Pisa to Florence via Chianti Cycle

View over Florence in Italy

Highlights of cycling Tuscany

Architectural wonders of Pisa

Cycle through olive trees in Tuscany

Cycle through the beautiful city of Florence

Sample wine, olive oil and biscotti in the Chianti region in Tuscany

Discover the sights of Florence by bike

View over Florence in Italy

Highlights of cycling Tuscany

Architectural wonders of Pisa

Cycle through olive trees in Tuscany

Cycle through the beautiful city of Florence

Sample wine, olive oil and biscotti in the Chianti region in Tuscany

Discover the sights of Florence by bike

2026 Bike & BargeReady to Book

Duration

7 days

Activities

self guided cycle

Accommodation

6 nights in 3-4 star hotels

Meals

6 Breakfasts

Price

$1435USD

Overview

Trip Code: TCV

Trip highlights

Cycling through classic Tuscan landscape of rolling hills, vineyards, olive groves and quintessential hill top towns
Exploring the renowned cities of Pisa and Siena
Enjoying the superb wines of the Chianti region
Discovering the towers of San Gimignano and the thermal waters of Casciana Terme
Florence, which welcomes you with its Renaissance splendour

Tuscany needs little introduction, having been the holiday destination of choice for centuries. Cycling through classic Tuscan landscapes of rolling hills interspersed with verdant vineyards and cypress trees lining the roads is one of life's great pleasures. Culture, history and excellent cuisine is ever present as you pedal between towns. From Pisa and its leaning tower, pass through medieval Siena, along the Via Francigena and a route of vineyards and olive groves, all the way to Florence, the cradle of the Renaissance. At night soak up the atmosphere in piazzas and trattorie, and join the passeggiata, an evening stroll often accompanied by a gelato.

Trip Grading

moderate to challenging

More info about grading system

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Itinerary

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Day 1
Arrive Pisa

Make your own way to Pisa, the city famous for its magical Piazza dei Miracoli (Square of Miracles) with characteristic Leaning Tower. A UNESCO World Heritage site since 1987, Pisa has a large number of monuments as well as the friendly and lively atmosphere of a university city. We can assist with booking pre-tour accommodation on request.

Meals: Nil

Day 2
Cycle along the Arno to Casciana Terme (50km/31.2mi)

The cycle route begins along the river Arno where you soon reach Pontedera, a rather modernized district, home to the wine company Castellani, and a sweets factory called Amedei. Continue through olive groves and vineyards, perfect for an immersion in nature. Finally you will reach the thermal town of Casciana Terme, famous for its Etruscan roots and where thermal water is said to have been discovered by Countess Matilda of Tuscany in the 12th century. Elevation: +290m/951ft/-180m/590ft

Meals: B

Day 3
Cycle the Via Francigena to San Gimignano or Colle Val d'Elsa (50 or 70km/31 or 44mi)

Following the Via Francigena pilgrim route, today's cycle leads through vineyards and rolling hills to the medieval hilltop town of San Gimignano. With its UNESCO listed centre, the town is encircled by 13th-century walls and is best known for its skyline of medieval towers. In the evening, treat yourself with the local exquisite cuisine! Elevation: +755m/2477ft/-545m/1788ft Subject to availability, the alternative overnight stay may be in Colle Val d’Elsa (70km/44mi, elevation +1000m/3280ft, -980m/3215ft)

Meals: B

Day 4
Cycle to the medieval town of Siena (45 or 25km/28 or 15.6mi)

Following the centuries old Via Francigena, you'll have views of Mount Maggio and the castle of Monteriggioni, Dante's subject in his famous literary pieces. The superb medieval town of Siena is ahead; you'll recognise it by the historic brick buildings and the crown of Torre del Mangia. Take time to sit in Piazza del Campo, where the famous Palio horse race takes place each year in July and August. Elevation: +740m/2428ft/-675m/2215ft If your stage starts from Colle Val d’Elsa, today's ride is 25km/15.6mi, elevation +445m/1460ft-242m/794ft

Meals: B

Day 5
Cycle to Greve in Chianti (55km/34.5mi)

Today's first stop is Castagnolli, where you can admire Brolio Castle, home to the Ricasoli family and today a well-managed wine cellar. Continue to Radda in Chianti, a classic Chianti village nestled in the verdant hills among remnants of the Etruscan age and Panzano, a lush green district with a countryside charm. Greve in Chianti is up next, where the famous Chianti Classico Wine Festival is held every year in September. A sip of the local wine will fire up your senses. Elevation: +935m/3068ft/-1045m/3428ft

