Tuscany Biking Tour

Tuscany Biking Tour
  • Duration

    6 Days / 5 Nights

  • Lodgings

    3 & 4 star

  • Activity Level

    Moderate

  • Tour Dates

    2024 Dates

    Apr 7-12, 14-19, 21-26, May 12-17, 19-24, Sep 8-13, 22-27, Oct 6-11

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Tuscany Bicycle Tour  "The Eternal Art & Wine Festival"

During this biking tour of Tuscany you spoil yourself with traditional Tuscan cuisine and lose your sense of time as you cycle past fields of red poppies and sunflowers surrounded by cypress trees and olive groves; an agrarian wonderland. 
This Italian region, best known as the heart of the Renaissance, is fully explored from memorable inns, farm stays and converted palaces. Savor full course meals and witness a cultural history dating back to the days of Italy's original inhabitants-the Etruscans.

 

Days 1-2: Chianti Classico Farm Stay
From a beautifully restored Tuscan farmhouse/winery, bike along quiet roads to the three villages that formed the Chianti Alliance centuries ago. Visit Tuscany's forgotten abbeys and hamlets then enjoy a private winery tour and taste their supple reds, fresh honeys and rich olive oil then relax by the vanishing edge pool spilling into the countryside of endless vineyards. 

Days 3-4: Abbeys, Saffron & Pilgrim Trails
Soft, colorful, rolling hills of vineyards and sunflowers provide the backdrop to pre-Roman Etruscan remnants on your route to San Gimignano’s "medieval skyscrapers.” Then ride past Voltera an Etruscan and Romans stronghold and into the fortressed Tuscan hill town Monteriggioni. In Siena you’ll witness a unique blend of medieval and Renaissance treasures during your city tour then a night on your own to enjoy the medieval atmosphere. 

Days 5-6: Pienza
Pedal through contrasting landscapes leading into the land of Brunello wines, Abbeys, Roman baths and historic hill towns. Cruise along a high ridge and the changing hill¬sides of ash gray, deep green and bright yellow to the perfectly planned city of Pienza, where pecorino cheese is renowned. 

Inclusions

  • All 3-star accommodation with breakfast
  • All full course dinners, but one and 1 gourmet picnic lunch
  • Winery Visits & tasting
  • Private City Tour of Siena & Visit of Etruscan Tombs
  • BIKE RENTAL of quality upright 27-speed touring bikes equipped with handlebar bags (your clipless pedals can be mounted
  • but remember to bring your shoes, bike gloves and shorts.)
  • Quality road bikes or e-bikes are available upon request
  • Route note, maps and chalk marked routes
  • All tour transfers including meet/depart, van support and luggage transfer
  • Multi-lingual guide(s)
  • All entrance fees mentioned in itinerary

Not included

  • Airfare, beverages, trip insurance (strongly recommended), personal items, guide tips...

Highlights include

  • Lodging at winery/villa
  • Wine tastings & tours
  • Medieval hamlets & historic market towns
  • Stay in center of San Gimignano
  • Private Siena city tour
  • Abbeys & fortresses
  • Pienza & pecorino cheese
  • Brunello winery visit
Tuscany Biking Tour

Tuscany Bicycle Tour  "The Eternal Art & Wine Festival"

Tuscany first attracted the Etruscans in 800 BC and each succeeding culture has added to the region's allure and charm. Marvel at the artistry of towns like Florence and Siena, which quickly give way to the rolling hills of olive groves and vineyards. 

Florence, the center of the Renaissance, is the meeting point of your tour. From here we transfer south to explore the pristine beauty of the Tuscan Chianti Classico countryside. You ride along quiet country roads that wind through the hills and valleys of colorful fields of poppies, sunflowers and along the vast rows of vineyards that produce the delicious deep red Chianti wines and the crisp white Vernaccia wines of San Gimignano.

We visit medieval fortresses, ancient Abbeys, Etruscan porticos and Renaissance palazzi. One vista after another leaves a lasting impression as we ride up to hilltop towns that offer stunning panoramas of the valleys below. You glide through the surreal ashen landscape of deeply fissured hills known as "crete", into the land of Brunello wines and through the inspiring scenery from where the "English Patient" was filmed.

To visit Tuscany is to step back-to a time when people lived to appreciate the simple things in life: an orange sunset, a ripe peach, the shade of an olive tree, a church bell at dawn. As you walk through the countryside, you too will soon understand what drew some of history's greatest figures to this magical area. Tuscany is truly a feast for both the body and the spirit.

