Italian region. This journey is designed for those who dream of pedaling through a landscape reminiscent of a Renaissance painting. This cycling trip is offered as a self-guided cycling tour, giving you the freedom to explore at your own pace.

Beginning in the artistic heart of Florence, your route unfolds into the rolling hills of the Chianti region, a landscape famed for its vineyards, historic castles, and lush forests. You will journey towards the magnificent city of Siena, a jewel of medieval architecture, before continuing to the tower-crowned village of San Gimignano and the ancient Etruscan city of Volterra. Your adventure concludes in Pisa, home to world-renowned landmarks. This thoughtfully designed cycling trip in Italy reveals the diverse facets of Tuscany, from its celebrated countryside and legendary cities to its world-class cuisine.

Itinerary

Carte ITALV0022
See interactive map

Program

Arrival in Florence. Check-in at your hotel, available after 3pm. Individual sightseeing tour of the city of Florence: start from the Piazza della Signoria, pass by the Uffizi Museum and the Ponte Vecchio, to finally arrive at Palazzo Pitti. A perfect itinerary for an introduction to the region’s history and world-famous art.

Accommodationhotel in Florence

After picking up your rental bikes, you leave the city of Florence. You quickly find yourself in a bucolic landscape, entering the legendary Chianti region. You can stop for a wine tasting along the route, at the beautiful Palagio Castle. Your first stage ends in Greve in Chianti. The heart of the village is the central square, where you find small shops selling local products and a lively atmosphere.

Accommodationhotel in Greve in Chianti
DistanceLength : 45km/28mi by bike

Today you cycle in the heart of the region called “Chianti Classico”, on the scenic Wine Route (Strada del Vino), which winds among vineyards and rolling hills. Take your time to admire the colours and panoramic landscapes of the Chianti Valley. You cross the villages of Mercatale and Panzano before arriving at Radda, a superb little village with medieval origins, with its historic walls still visible and the Podestà.

Accommodationhotel in Radda in Chianti
DistanceLength : 35km/21.8mi by bike

The discovery of the Chianti region continues towards the village of Gaiole. The landscape is dotted with castles and wine estates. We suggest a break at Meleto Castle or at the famous Brolio Castle, to taste the wine of the Ricasoli family. In the afternoon you arrive in the magnificent historic city of Siena, proud of its traditions, which still retains a medieval atmosphere. It is hard not to succumb to the charm of the unique atmosphere of the city center. Possibly the highlight of your trip, the Piazza del Campo is one of the most beautiful squares in the world!

Accommodationhotel in Siena
DistanceLength : 45km/28mi by bike

Take a little more time to complete the tour of Siena, before setting off for today’s relaxing stage, which runs partly along the Via Francigena. It is in a typical Tuscan landscape that you arrive at Monteriggioni, a village surrounded by mostly intact medieval walls including towers and two gates. Today the cycling stage ends in Colle Val d’Elsa, a village known as the Bohemia of Italy. The production of crystal in Val d’Elsa began in the 15th century and remains the most important Italian production of crystal today.

Accommodationhotel in Colle Val d’Elsa
DistanceLength : 30km/18.6mi by bike

Today you reach the emblematic village of San Gimignano, which dominates from its hill the entire valley of the Elsa River. This village is listed as a UNESCO World Heritage Site. It is crossed by the Via Francigena and boasts thirteen medieval towers. The wider and taller the tower, the wealthier the family that built it. You end the stage with a challenging climb to Volterra. Your efforts will be rewarded by the beauty of the ancient Etruscan city that became Roman. Its Roman amphitheatre is breath-taking!

San Gimignano @ Adobestock

Accommodationhotel in Volterra
DistanceLength : 45km/28mi by bike

The last day of your Tuscan journey will be gentler cycling as the landscape begins to change. The hills will be more and more rounded as you approach the valley of the Arno River. You start with a beautiful descent, crossing small villages with a calm and peaceful atmosphere. You will then arrive in Pontedera. This city is the birthplace of the Vespa, a true icon of the Italian Dolce Vita since 1946. If you have time, you can visit the museum, in the historic production building. A short transfer by train (not included) is needed to reach Pisa.

