Giada's Guide to Tuscany
The rolling hills of Tuscany are Giada’s favorite place to recharge, and the landscape might be Italy’s most idyllic backdrop for a countryside escape. At the heart of the region is its capital, Florence, considered the cradle of the Renaissance thanks to its rich history as a center of art and architecture. Its rugged countryside is equally breathtaking, with scenic valleys dotted with rustic villas, medieval fortress towns, and sun-drenched vineyards and olive groves that we can thank for some of the best Italian wines and olive oils. In addition to Chianti wine, full-bodied reds such as Montalcino and Montepulciano are produced here, along with rich olive oils known for their gentle bitterness and herbal flavors.
One of Giada’s favorite Tuscan towns, Montalcino, is known for its brunello wine, so drink up! It’s also home to great restaurants and shopping. Southwest of Florence, picturesque San Gimignano is a small, walled medieval town in the midst of the rolling hills of Tuscany. Another medieval city, Siena is one of the region’s more crowded destinations but still retains lots of charm (and if you’re searching for somewhere with a bit of nightlife, this is it). Meanwhile, quaint Pienza, with its urban garden-lined alleys of brick and cobblestone, can be combined as a day trip with Montepulciano, a city on a hill that you can only hike up to or reach by bus (cars need to be parked outside of the city’s walls).
Here is our guide to exploring Tuscany, from the art and culture of Florence to the rugged countryside of our favorite small towns.
Getting Around
In the northern part of the region, Florence and Pisa have the largest international airports serving Tuscany (Amerigo Vespucci Airport in Florence and Galileo Galilei Airport in Pisa). Direct flights to Florence are available from the U.S., and most major carriers fly into Pisa through Europe or the U.K.
Tuscany is a sprawling region with small towns scattered throughout the countryside some are worth exploring for a few days, and others make for a quick day trip. Because it’s such a large area, the best way to get around Tuscany is by car. Rent a car from the airport or train station when you arrive to make your way across the region, or book a private driver to take you from place to place (we like mydaytrip.com for easy door-to-door service). Or if you prefer, you can choose a city like Florence to make your home base and design your itinerary around day trips. If you’re feeling adventurous, zip around the countryside in an Ape (these small three wheeled vehicles are iconic in Italy!).
Florence: Eat
All’Antico Vinaio
Back in the day, Florence was a workers’ town, where cheap, filling food like sandwiches was in high demand. The panini here are still the best in Italy, both for their variety and the speed with which they’re constructed. Get the la Favolosa here, piled with salami and a pecorino cheese spread on freshly baked schiacciata bread (like focaccia, but risen longer for more flavor).
Il Latini
Dinner at Il Latini is always a party - tables are long, banquet style arrangements, so you'll almost definitely be seated with strangers who'll quickly become friends. And while you can order a la carte, it's best to put yourself in the kitchen's hands and go with the set menu. You'll end up with 5-course meal served family style that is crowned by a glorious bistecca Fiorentina that's bigger than the plate it's served on.
Trattoria Cammillo
4 Leoni
Florence: Do
Madova
Leather goods are a Florentine tradition—fitting for a city that specializes in beef! There are many quality glove makers in town, but this 100-year-old institution at the base of the Ponte Vecchio is the best of the best. Let the experts measure your hands to find the perfect fit, and on't leave without trying a pair made from cinghale, wild boar leather, which feels like unbelievably soft suede.
Mercato Centrale
Officina Profumo-Farmaceutica Santa Maria Novella
Uffizi Gallery
Florence: Stay
Portrait Hotel
One of two sister properties that flank the Arno river owned by the Ferragamo family, this hotel is just as stylish as you would expect. Rooms are sleek and minimal, filled with luxurious touches like cashmere blankets and a high quality hair dryer and straightener in the bathroom.
Helvetia & Bristol
Siena: Eat
La Taverna di San Giuseppe
In a rustic, 12th-century building, this beloved taverna serves traditional Tuscan dishes like ribollita, pappa al pomodoro, handmade pici, and cinghiale (wild boar) when it’s available. Be sure to book in advance, as it’s ever-popular with locals and travelers alike.
Osteria Le Logge
For more than 45 years, this osteria just steps from the Piazza del Campo has been serving refined Tuscan fare in a warm, casual room that was once a grocer’s shop. The owners run a winery in Montalcino, so be sure to sample some of their brunello alongside the other lovely Tuscan wines in their cellar—in this case, an ancient Etruscan cavern.
Pizzeria Poppi
This small counter-only pizzeria is famous for ciaccino, a local focaccia that’s baked thin in large rectangular trays and stuffed with mozzarella and prosciutto cotto. Though it looks unassuming from the outside, one bite will have you in gooey, cheesy bliss.
