Regional Tours
Medieval Tuscany
There are many Medieval cities and towns and over 150 medieval Castles in the Tuscan area. Our private program begins in Siena, which has managed to preserve its medieval character completely. The medieval festival of the Palio is still held twice yearly by its very decidated citizens.You will visit San Gimignano the hill top town of towers is one of the most charming and picturesque of all the Tuscan hill towns. The town once had 70 towers which were symbols of wealth in the medieval time. Only 14 remian today. The program includes 2 famous wine areas Montepulicano and Chianti where you can see the importance of wine in the history of the region and of course taste some great wines. Lucca an extraorinary example of a medieval walled city will also be visitied.The program The tour will end in Florence, centre of art and culture.
Highlights
Cities Visited:(Siena, Montepulciano, San Gimignano, Chianti, Florence, Lucca)

1 . 2 . 3 . 4 . 5 . 6 . 7 . 8 . 9 . 10 . 11 . 12 . 13 . 14 . 15 . 16 . 17 . 18 . 19 . 20 . 21 . 22 . 23 . 24 . 25 .
Day 1 - Arrival in Siena
Upon arrival in Siena check into your hotel and enjoy the rest of the day at leisure.Transfers from your point of arrival can be arranged.
Day 2 - Siena and Montepulciano
This morning meet your local English speaking guide for a walking tour of Siena. The walk will not be too physically challenging, and will offer a new and entertaining way to become familiar with the extraordinary beauty of this medieval town. Your route will take you away from the ordinary tourist routes, as your guide illustrates Siena's eventful past through tales of bankers, pilgrims, artists and Saints.In the afternoon meet your private driver for your excursion to Montepulciano, the ancient fortified town, famous for its antique cafes that, in a not too distant past, were the meeting place of many artists from all over the world. You will have a chance to stroll through the picturesque town. You will then head for the Gattavechi winery where you will taste the town's famous Nobile wine, a mellow-flavored red with a mildly floral aroma that features a distinctive iridescent orange tone. Return with your driver to Siena for the night.
Day 3 - San Gimignano
Morning at leisure to explore Siena on your own.This afternoon depart with your private driver for San Gimignano, one of the most charming and picturesque of all the Tuscan medieval hill towns. Here, together with a local guide, you will discover this town of towers. At one time there were more than 70 towers, built as symbols of wealth and as a security precaution by the town's prosperous merchants, but only 14 remain today. Walk through the wonderfully preserved town square at the Piazza della Cisterna and visit the 13th century town hall - the Palazzo del Popolo. There are good views from the Rocca Citadel and the entire town is an excellent place to stroll and soak up the atmosphere.
Day 4 - Chianti - Florence
Today after checking out of your hotel meet your private driver for a morning of sightseeing in the Chianti region before arriving in Florence. Chianti is considered one of the oldest wine regions in the world, as evidenced by the medieval castles and ancient towns that line the hillsides. Chianti dates back to the days of the Etruscans. The name is most likely taken from the noble family name of the Clantes. In the 13th century the "Lega del Chianti" was created to unite the three most important areas, Castellina, Radda and Gaiole. The black rooster became the symbol of the Lega del Chianti.You will stop in the medieval town of Greve, the unofficial capital of the Chianti Region. It came to prominence in the 13th and 14th centuries as a major trading center. The town square(which is more of a triangle) is filled with dozens of wine and gift shops and cafes. It is the host of the Chianti wine festival each September. Your tour will include a visit to a Chianti winery and a wine tasting.Continue to your accommodations in Florence.
Day 5 - Classical Florence Tour
Your private guide will meet you at your hotel for your private walking tour of the city. Florence's rich past as the cultural centre of the Italian Renaissance can still be seen today in the wealth of art gathered here, and in the preservation of its splendid architecture. The tour includes visits of the Duomo and the Baptistry, the Piazza della Signoria, Ponte Vecchio, and the famous Accademia Gallery. Balance of day at your leisure. Optional Uffizi gallery reservations or guided tours available.
Day 6 - Lucca
This morning meet your driver for your half day excursion to Lucca, one of the Italy's finest mediaeval treasures. The centre is relatively unspoiled and is sprinkled with palazzi, towers and almost countless splendid churches. You will meet your local guide for your tour of this wonderful town.Return to Florence in the afternoon.
Day 7 - Departure
After checking out of your hotel, depart for your onward travel. Transfers can be arranged for your next point or the airport or rail station.
Accommodations
Siena Hotel Garden (or similar)
Florence Grand Hotel Cavour (or similar)
Sightseeing
Private half day walking tour of Siena with local guide
Private half day excursion to Montepulciano with winery visit and wine tasting
Private half day excursions to San Gimignano including local guide
Private excursion to Chianti with tour of Greve and local Chianti winery and wine tasting
Private 4 hour walking tour of Florence, including entrance to the Accademia and Santa Croce church
Private half day excursion to Lucca including local guide
Transfers
Private transfer from city to city as per itinerary with English speaking drivers
Meals
Breakfast at hotels daily
Wine tasting in Montepulciano and Chianti
Services
Assistance from our Road to Italy office in Rome and local representative offices throughout Italy
Local emergency contact number daily
Does not include
Airfare
Travel Insurance (highly recommended) Link to Insurance page
Tips and gratuities to drivers and local guides
Alternative Hotels available to suit your budget
Siena - Case al Vento

Casa al Vento is the essence of Chianti : flavour and wellness. Borgo Casa al Vento is the fruit of an everlasting love, and of ....
MORE
Alternative Hotels available to suit your budget
| Villa Medici(5L) | Castello del Nero(5L) |
| Savoy - Florence(5L) | Santa Croce Relais(5L) |
| Plaza Lucchesi(4S) | Pierre(4) |
| Degli Orafi(4) | Berchielli(4) |
| Botticelli(3) |
Florence - Grand Hotel Cavour

The Grand Hotel Cavour is to be found in the historical heart of Florence, very near to the house where Dante Alighieri was born. ....
MORE
Average land cost for this program
Per person based on number of people travelling together.
Based on 2 people
Euro 2030 per person
Based on 4 people
Euro 1430 per person
Based on 6 people
Euro 1210 per person
This program can be priced for any number of people.Cost may vary depending on dates chosen & ANY weekend, holiday and trade fair date surcharges.
For a quote on your dates & number in your party please contact us.
1) Consult with our tour designers
Contact our office by phone or e-mail and speak to one of our tour designers who will answer any question you have about our suggested tour. They will listen attentively to your ideas and plans and suggest changes to personalize the tour based on your interests and budget.
Tel: 416 964 7600
Toll: 1-800-848-8163
reservations@roadtoitaly.com
2) We send you a Proposal
Shortly after your initial contact with our tour designers, you will receive a draft proposal based on your earlier discussions, normally within 2 business days. This proposal is a no obligation draft for your review and comments. Any additions or modifications will be implemented and a new proposal will be forwarded to you for approval.
3) You like what you see!
Upon meeting your requirements and expectations, you will be requested to send a deposit in the amount of 25% of total. Final Payment is due 45 days prior to scheduled departure date.
4) Buon viaggio!
Approximately, 2 weeks prior to departure you will receive a personalized and detailed day by day itinerary booklet and the necessary vouchers for the services to be provided, along with a general information section on the various regions of Italy.
The booklet and vouchers will include all the important information; addresses, phone & mobile numbers for all your service providers, hotels as well as the phone number of our office in Rome.
Take advantage of the experience of our tour designers
call for a no obligation, personal consultation to create a worry free Italy vacation of your dream. If you do not find what you are looking for on our list, we can make further arrangements.