Be ready to ride as a short transfer from the busy streets of Florence is the start of our first ride following the quiet country paths into the wondrous Chianti countryside. One moderate climb allows us to fully enjoy the wonderful views of this famed wine region as well as explore the nearby Abbey and enoteca. Our destination is a beautifully restored farmhouse winery located near an ancient market town in the heart of the Chianti Classico region. Here we get a chance to relax and explore the grounds with a welcome glass of Chianti/Rose or laze around the farms impressive vanishing edge pool before we sit down for a memorable Tuscan feast--Florentine T-bones anyone?

Lodgings for two nights at a family run farm/winery offering us the unique experience associated with the agriturismo.

From our farmstead we complete our exploration of the famed Chianti wine region. You'll experience an up-close look at the scenery that has made Tuscany synonymous with that "Taste of Tuscany" everyone expects to see. You cycle along quiet country roads lined by oak groves, vineyards and farmlands you ride between the 3 main villages that formed the "Chianti Alliance" centuries ago, Radda, Gaiole and Castellina in Chianti with an optional visit to nearby Greve.

Along the way you tour of the ancient Abbey of Coltibuono, where the art of wine, honey and olive oil production has been refined for centuries. We not only taste the goods here, but also enjoy an Andiamo gourmet picnic lunch featuring assorted local specialties within the setting of spectacular views over the eastern edge of the Val d'Arno. Our loop takes back into heart of the wine region and begs us to stop for a tasting or even better a gelato that you are sure to associate with everything Italian. On our return we enjoy a private tour & tasting at the winery of our host.

The soft colorful landscapes of fine lines formed by the numerous vineyards, gently rolling hills and fields of sunflowers are unforgettable within this idyllic cycling route of the Chianti that includes a stop at the important Etruscan tombs of 400 BC. We then tour the charming Castellina in Chianti before gliding downhill along a 20-km gently sloped route that embraces everything fun about biking and wonderful about Tuscany.

We end the ride with a backdoor approach to the "medieval skyscrapers" of San Gimignano and shift gears from the rugged mountainous terrain of red grapes and into the more rolling countryside white grapes offer that cruises through the medieval gate on the quiet side of town and leading into the heart of the town we stay.

Lodgings are in a 3-star converted palace within the heart medieval walls. The atmosphere and hotel views are magical & there are lots of fun cafés and romantic quaint squares.

This day's ride is one of my favorite rides from any tour. Our route takes us to Siena, ancient arch-rival of Florence, along a route that moves away from the vineyards and through a land of wheat fields, orchards and goat farms. Early on there are plenty of photo-ops looking back on the towers of San Gimignano and later Voltera. The road continues along a quiet country road to Isola d'Abazzia (island abbey) which we will explore before reaching the completely walled multi-towered medieval outpost, Monteriggione.

In these times no soldier of rank lived within the walls, but it was an important fortress for the Sienese foot-soldier during their battles with Florence. Once Siena was conquered, the Florentines considered the fortress insignificant. We take time to explore the grounds that until 1960, when it was slowly brought back to life, it was populated by fewer than 20 people. Everyone has the option to shuttle a short distance into Siena or add another 10 miles of country riding to the outskirts of Siena.

Soon after arrival you enjoy a very informative privately guided tour of Siena where we visit what is considered by many the most beautiful square in the world and the amazing Duomo and learn about the famous "Palio" horse race, then have the rest of the night free to explore on your own.

Lodgings are at a very friendly & quiet 3-star city hotel near the medieval town gate & features large rooms and a nice garden.

Out of Siena we soon find ourselves back in the quiet countryside of sweeping wheat fields, Abbeys, Roman baths and historic hill towns. It doesn't take long for you to reach for your camera in an attempt to capture the vast panoramas of rolling hills of strange landscape of bare, ash gray soil of deeply fissured hills known as "crete." Tall cypress pine trees line the pathways to one distant estate after another creating a surreal feeling as if you have stepped into a land of fantasy. This impressive road takes us to a remarkable 13th century Abbey that features the noteworthy frescoed cloisters by Signorelli and Sodoma.

After lunch at the Abbey we ride into the land of Pecorino cheese, and Vino Nobile wine or better known as "the king of wines". Just before reaching the entrance of the town walls of Pienza, we stop to visit the sit of where the film "The English Patient" was made. Then ease into the center of town and our 4 star lodging.

Lodgings: 4 star, 15th century Palace at the Medieval Center.

Transportation Logistics

The following is a list of train schedules for transportation to and from the tour start and end locations. Train departure times and tracks are subject to change, so verify before boarding.

