Siena Travelers Recommend

Discover one of Tuscany’s best preserved medieval towns in the historic city center of Siena, a UNESCO World Heritage Site. Then, pair those urban piazzas with scenic countryside as you explore the surrounding wine country of Chianti and Val d’Orcia. Here are your best options for spending two days in Siena.

Day 1: Siena, Inside and Out

**Morning:**Begin your day by getting to know the Siena Cathedral (Duomo di Siena) from top to bottom. Beat the crowds by booking skip-the-line tickets so you don’t have to wait to enter the complex and can take your time exploring the Gothic church, crypt, baptistry, museum, and Piccolomini Library. 

**Afternoon:**From Siena’s soaring cathedral, move on to its medieval historic center, centered around the Piazza del Campo. Join a private walking tour to take in all the town highlights in just a few hours, from the imposing Palazzo Pubblico and Torre del Mangia to the cobbled lanes lined with shops.

**Night:**After a day of art and architecture, it’s time to unwind with an evening of food and wine. An informal cooking class or wine tasting workshop offers a hands-on way to learn about—and sample—Tuscany’s regional cuisine and cap off your first day in Siena.

Day 2: Wine, Crafts, and Views

**Morning:**You’ve seen the sights in town, now head for the hills. Join a wine-tasting day trip to Montalcino or San Gimignano, or travel by Vespa scooter or vintage Fiat 500 to the wineries just outside Siena. Outdoor enthusiasts can join a hiking or e-bike wine tour with tastings and lunch.

**Afternoon:**Siena is famous for its prestigious wine, traditional crafts, and fairytale scenery. You’ve crossed wine off the list, so devote the afternoon to learning the history of majolica production with a ceramics workshop, or join a guided photography tour to capture choice shots of the town and its views.

**Night:**Make your final evening memorable by watching the sun set over the medieval old town and rolling countryside beyond. Head to the panoramic Piazza del Mercato with a night tour, or climb to the top of the Torre del Mangia for sweeping views across the Sienese hills.

Siena is more than just a postcard-perfect medieval hilltown. The UNESCO-listed gem is also the ideal base for exploring Chianti, the Val d’Orcia, and the Crete Senesi—a quintessential Tuscan landscapes dotted with tiny villages and rolling vineyards. Here are a few ways to take in Siena and the surrounding countryside in three days.

Day 1: Explore the Town

Delve into the rich culture and history of this time-capsule town by devoting the day to exploring Siena’s delights, large and small. Begin your visit with skip-the-line access to the soaring Gothic Siena Duomo. Early morning tickets leave you time to linger in the magnificent church and savor works by Donatello, Michelangelo, and Bernini (and help you avoid the tour-bus crowds that flock to the complex later in the day).

Afterwards, get to know the medieval center of the city with a walking or Segway tour that touches on its architectural treasures, such as the Piazza del Campo, Palazzo Pubblico, Mangia Tower (Torre del Mangia), and Basilica of San Domenico. Some tours also provide insight into the town’s famous Palio festival with a stroll through the contrade districts, and most pause in the Piazza del Mercato for photo ops from the scenic overlook and a chance to explore the quiet artisan-lined back streets.

Day 2: Outside the Walls

Located just outside Siena’s imposing medieval city walls, the undulating Crete Senesi region offers some of the most striking views in Tuscany. Admire this landscape from the air on a hot-air balloon flight or from the ground with a guided hike through the hills. Foodies can combine countryside and cuisine by joining a truffle hunt or a cooking class, and wine lovers can visit the local wineries on a tuk-tuk, all-terrain vehicle, or e-bike winery tour.

True oenophiles may want to head a bit further afield to sample prestigious Chianti or Brunello di Montalcino wines where they are produced. Opt for a day trip that provides transportation, and you can imbibe with peace of mind. Most wine-tasting tours include stops at a winery or two for tastings as well as free time in the scenic hill towns like Radda, Castellina, or Montalcino and an informal Tuscan lunch.

Day 3: Adventures Across the Border

After exploring the city and its surroundings, take advantage of Siena’s strategic location in the center of Tuscany, and take a day trip to the furthest reaches of the region—or even across the border into Umbria, Liguria, or Emilia-Romagna. Unforgettable Tuscan destinations include the hill towns of San Gimignano, Volterra, and Montepulciano and the scenic streets of Pienza.

