6 Unforgettable Tuscany Itineraries: Your Guide to Exploring Italy's Most Beautiful Region
6 Unforgettable Tuscany Itineraries: Your Guide to Exploring Italy's Most Beautiful Region
Tuscany, with its rolling hills, medieval villages and world class cuisine, is a dream destination for
travelers seeking the perfect blend of culture, history and natural beauty. Whether you're planning
a quick getaway or an extended vacation, this enchanting region of Italy offers countless treasures
waiting to be discovered. In this comprehensive guide, we've curated six examples of incredible Tuscany itineraries that showcase the best this magical region has to offer.
From the Renaissance splendour of Florence to the medieval charm of Siena and the picturesque vineyards of Chianti, these carefully crafted routes will help you experience the authentic heart of Tuscany.
With chauffeured transportation and an expert tour guide at your side, embark on a journey
through one of Italy's most beloved destinations.
Table of Contents
- Classic Tuscany: The Perfect 7-Day Itinerary
- Tuscan Wine Country: A 5-Day Vineyard Tour
- Medieval Tuscany: Exploring Hill Towns in 4 Days
- Art & Culture: A 6-Day Renaissance Immersion
- Coastal Tuscany: 3 Days Along the Tyrrhenian Sea
- Hidden Gems: Off-the-Beaten-Path 4-Day Adventure
- Practical Travel Tips for Tuscany
- Frequently Asked Questions
Classic Tuscany: The Perfect 7-Day Itinerary
This week-long itinerary offers the quintessential Tuscan experience, balancing city exploration with countryside relaxation.
Day 1-2: Florence
Begin your Tuscan adventure in Florence, the cradle of the Renaissance. Spend two full days exploring this magnificent city:
- Day 1: Visit the iconic Duomo (Cathedral of Santa Maria del Fiore) and climb to the top for panoramic views. Continue to the Uffizi Gallery to admire masterpieces by Botticelli, Leonardo da Vinci and Michelangelo. End your day with sunset views from Piazzale Michelangelo.
- Day 2:
Start at the Accademia Gallery to see Michelangelo's David. Explore the Ponte Vecchio and the artisan workshops of the Oltrarno district. Enjoy a leisurely lunch at Mercato Centrale before visiting the Pitti Palace and Boboli Gardens.
Day 3: Chianti Wine Region
Head south into the famous Chianti wine region:
- Drive the scenic Chiantigiana Road (SR222) through vineyards and olive groves
- Visit charming towns like Greve and Castellina in Chianti
- Enjoy wine tastings at family run vineyards, sampling the renowned Chianti Classico
- Have lunch at a countryside trattoria featuring local specialties like ribollita and pappardelle with wild boar ragu
- Overnight stay in a converted farmhouse or agriturismo for an authentic experience
Day 4: Siena
Dedicate a full day to exploring the medieval city of
Siena:
- Marvel at the stunning Gothic architecture of Siena Cathedral
- Relax in the shell shaped Piazza del Campo, home to the famous Palio horse race
- Climb the Torre del Mangia for spectacular views
- Wander through the 17 contrade (districts) of the historic center
- Sample local pastries like ricciarelli and panforte
Day 5: Val d'Orcia
Drive through the
UNESCO listed
Val d'Orcia, one of Tuscany's most photogenic landscapes:
- Visit the picture perfect town of Pienza, known for its Renaissance architecture and pecorino cheese
- Explore the wine town of Montalcino, home of the prestigious Brunello di Montalcino
- Relax in the thermal baths at Bagno Vignoni with its unique central pool
- Stop for photos at the iconic cypress lined roads and farmhouses that grace countless postcards
- Overnight stay in the region to fully appreciate the magical atmosphere
Day 6: Montepulciano and Cortona
Continue your exploration of southern Tuscany in the
Val di Chiana
- Spend the morning in Montepulciano, famous for its Nobile wine and dramatic hilltop setting
- Enjoy lunch overlooking the surrounding countryside
- Continue on to Cortona, the town made famous by the film Under the Tuscan Sun, for the afternoon.
- Wander its steep medieval streets and enjoy panoramic views of the Val di Chiana valley
- Return to your accommodation in the countryside for a final evening under the Tuscan stars
Day 7: San Gimignano and Return to Florence
On your final day, head back toward Florence with important stops along the way:
- Visit San Gimignano, known as the "Medieval Manhattan" for its striking towers
- Enjoy a gelato in the main square from award-winning Gelateria Dondoli
- Take a final scenic drive through the Chianti region
- Return your rental car in Florence before departing
Tuscan Wine Country: A 5-Day Vineyard Tour
This five day itinerary offers the ultimate taste of Tuscany, balancing immersive wine tastings with
scenic countryside exploration
Day 1: Florence to Chianti Classico
From Florence, drive to the heart of Chianti Classico, marked by the black rooster logo.