*Meeting your tour by train if not staying in Florence: 
Trains from Rome to Firenze/Florence (tour start): ~1.5 hours 
#9310 Roma Termini -9:00am--arrival Firenze S. M. Novella ---10:37am

From Pisa: ~1 hour 
#3110 Pisa Centrale -10:27 am--arrival Firenze S. M. Novella ---12:45 pm 

From Milan: ~3.5 hours
#9433 Milano Centrale -10:00am-- arrival Firenze S. M. Novella ---12:45 pm

Departing your tour: 
From Chiusi to Rome: ~1.5 hr (departs every half hr.) 
#577 Chiusi-Chianciano Terme -09:35 am--arrival Roma Termini ---11:03 am 

*Departure times and track are known to change on a moments notice, thus verify before boarding

Highlights include

  • Lodging at winery/villa
  • Wine tastings & tours
  • Medieval hamlets & historic market towns
  • Stay in center of San Gimignano
  • Private Siena city tour
  • Abbeys & fortresses
  • Pienza & pecorino cheese
  • Brunello winery visit
Tuscany Biking Tour
Days 1 & 2: Fattoria Rignana

Days 1 & 2: Fattoria Rignana

Surrounded by 120 hectares of vineyards, woodland and olive-groves, the Fattoria di Rignana is situated in the very heart of the Florentine Chianti district. The farm dates back to the 11th century, when Rignana was a castle controlled by the Commune of Florence along the Sienese border. The main Villa belonged to the noble Ricci family in the 17th century. Today Rignana produces wine and oil, of which 16 hectares are covered by vineyards and olive trees.

 
Days 3: Hotel La Cisterna

Days 3: Hotel La Cisterna

A beautiful converted 12th century palace is situated in the very center of town surrounded by the town's main towers. We do our best to provide you with their finest rooms: either with a countryside view or with a view of the main square.

 
Day 4: Hotel Santa Caterina ***

Day 4: Hotel Santa Caterina ***

Located in Siena, this 18th century converted villa is a small cozy hotel situated just a few meters away from " Porta Romana " one of the medieval gate entrances to the historical center of Siena. This hotel offers a magnificent garden and amazingly friendly staff.

 
Day 5: Hotel Il Chiostro ****

Day 5: Hotel Il Chiostro ****

A converted palace located in Pienza situated in the Medieval center overlooking the Val D’orcia.

 

*Please note: while these hotels are typically featured, we occasionally reserve other hotels of similar style and quality due to availability. Please call us if you have any questions about the exact hotels selected for any of our tours.

Tuscany Biking Tour

    DAY-TO-DAY DISTANCES & HIGHLIGHTS
    All the towns & lodgings we stay are highlights in themselves

    Day 1: Ride 29 km / 18.5 miles-lots of downhill, end with uphill. Highlights: visit of Badia Passingano & Chianti Classico wine tasting at farmhouse/winery we stay.

    Day 2: Ride 45 or 62 km/28 or 40 miles-Chianti Classico loop some shorte climbs. Highlights: Visit Badia Coltibuono, gourmet lunch, sample wine and honey & visit famous Chianti Alliance townships & tiny hamlets.

    Day 3: Ride 48 km/ 30 miles two climbs & one 12-mile long downhill. Highlights: Etruscan tombs, visit market town & tour San Gimignano.

    Day 4: Ride 43 or 64km / 27 or 42 miles-easy early short climbs or moderate ride starts with long climb then long downhill. Highlights: Visit multi-towered medieval outpost, Monteriggioni & Island abbey, Siena City tour.

    Day 5: Ride 57 km / 36 miles-moderate ride with many short climbs. Highlights: Visit of the Benedictine Abbey Monte Oliveto Maggiore (frescos by Sodoma and Signorelli), Pienza and taste pecorino cheese.

    Day 6: Departure day…Chiusi train station as pre-arranged.


KEEP IT PRIVATE ON AN EXISTING TOUR or CUSTOMIZE YOUR TRIP

If you have at least 6 participants we can keep it private on any of our sheduled tours or on an alternative date (subject to availability). For less than 6, prices may vary and for more than 12 discounts may apply.

To help us get started complete the form below. You can also call us M-Sat 9-5 PST (USA), or to the right, schedule a call or send us a message. 

Sometimes a custom trip is participating in one of our exisitng trips on a private basis with a few alterations to trip length, activity level, or adding some side trips. Other times we get to work to create a unique itinerary specific to your groups desires or budget. We then use our expertise to organize a tour especially tailored to your vision.

The first thing we do is get to know you a little. We learn your interests and preferences, find out who’s going and why. Family, friends or associates? Birthday, reunion or corporate retreat? When you speak with our tour designer he/she will work together with you to design a trip that is sure to create great anticipation and excitement for all.

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