Meals: B

Day 6
Cycle to Florence (35km/22mi)

A shorter cycle day today with free time on arrival to explore one of the world's most beautiful cities. The first leg is to the small town of Mercatale, where there are wine-tasting opportunities at its local wine cellars. After ten kilometres, visit Impruneta, a neighbouring district filled with terracotta art. Back on your bike, Florence is waiting for you! We recommend not missing the Duomo, the Piazza della Signoria, the Uffizi Gallery, the Ponte Vecchio over the Arno River, and Michelangelo's statue of David. Overnight in Florence. Elevation: +660m/2165ft/-840m/2756ft

Meals: B

Day 7
Trip concludes

After breakfast the trip concludes. We can assist with booking extra nights on request.

Meals: B

Map

Elevation

The map and elevation chart are for illustrative purposes only and meant to provide general guidelines.
On self guided trips, actual route information provided before departure will be more detailed.

Inclusions

What's included

6 breakfasts - varied buffet breakfasts are served at each hotel
6 nights accommodation in 3-4 star hotels on a twinshare basis with private facilities
Rental touring bike with helmet, pannier, puncture resistant tyres and gel saddle (electric bike available on request - supplement applies)
Luggage transfers, 1 piece maximum 20kg per person - supplement applies for excess
Digital information pack including route notes, maps, navigational App (can be used offline), GPS Tracks and travel guide per room booked
Bike insurance against theft & damage
Emergency hotline

What's not included

Travel to Pisa and from Florence
Meals not listed as included, drinks
Travel insurance - mandatory
Guide - this is a self guided cycling holiday
A supplement will apply if you book a single room
Entrance fees not listed as included
Transfers not listed as included
Transfers by taxi if you need to skip or shorten a stage (option to shorten day 2 only, by train)
Excess luggage
We recommend bringing a handlebar phone holder – to follow the route more easily using the app / GPX files
Local hotel taxes - payable locally directly to the hotel (allow eur15-20 pp)
Items of a personal nature

Bike information

Hybrid Bike

During the trip you will be provided with a 27 speed bike with handbrakes. This will generally be a citybike available in various sizes in unisex models, the bike size will be determined based on your height. You will also receive a pannier to carry your gear for the day, along with a handlebar bag, bike computer, lock and repair kit. Helmets will be provided locally.

Electric Bike

An electric bike is available on request. A supplement applies, see below. The electric bike provided has a low-entry frame and a battery with an average range of 90km.

Electric bikes, or e-bikes, are designed to make cycling easier. The pedaling ‘boost’ provided by an e-bike opens up more options, allowing people of different fitness levels to cycle together or for cyclists to take on routes they may otherwise consider too tough for their current fitness capabilities. Please note that e-bikes are heavier than normal bikes and given the higher speed possible, should only be ridden by confident cyclists. Minimum age for e-bike rental is 18 years (or 14 -17 years with waiver signed by parent or guardian) and a minimum height requirement is 147cm / 4ft10in.

Grading

moderate to challenging

Grade 4 - This trip involves 5 days cycling with daily cycles of 25-70km/15.5-44mi, over a hilly landscape with some steeper sections and to hilltop towns. Though the daily distances are not so far, the route can be strenuous at times - there are numerous climbs and descents, including some steep inclines - the elevations are noted each day. Much of the cycle is on paved roads with low traffic (95%) with part of the trip on unpaved surfaces. It is important to be in good physical shape to fully enjoy this trip. It is considered suitable for cyclists with a good to high level of fitness. You need only carry your personal items including a water bottle. Your luggage is transported for you between hotels. *For safety reasons, we insist that cycle helmets be included as a compulsory item on your equipment list. If you are concerned about your overall cycling fitness, we recommend you consider an e-bike.

Departure dates

Every Saturday from 29 Mar to 11 Oct

Notes

Mid Season

High Season

DN1

High season is from 10 May to 5 September, Mid season is from 19 Apr to 9 May and 6 to 26 Sep. Supplement applies to high and mid season departures.

Note:

Due to logistics this trip is not suitable for solo travellers. It is possible for single travellers to book on a date which already has travellers. Contact our team for more details.

Note:

Other departure dates are available for groups of 6 or more.

Note:

Trip not available 14 Jun due to an event in Florence. Dates on request during the Palio event in Siena in July and August.

Want to organise a private group?

Fundraising events, sporting groups, family treats; learn how you can organise a Private Group from just 6 travellers.

Priceper person from

$1435USD

Options & Supplements*

Electric Bike SupplementUSD$170
Single SupplementUSD$390

*Prices listed are per person

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