Day 1: Chianti Countryside, Honey, Wine and Olive Oil

In the heart of the Chianti Classico region, near a medieval market town, we spend two nights on a beautifully restored farmhouse/winery that was centuries ago home to the local bishop. We bicycle from just outside Florence and head straight into the farmlands and tiny hamlets of the Chianti hills. We get a good feel for this famous wine region during our short warm-up and will have plenty opportunity 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 vanishing-edge swimming pool that looks over the rolling hills and vineyards before we sit down for a memorable Tuscan feast—Florentine T-bones anyone? Lodgings: for two days are 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.

Lodgings: 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, Tiny Hamlets & Val d’Arno

From our farmstead we complete our exploration of the famed Chianti wine region. Enjoy our loop ride that criss-crosses through the scenery that has made Tuscany synonymous with that “Taste of Tuscany” everyone expects.  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 (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. We end the day with a private tour & tasting at the winery of our host before setting off for another feast.

Lodgings: Same as previous night.

Dinner: Another locals’ favorite serving excellent Tuscan cuisine & offering outstanding wines.

Day 3: The 1st Italians &the Middle Ages

The soft colorful landscapes of fine lines formed by the numerous vineyards, gently rolling hills and fields of sunflowersare unforgettable within this idyllic walking 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 tiny back road leads us to the medieval gate on the quiet side of town and our arrival time allows for plenty of time to explore the streets of this incredibly charming town (location of the film “Tea with Mussolini”).

Lodgings: 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: Pilgrim Route & Italy’s Most Beautiful Square

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.

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

Dinner: Outdoor café on the famous “Il Campo” Square.

Day 5-6: Marble Mines & Turquoise Sea

During our transfer we offer the option to stop in Pisa to see the Leaning Tower. We later stop above Carrara, capital of the marble trade, where the white marble covers the roadside.  Our destination is the surreal marble mines frequented by notable sculptors such as Michelangelo.  Get up close to the activity, then lunch in a tiny worker’s village that commands spectacular views of the region.   

At the blue green seas of the Cinque Terre Coast we hike between the five villages. From the southernmost village, Riomaggiore we 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 to start clicking away.  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 which offers a nice beach beckoning you for a swim we complete our circuit of the five villages. Many guests who wish to spend a more leisurely day walking will do the walks before lunch and casually make use of the trains between the last two villages for the remainder of the day.

Lodgings: 4-star converted castle above the sea.

Dinner: Outstanding restaurant with “Godfather” ambience.

Day 7-8: Camogli & Portofino

Out of impressively frescoed Camogli we hike into Portofino National Park where a completely different nature is on display from 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 an ancient Abbey 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.)

We then walk through the south end of the park into 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.

Dinner: My favorite seafood restaurant in Italy—sea bass baked in salt anybody?

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