- Visit Castello di Brolio, where modern Chianti wine was born
- Participate in guided tastings at Antinori nel Chianti Classico, a stunning architectural marvel
- Overnight stay in a wine resort or converted castle
Day 2: Exploring Chianti Villages
Visit smaller, family run wineries around Radda in Chianti
- Enjoy a cooking class focusing on wine pairings
- Explore the charming medieval village of Volpaia
- Taste wines directly from the barrel at a traditional cellar
- Second overnight stay in Chianti
Day 3: Montalcino and Brunello
Journey to
Montalcino, home of the prestigious Brunello di Montalcino
- Tour the imposing 14th century fortress
- Visit iconic wineries like Biondi Santi (the birthplace of Brunello) or Castiglion del Bosco
- Learn about the strict production methods that make Brunello so special
- Overnight stay in Montalcino or nearby in the Val d'Orcia
Day 4: Montepulciano and Vino Nobile
- Head to
Montepulciano to taste the
Vino Nobile di Montepulciano
- Tour historic cellars built underneath the medieval town
- Visit Avignonesi or Poliziano vineyards
- Enjoy lunch with a view of the Val di Chiana
- Overnight in
Montepulciano
Day 5: Bolgheri and Super Tuscans
Drive west to coastal
Bolgheri, home of the revolutionary Super Tuscan wines
- Tour the famous Cypress Avenue immortalized by poet Giosuè Carducci
- Visit prestigious estates like Ornellaia or Sassicaia
- Enjoy a seafood lunch by the Tyrrhenian coast
- Return to Florence in the evening
Medieval Tuscany: Exploring Hill Towns in 4 Days
This itinerary focuses on Tuscany's captivating medieval hill towns, each perched dramatically atop rolling hillsides.
Day 1: Siena
Begin in the Gothic splendor of
Siena
- Tour the spectacular Duomo with its intricate marble floor
- Visit the Museo Civico in the Palazzo Pubblico
- Learn about the Palio horse race and its traditions
- Overnight in
Siena
Day 2: San Gimignano and Volterra
Visit two beautifully situated hill top towns
- Drive to San Gimignano to see its 14 remaining medieval towers
- Climb the Torre Grossa for breathtaking views
- Continue to Volterra, an ancient Etruscan town famous for alabaster crafts
- Visit the Roman Theater and Etruscan Museum
- For overnight stay return to
Siena or stay in
San Gimignano
Day 3: Monteriggioni and Certaldo
Continue exploring two more charming medieval towns
- Visit the perfectly preserved walled town of Monteriggioni
- Walk the complete circuit of medieval walls
- Continue to Certaldo Alto, reached by funicular
- Explore the house of Giovanni Boccaccio, author of the Decameron
- Overnight in the area
Day 4: Lucca and Barga
Experience the charms of
Lucca & Barga
- Travel to Lucca and walk or cycle its intact Renaissance walls
- Visit the unusual Guinigi Tower with oak trees growing on top
- Drive into the Garfagnana region to visit Barga, one of Tuscany's most beautiful villages
- Enjoy spectacular mountain views before returning to your departure point
Art & Culture: A 6-Day Renaissance Immersion
This itinerary is perfect for art lovers and history enthusiasts wanting to dive deep into Tuscany's
cultural heritage.
Day 1-2: Florence Art Tour
Learn, discover and expand your art knowledge with an expert art historian tour guide.
- Day 1: Focus on the major museums - Uffizi, Accademia, and Bargello
- Day 2: Explore lesser-known gems like Museo dell'Opera del Duomo, San Marco Museum, and Palazzo Medici Riccardi
- Attend an evening concert of classical music
Day 3: Prato and Pistoia
Explore two of Tuscany’s famous towns know for their historical textile industry and vibrant artisan traditions.
- Visit Prato to see Filippo Lippi's frescoes in the cathedral
- Continue to Pistoia for its beautiful Romanesque churches
- See the Ospedale del Ceppo with its glazed terracotta frieze
- Return to Florence
Day 4: Arezzo
Take a day trip to Arezzo renowned for its antiques fair, rich medieval and Renaissance architecture
and history
- Marvel at Piero della Francesca's "Legend of the True Cross" frescoes in the Basilica of San
- Francesco
- Visit the Casa Vasari, home of the famous artist and historian
- Explore the antique market if visiting on the first Sunday of the month
- Return to Florence
Day 5-6: Pisa and Lucca
Day 5: Head to Pisa to see not just the Leaning Tower but the entire Piazza dei Miracoli complex
- Visit the Camposanto with its remarkable frescoes
- Continue to
Lucca for overnight
Day 6: Explore Lucca's churches, including
San Martino Cathedral and
San Michele in Foro
- Visit the Puccini Museum dedicated to the famous composer
- Return to Florence
Coastal Tuscany: 3 Days Along the Tyrrhenian Sea
Discover Tuscany's less-visited western coastline with this refreshing itinerary.
Day 1: Livorno and Bolgheri
Experience the vibrant town of Livorno and the charming village of Bolgheri
- Start in port city Livorno with its canals and seafood cuisine
- Visit the Central Market for lunch
- Drive along the scenic Viale Italia with views of the Terrazza Mascagni
- Continue to Bolgheri for wine tasting and dinner
- Overnight in Bolgheri or Marina di Castagneto
Day 2: Etruscan Coast
Discover the
Etruscan Coast, where ancient charm meets sunlit beaches and seaside allure.