Ristorante Gallo Nero
This warm, romantic restaurant is tucked away on the ground floor of what used to be a 13th century palace and feels like you're eating in a medieval wine cellar. The artfully presented dishes are definitely a step up from traditional Italian spots, and the pastas are wonderful. It can also be a really nice reprieve from the crowds!
Siena: Do
Aloe&Wolf
Fashion lovers come to this boutique for a treasure trove of vintage designer clothing and accessories. This isn’t any ordinary thrift shop! You’ll love the unique, high-fashion finds you’ll end up taking home with you.
Duomo di Siena
Locals know that this cathedral is the grandest in all of Tuscany (yes, even more impressive than Florence!). One look at its dramatic black-and-white striped marble interior modeled on the city’s crest and you’ll agree; it’s a marvel of medieval artistry from floor to ceiling. Be sure to set aside plenty of time to explore every corner of this cathedral complex, or you’ll miss precious details like the altar sculptures by Michelangelo. If heights don’t daunt you, take the guided “Gate of Heaven” tour, which gives a rare bird’s-eye view of the frescoes and stained glass from walkways that are tucked under the roof.
Piazza del Campo
This grand, central public space outside the city government building is one of the most unique in Italy. Its odd shell-like shape paved in red bricks that are divided into pie slices is a symbolic reference to the Noveschi (the Nine), the group of powerful oligarchs who ruled Siena at the height of its influence. The palazzos that line the square were the homes of these important families; by careful agreement, no one building is any taller than the others, signifying that they held power equally.
Via di Città
The town of Siena was masterfully planned from start to finish as a grand display of power and precision. Walk along this main artery that symbolically connects religion and politics (it runs from the government seat in Piazza del Campo to the grand cathedral complex) to wonder at the vision of the medieval leaders who made it happen. In between lie the grand palazzos of many important families, the stone facades of which you can admire as you stroll and shop.
Siena: Stay
Grand Hotel Continental Siena
This opulent hotel in a 16th-century palazzo might just be the most luxurious place to make your home base in Tuscany. With four-poster beds and lush tapestry canopies in most rooms, you’ll feel like a member of the Italian nobility yourself, especially when you sample the daily wine tastings in the underground cellar.
Pienza: Eat
Fredo Gelateria
In the center of town, this shop makes the most delicious artisanal gelato from premium ingredients all sourced by hand from local farms and orchards. Any fruit flavor is not to be missed! Not in the mood for a frozen treat? They also make delicious traditional Tuscan pastries like pane dei santi, a rich bread enjoyed in the fall around All Saints’ Day.
Piccolomini Cafe
This charming cafe in a quaint plaza makes for a great lunch spot with lots of outside seating. The best time to come is for aperitivo hour when you can enjoy an Aperol spritz or negroni and snack on homemade focaccia and cheese. For a traditional meal, order the pici, a thick hand-rolled pasta from Siena that looks like oversized spaghetti.
Podere il Casale
This organic cheese farm is home to an exceptional farm-to-table restaurant that uses fresh ingredients from their garden and the animals on the farm. Take in the stunning views of the Val d’Orcia—a valley with rolling hills that’s been designated a UNESCO World Heritage Site—from the panoramic terrace. If you’d like to make a full day of it, Podere il Casale also offers cooking classes and activities like pizza and pasta making, bread baking, cheese making demos, and truffle hunting.
Pienza: Do
Palazzo Piccolomini
This lavish palace was once the summer home of Pope Pius II. Today, it holds a ground-floor museum that shows how the 15th-century pontiff lived (spoiler alert: very well!), a small wine shop with a great selection of local wines, and a stunning rooftop garden that offers incredible views of the Orcia Valley below.
Officine 904
Visit this family-run fashion shop for unique and trendy bags, purses, wallets, and more made from the high-quality soft leather for which Tuscany is known. Partners in life and business, Paolo Porcu Rodriguez and Silvia Pavanello are the visionary artisans behind the studio and all their timeless design.
Pienza: Stay
Montepulciano: Eat
Agriosteria Tenuta Astrone
This cute farmhouse restaurant south of Montepulciano is known for its Tuscan burgers, which arrive deconstructed with the lettuce, cheese and bread on the side. They cook the meat in terracotta pots, which change color in response to the heat of the flame. It’s a visual way to tell how the meat inside is cooking, an ancient local method of cooking that’s fascinating to watch.
Godimento Di Vino
The name of this restaurant means “Enjoyment of Wine,” and that’s certainly what you’ll do as you browse the extensive cave filled with local vintages. Located in a rustic stone building on a winding, quiet side street, this cozy spot serves classic Tuscan fare for which the knowledgeable staff is always ready to recommend the perfect pairing.
