Compare Tuscany: Cycle Siena & Chianti by Exodus Travels vs Under the Tuscan Sun: Italian Adventures With Your Family by Road Scholar

Day 1 Start at your hotel in the Orcia Valley

We start in the Orcia Valley, staying in one the local hilltop towns, San Quirico D'Orcia or Pienza. There’ll be a welcome briefing at the hotel, where we gather as a group to go over the trip ahead.

Day 2 Circular ride through classic Tuscan countryside via the wine town of Montepulciano and thermal spa village of Bagno Vignoni

Today we enjoy a circular ride in the Orcia Valley. Taking in Pienza and San Quirico d'Orcia, we cycle to the beautifully situated wine centre of Montepulciano, best known for producing vino nobile. We then head towards the medieval village of Monticchiello and on to the well known thermal bath of Bagno Vignoni, before making our way back to the hotel.

Day 3 Ride through vineyards and the walled town of Murlo to Siena

A classic day's riding, showing Tuscany at its most picturesque. Following back roads, we head out of San Quirico with a first stop at Montalcino. We then descend on the road to Buonconvento and ride back up to Murlo, passing by Bibbiano. From here, we ascend the short but steep Rospatoio Pass and take a lovely road section via Ville di Corsano as we approach the splendid gothic city of Siena. If staying in Pienza (26 August 2023 departure), today's ride is an extra 6mi (10km).

Day 4 Free day in Siena to explore or relax

Siena is one of the best-preserved medieval towns in Italy and home to the grand Piazza del Campo. There is plenty to see in Siena and its sights are best explored on foot as the town is compact but hilly. There are many museums and buildings of interest to visit, such as the impressive duomo (cathedral). Alternatively, you may choose to head out for an unguided ride.

Day 5 Ride via Gaiole and Radda to Castellina in Chianti

From Siena, we head directly into the heart of Chianti. Our picturesque route takes us via some lovely small villages and hamlets, plus spectacular vineyards and castles, such as Castello di Brolio. Here there is the option to taste some of the finest regional wines. We then cycle on to Gaiole for lunch and, after a gelato stop in Radda, follow our final section to Castellina in Chianti, where we stay for two nights.

Day 6 Circular ride through the Chianti hills via towers of San Gimignano and Monteriggioni

From Castellina, we ride through rolling countryside before taking a scenic descent into the lower valley. From Poggibonsi, we head towards the distant towers of San Gimignano, nestled between hills and small hamlets. The Unesco-recognised town, famous for its towers, vernaccia wine and saffron, is one of the most visited and interesting sights in Tuscany. We spend a few hours enjoying the atmosphere, walking by the walls and admiring the high towers. Our return involves a long but beautiful climb before reaching Castellina and a well-deserved gelato.

Day 7 Cycle to Florence via Panzano and Greve in Chianti

Our final ride passes through Panzano towards the market town of Greve in Chianti. This is considered one of the most scenic roads in Tuscany, which links Florence to Siena via the Chianti hills. On arrival in Greve in Chianti, we have time to admire the triangular piazza that hosts the Chianti wine festival before heading towards Strada and Impruneta, known for their terracotta production. In Impruneta, we stop for lunch. We finish by taking a panoramic road towards Florence, cycling all the way to Piazzale Michelangelo. We will arrive in Florence in the early afternoon, giving you time to start exploring this wonderful Renaissance city, including the cathedral and Baptistery of Saint John. Don’t miss the Ponte Vecchio, a medieval stone bridge lined with jewellers, which connects the two banks of the river Arno.

Day 8 End Florence.

The trip comes to an end after breakfast. However, if you’d like a little longer to explore this magnificent city, please speak to your sales representative.

Day 1 In Transit to Program In Flight

Day 2 Arrive Montecatini, Check-in, Orientation, Welcome Dinner Montecatini Terme

Hotel check-in from 2:00 p.m. Walking less than 1 mile.

After checking-in at the hotel and getting your room, take some time to freshen up and relax before our Orientation session. Orientation. The Group Leader will greet everyone and lead introductions. We will review the up-to-date program schedule, discuss roles and responsibilities, logistics, safety guidelines, emergency procedures, and answer questions. We will review COVID-19 protocols and will adhere to local COVID-19 guidelines and requirements throughout the program. This is a Road Scholar Grandparent program. Grandparents are responsible for their grandchildren at all times. If/when separate age group activities are conducted concurrently, program staff will supervise. Minors are never to be left unsupervised. Except breakfast, meals will be plated (each dish served to guests by a waitstaff) from a set menu unless otherwise specified. Water is included with all meals and other beverages including wine, tea and coffee will be available for purchase unless otherwise specified. Transportation will primarily be provided by motorcoach unless noted otherwise. Periods in the schedule designated as “Free time” and “At leisure” offer opportunities to do what you like and make your experience even more meaningful and memorable according to your personal preferences. The Group Leader will be happy to offer suggestions. Program activities, schedules, personnel, and indicated distances or times may change due to local circumstances/conditions. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding. Next, we will set out for a neighborhood walk with our Group Leader to locate ATMs, pharmacies, grocery stores, restaurants, etc. Returning to the hotel, we’ll gather for a Welcome Reception to become acquainted with our Group Leader and fellow Road Scholars.

