# Day Trips from Chianti: Siena & the Wine Road | Doorways > Meander the SS222 wine route to Siena, market mornings, hill towns and cellar visits, our favorite day trips from a Chianti villa base. Source: https://villavacations.com/travel-guide/chianti-day-trip-ideas/ Travel Guide · Day Trip Ideas # Day Trip Ideas from Chianti [Day Trip Ideas](https://villavacations.com/category/day-trip-ideas/) By Kit Burns · June 1, 2026 ![Day Trip Ideas from Chianti](https://villavacations.com/wp-content/uploads/2026/06/chianti-day-trip-ideas-body-02.webp) ## Day 1- Exploring South ![skyline-at-sunset-siena-italy-2.jpg](https://villavacations.com/wp-content/uploads/2026/06/chianti-day-trip-ideas-body-01.webp) Meander south from Castellina in [Chianti](https://villavacations.com/destinations/chianti/) to [Siena](https://villavacations.com/destinations/siena/) on the beautiful SS222 wine route. In Siena visit the Cathedral, Baptistery 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 ![piazza-del-duomo-and-san-gimignano-siena-italy-2.jpg](https://villavacations.com/wp-content/uploads/2026/06/chianti-day-trip-ideas-body-02.webp) 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](https://villavacations.com/destinations/chianti/) 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](https://villavacations.com/destinations/florence/), [Tuscany](https://villavacations.com/destinations/tuscany/) ![florence-parade-duomo-2.jpg](https://villavacations.com/wp-content/uploads/2026/06/chianti-day-trip-ideas-body-03.webp) 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, Baptistery, Giotto's Tower and Orsanmichele. Return another day for the rest. ## Day 4-Volterra Basilica di San Francesco, [Assisi](https://villavacations.com/destinations/umbria/), Tuscany ![piazza-del-duomo-and-san-gimignano-siena-italy-2.jpg](https://villavacations.com/wp-content/uploads/2026/06/chianti-day-trip-ideas-body-04.webp) Volterra is one of our favorite hill towns, known for its stark architecture, its altitude, the excavations, the Etruscan museum, the Museo Guarnacci. Enjoy a local specialty, cinghiale (wild boar), for lunch. On the way home stop at famous [San Gimignano](https://villavacations.com/destinations/siena/) 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 ![chianti-daytrip-winery.jpg](https://villavacations.com/wp-content/uploads/2026/06/chianti-day-trip-ideas-body-05.webp) 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](https://villavacations.com/destinations/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 ![Gucci-outlet-The-Mall-Firenze-1240x700.jpg](https://villavacations.com/wp-content/uploads/2026/06/chianti-day-trip-ideas-body-06-1024x578.webp) Pick up your custom shoes in Panzano. Visit the Basilica de San Francesco in Arezzo 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 ![vineyard-chianti-alt-2.jpg](https://villavacations.com/wp-content/uploads/2026/06/chianti-day-trip-ideas-body-07.webp) 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](https://villavacations.com/destinations/cortona/), home to Under the [Tuscan](https://villavacations.com/destinations/tuscany/) 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](https://villavacations.com/destinations/siena/), 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. ## More from our Siena guides - [Where to Stay in Siena: Inside the Walls or a Villa in the Hills](https://villavacations.com/travel-guide/where-to-stay-in-siena/) - [The Best Time to Visit Siena, Month by Month](https://villavacations.com/travel-guide/best-time-to-visit-siena/) - [The Palio di Siena Explained: The Race, the Contrade and How to See It](https://villavacations.com/travel-guide/palio-di-siena/) - [What to Eat in Siena, From Pici to Panforte](https://villavacations.com/travel-guide/what-to-eat-in-siena/) - [Day Trips from Siena: Val d’Orcia, the Crete Senesi and the Towers of San Gimignano](https://villavacations.com/travel-guide/day-trips-from-siena/) - [Wine Country Near Siena: Chianti Classico, Brunello and Vino Nobile](https://villavacations.com/travel-guide/wine-country-near-siena/) - [Siena vs. Florence vs. San Gimignano: How Many Days, and Where to Base Yourself](https://villavacations.com/travel-guide/siena-vs-florence-vs-san-gimignano/) - [Large Villas in Chianti and Siena for 16 or More Guests](https://villavacations.com/travel-guide/large-villas-chianti-siena-16-guests/) - [Siena villas and destination guide](https://villavacations.com/destinations/siena/) Planning a trip to Italy? Add Doorways as a preferred source on Google, so our new guides are more likely to show up when you search. [Add us on Google](https://www.google.com/preferences/source?q=villavacations.com) Stay in ## Hand-selected villas in *Chianti* Chianti ### Villa Amarika 7 Beds·7 Baths·14 Guests Chianti ### Villa Colli 7 Beds·7 Baths·14 Guests Chianti ### Villa Danica 5 Beds·5 Baths·10 Guests [Browse All Villas](https://villavacations.com/villas/?destination=Chianti) About the author ### Kit Burns Kit Burns is a contributing editor at Doorways. A long-time guidebook writer with deep ties across Italy, Kit covers the practical side of a villa week — the restaurants, the day trips, the places worth driving an hour for. He travels with a notebook, a paper map, and very little else. Travel Guide ## More *stories* Day Trip Ideas · October 28, 2026 ### Day Trips from Siena: Val d’Orcia, the Crete Senesi and the Towers of San Gimignano Day Trip Ideas · October 26, 2026 ### The Garfagnana and Serchio Valley: Lucca’s Wild Back Country Day Trip Ideas · June 1, 2026 ### Day Trips from Amalfi Town and the Amalfi Coast --- Doorways Villa Vacations, Italian villa specialists since 1994. Book through a travel advisor: https://villavacations.com/contact-us/