Tuscany Unplugged (24 September – 9 October 2016

Tuscany Unplugged

24 September – 9 October, 2016Cypress_road.jpg

Tuscany elicits visions of rolling hills covered with vineyards, wheat, olive orchards and cypress trees, all dotted with villas and Etruscan villages perched atop the highest hills.   We envisioned a different approach to a cycle tour of Tuscany when we first started making plans to return after many years of absence.  The notion was to “unplug” from the tourist squirrel cage.  To that end we created a blend of characteristically old Tuscan villas and villages throughout the landscape as seen from roads less traveled.  And we added a mixture of lodging and dining experiences to the tour to better appreciate the rich variety of flavors and personalities that are quintessential Toscana!  

Day 1 Florence, Italy (Firenze)  (9km, 150m)

Welcome to Firenze, the birthplace of the Renaissance and one of our favorite cities! Our lodging in Florence offers a unique experience to reside in an Italian villa built in the Liberty style in 1917. Your spacious room includes a full kitchenette, a quiet garden on the back of the villa, and a central location from which to explore Florence. A variety of restaurants are within an easy walk or bike ride. Our hostess, Angela, is a wealth of knowledge and freely shares her knowledge of local sites and roads.


Day 2 – Laterina, Italy (70km, 1000m)

The ride from Florence to Laterina is the perfect introduction to Tuscany. Enjoy the ups and downs, views of vineyards, and the colorful tapestry of Tuscany.  Heading into the Florentine Hills, near the town of San Donato, a compelling wine making and olive oil factory dominates the hilltop. Fattoria Torre A Cona is an 18th century villa whose cellars protected famous works of Michelangelo and Donatello during WWII, including statues of the Medici Chapels and the Duomo of Florence.  Our lodging is located on the grounds of a former factory producing bricks and tile, and features a swimming pool, and an evening of extensive wine tasting, local cheese, and foods. The wine shop, on the premises, offers direct shipping to the U.S. for your wine purchases.


Days 3 u0026amp; 4 – Cortona, Italy  (81km, 980m)

Our ride from Laterina to Cortona is rewarded with lodging within the walled city. Cortona is perhaps best known these days as the setting for the book and movie “Under the Tuscan Sun”. Gorgeous, hillside Cortona has a long history dating back even before its time as an important Etruscan center. Top attractions include the Duomo (Cathedral), the small Museo Diocesano across the piazza with its superb art collection, and the fascinating Museo dell’Accademia Etrusca with its assembly of Etruscan and Roman era items. Cortona is also bursting with splendid churches spanning many periods.   Our stay over day will allow for resting and purusing the museums, art galleries, and maybe going for a ride above the town.


Day 5 – San Quirico D’Orcia, Italy  (47km, 850m or 77km, 1360m)

San Quirico is a quiet contrast to Cortona with approximately 2,500 inhabitants, San Quirico was once a main stop on the road connecting Northern Italy to Rome.  The walled city has four entrances, cyclists will be entering from the east. Horti Leonini, late Renaissance gardens, are a 5 minute walk from the hotel. The entrance is off of the Piazza della Liberta. Created in 1575 during the rebuilding of walls damaged in the war between Siena and Florence, the gardens today also include a modern rose garden and statues created in the 1990’s. Enjoy a gelato from one of several options and stroll through the gardens.


Day 6 – Montalcino, Italy  (85km, 1250m or 101km, 1720m)

Montalcino is the city of Brunello red wines. Our hotel is perched on the hillside offering spectacular views of the valley and the perfect spot to relax with a glass of refreshment. The center of the medieval town is dominated by the imposing Rocca or fortress built in 1361.

Days 7 and 8 – Massa Marritima, Italy  (85km, 1250m or 101km, 1720m) Quiet_road_views.jpg

Our hotel is located on the hilltop, at the corner of the pedestrian only (touristica) streets of the walled city. An outside entrance to the gardens at the back of the hotel will be our bicycle entrance and storage. The gardens and swimming pool will offer a place to relax after a solid day of cycling; climbing, ridge surfing, and more climbing!  Saturday night will be dinner on your own, with many options within a short walk.


Days 9 and 10 – Volterra, Italy  (85km, 1600m or 89km, 1850m)

Volterra’s rich Roman and Etruscan history are waiting for you to enjoy!   Our two night stay will provide time to explore Volterra. Plenty of shopping opportunities here for alabaster stone keepsakes, jewelry, leather or bronze goods. You can rent an AudioGuide at the Tourist Information Office (Ufficio Turistico) in Piazza dei Priori 20 to learn more about the Roman amphitheatre and other Etruscan history.


Day 11 – San Gimignano, Italy  (34km, 500m or 52km, 850m)

Near the edge of town we found a nice hotel managed by Tobias, an avid cyclist, where you and your bike will be welcomed with smiles.  The hotel is only 500 meters from the town of San Gimignano, dinner will be on your own this evening. Enjoy this famous Tuscan town, photographed for its many towers. Towers were added fortification to wealthy homeowners houses during the medieval times.  Dinner on your own in San Gimignano. Enjoy!!

Days 12,13, and 14 – Castellina in Chianti  (36km, 600m or 55km, 750m)

Three nights in this charming town will allow for a day trip into Siena, wine tasting (we recommend Mazzei Winery), or leisurely rides in the Chianti region. Another beautiful hillside location, with pool, and lovely views from the decks of the hotel.

Day 15 – Florence, Italy  (52km, 540m)

Our final day of riding and the return to Firenze. We recommend a stop in Greve in Chianti. Watch for signs to the Ufficio Turistico (Office of Tourism). The piazza or town square offers a variety of shops, gelato, coffee, or lunch options. The Museo del Vino is open from 11:00AM – 4:30PM.


Day 16 — Florence airport departures


Planning DetailsFall_vines.jpg

Arrive into Florence, Italy airport by 24 September. We have hotel space reserved for earlier arrival dates, so let us know your flight itinerary to confirm extra room nights. 

Depart from Florence, Italy airport 9 September . Later departures may be arranged.   



Comfortable family operated Bu0026amp;Bs, inns and hotels well situated to enjoy local culture and flavors.



Group breakfasts and dinners featuring typical local flavors and dishes prepared individually for our enjoyment. Breakfasts provided by our lodging partners. Dinners generally include a variety of choices for each course (starter, first course, main course, dessert); paired with wines, beer and after dinner coffee. Most dinners served from the kitchens of our hotels, others taken in nearby restaurants. 


15 nights, 15 breakfasts, 13 dinners, daily road snacks/picnics, maps and route descriptions, luggage transfers, on-the-road ride guides, van support (sag wagon).


Lunches, 2 dinners, tips u0026amp; gratuities, airfare, museum entries, trams or lifts, trip insurance 


$4500 double occupancy per person 

$5250 single occupancy per person (3 spaces possible)