Day 1- Exploring South

Meander south from Castellina in Chianti to Siena on the beautiful SS222 wine route. In Siena visit the Cathedral, Bapistry and Museo dell' Opera del Duomo. Follow any alleys to the Piazza del Campo to relax and enjoy the scene as you imagine the spectacle of the Palio that takes place here in July and August. Have Sunday dinner midday, Italian-style, in Siena at one of the restaurants recommended in our Restaurant Guide.

Day 2- Exploring North

The magnificent Duomo di Siena

Continue your explorations of Chianti by moseying north from Castellina-in-Chianti on the same SS222 wine route through Panzano and Greve. Have your feet measured at Fragiani's in Panzano, choose your pelt and style and order your custom shoes to be picked up on Friday. Using your Chianti vineyard map and our recommendations for visits to wineries, stop along the way to taste and buy Chianti Classico wine to enjoy at your villa. Then, if you have time, stray from the SS222 and visit the abbey Badia a Passignano, Radda and Gaiole.

Day 3- Florence

Duomo, Florence, Tuscany

Take the train, or drive and park free at Piazzale Michelangelo. Admire the view from San Miniato and walk down into town. Make reservations in advance to visit the Uffizi. Take in the Duomo, Bapistry, Giotto's Tower and Orsanmichelle. Return another day for the rest.

Day 4-Volterra

Basilica di San Francesco, Assisi, Tuscany

Volterra is one of our favorite hill towns, known for its stark architecture, its altitude, the excavations, the Etruscan museum, the Museo Giarnacci corrige Guarnacci. Enjoy a local specialty, cinghiale (wild boar), for lunch. On the way home stop at famous San Gimignano for the famous skyline (you can climb up one of the towers) and then walk all the way around the fountain in the Piazza della Cisterna to ensure your return. Because San Gimignano has many tourists during the day, you can return at night for dinner or ice cream and a nicer experience.

Day 5 -Pisa & Lucca

Visit the Leaning Tower of Pisa's Campo dei Miracoli, along with the Cathedral. Relax midday at the beach in Forte dei Marmi or Lido di Camaiore and then visit Lucca. Rent bikes at the tourist office to ride around the city walls, or tour some of Tuscany's most impressive villas and gardens in the surrounding hills. In July or August, attend the Puccini Festival in nearby Torre del Lago. If you have kids, focus on the Parco di Pinocchio in Collodi and don't miss the Leonardo Museum in Vinci on your way home.

Day 6- See the Legend of the Cross and do some shopping

Pick up your custom shoes in Panzano. Visit the Basillica de San Francesco in Arrezzo to see Piero della Francesca's Legend of the True Cross. Continue to Montevarchi and San Giovanni Val d'Arno, with designer outlets like Prada, Gucci, and Dolce & Gabbana.

Day 7- Chianti Again

This is the time to explore wineries and hill towns you've missed. Some of our favorites are San Donato in Poggio, Monteriggioni (just north of Siena on the SI-FI superstrada), and Colle Val d'Elsa upper town and also lower town, where two of our favorite restaurants are located.

Day 8- San Galgano

This ruined Cistercian abbey is one of Tuscany's most unusual attractions. Bring a picnic, and stop at the little chapel on the hill to see the Italian Sword in the Stone.

Day 9- Hike the Cinque Terre

Early start today to hike the five villages of the Cinque Terre and on the way home to stop at Carrara to see the quarries where Michelangelo got his pure white marble for David. Perfect activity for kids before going to the Accademia tomorrow.

Day 10- The Accademia in Florence

Back to Florence, this time to visit the Accademia to see Michelangelo's David, as well as the beautiful frescoes by Fra' Angelico at San Marco. Other options include the library (and market) of San Lorenzo, the Synagogue, the Pitti Palace, and the Boboli Gardens.

Day 11- Under the Tuscan Sun

Spend the day in Cortona, home to Under the Tuscan Sun. Park near Piazza Garibaldi, where on a clear day, you can see all the way to Lake Trasimeno. Spend the morning visiting the Etruscan Museum or the churches of San Niccolo and San Domenico. Or follow the mosaic stations of the cross to the church of Santa Margherita. Finish your last minute shopping, and if you have time, stop at the Etruscan ruins and tombs of Camucia.

Day 12- Montalcino

Visit the enoteca in the fortress atop this classic Tuscan hill town to sample the famed Brunello wine, stopping to see the Sant' Antimo Abbey, just down the road. Make reservations ahead of time for dinner at Taverna dei Barbi, with an international reputation for Tuscan country cuisine. Explore Pienza, well known for its pecorino cheese; ask to taste the difference between the young (soft and mild) and aged (sharp) varieties.

Special recommendation - Make dinner reservations at La Fattoria in Tavarnelle Val di Pesa for the Friday night antipasto buffet and dinner. 

Rent a Villa in Lake Como

Make sure that you have a comfortable home to return to after your day trips. Our chianti vacation rentals include a mix of carefully selected luxury villas in Chianti. Contact us to begin planning your Italian villa vacation today.