You can also make a break for the Ligurian coast with a guided tour of the fishing villages of Porto Venere and the Cinque Terre and or double-down on art and culture by taking in the frescoed museums and churches of Cortona and Assisi, located on the border between Tuscany and Umbria. Alternatively, you can rev your engines with a guided tour of the Ferrari Museum near Modena and enjoy tastings of local balsamic vinegar and Parmigiano-Reggiano cheese. Then head back to Siena for one last night enjoying the city’s enotecas and wine bars.

Situated in the heart of Tuscany, Siena is just a stone’s throw from several of Italy’s most celebrated wine-producing regions. Wine lovers who make their base here will have plenty of chances to learn about—and taste—sought-after labels and rare vintages. Here’s what you need to know about wine tasting in Siena.

Must-Try Varietals

Wine lovers in this part of Italy can choose from among a number of famous wine-producing regions. North of town, between Siena and Florence, is the famous wine region of Chianti. Chianti is well known for its production of medium-bodied Chianti Classico reds, which are made using at least 80% sangiovese grapes, with the rest made of up blends that may include canaiolo, colorino, cabernet sauvignon, syrah, and merlot.

South of Siena lies Montalcino, where Italy’s famous Brunello di Montalcino wine is made using 100% sangiovese grapes. Also south of Siena is Montepulciano, whose Vino Nobile di Montepulciano red is again made mostly of sangiovese, with small amounts of other varietals such as canaiolo and mammolo blended in. White-wine lovers may want to make the journey northwest to the hill town of San Gimignano to try Vernaccia di San Gimignano, made using the white vernaccia grape.

Must-Do Experiences

• See medieval castles such as Castello Monteriggioni and Castello Di Meleto during a wine tour of Chianti.

• Hike to a winery on the vineyard-surrounded Via Francigena ancient pilgrimage route.

• Learn about the production of Brunello di Montalcino and Chianti wines during winery tours.

• Train your palate during a guided wine-tasting workshop.

• Drive a vintage Italian car through the Tuscan countryside before stopping at a local winery for a multicourse meal accompanied by Tuscan wines.

With one of the best preserved medieval cityscapes in Tuscany, Siena’s historic center boasts lively piazzas, soaring Gothic churches, and picturesque cobbled alleys. It’s also the backdrop to the raucous Palio festival and horse race held here each summer. Here’s how to discover this captivating city’s main highlights in just one day.

Morning: Explore the Historic Center

Consider the old town of Siena as an open-air museum centered around the Piazza del Campo and Siena Cathedral (Duomo di Siena), a Gothic masterpiece and one of Siena’s most impressive sights. The historic center, a UNESCO World Heritage Site, is compact and easily visited in a few hours. Put the city’s important urban landmarks, such as the Palazzo Pubblico and Torre del Mangia, into context by joining a small-group or private walking, bike, or Segway tour. Many tours offer a skip-the-line entrance to the Duomo to maximize your time. And, some guided tours include a stop at the Contrada Museum to learn about Siena’s famed Palio horse race, as well as a gelato break.

Afternoon: Taste the Flavors of Tuscany

Set deep in the Tuscan hills, Siena is the perfect spot to discover this region’s traditional cuisine. Spend your afternoon taking a food tour in the city center that samples some of the area’s best cheeses and salami, local truffles, and the city’s famed panforte and ricciarelli sweets. Oenophiles can opt for a wine tour to learn about the prestigious varietals produced in the vineyards of nearby Chianti, and those who want a more hands-on experience can join an informal cooking class to learn how to prepare Tuscan classics.

Night: Head for the Hills

The beauty of Siena’s historic center is matched by that of the surrounding rolling landscape, perhaps most striking at dusk. As the setting sun casts a golden light over the countryside, strike out for a scenic driving tour through the vineyard-covered hills of Chianti, with stops for wine tastings and dinner at a tiny hilltop village. Alternatively, saddle up and explore the environs on horseback, an option if traveling with older kids and an unforgettable way to top off your day of culture and cuisine in Siena.