Accommodationhotel in Pisa
DistanceLength : 55km/34.2mi by bike

Take your time to visit the famous and bright Piazza dei Miracoli, with its tower, cathedral, and baptistery. Remember that Pisa is not only a leaning tower, but it is also a beautiful city where you can stroll through the historic center or along the river. End of the trip after breakfast and hotel check-out (~10am).

Occasionally, adjustments to the planned itinerary may be necessary. This could stem from trip logistics (such as fully booked accommodations, trail closures, or adverse weather conditions, etc.). It’s important to understand that these modifications are always implemented with your best interests in mind, prioritizing your safety and comfort.

Dates, prices and booking

Period
Participants
Price per person
Book

Trip details

Depart starting any day of the week from April 1st to October 31st.

Price Per Person2 to 3 People4 to 5 People6+ People
20261480 €1280 €1230 €
20271540 €1330 €1280 €

Accommodation: 3* hotels and 4* hotels (some hotels with a swimming pool).

All accommodation in double room with private bathroom. It is possible to book a single room (with a supplement fee).

Extra nights, price per person, per night with breakfast:

Price Per PersonDouble roomSingle room
Florence130 €150 €
Pisa90 €120 €
Siena130 €150 €
Price includes
  • Accommodation in B&B (7 nights) in double room
  • Breakfast (7)
  • Luggage transfers (1 piece of luggage + 1 hand bag per person)
  • Digital travel packet
  • Access to our phone travel app during the trip
  • Telephone assistance
Price excludes
  • Travel to/from Florence (flights, train, bus, etc.)
  • Drinks
  • Lunches and Dinners
  • Tourist taxes
  • Return journey from Pisa to Florence
  • Train ride Pontedera – Pisa on Day 7 (~3€)
  • Bike rental
  • Insurance
  • Booking fees
  • Entrance fees to tourist attractions
  • Personal expenses
  • Everything which is not listed in the “Included in Trip Price” section
Options & supplements
  • Single room supplement: +410 €
  • Hybrid bike rental: 190 €
  • E-bike (Hybrid) rental: 290 €
  • Gravel bike rental: 330 €
  • E-Gravel bike rental: 430 €
  • Return transfer by private bus, subject to availability: 150 € / person (personal bike included)

Your travel advisors

Francesca Bigolin

Francesca Bigolin

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Anna Castaldo

Anna Castaldo

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Tania Gherli

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Technical and practical information

Difficulty level 3/5 (on E-bike) or 4/5 (on Bike):

Level 3/5 when using an E-bike. Stages of 30 to 55km/18.6 to 34.2mi. The route is hilly with challenging climbs and descents, especially the climb to Volterra on Day 6. Participants are asked to be in good physical condition and to have already practiced cycling for several days in a row prior to this trip. If you do not use an E-bike the difficulty level turns to 4/5. The daily stages take place on secondary roads, generally asphalted, and on some dirt roads. You will ride on slightly busier roads as you approach larger cities. There are no bike paths in the Chianti region, be aware that you will share the road with vehicles.

You only carry your daily belongings in a small bag or saddle bag. You’ll get your luggage at your hotel in the evening: your luggage is transported by taxi. We ask you to limit your luggage to 1 piece of luggage + 1 hand bag per person, 20kg/44lbs maximum. If you need to transfer more than one piece of luggage, please inform us at the moment of booking (a supplement will be charged).

Possible for groups of 2 and above.

Starting any day of the week from April 1st to October 31st, 2025

8 days / 7 nights / 6 days of cycling

Start

On Day 1 in Florence at hotel check-in (~3pm).

