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 enjoy a splendid easy walk to the 1000 year old township of Badia Passignano. 

This ancient Abbey town was founded by the Vallambrosa monks and later taken over by Napoleon edict. It was only until the 1990’s that the monks were able to reclaim the Abbey. We get a good feel for this wine region during our short walk and will have plenty opportunity to explore the tiny village that leads to our farmstead.  At the end of the walk 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 nights at a family run farm/winery offering us the unique experience associated with the agriturismo. 

From our farmstead we continue our exploration of the famed Chianti wine region. Enjoy casual walks within the scenery that has made Tuscany synonymous with that “Taste of Tuscany” everyone expects.  Along quiet country roads and trails lined by oak groves, vineyards and farmlands you walk 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. On our return we enjoy a tour of the winery & 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 walking route of the Chianti that includes a stop at the important Etruscan tombs of 700 BC.  Our walk takes us into the rural trails of the white wine region and offers us a special back route to the “medieval skyscrapers" of San Gimignano.  This incredibly scenic tiny path leads us to the medieval gate on the quiet side of town. Our arrival allows for plenty of time to explore the streets of this renowned charming town (location of the film “Tea with Mussolini”).

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

From a tiny quaint village known for its production of the famed Vernaccia white wine we walk along a wooded path and into a peaceful nature reserve that was once an ancient Etruscan salt road and leads to a fascinating ruinous village and castle.  This long-forgotten site of Castelvecchio not only offers us splendid views, photo-ops & exploration, but has recently roused archaeological interest and allows us the chance to visit a site still being uncovered. 

The afternoon offers us two great options.  We can either end our walk here to visit the significant Etruscan and medieval-town of Voltera where the finest Etruscan museum is considered a “must see”. Or we continue walking from the fortress, in which case we’d follow a trail that is lined by poppy and sunflower fields along a quiet country road to Isola d’Abazzia (island abbey) which we will explore before walking up to the completely walled multi-towered medieval outpost, Monteriggione. No soldier of rank lived within the walls, but it was an important fortress for the Sienese foot-soldier during their middle age 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, was populated by fewer than 20 people. For those interested in a Vernaccia wine tasting, both options allow for a return to the tiny hamlet we began our morning. Another wonderful dinner is planned in the old city.

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

After a short transfer we soon find ourselves at the blue green seas of the Cinque Terre Coast, where we hike between the first three of the five villages. We begin 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 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. 

Hotel: 3-star near the sea & steps to town.

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 of our tours, 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 San Futtuoso 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 cafes, 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