Montepulciano: Do
Avignonesi Winery Tour
Vino nobile de Montepulciano is a sangiovese-based red blend that, along with its cousins chianti and brunello di Montalcino, helped make Tuscan wines the international powerhouse they are today. Though they are primarily made with the same grape, the unique conditions of each small town and the methods used by local winemakers can change the final product dramatically. Montepulciano’s version is medium-bodied but can age well for decades, striking a lovely middle ground for red wine fans. Taste it and other local wines (dessert wine lovers must try their vin santos!) at this gorgeous, welcoming winery.
De’Ricci Cantine Storiche
As a center of wine production since the Etruscan era, it’s no surprise that Montepulciano was built on wine—literally! Below the streets of the town are a network of caverns built into the stone centuries ago to age and store wine at the perfect temperature year-round. Many of the wineries in town offer tours and tastings; this one is the most stunning, with a vaulted ceiling of terracotta bricks reminiscent of a grand cathedral and a labyrinth of ancient tunnels.
Fortezza Medicea
This 13th-century fortress was once a defensive structure for the Medici family as they consolidated their power across the region; today, it serves a much more friendly purpose as the headquarters of the local wine consortium, which manages the production of vino nobile de Montepulciano, among others. Learn about this beloved local wine and taste plenty of samples, then head outside to stroll the manicured, shady gardens that overlook the Val d’Orcia below.
Palazzo Comunale
If you’ve traveled through Florence on your way to Montepulciano, the design of this local town hall might look familiar: It was modeled after the Palazzo Vecchio in the capital city on the order of Cosimo de Medici. Turn left in the building’s courtyard to enter the bell tower, from which you’ll get amazing views of the valley that extends below you. A terrace level is accessible by elevator, but if you can brave the narrow stairs from the terrace up to the top of the belfry, you’ll be able to see all the way to Siena.
Piazza Grande
One of the few truly flat spaces in this extremely hilly town, this central piazza has been the heart of life in Montepulciano since the Middle Ages. It’s bordered by the duomo, town hall, and the palazzos of several formerly prominent families, all of which are breathtaking to see. On one side, you’ll see a stone well topped by a griffon and lion, the coat of arms of the powerful Medici family (if you’re traveling through the region, you’ll spot this symbol in many places!).
Montepulciano: Stay
Monteverdi
About a half-hour drive south of Montepulciano, this hotel nestled in the hills of Tuscany is Giada’s happy place! Monteverdi has a little bit of everything: a great spa to relax in, culinary classes where you can learn how to make pastas with their in-house chefs, an art gallery, and scenic hiking trails. Sign up for an on-property cooking class with chef Giancarla at their Culinary Academy.
Montalcino: Eat
Il Giardino
Run by a husband (the manager) and wife (the chef), this intimate restaurant’s arched interior and neutral tones set the tone for a cozy meal. The pastas and plates here like pistachio-crusted lamb chops and stuffed rabbit are a bit more refined and elegant than traditional Tuscan restaurants, and they also offer an extensive wine list. Order a local rosso di Montalcino or brunello di Montalcino wine with your meal!
La Sosta
This charming wine bar and restaurant in the heart of town is steps from the medieval fortress. Be sure to sit outside on the back terrace for the best panoramic views. In addition to an excellent wine selection, they have an amazing blanched green bean salad with walnuts that's lightly dusted with an anchovy-and-caper dressing—it was so good, Giada went back for it again the next day!
Locanda Demetra
This farm-to-table restaurant and cooking school owned by three siblings has a covered outdoor terrace overlooking the Tuscan hills, making it a great place to unwind and enjoy an Italian lunch at a leisurely pace. They make a delicious brunello jam from their grapes, which are unique to the Montalcino area.
Ristorante Taverna del Grappolo Blu
This cozy restaurant is our pick for a classic Italian meal where you can enjoy Tuscan charcuterie, pasta, and wines. Inside has a rustic ambiance, while outdoors, you can grab a cozy bench for two with a view of the Tuscan countryside.
Porta al Cassero
If you're looking for a quick and casual meal, this osteria offers a menu of salami and cheeses to start and traditional Tuscan dishes like pici with ragu, polenta, wild boar and bean stew, or roast rabbit. Come here for a simple homestyle lunch!
Montalcino: Do
Casanova Di Neri
Visit this winery to learn about the unique wines you can find in Montalcino, from brunello to rosso and toscana. On weekdays, you can take part in a wine tasting experience in their farmhouse. Not only are the folks here generous with their wine pours, the professional staff are generous about sharing their knowledge, too. You'll walk away feeling like an expert about wines of the region.
Farmacia Salvioni 1905
This old (founded in 1905!) but beautiful historic pharmacy sells its own cosmetics line that started in the same laboratory where brunello wine was created. Browse products like serums, creams, perfumes and supplements featuring natural ingredients like grape extract and plant stem cells, then head out the back of the shop for a surprise: a small terrace with a stunning Tuscan view!