Finish

On Day 8 in Pisa after breakfast and hotel check-out (~10am)

Self-guided tour, without a human guide. A digital travel packet will be sent by email that includes: the list of your accommodations,all the detailed information you need to make your trip a success (documents in French or English as guests request), and access to our phone travel app for navigating bike rides and accessing local maps. The application is available in English.

Accommodation

3* & 4* hotels (some hotels with a swimming pool). Accommodation in double room with private bathroom. It is possible to book a single room (with a supplement fee).

Meals

Breakfast is always included. For lunch: you can eat along the rides daily by buying your picnic supplies in local grocery stores or stopping at a restaurant. For dinner: there are many restaurants/pizzerias in the proximity of your hotels. *It is important to inform us about any food allergies or dietary requirements upon booking.

Extra Nights

It is possible to add extra nights before or after your tour in Florence, Siena or Pisa. Please contact us for availability.

Bike rental

The bikes we offer come in a variety of models:

Hybrid bikes

27 speeds Shimano Alivio. Women or men frames. Alluminium/steel frame. 28'' wheels. Handlebar V-brakes.

VTC

E-Bikes

Depending on the size and on availability, we will either rent an E-Bike or an E-MTB (electric mountain bike).

E-Bike (Hybrid): women or men frames. Winora brand or similar 25kg, 28'' wheels, 8 Shimano Acera speeds. Bosch battery and engine.

VAE

E-MTB (Mountain bike): Haibike brand or similar 25kg, 289' wheels, 9 Shimano Alvio speeds. Bosch battery and engine.

E-MTB

Bike rentals include: Helmet, lock, repair kit, lateral saddle bag, handlebar mobile support (one each two persons).

Trip Starting Destination

This tour starts in Florence, Italy

Trip Ending Destination

This tour ends in Pisa, Italy

By Plane/Train

Regular airlines or low-cost airlines to Florence, Bologna (100km/62mi) or Pisa (80km/50mi):

Florence - Firenze Amerigo Vespucci (FLR) Bus: - From Florence airport to Florence train station: ATAF bus, leaving every 30 minutes from 5:30AM to 12:30PM, to Florence Santa Maria Novella train station (20 minutes ride, approx. 6€)

Bologne – Bologna Guglielmo Marconi (BLQ) Bus + Train: - From Bologna airport to Bologna train station: Marconi Express train, departure every 7 minutes (12.80€) From Bologna Airport to city centre in 7 minutes | Marconi Express Bologna Shuttle - From Bologna Centrale train station to Florence: direct high speed train AV (journey is around 40 minutes, tickets from 30€)

Pise Galileo Galilei (PSA) Bus + Train: - From Pisa airport to Pisa train station: Pisa Mover, connection every 5 minutes, ticket is approx. 6.50€. You can buy tickets directly at the airport terminal or at the self-service machines. - From Pisa Centrale train station to Florence: direct train R or RV (journey is around 1 hour, tickets from 9€)

For more information on trains: EN - Trenitalia *Please note, schedules must be checked before travel, we cannot be held responsible for any changes.

By Car

You can park your car in Florence, at the hotel (payment on site)

By Bus

- Flix Bus: https://www.flixbus.com/ - Bla Bla Car (bus and carpool options): https://www.blablacar.co.uk/bus

Swimming

A number of our trips lend themselves to swimming, either during the stage or at the end of the day. It would be a shame not to take advantage of them. Please note, however, that you are the sole judge of whether or not to go for a swim, and that you do so under your own responsibility and at your own risk.

Responsible tourism

Travelife Partner

Since 2025, Grand Angle has been recognized as a Travelife Partner, an international label that certifies our responsible practices regarding the environment, ethics, and sustainable management, both within our company, with our partners, and in the organization of our trips.

This label, the second level of a rigorous international certification, attests to our concrete actions in favor of responsible tourism. We are actively working toward the next level, Travelife Certified, in line with our sustainable development policy.

It is the client’s responsibility to arrive prepared with the items listed below to help ensure a safe and enjoyable trip.

The following items are required for this trip unless otherwise noted. When packing, think layered clothing systems that work together and can be easily added or removed.

