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. Your walks follow quiet country roads that wind along 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 walk up to hilltop towns that offer stunning panoramas of the valleys below.
After your rides, relax and enjoy la dolce vita with a gelato ice cream, a foamy cappuccino, or maybe try a glass of Vernaccia on a terrace over-looking the very vineyards where it was made. At night, watch the stars come out knowing that your only decision is which of the many delicious choices you'll have to order for dinner. The ample dinners personify Italian cuisine and are made with the freshest local ingredients: try the famous Florentine steak, explore new tastes with some wild boar or enjoy the great fresh pasta with a variety of sauces. Then complete your meal with a creamy tiramisu, or a plateful of cantucci dipped into the sweet dessert wine, Vino Santo.
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.
Day 1: Chianti Countryside, Honey, Wine and Olive Oil
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.
Dinner: Our farmstead has one of the finest kitchens in Tuscany--a favorite amongst locals
Day 2: The Chianti Alliance
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. Along quiet country roads and trails 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.
Lodgings same as previous night.
Dinner: Optional Cooking class evening serving up excellent Tuscan cuisine & offering outstanding wines.
Day 3: Etruscan Legacy & Medieval Towers:
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 700 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 of 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 albergo within the medieval walls. The atmosphere and hotel views are magical & there are lots of fun cafés and romantic quaint squares.
Dinner: Excellent trattoria specializing in local favorites like saffron sauces & wild boar
Day 4 - 5: Italy's Most Beautiful Square, Wheat Fields & Goat Farmers:
This day's ride is one of my favorite rides from any tour. Our route takes us to 
Siena, ancient archrival 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.
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
Fattoria Rignana*** is surrounded by 120 hectares of vineyards, woodland and olive-groves, and 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 Comune 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.
La Cisterna *** is a three star hotel in the historic center of San Gimignano. This 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. 
Hotel Santa Caterina *** in Siena, is an 18th century villa converted into 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.