Expertly curated by Jordie via experience, extensive research, and inside tips from her Tuscan wedding planner—here is a guide to towns/regions in Tuscany worth the visit.
Jordie and Andrew will be exploring Tuscany and the Tuscan Archipelago following the wedding— please feel free to reach out for more insider tips or to honeymoon-crash.
ABOUT: Siena is a popular medieval city with a UNESCO-listed historic center (Piazza del Campo) and one of the most iconic cathedrals in the world. The tower, Torre del Mangia, serves as a gathering place and venue for the famous Palio horse race. The city's Gothic cathedral, Duomo di Siena, is adorned with intricate marble facades and is a testament to Siena's medieval architecture and religious devotion.
FAMOUS FOR: Palio horse race
DO/ SEE/ EAT:
La Taverna di San Giuseppe: Rustic Tuscan cuisine and warm hospitality.
Osteria da Divo: Regional dishes in an incredible, cave-like atmosphere
ABOUT: Charming hilltop town known for its rich medieval history. Its unique location offers stunning views over the Val di Chiana and towards Lake Trasimeno. The town is characterized by narrow, winding streets, historic buildings, and a vibrant cultural scene.
FAMOUS FOR: Frances Mayes's Under the Tuscan Sun is set in Cortona
DO/ SEE/ EAT:
There are many Piazzas (or town squares) to enjoy an espresso/people watch. Piazza Garibaldi, has a sweeping panorama of the Val di Chiana and Lake Trasimeno. Piazza della Repubblica is the main square dominated by Palazzo Comunale (Town Hall) with its striking clock tower in the photo!
Cortona Bistro: A casual charming bistro offering a blend of traditional and contemporary Tuscan dishes.
ABOUT: Arezzo is a vibrant city in the southeastern part of Tuscany. Less popular than its siblings like Siena and Pisa, this regional capital dates from Etruscan times, set on hilltop overlooking the Arno river plain. The focal point is the town square (Piazza Grande) which is lined with restaurants and shops and hosts a huge antiques market.
FAMOUS FOR: It's antiques market (fist Sunday of the month)
DO/ SEE/ EAT:
Take a stroll along Corso Italia for shopping and great coffee shops.
Antica Osteria l'Agania: A family-run restaurant serving classic Tuscan cuisine. It's known for its warm hospitality and rustic setting.
ABOUT: Pienza is a tiny Renaissance village in southern Tuscany with sweeping panoramic views of Val d'Orcia. In the historic center, you'll find the stunning Piazza Pio II and the Duomo. Corso Rossellino is the main street of Pienza, lined with charming shops, cafes, and restaurants. Explore the surrounding Val d'Orcia, and take in the cypress trees and picturesque landscapes.
FAMOUS FOR: Pecorino cheese
DO/ SEE/ EAT:
Sette Di Vino: Old-fashioned osteria with tables on a tranquil square, for regional, homestyle Italian dishes.
Trattoria da Fiorella: Tuscan antipasti, handmade pasta & Florentine steak at a charming trattoria with a leafy courtyard.
Buongusto Gelateria: Gelato how its supposed to be 🤌
Bar Il Casello: Enjoy a glass of wine and the most stunning views in all of Tuscany.
ABOUT: Montalcino, just west of Pienza, is a beautiful village immersed in Val d'Orcia, renowned all over the world for the production of its famous Brunello red wine.
FAMOUS FOR: Brunello red wine.
DO/ SEE/ EAT:
Fortezza di Montalcino: A 14th-century fortress offering panoramic views and wine tastings.
Ristorante Boccon DiVino: A family-run restaurant with a focus on traditional Tuscan dishes and an extensive wine list. Gorgeous views of the Val d'Orcia
ABOUT: Nestled in the heart of the Chianti wine region, Greve in Chianti is a quaint town known for its picturesque piazzas, vibrant local markets, and, of course, its world-famous Chianti Classico wines. The town serves as a perfect hub for exploring the surrounding vineyards and olive groves.
FAMOUS FOR: Chianti Classico wine.
DO/ SEE/ EAT:
SO many vineyards nearby to explore + visit for a tasting.
I'Desìo: Think "family dinner on a Sunday". Red tablecloths, traditional Italian food, gorgeous views of the Chianti region.
ABOUT: Gaiole in Chianti is a picturesque village nestled in the heart of the Chianti wine region. Gaiole is smaller and quieter compared to Greve. It has a more laid-back, rural feel, making it ideal for travelers looking for a peaceful, authentic Tuscan experience.
FAMOUS FOR: Chianti Classico wine.
DO/ SEE/ EAT:
SO many vineyards nearby to explore + visit for a tasting.
Pro tip: Many of these family-run vineyards are set up as BnBs and are a perfect home-base for exploring Tuscany.
ABOUT: San Gimignano, often referred to as the "Medieval Manhattan" for its skyline of towers, is one of Tuscany's most iconic towns. Its well-preserved medieval architecture and rich history make it a UNESCO World Heritage site. Note that it is quite popular and can be busy in the summer months.
FAMOUS FOR: The iconic medieval towers
DO/ SEE/ EAT:
Gelateria Dondoli: award-winning gelato from one of Italy’s most famous gelaterias
ABOUT: Pitigliano is a medieval town with Etruscan heritage, found in the Maremma region at the southern tip of Tuscany in central Italy.
FAMOUS FOR: Nicknamed “Piccola Gerusalemme” (Little Jerusalem), thanks to its historical Jewish community dating back to the 1400s.
DO/ SEE/ EAT:
Get lost in Pitigliano’s alleys and side streets and shop for local goods, especially the Via Roma, Via Vignoli and Via Zuccarelli.
La Casa di Gea Pizzeria: for some Suppli or Pizza to go.
ABOUT: Montepulciano is a charming medieval hilltop town renowned for its Vino Nobile, one of Italy's finest wines.
FAMOUS FOR: Vino Nobile red wine
DO/ SEE/ EAT:
Palazzo Comunale: Climb the tower for panoramic views over the Val d’Orcia.
La Schiaccia dell'Opio: for sandwiches. (Think: a local All'Antico Vinaio)
Hit up one of the many wine bars (like La Bottega del Vino) for wine and a spuntino.
ABOUT: Colle Val d’Elsa, often referred to as the “City of Crystal,” is a charming town nestled in the heart of Tuscany and is not a popular tourist destination making it quiet most of the year.
FAMOUS FOR: Production of crystal glassware.
DO/ SEE/ EAT:
Sentierelsa Trail: a beautiful hiking trail that runs along the River Elsa and leads you to the Diborrato Waterfall.
more suggestions including vineyard and hotel reccomendations to come