  • Cycling Shoes – sport shoes that are comfortable for cycling in.
  • Socks – one pair for every day or two days of the trip. Sport specific padded socks, no cotton please!
  • Sun Hat – wide brimmed hat or baseball cap/bandana combo
  • Cycling Gloves – padded gloves used specifically for cycling.
  • Cycling Shirts – non-cotton, breathable short sleeve and/or long sleeve shirts (Note: long sleeve shirts provide better sun protection)
  • Cycling Pants & Shorts – nylon pants AND shorts, zip-offs or leggings
  • Windbreaker Layer – a light jacket or pullover
  • Warm Top – mid-weight sweater or pullover of wicking material such as merino wool, fleece or polypropylene
  • Insulating Jacket – down-fill or synthetic-fill insulated “puffy” jacket or warm, lightweight fleece jacket (may not be needed in summer months)
  • Rain Gear – waterproof jacket and pants or high-quality poncho, breathable fabric such as Gore-Tex® or coated nylon. For the pants look for side zippers that will easily allow pulling them over footwear.
  • Casual Clothing & Footwear – comfortable clothes and shoes to wear in the evening after activities.

Important Note: Please, no cotton hiking/cycling clothes. Synthetic clothing is very efficient in drying quickly. Merino wool material clothing is also efficient in drying quickly, is comfortable to wear and has the advantage of not developing a bad odor after use.

  • Saddlebag – If choosing to use a rental bike on this trip, a saddlebag is included with rental
  • Personal Luggage – small duffel bag, suitcase or backpack – for extra items and casual clothes
  • Cycling Helmet – (Mandatory for this trip) comfortable fitting, with rain cover. If choosing to use a rental bike on this trip, a helmet is included with the rental.
  • Hydration System – 2+ liters capacity, either water bottles or bladder/hose system (if planning to wear a backpack during cycling) and an additional water bottle
  • Headlamp – preferably with an L.E.D. bulb that works with AA or AAA batteries (Note: always test headlamp before trips and travel/pack without batteries in device)
  • Picnic/Lunch Kit – knife, plate or bowl, box with closeable lid, utensils, etc.
  • Phone & Charger – local sim card or international plan may be needed. Consider bringing a small power bank to use to recharge devices during trip activities.
  • Map or Phone Holder – for handlebars, included with bike rentals
  • Waterproof Travel Case or Pouch – used to keep important documents (i.e. passport, health/travel insurance, etc.) & phone safe from weather/water
  • Sunglasses, Sunscreen, & Lip Balm
  • First Aid Kit – see first aid kit suggestions below*
  • Personal Toilet Paper Kit – most public restrooms outside of lodging will have toilet paper available, but it is good to be prepared with a personal toilet paper kit to potentially use during portions of this tour. Along the trail, there may be the need to use natural settings for toilets (i.e. digging catholes, etc.) when there are no public toilets available. Kits should include toilet paper, wet wipes, sanitizer & sealable plastic bag(s) for carrying out used paper/wipes.
  • Toiletries
  • Contact Lenses & Glasses – if wearing contact lenses, please also bring back-up pair of glasses and contacts.
  • Prescription Medication – with emergency back-up supply
  • Money – It is good to have some local currency, often smaller local businesses do not accept credit cards and/or prefer cash. Some public restrooms require small amounts of cash to use.

Optional Items & First Aid Kit Suggestions

  • Backpack – a small sized comfortable pack with a waterproof cover. Taking a backpack is useful as it makes it easy to carry your belongings when you go on a short walking trip along the way. If your bike has a rack system this bag can be easily attached or even packed within a saddlebag.
  • 2-3 Face Masks; 1-2 Over-the-counter Rapid Antigen COVID-19 Tests (recommended but optional)
  • Travel Power Adapter – Electric power voltage Italy is 230 V / 50 Hz and the plugs are F & L type
  • Support Braces – consider bringing any joint braces that may be currently needed or from past injuries (i.e. knee, ankle, elbow, etc.)
  • Sleep Mask & Ear Plugs
  • Bug Repellent
  • Quick Drying Towel or Bandana(s)
  • Swimsuit

