Top hill towns of Tuscany IN 5 DAYS

Tuscan hill towns and villages boast fantastic views, charming old streets, great museums and plenty of history to tell. They are often surrounded by thick defensive walls and vaunt ancient gates and watch towers. These villages are often rich in art, too.

Day 1: Montecatini Terme – Tuscany

Arrival in the beautiful thermal town of Montecatini Terme, in Tuscany. Accommodation at a 3 star hotel, dinner and evening at leisure.

Tip! Don’t miss a ride to Montecatini Alto, the oldest part of the town, situated on a hill. Enjoy the view and the ride by the historical Funicular.

Day 2: Etruscan villages of San Gimignano and Volterra

San Gimignano thanks to its appearance with high medieval towers, has earned the nickname “Tuscan Manhattan”. It was a natural stop for pilgrims walking to Rome. It can be considered one of the best preserved medieval towns of all Italy. Don’t miss Piazza della Cisterna, then climb the Torre Grossa, the Church of Sant’Agostino with a wonderful 15th-century fresco cycle by Benozzo Gozzoli.

After visiting San Gimignano, we will stop for wine tasking with snacks in one of the local Fattorias.

Volterra has a long Etruscan history and affords interesting sightseeing. Don’t miss the heart of the medieval town, Piazza dei Priori, with the wonderful Palazzo dei Priori, now the city hall, and Palazzo Pretorio, whose tower is traditionally known as the Tower of the Little Pig. Visit the Romanesque cathedral and its baptistery. The Roman amphitheatre also deserve a visit.

Dinner at the hotel.

Day 3: Spellbinding Siena and a hidden gem Montereggioni

Siena is definitely a key attraction during a trip to Tuscany. It is famous for its Palio that take place twice a year, and for its characteristic narrow streets flanked by brick buildings. The historic city is listed as a world heritage site by UNESCO and is filled with beautiful and interesting places to visit: Piazza del Campo, Torre del Mangia, the Cathedral…to mention only a few!

On the way back, we will stop in Monteriggioni – a charming village, where time seems to stand still.

Monteriggioni has a castle that was built for defensive purposes by the Sienesi between 1214 and 1219. It is referenced in Dante Alighieri’s “Divine Comedy”. The roughly circular walls presents 14 towers that can be seen from a distance. Have a walk in the main piazza – Piazza Roma, with its splendid Romanesque church. Stroll along the narrow streets and breath in the Middle Ages. Dinner at the hotel.

Day 4: Under the Tuscan sun…in Cortona!

From the hilltop there are splendid views over the surrounding valley with its cultivated fields and you can also see Lake Trasimeno.

Even though Cortona is quite small, it boasts beautiful churches and museums featuring Etruscan and Renaissance artefacts. You can’t miss Piazza della Repubblica, where the Palazzo Comunale stands, the Diocesan Museum (with the painting of the Annunciation by Beato Angelico) and the MAEC (the Etruscan Academy Museum of the City of Cortona).

ALTERNATIVE: On the way back we may stop at a cosy fattoria for a dinner and wine tasting!

Day 5: Departure

After breakfast, check out and journey home.

Our best offer:
from € 184,00 per person per 4 nights in a double room 
from € 56,00 single room supplement per 4 nights
(max. 5 single rooms)

The price includes:

  • Accommodation at a 3 star hotel (4 nights HB)
  • Wine tasting in the area of San Gimignano
  • Tour assistance during all three days of excursions

The price does not incluse: beverages, transfers, parking fees, city taxes, entrance fees

Price valid for a group of minimum 25 participants.