In the heart of the Chianti Classico region, near a medieval market town, we spend two nights at a beautifully restored villa/winery that was centuries ago home to the local bishop. From just outside Florence we bike straight into the farmlands and tiny hamlets of the Chianti hills. This famous wine region unfolds during our short warm-up with plenty of opportunities to explore the tiny villages that lead to our farmstead.

At the end of the ride you get a chance to sample the three types of wine that our host produce as well as try their honey and olive oil. Then relax around the infinity pool that looks over the rolling hills and vineyards before we sit down for a memorable Tuscan feast—Florentine T-bones anyone?

Lodgings & Dinner: Enjoy two days at a family run farm/winery offering us the unique experience associated with the agriturismo. There is a beautiful restaurant here and it is locally renowned for its fabulous traditional Tuscan cuisine.

We ride deeper into the famed Chianti wine region as we criss-crosses through the scenery that has made Tuscany synonymous with that “Taste of Tuscany” everyone expects.  Our path follows quiet country roads lined by oak groves, vineyards and farmlands with time to visit the 3 main villages that formed the “Chianti Alliance” centuries ago, Radda, Gaiole, and Castellina in Chianti(optional visit to nearby Greve.)

Along the way you tour 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 and a 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 gelato that you are sure to associate with everything Italian. We end the day with a private tour & tasting at the winery of our host before setting off for another feast. 

The soft colorful landscapes of fine lines formed by the numerous vineyards, gently rolling hills and fields of sunflowers are unforgettable within this idyllic route of the Chianti that includes a stop at the important Etruscan tombs of 700 BC. We have enough time to explore the last of the villages that formed the Chianti Alliance before lunch and then a 20-km gentle downhill cruise takes us into the rural pathways approaching the “medieval skyscrapers” of San Gimignano from the seldom traveled side of town.

This incredibly scenic back road leads us to the medieval gate locals access and our arrival time allows for plenty of time to explore the streets of this incredibly charming town (film location in “Tea with Mussolini”).

Lodgings: A converted palace in the heart of the medieval town. Rooms with views of the square or countryside.

This day's ride is one of my favorite from any tour. Our route leads us to Siena, ancient arch-rival of Florence, following a country road that moves away from the vineyards and into 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 then towards Voltera.

The quiet country road passes by Isola d'Abazzia (island abbey) which we explore before reaching the multi-towered walls of the medieval outpost, Monteriggione. In olden times no soldier of rank lived within the walls, but it was an important fortress for the Sienese foot-soldier stationed to do battle with Florence. Once Siena was conquered, the Florentines considered the fortress insignificant. We explore the grounds that until 1960, when it was slowly brought back to life, was populated by fewer than 20 people. Option to shuttle a short distance into Siena or add another 10 miles of country riding to the outskirts of Siena before our city tour.

Today is a transfer day and it isn't long before we find ourselves along the blue green seas of the Cinque Terre Coast, where we will hike between the five renowned villages. We start from the southernmost village, Riomaggiore and walk along the romantic lover's lane to stunning Manarola then break away from the crowd to the tiny olive oil producing village Volastra. 

High above Manarola our trail enjoys the ultimate Cinque Terre view that everyone hopes to see and takes us through a lush valley filled with wild flowers & vineyards. In Corniglia, built on a sheer cliff above the sea, we take our time wandering through the narrow alleyways of colorful houses and shops that lead to the town’s castle of 1273.  Squarzafico, the Captain of the Genoese Republic, besieged the original inhabitant of the castle, Nicolao Fieschi, who had sided with King Charles of Anjou later Nicolao was quoted as wondering why he ever sided with that King in the beginning. This is one of the many legends we examine within these stonewalls.    

Bright yellow lemon trees with deep green leaves in front of the sparkling blue ocean impress even the novice photographer. After lunch we hike along the coast and up into the vineyards of the famed Sciacchetra wine producers. As we leave Corniglia for Vernazza (most visitors’ favorite) and Monterosso a Mare we complete our circuit of the five villages. Many opt to spend a more leisurely day and do the walk before lunch and casually make use of the trains between the last two villages for the remainder of the day.

Lodgings: 3-star along the sea.

From impressively frescoed Camogli we hike into Portofino National Park where a completely different nature is on display compared to the previous days. This is one of our favorite hikes from any tour and begins through lush gardens and olive groves to a hillside town where the views from the church still impress the locals. We make our way along an unusual trail that's carved into the cliffs and leads to a tiny cove accessible only by foot or boat. Here the ancient Abbey San Fruttuoso and the “Torre Andrea Doria,”a medieval lookout tower, are explored. We offer a boat ride 15m off shore to see 18m below these incredibly clear waters the "Christ of the Depths" (a statue dedicated in memory of lost sailors and is said to now protect scuba divers.)

Entering the south end of the park we pass by some WWII relics and enjoy stunning views of the Italian Riviera. We soon find ourselves in the famous town of Portofino where the yachts can be as big as the mansions that dot the hillsides.

Before heading back to Sestri Levante, we visit Santa Margherita's palm tree-lined waterfront. This popular town, decorated stylishly with flowers, is filled with cafés, beautiful boutiques & colorful fruit and pastry shops. There's enough time for a final shopping and exploration of colorful Sestri Levante before our grand farewell dinner. 

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