After years of experience planning adventure travel around the world, we’ve learned that anything can happen, and every traveler should carry a basic personal first aid kit. We want to ensure our guests are well-prepared and make smart informed travel decisions. In many of the places we operate trips, it may be challenging to find certain medications and/or first aid supplies, and sometimes common items you desire may not be available in the destination you are travelling. That’s why it’s good to be prepared and carry a small supply of first aid supplies, any prescription medication, and/or over-the-counter medications you may require during your travels.

We recommend discussing your travel plans, vaccination requirements, and any medication usage with your primary healthcare provider before embarking on our trips. This helps ensure you have a safe and enjoyable travel experience.

Here is a basic list of what we think makes a good personal travel first aid kit:

  • Medications – Brands of your choice, all medications should be either prescribed directly by your doctor or discussed with a doctor prior to use.
  • Electrolyte Replacement/Drink Mix – brand of choice
  • Creams – Antibiotic ointment, Anti-Itch: Hydrocortisone, Arnica
  • Eye Problems: Dry/Itchy – Eye drops
  • Feminine Hygiene – Tampons
  • Wound Care – a various pack of bandages, antiseptic swabs
  • Blister Care – blister kit made up of items of your choice
  • Sun Protection – sunscreen, SPF lip balm
  • Various Items – Athletic tape/"KT Tape", Nail clippers, Tweezers, Small bottle of hand sanitizer, Sewing kit (clothing/button repairs), Disposable surgical gloves (1-2 pairs)

PACKING FOR TRAVEL: It is recommended that you prepare your items in the following manner for your travels to this trip.

“Carry-on Bag(s)” - This is the bag you will bring with you on the plane. We recommend all your pertinent information be in this bag (passport, travel documents, etc.) as well as your most important gear items (footwear, jacket, prescription medication, etc.) in case any checked luggage items becomes lost or delayed.

“Checked Bag(s)” - This bag will be checked and contain the rest of your personal items (clothing and gear, etc.).

Important Note: Again, it is recommended to either wear or pack in your “Carry-on Bag” the main gear items you need for this trip vs. putting them in your checked “Travel Bag” (in case luggage is delayed). Lost or delayed luggage has become more and more common in major airports for international travel since the global pandemic.

LUGGAGE MANAGEMENT DURING TRIP: During this trip, the packing system needs to be in 2 bags.

Extra Luggage - “Checked Bag(s)” & “Carry-on Bag(s)”: This bag will contain all the items you want to bring along on the trip. It will be transferred by vehicle, and you will have access to it at the end of each day of activity at hotels, but not throughout the day. Luggage transfers are limited to 1 bag/item per person, 20kg/44lbs maximum weight.

Extra luggage is not allowed on this trip beyond the 1 bag requirement and is not easily stored due to different starting and ending destinations.

Saddlebags/bike bag (not provided unless you add bike rental): All guests will need a bike saddle bag, which they will be responsible for carrying during trip activities. Items in this bag should include anything you may need throughout the day during the trip. (i.e. rain gear, warm layers, water, sunscreen/lip balm, snacks/food, camera/phone, etc.)

To Transport Your Belongings: If you don’t have a saddlebag & rack on your bike, bring a 30-40L backpack with a waist strap to carry what you need for the day (i.e. rain gear, warm layers, water, sunscreen/lip balm, snacks/food, camera/phone, etc.) as you cycle. If you have a rack on your bike, you can attach your bag with the help of bungee ropes or paracord. Rented bikes are equipped with a saddlebag where you can store your belongings. You should still bring a small backpack with you, so that you can easily take your belongings with you when you are visiting attractions along the route.

Country: Italy Capital: Rome

Documents

Travellers from the European Union, including children, need a valid identity card or passport. Check with the authorities in your home country for the conditions of entering this destination.