Montalcino 564
Owned by a husband-and-wife duo who run several shops around Montalcino, this is an Italian fabric store that also doubles as a wine shop. It’s a great place to buy souvenirs like home accessories, and the owner can make anything you want out of his gorgeous textiles made from linen, hemp and natural cotton. It’s a great place to bring home one-of-a-kind keepsakes like tote bags or towels that you’ll be able to use every day.
Villa i Cipressi
This estate farm started producing honey more than three decades ago, and expanded into grape and olive vineyards to make brunello di Montalcino, rosso di Montalcino and grappa di brunello and extra virgin olive oil. Visit the winery to learn how they make these regional wines, and see the apiary to learn about the honey production process and taste all the types of local honeys they offer!
Montalcino: Stay
Villa Palazzetta
This stunning villa overlooking Montalcino and its valley is elegant and homey all at once. Nestled in the Tuscan hills, the property has its own vineyard and an olive orchard but is less than a 10-minute walk to the historic center of town. You'll want to spend all day by the pool with its incredible views of Val d'Orcia!
San Gimignano: Eat
Gelateria Dondoli
Rightfully famous for its innovative flavors, this gelato shop run by the charismatic Sergio Dondoli is a must-visit in this picturesque town. Sample saffron and pine nuts, grapefruit and sparkling wine, chocolate with cherries and chili, and many more flavors, all made with local raw milk and hand-picked fruits and nuts from across Italy.
Ristorante Il Pino
On a quiet side street near the arch of Porta San Matteo, this lovely family-run restaurant has been around since 1929 and is known for traditional Tuscan dishes prepared with local ingredients. Dine by candlelight in the warm, rustic setting with exposed bricks, medieval arches and original cross-vault ceiling from the 1200s. Beef is their specialty, so be sure to order the carpaccio and bistecca alla fiorentina!
Osteria del Carcere
At this cozy, welcoming wine bar, enjoy casual snacks like Tuscan salumi and cheeses, bruschette, and warming soups, all paired with local wines. Ask the friendly staff for a recommendation—they’ll be sure to pour you something utterly delicious!
San Gimignano: Do
Camminamento delle Mura
San Gimignano is one of the many Tuscan towns surrounded by an ancient fortified wall, a remnant from the turbulent medieval era when warring families fought for control of the region. Recently restored after an earthquake, this walkway atop a section of the town’s walls offers magnificent views of the countryside.
Torre Grossa
In the Middle Ages, wealthy families in San Gimignano each built their own towers to show off their power—at one time, there were 72 towers looming over the small city. Today, just over a dozen remain, but the tallest is this one attached to the local town hall. Climb the 218 steps to the top for a panoramic view of the vineyards and rolling hills surrounding this picturesque town.
Visit a Local Artisan
The main street of San Gimignano is lined with tons of wonderful artisans’ shops, from leather goods to ceramics, carved alabaster from nearby Volterra, and, of course, lots of delicious food and wine to take on your travels. Stroll up the pedestrian walkway and pop in wherever catches your eye—we guarantee you’ll find some memorable souvenirs.
San Gimignano: Stay
Hotel La Cisterna
Set in a 14th-century building in the historic heart of San Gimignano, Hotel La Cisterna overlooks the ancient Piazza della Cisterna. Choose a room with a memorable view of the medieval piazza or the endless Tuscan countryside—you can’t go wrong either way. As a bonus, the hotel’s on-site restaurant, Le Terrazze, is the only eatery in the piazza with a panoramic view. From April through October, they also run a bar on the terrace that opens in the afternoon. It’s one of Giada’s favorite spots for an aperitivo!
Hotel L'Antico Pozzo
This elegant, 18-room boutique hotel is full of charm and tucked away from the crowds touring San Gimignano (fun fact: It’s owned by the same family as Ristorante Il Pino around the corner). Descend the stone staircase into the lobby and continue deeper to discover their underground cellars. The hotel’s medieval structure has been well-preserved and beautifully furnished to offer comfortable, traditional-style guestrooms. Room types here are named after Italian poets; the spacious, high-ceilinged Dante Rooms are our favorite.
Get a taste of the region
Tuscan Sweet Mustard Large
- Discount Price Member
- $18.00
- Regular Price / Regular
- $20.50
- Unit Price
- per
Organic Fagioli Cannellini Beans
- Discount Price Member
- $7.00
- Regular Price / Regular
- $7.50
- Unit Price
- per
Organic Pappardelle Pasta
- Discount Price Member
- $10.00
- Regular Price / Regular
- $11.00
- Unit Price
- per
More from Tuscany
Giada's Guide to Florence
Making Florence your home base? See the rest of Giada's recommendations on where to eat, do and stay in Florence
