Rolling hills covered in vineyards and olive groves, medieval towns that transport you to another era, a stunning Mediterranean coastline, and mouthwatering cuisine made with fresh local ingredients—this is Tuscany in a nutshell. The heart of Italy, home to Florence (a perennial favorite in Travel + Leisure’s World’s Best Awards), is a dream destination for travelers—myself included.
Since I live in Rome, Tuscany is just a short trip away, and I take every opportunity to visit. Over the years, I’ve wandered through cities like Siena, Lucca, Pisa, San Gimignano, and Volterra; soaked in Saturnia’s thermal springs; lounged on the beaches of Forte dei Marmi and Porto Ercole; toured countryside wineries; and even learned to make pici and other regional dishes in cooking classes.
But Tuscany is so vast and packed with incredible experiences that picking just the best is nearly impossible. That’s why I turned to two experts: Giulia Scarpaleggia, a cookbook author who writes the Letters from Tuscany Substack and hosts cooking classes in Colle di Val d’Elsa, and Christian Scali, a lawyer and co-owner of Villa Ardore, who splits his time between California and Tuscany. Below, you’ll find their top recommendations for hotels, activities, shopping, dining, must-visit towns, and getting around.
Top 5 Can’t-Miss Experiences
- Stay at Borgo San Felice, a luxury hotel with a Michelin-starred restaurant set in a historic countryside village.
- A wine tasting is a must—Antinori Nel Chianti Classico is one of the region’s finest wineries.
- Don’t miss the Arezzo Antiques Fair, Italy’s oldest and largest outdoor antiques market, held the first weekend of every month.
- Dine at Ristorante Il Pellicano, a Michelin-starred spot at the iconic Hotel Il Pellicano, where gourmet tasting menus come with breathtaking views.
- Explore Siena, one of Italy’s best-preserved medieval cities—plan at least a full day here.
Best Hotels & Resorts
Borgo San Felice
This Relais & Châteaux property revived a medieval hamlet near Siena. Rooms are tucked into old stone buildings with traditional decor. Guests can lounge by the pool, indulge in spa treatments inside a converted olive mill, dine at the Michelin-starred restaurant, or enjoy homemade pasta at the casual osteria.
Il Salviatino
Scali and his husband adore this five-star family-owned hotel in Fiesole, just outside Florence. “It’s full of special touches—frescoed ceilings, a panoramic terrace with manicured gardens, and sweeping views of the Duomo,” he says. The 15th-century villa recently underwent a renovation, refreshing its 39 rooms and adding a new spa.
Agriturismo Il Rigo
For an authentic Tuscan stay, book an agriturismo—a rustic farmhouse B&B. “At Il Rigo, you feel like family. Luisa and her husband Mathias run it personally, making everyone feel at home,” says Scarpaleggia.
La Roqqa
This sleek new boutique hotel in Porto Ercole (Monte Argentario) features designer furniture, a rooftop Italian restaurant, and a private beach club with plush sunbeds and a laid-back eatery.
Villa Ardore
Scali and his husband restored this 16th-century Chianti farmhouse into a luxe private retreat for up to 16 guests. With an infinity pool overlooking vineyards, a spa, vegetable garden, bocce court, and full kitchen, it’s perfect for families or groups seeking peace without sacrificing access to Tuscany’s highlights.
Best Things to Do
Visit Siena Cathedral
Scarpaleggia recommends admiring its intricate marble mosaic floors—either from ground level or via the Porta del Cielo (“Heaven’s Gate”) tour. Don’t miss Pinturicchio’s frescoes in the Piccolomini Library.
Wine Tastings
A visit to Antinori Nel Chianti Classico is a must—this architectural marvel is run by one of Italy’s oldest winemaking families (26 generations and counting!). Book ahead—tours sell out fast.
Contemporary Art at Galleria Continua
“For modern art in a historic setting, Galleria Continua in San Gimignano is unmatched,” says Scali. Housed in a former cinema, it contrasts beautifully with the town’s medieval backdrop.
Hit the Beach
Prefer rugged cliffs or chic beach clubs? Monte Argentario offers dramatic coastal diving, while Forte dei Marmi (a Florentine favorite) has golden sands and marble-paved promenades.
Take a Cooking Class
Scarpaleggia’s half-day classes in Colle di Val d’Elsa start at the market or in her kitchen studio. You’ll learn to make pici pasta, chicken cacciatore, and olive oil cake before enjoying your four-course meal.
Best Shopping
Arezzo Antiques Fair
“A magical weekend hunt for rare collectibles and design pieces,” says Scali. Held the first weekend of each month.
Berti
A family-run knife workshop in Scarperia since 1895. Visit to see traditional craftsmanship and pick a hand-forged blade.
Ceramiche Artesia
A tiny Certaldo Alto ceramics studio where artisans hand-paint pieces like pomegranate platters and geometric bowls.
Best Restaurants
Osteria di Fonterutoli
Scali raves about this elegant winery estate spot. “The garden views are stunning. Try the eliconi pasta with wild boar ragù and mushrooms.”
Trattoria Bel Mi’ Colle
Scarpaleggia’s hometown favorite in Colle di Val d’Elsa. “The beef tongue and stuffed chicken neck appetizers are musts—and the cheese selection is incredible.”
Enoteca I Terzi (Siena)
A wine bar with 1,800+ labels on display. Start with a meat-and-cheese board, then opt for bistecca alla fiorentina or seasonal dishes like radicchio risotto.
Gigliola (Lucca)
A modern osteria for brunch, aperitivo, or dinner. “Their bread, fresh pasta, and natural wines are superb—plus unexpected dishes like falafel.”
Il Pellicano
The Michelin-starred restaurant at Hotel Il Pellicano is one of Tuscany’s most romantic spots. Choose a tasting menu or à la carte dishes on the sea-view terrace.
Best Time to Visit
Tuscany shines year-round. Summer brings crowds and high prices; winter sees some countryside hotels close, but cities like Florence and Siena remain lively. Spring and fall offer ideal weather.
Scali’s pick? “May—the countryside is lush, the weather perfect.”
Festivals to note:
- Palio di Siena (July/August)
- Lucca Summer Festival (June)
- Bravìo delle Botti (August, Montepulciano’s wine-barrel race)
- White Truffle Festival (Fall, San Miniato)
How to Get There
Fly into Florence (FLR) or Pisa (PSA), or arrive via Rome/Milan and take a train or drive.
Cities to Visit
Siena
A perfectly preserved medieval rival to Florence, with its iconic fan-shaped Piazza del Campo.
Pietrasanta
“The marble capital of Versilia, where artists turn the city into an open-air sculpture gallery,” says Scali.
Lucca
A Roman-founded gem with tree-topped towers, an oval piazza built over an amphitheater, and bike-friendly ramparts.
Val d’Elsa
“A hidden valley along the Via Francigena, with rolling hills, vineyards, and quiet charm,” says Scarpaleggia.
Pienza
A UNESCO-listed Renaissance town in Val d’Orcia, famous for its pecorino cheese.
How to Get Around
Trains (Trenitalia) work for cities, but renting a car is best for the countryside. Book early in peak season!