Health/Insurance

Do not forget your card and/or policy details for your health insurance and/or travel insurance.

Country code for calling Italy: +39

European Emergency Number: 112

Italian Tourist Information Office

Phone: +390142660366.

Website: https://www.italia.it/en

Central European Time (CET/UTC+1) and Central European Summer Time (CEST/UTC+2) during daylight saving time.

Italian, some english spoken in tourist areas

Italy is a Member-State of the European Union and uses its uniform currency – the Euro €. Italy, as is the case with the other Member-States of the E.U. uses eight coins as follows: 1, 2, 5, 10, 20 and 50 cents and 1 and 2 Euros. The banknotes are issued in the following denominations: 5, 10, 20, 50, 100, 200 and 500 Euros. Currency exchange rates are clearly displayed in every bank that accepts currency exchange, while credit card holders may acquire money from the ATMs of the collaborating banks. Italian banks are open for the public from 8:00 to 13:00 and from 14:30 to 16:30 Monday to Friday. They are closed on Public Holidays. Euros can also be exchanged for notes of other foreign currencies at exchange offices that are situated at the airport and certain main ports, in the larger cities, as well as at many tourist destinations. A passport is required when exchanging currencies. Italy more than other EU destinations, still prefer cash in most settings, but credit card use is becoming more and more available.

Tuscany is a transition region between the North and the Mediterranean climate of the Mezzogiorno. The topography of Florence and Siena means that in summer, it can be very, very hot… as well as being prone to torrential rain (especially in August). The best seasons are spring (May and June) and autumn, with pleasant temperatures (around 25°C).

Source: www.routard.com

Geography of Tuscany

Geography, whether human, economic or electoral, gives Tuscany a pivotal position between the North and the Mezzogiorno. Almost enclosed to the north and east by the Apennine mountains, and open to the vast plain of Roman Lazio, this region is too diverse to form a homogeneous whole.

To the south, on the Sienese side, towards the abbey of Monte Oliveto, are the famous Crete senes, dating from the time when the entire region was covered by the sea.

This fertile land slopes gently down to the Val d’Orcia, where wheat, sunflowers, olives and vines are grown, before coming up against the volcanic Amiata region.

To the west, the metal-bearing mountains mark the boundary between Maremma and Tuscany, beyond the green valleys and forests of the Montagnola and Val di Merse, lands of lumbering and timber exploitation.

In the center, between Siena and Florence, the Chianti region is a land not only of vines, but also of fruit and olive trees. The richness of this wine, over 90% of which is made from Sangiovese grapes, lies in its substratum, made up of sandy, stony, clay and sandstone deposits, combined with the microclimates created by the wide variety of exposures of the plots.

Val d’Arno: the region’s main (not to say only) axis, it accounts for most of the population of both regions. Crossed by the Autostrada del Sole (A1), it is the heart of Tuscan activity.

The Arno River

Only 241km long, the Arno rises at Monte Falterona (1,385m) in the Apennines, then loops southwards through Florence and flows westwards past Empoli, Pontedera and Pisa. At the end of its course, it descends to the Ligurian Sea, where it empties 10km north of Livorno. In Florence, this river marks the separation between the two banks: Oltrarno (left bank) and Lungarno (right bank).

Every year in October and November, the level of the Arno rises irresistibly, without causing flooding. However, some observers believe that the risk of a new catastrophe has not been completely averted. In spite of the canalization work undertaken after 1966 and the construction of dykes, Florence would still not be safe from another destructive flood.

Around 1503-1504, Leonardo da Vinci presented the city of Florence with a project to divert the Arno and build a kind of canal linking the Medici city to the sea. Leonardo’s concern was the same as today: to avoid terrible floods! Source: www.routard.com

Reviews

3,5 · 2 reviews

Danielle 12/27/25

—  We are disappointed with the hotels...

Eric 12/27/25

—  Tuscany is not the best cycling destination

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