Tuscany travel can combine hilltop towns, historic city streets, vineyard visits, and time by the Mediterranean. This family itinerary covers a two-week trip with a nine-day stay near Arezzo, followed by stops in San Gimignano, Lucca, and Tellaro. The experience also shows why a flexible schedule matters: long drives, summer heat, crowds, and the appeal of a quiet day at home can all shape a trip.
Planning included research, organizing clothing and art supplies, and building an itinerary. For a group traveling with teenagers, it helped to balance sightseeing with rest days rather than scheduling an excursion every day. The family rented two cars during the first part of the trip, and frequent drives eventually made slower days at the villa especially welcome.
Tuscany Travel: Staying Near Arezzo
Villa Barbazzano
The first nine days were spent at Villa Barbazzano, about 45 minutes south of Florence in Val di Chiani. The villa has nine bedrooms and sleeps up to 20 people, making it suitable for a large family gathering. The group of eight had room to spread out, enjoy the pool and pool house, and take in the gardens and sunsets.
Having a comfortable base made it easier to take unscheduled breaks. Arezzo, the closest larger town, is about 20 minutes away and became a convenient destination for several short visits and meals. When planning a villa stay, consider travel time to nearby towns as well as the comfort of the property; a restful base can be just as valuable as a full sightseeing schedule.
Florence
Florence was explored on a day with intermittent thunderstorms. Ponchos and umbrellas helped the group continue sightseeing, although the weather made the city feel very different from a sunny-day visit. A guide led a walking tour that was planned for four hours and lasted three. For a group with teenagers, a shorter tour of around two hours may be a more comfortable option.
The guide, Chiara from Florence Custom Tours, was described as friendly, patient, and knowledgeable. The group missed entry to the Duomo by a few minutes but still enjoyed seeing the landmark from the city streets and viewing Michelangelo’s David. Ciro & Sons, near the train station, was a convenient stop for pizza before the return journey. Check attraction hours and meeting locations in advance, especially when the day includes a timed tour or train travel.
Montepulciano
Montepulciano was less than an hour’s drive from the villa and offered classic Tuscan scenery along the way, including rolling hills and vineyards. The town’s steep lanes lead up to Piazza Grande, where the group stopped for pizza and gelato before climbing the Montepulciano Tower. Its elevated view across the surrounding landscape was a highlight of the visit.
The tower’s stairs become taller and narrower near the top, so the climb may not suit visitors with limited mobility. After sightseeing, the town’s shops made it a good place to browse for leather bags and hats. Wear comfortable shoes for the hills and allow time to explore without rushing.
Il Borro and Riecine
About 20 minutes from the villa, Il Borro offered a picturesque setting for a relaxed outing and a meal at the resort. The meal was enjoyable but expensive, so checking prices before dining can help with budgeting. The nearby village-like setting also made for a pleasant change of pace after busy sightseeing days.
Riecine, about an hour from the villa, was the first vineyard visited. The winery’s modern production building featured murals by local artist Marco Zedone. The tasting included red wines and a rosé. Vineyard visits can add variety to a Tuscany itinerary, but it is useful to confirm tour and tasting arrangements before setting out.
Piancornello
Piancornello is an organic vineyard that does not offer public tours; the visit was arranged through a friend. The two-hour bus ride on winding roads was difficult for some travelers prone to motion sickness. In return, the group shared a home-cooked meal and saw grapevines described as 50 years old. They also learned about the work involved in grape harvesting, which the vineyard said typically takes place in early October.
Arezzo
Arezzo was visited three times during the stay. Highlights included Giorgio Vasari’s frescoes, the shops along Corso Italia, and meals in Piazza Grande, a medieval square decorated with coats of arms. Parts of the film Life is Beautiful were filmed in the town. Menus did not always offer the fresh salads the group hoped to find, so travelers with specific dietary preferences may want to check menus ahead of time.
From San Gimignano to Lucca
San Gimignano
On the way west toward the coast, the group stopped in San Gimignano, a walled town known for its towers. The center was busy with tour groups, but quieter streets offered a break from the crowds. The town’s towers were built as displays of wealth rather than for military use. A little flexibility when exploring can help visitors find less crowded corners, even on a popular route.
Lucca
Lucca, about two hours from San Gimignano, provided a striking contrast to the hill towns. The city is enclosed by a broad wall that also functions as a park and path for walking and cycling. Visitors should expect to park outside the historic center and continue on foot; the group found a nearby garage and walked with its luggage to an apartment.
Inside the walls, cobblestone streets, colorful buildings, and small shops are easy to explore on foot. The group climbed Torre Guinigi, known for the trees growing at its top, and visited the oval Piazza dell’Anfiteatro several times. Dante e Gentucca was a favorite stop for pizza, while the church opposite the shop hosted nightly Puccini concerts. Lucca is Puccini’s birthplace and also hosts the Lucca Summer Music Festival; Bob Dylan was performing during this visit.
The drive also passed near Carrara, known for its white marble quarries. If that is an area of interest, research possible visits before traveling through, since the group wished they had planned time to stop. In Lucca, the compact historic center makes comfortable walking shoes and a little free time useful additions to the day’s plan.
A Coastal Day Trip to Tellaro
The original plan was to visit Cinque Terre, but high temperatures of 94 degrees Fahrenheit and Saturday crowds led the apartment manager to recommend another destination. Tellaro, about a 40-minute drive from Lucca, became the alternative. The small coastal town was quiet during the visit, although parking took some effort.
From town, a street leads down toward the sea. The group found a shallow access point near a rock quarry, then continued along the path to rocky places for swimming. The rocks were slippery, so careful footing was important. Tellaro offered a memorable Mediterranean swim and a less crowded day by the water. Travelers considering a similar outing should take water shoes or footwear with good grip and check local access conditions.
A Simple Travel Craft: Printed T-Shirts
As a creative project for the trip, shirts were printed using a hand-cut rubber stamp. The rubber was too soft to hold the ink well, so the results were less successful than hoped. For a future project, linoleum was considered a better material for carving a stamp. Test printing on scrap fabric first to check the design and ink before working on finished shirts.
Planning a Tuscany Travel Itinerary
This route brought together countryside stays, historic towns, a vineyard visit, and a coastal stop. The most useful planning lessons were to leave room for rest, account for winding roads and travel time, and check tour locations and opening hours before departure. Tuscany travel can be rewarding without trying to see everything in one trip; a balanced itinerary leaves time to enjoy both planned highlights and unexpected discoveries.
