Italy: Tuscany Explorer

Departures: Italy

Tuscany Explorer

This self-drive trip, which includes some guided tours allows you to discover the great cities and beautiful towns of Tuscany at your own pace. Visit Florence, Vinci, San Gimignano, Volterra, and Siena, explore museums, Etruscan monuments, famous wineries and plenty of sights in between. Finally the road leads to Pienza, where beautiful palaces and cathedrals crown the hilltop and is your base to explore the lovely Val d’Orcia. The rich culture and lovely landscapes of Tuscany will awaken your taste buds and soothe your soul.


We believe that to travel responsibly, a portion of our tour cost should benefit communities in need. For this trip, our donation will go to a non-profit organization we support that is having a very positive impact around the world: DOCTORS WITHOUT BORDERS—a humanitarian-aid organization that provides ongoing emergency medical aid around the world.


Starting at $4190*

For more information and to get started, contact us at How to Book.


May, October 2019

Day 1

Arrive Florence

Arrive Florence according to your flight details. After clearing customs, you’ll be met and transferred to your hotel.

Florence — the capital of Tuscany and a World Heritage Site since 1982 — lays claim to a priceless heritage, but it’s much more than a city filled with majestic Renaissance artworks. It also offers the visitor many museums, gardens, small piazzas, and contemporary art exhibitions to discover.

Day 2


After breakfast, enjoy a guided morning walk that hits the principal sights – Piazza Duomo, Piazza della Signoria, Mercato del Porcellino, San Lorenzo and Ponte Vecchio. You’ll stop to meet a local artisan and learn a few of their secrets. Your guide will offer tips and suggestions for further sightseeing, shopping and restaurants while you are in Florence.

Afternoon at leisure. This evening indulge in a traditional Tuscan meal, prepared for you by a local chef!

Day 3


Visit both the Accademia Gallery, home of Michelangelo’s ‘David’ and the Uffizi Gallery, housing a priceless collection of art pieces mainly from the Renaissance, with front-of-line tickets. Your visits are self-guided, although a guide can be included at additional cost.

If you’re not interested in visiting Florence museums, you may decide to spend a day exploring the city on your own, indulging in a coffee while people-watching, shopping and meeting the locals.

Day 4


Pick up your car rental (not included) and drive to the town of Vinci. On the way you may choose to stop at Montelupo Florentino – a city renowned for its vibrant ceramics. The Ceramics Museum of Montelupo Florentino is a wonderful diversion to take on your way.

Vinci, the birthplace and home of the legendary Leonardo de Vinci, houses the Museo Leonardiano — The Museum of Leonardo de Vinci — as well as the ancestral home of Leonardo de Vinci — the Casa Natale di Leonardo. Stop, stretch your legs, eat a delicious Tuscan lunch and marvel at the genius of Leonardo di Vinci’s creations.

Day 5


Explore charming Colle Val d’Elsa today. Walk through the historic center, visit the Duomo and enjoy the medieval atmosphere. World-renowned for its crystal production, Colle di Val d’Elsa accounts for 95% of Italian crystal glass production. You’ll find several workshops in the town center, where you may find some treasures to take with you.

Spend the afternoon walking through San Gimignano, climbing to the top of Torre Grossa to get a magnificent view of the city. Escape the crowds with a visit to the 14th century Romanesque and Gothic Fonti, built over the original wells dating back to the 9th century.

Day 6


Take the short drive this morning to the lovely walled town of Volterra, with stunning views of the surrounding valleys and vineyards. Its history dates back to the 7th century BC and you’ll find many interesting ruins and structures from the Etruscan, Roman and Medieval periods there. It’s easy to explore by walking and well worth a visit.

Day 7


One your way to Siena this morning, stop for a pre-arranged winery visit, with tastings and lunch at an estate that dates back to 1076. Renowned for its Sangiovese grapes, enjoy the estate, their Chianti Classico and olive oil. Lunch is included.

The great city of Siena had humble beginnings as an Etruscan hill town, like many other small villages and towns of Tuscany. Within the city itself lie many spectacular landmarks such as the Piazza del Campo. Siena offers everything one could expect of an Italian metropolis; wondrous foods, sights, sounds, and a vibrant nightlife. Exploring the city will take time, so enjoy the next several days here sampling everything this ancient city has to offer.

Day 8


Siena, intact for centuries, looks much as it did in the 14th century, and the conservation of its unique, coherent medieval architecture is one of the main reasons to visit this charming city: it was the first municipality in Europe to stop traffic from entering the old city center, back in 1966.

Embark on your morning exploration of Siena with your guide, where you’ll enjoy the breathtaking view of Siena from the top of Torre del Mangia. Appreciate medieval frescoes, the architecture and other art treasures found in the Complex of Santa Maria della Scala as well as other Siena highlights.

Day 9


The history of Chianti has always been deeply linked to its wines, making it the perfect place to sample traditional Tuscan food and wine. The towns here make up the production zone of world-renowned Chianti wine. Sangiovese grapes, at the heart of Chianti Classico, stretch over the hills of this region, dotted with towns and villages whose streets emit the aromas of the nearby wine cellars.

Take the short drive out to a small vineyard, where you’ll enjoy a walk through the estate and wine tasting (included). You may choose to have lunch here (not included) or stop in at another vineyard or olive oil producer to visit in this wonderfully scenic area of Tuscany.

Day 10


Indulge your whims with a day to yourself to explore Siena. Be sure to visit Siena’s 13th century City Hall, which houses the Civic Museum and a series of frescoes known as some of the most important works of 14th century Italy. As you walk through the streets of this old Etruscan city, be sure to sample the cakes and cookies made here, known as the sweetest in Tuscany.

Day 11


Leave Siena behind and head towards Pienza. Along the way, stop at the Abbey of Monte Oliveto Maggiore for a tour of this magnificent Abby and lunch (included).

In the heart of the Val d’Orcia, Pienza is a great town from which to explore this magical corner of Tuscany. Located between the towns of Montepulciano and Montalcino, Pienza is a UNESCO World Heritage city, and a splendid example of 15th century Renaissance architecture. One of its main products is Pecorino cheese, which gets its aromatic flavor from sheep who graze in the scenic Val d’Orcia.

Day 12


The Val d’Orcia is covered in oak forests, olive groves and vineyards that produce Brunello and other fine Tuscan wines extending across the hillsides, nestled in between monuments and villages. The oldest extinct volcano in Italy, Monte Amiata, provides a stunning backdrop for this idyllic valley.

During your time in Pienza, choose to explore the many nearby towns and points of interest of the Val d’Orcia, including Montalcino, San Quirico d’Orcia and San Galgano Abbey, among others. We will provide you with a long list of suggestions for your stay here!

Day 13


A day to discover the sights of Pienza and/or the surrounding countryside.

You may wish to visit The Palazzo Borgia, one of Pienza’s many palaces. Within the walls of this splendid building is the Diocesan Museum which is full to the brim with beautiful examples of local textile work as well as a collection of religious artifacts from the city’s time as a Papal retreat.

Strike out to explore more of the Val D’Orcia, with it’s gorgeous hillsides, agroturismos and charming towns.

Day 14


Say goodbye to Italy and the charming province of Tuscany! Depart Pienza by car for the two and a half hour drive to the airport in Florence. Drop off your rental car and take the shuttle to the airport, and your homeward bound flight.

For pricing and hotel information, contact us at How to Book. The specifics of this itinerary are subject to change based on local conditions at the discretion of Ponte Travels.

• Rates shown are per person, double occupancy. Airfare not included.