At leisure. Continue getting to know your fellow Road Scholars, settle in, and get a good night’s rest for the day ahead.

At the hotel restaurant.

Day 3 Italian Class, Montecatini Terme, Funicular to M. Alto Montecatini Terme

Getting on/off a funicular. Walking up to 4 miles throughout the day, extended periods of standing; cobblestones, mostly level urban stone streets/sidewalks, unavoidable steps/stairs.

Impariamo l’italiano! We will gather in the meeting space for a general introduction to Italian. We’ll learn how to greet people, order a coffee, ask directions, and more from our Group Leaders. We’ll then walk across the street for an expert-led field trip to the Terme di Tettuccio complex, the center of Montecatini Terme. These thermal springs have been popular since Roman times and gained even more popularity during the 15th century when Medici Grand Dukes restored the buildings and grounds.

Next, we’ll set out on an expert-led walking field trip through Montecatini Terme to learn more about this popular Tuscan resort town. After some time for independent exploration, we’ll take the funicular up to the hillside town of Montecatini Alto.

We will take the funicular back down into Montecatini Terme. Returning to the hotel, the remainder of the evening is at leisure.

At the hotel.

At a restaurant in Montecatini Terme.

At a restaurant in Montecatini Alto.

Day 4 Welcome to Tuscany Lecture, Train to Pisa, Leaning Tower Montecatini Terme

Getting in/out of mini-van; on/off a train; riding about 35 miles, approximately 1.25 hours riding time, Walking up to 5 miles throughout the day, extended periods of standing; cobblestones, mostly level urban stone streets/sidewalks, unavoidable steps/stairs. No elevator at Leaning Tower; 269 steps to top.

In the hotel meeting room, we’ll be joined by a local expert for a lecture about the region of Tuscany. We’ll then board a minivan and ride to a pizzeria near the train station.

We will walk to the nearby Montecatini Terme station and board a train to Pisa. Upon arrival, it’s a short walk to the Piazza dei Miracoli, also known as Piazza del Duomo, where we will meet a local expert who will lead our field trip to explore the Duomo and baptistery. The lacy white marble tiers of the buildings contrast with the wide green lawns, unusual for a city cathedral. Until the port of Pisa silted up, the city was a strong maritime republic along with Genoa, Amalfi, and Venice. The city’s wealth is demonstrated by the civic and religious pride of its inhabitants who funded such a grandiose construction — that began to lean shortly after it was constructed in the 12th century! For those with energy and stamina, we’ll climb 269 steps to the top of the Leaning Tower of Pisa. We’ll return to Montecatini Terme by train after our field trip.

At leisure.

At the hotel.

At a pizzeria near the train station in Montecatini Terme.

This meal has been excluded from the program cost and is on your own to enjoy what you like in Montecatini Terme. Please refer to the list of restaurants in the program materials. The Group Leader will be happy to offer suggestions.

Day 5 Vinci Field Trip, Museo Leonardiano, Agriturismo Montecatini Terme

Getting in/out of vans; driving about 35 miles throughout the day, approximately 1.5 hours riding time. Walking up to 5 miles throughout the day, extended periods of standing; dirt pathways, cobblestones, mostly level urban stone streets and sidewalks, unavoidable steps/stairs.

We will set out on a field trip to Vinci, birthplace of Leonardo da Vinci, the incomparable Renaissance artist, architect, engineer, mathematician, and scientist. We will begin at the museum where there are models of Leonardo’s inventions based on his drawings, then walk about 1.25 miles on the “strada verde” — green route — an ancient path of olive groves lining the road to reach Vinci. We will then enjoy an expert-led visit to the house where he was born in Anchiano.

Next, we’ll ride a few miles west of Vinci to an agriturismo, where we’ll explore the farm and vineyards. The host will explain the production of extra virgin olive oil and wine and will also lead a cooking demonstration for an illustrated presentation about rustic cooking in Tuscany. We will assist in making the meal.

Riding back the hotel in Montecatini Terme, the remainder of the evening is at leisure.

At the hotel.

At a restaurant in Vinci.

At the agriturismo.

Day 6 Florence Full Day Field Trip, Museo Galileo, Palazzo Vecchio Montecatini Terme

Getting on/off a shuttle bus, on/off a train; riding about 60 miles throughout the day, approximately 2 hours on the train. Walking up to 6 miles throughout the day, extended periods of standing; cobblestones and mostly level urban stone streets/sidewalks, unavoidable steps/stairs. Elevator available at Museo Galileo.

We will take a shuttle from the hotel to the station and catch a train to Florence for the day. Science aficionados in particular will enjoy a field trip to the Museo Galileo where a docent will our explorations. We’ll see centuries-old astrolabes, globes, and scientific instruments. A highlight of the collection is the telescope Galileo Galilei used to observe the heavens. Detailed story boards describe the objects’ stories and how they work.

At two gelaterie in the historic center, we will taste one of Italy's most famous desserts. Gelato is similar to American-style ice cream, but milk is used instead of cream and the final product has a smoother texture. After a couple of robust samples en route to our cooking school, a local artisan will show us how gelato is made using seasonal flavors and local ingredients. We will have some time for independent exploration, then walk back to Santa Maria Novella station for the train ride back to Montecatini Terme.

Returning to the hotel, the remainder of the evening is at leisure.

At the hotel.

At a restaurant in the Piazza della Signoria.

On your own to enjoy what you like.

Day 7 Market Day, Train to Pistoia, Underground Pistoia, Free Time Montecatini Terme

Getting on/off a shuttle bus, on/off a train; riding about 20 miles throughout the day, approximately 2 hours on the train. Walking up to 5 miles throughout the day, extended periods of standing; cobblestones and mostly level urban stone streets/sidewalks. Unavoidable steps/stairs.

In Montecatini Terme, Thursday is Market Day! We will walk with our Group Leader to the local market to see vendors from all around the area setting up their carts along the streets with leather goods, pottery, scarves, souvenirs, etc. Stalls also display and sell fresh cuts of meat, salumi, cheeses, breads, and other delectable foods. From the market, we will walk to the station, board a train, and ride to the nearby town of Pistoia. Upon arrival, we will walk to the entrance of Pistoia Underground, where we’ll learn from a local historian about medicine, city planning, architecture, and daily life during the Middle Ages. At the Museo dello Spedale del Ceppo, we will see and learn about building’s role as a hospital from 1277 until 2013. We will also see the fascinating late-18th-century anatomical theater.

We will take the train back from Pistoia to Montecatini, where the remainder of the afternoon is free. Take this opportunity for personal independent exploration to see and do what interests you most. The Group Leader will be happy to offer suggestions.

At leisure.

At the hotel.

At a restaurant in Pistoia.

On your own to enjoy what you like in Montecatini Terme.

Day 8 Lucca Full Day Field Trip, Biking on the Walls, Free Time Montecatini Terme

Getting on/off a train; riding about 40 miles throughout the day, approximately 1 hour on the train. Walking up to 5 miles throughout the day, extended periods of standing; cobblestones, mostly level urban stone streets/sidewalks; unavoidable steps/stairs without handrails. Biking about 4 miles; vehicle-free, paved pathway.

We’ll catch a morning train to the town of Lucca, where we will meet a local expert at the station who will lead us on a pleasant walking field trip along a portion of the surrounding defensive walls. Along the way, we’ll learn how the walls were built 500 years ago to defend the city from invaders and how they now serve a peaceful purpose as a favorite walking path for walkers and recreational bike riders. The high walls provide a wonderful panorama of the city.

We will regroup at an announced time and place, then bike atop the 16-foot medieval walls to get another perspective of this unique town. From the time Lucca was a Roman colony, a protective wall fortified the city within from invaders. With urban expansion, the original walls were extended in the 17th century. Today, the 2.6 miles of the wall that encircle Lucca have been turned into a wide tree-lined path — the favorite promenade of local residents of all ages. We’ll return to the station in Lucca to catch a train back to Montecatini where a shuttle will be waiting to take us back to the hotel. The remainder of the afternoon will be free for independent exploration to see and do what interests each of us most.

At leisure. Prepare for check-out and departure in the morning.

At the hotel.

On your own to enjoy what you like in Lucca.

At a local restaurant. Share favorite experiences with new Road Scholar friends during our farewell dinner.

Day 9 Program Concludes, In Transit From Program In Flight

Hotel check-out 11:00 a.m. See your program’s “Getting There” information regarding transfers.

If you are returning home, safe travels. If you are staying on independently, have a wonderful time. If you are transferring to another Road Scholar program, detailed instructions are included in your Information Packet for that program. We hope you enjoy Road Scholar learning adventures and look forward to having you on rewarding programs in the future. Don’t forget to join our Facebook page and follow us on Instagram. Best wishes for all your journeys!

At the hotel depending on departure times; for those with early departures, the hotel will prepare a bagged breakfast. This concludes our program.