- Explore the beautiful beaches of the Costa degli Etruschi
- Visit the charming village of Populonia with its Etruscan ruins
- Take a boat trip to Elba Island (optional)
- Enjoy a seafood dinner in San Vincenzo
- Overnight stay in the area
Day 3: Argentario Peninsula
Enjoy the Argentario Peninsula with its gentle cliffs and clear turquoise coves.
- Drive south to the dramatic Monte Argentario peninsula
- Visit the charming harbor towns of Porto Santo Stefano and Porto Ercole
- Take a scenic drive around the peninsula
- Relax on the connected sandbar beaches
- Return to your departure point or continue south
Hidden Gems: Off-the-Beaten-Path 4-Day Adventure
Escape the crowds with this itinerary focused on Tuscany's lesser-known but equally beautiful destinations
Day 1: Maremma Region
Explore the wild Maremma region in Southern Tuscany
- • Visit the Tarot Garden created by artist Niki de Saint Phalle
- • Discover the Etruscan ruins of Sovana and Pitigliano
- • Stay overnight in a converted farmhouse
Day 2: Garfagnana Valley
Experience the Garfagnana Valley, where forests and mountain villages create a peaceful retreat.
- Drive north to the mountainous Garfagnana region
- Visit the spectacular Grotta del Vento cave system
- Explore medieval villages like Castiglione di Garfagnana
- Try rustic mountain cuisine
- Overnight stay in the area
Day 3: Casentino Forest
Wander through the ancient
Casentino Forest National Park
- Discover the remote La Verna and Camaldoli monasteries
- Hike through pristine woodlands
- Stay overnight in a mountain lodge
Day 4: Mugello Region
Explore the Mugello, birthplace of the Medici family
- Visit the Villa Demidoff park with its colossal sculpture of Apennine Colossus
- Tour the Convento di Bosco ai Frati with works by Donatello
- Return to
Florence
Practical Travel Tips for Tuscany
Best Time to Visit
- Spring (April-May) and Fall (September-October) offer ideal weather and fewer crowds
- Summer (June-August) brings hot weather and peak tourist numbers
- Winter (November-March) offers lower prices and a more authentic experience, though some attractions have limited hours
Transportation
- Rental Car or private driver/car service is highly recommended for exploring the countryside and hill towns
- Trains connect major cities like Florence, Pisa, Lucca and Siena
- Buses reach smaller towns but have limited schedules
- Consider hiring a private driver for wine tours to avoid drinking and driving
Accommodation Options
- Agriturismi (farm stays) offer authentic rural experiences
- Historic villas provide luxury accommodations with heritage
- Boutique hotels in cities and towns balance convenience and charm
- Apartments are ideal for longer stays or families
Dining Tips
- Lunch (12:30-2:30 PM) and Dinner (7:30-9:30 PM) are typical meal times
- Many restaurants close between lunch and dinner
- Reservations are recommended for popular restaurants
Cultural Etiquette
- Greet locals with "Buongiorno" (good day) or "Buonasera" (good evening)
- Dress modestly when visiting churches (covered shoulders and knees)
- Always validate train and bus tickets before boarding
- A small tip (5-10%) is appreciated for good service but not mandatory
Conclusion
Tuscany offers an enchanting blend of art, history, cuisine, and natural beauty that captivates travelers from around the world. Whether you're sipping wine in the rolling hills of Chianti, admiring Renaissance masterpieces in Florence, or wandering through medieval villages frozen in time, this magical region provides experiences that will stay with you long after you've returned home.
Use these six itineraries as inspiration for your own perfect Tuscan adventure, mixing and matching destinations based on your interests and available time. However you choose to explore this remarkable region, you'll soon discover why Tuscany has been capturing hearts for centuries.
Buon viaggio!
Frequently Asked Questions
How many days do I need to visit Tuscany?
While you could see the highlights in 3 to 4 days, ideally plan for 7 to 10 days to truly experience the region without rushing. This allows time to explore both cities and countryside at a relaxed
pace.
Is it better to base yourself in one place or travel around Tuscany?
For a week long trip, consider staying in 2 to 3 well located bases. Florence is ideal for exploring northern Tuscany, while Siena or an agriturismo in Val d'Orcia works well for the south.
Do I need a car in Tuscany?
While you can visit major cities like Florence, Siena and Pisa by train, a car is essential to truly experience the Tuscan countryside, hilltop towns and vineyards. Rent a smaller vehicle to navigate narrow village streets more easily or consider hiring a private driver, especially for wine tours to avoid drinking and driving.
When is the best time to visit Tuscany?
May, June, September and October offer ideal weather and manageable crowds. July and August are hot and crowded, while winter months (November-March) are quieter but may have limited opening hours at some attractions.
What are the must-try foods in Tuscany?
Don't miss these Tuscan specialties:
- Bistecca alla Fiorentina (T-bone steak)
- Ribollita (bread and vegetable soup)
- Pappardelle al cinghiale (pasta with wild boar sauce)
- Pecorino di Pienza (sheep's milk cheese)
- Cantuccini (almond biscuits) dipped in Vin Santo
Can I visit Tuscany on a budget?
Yes! Consider these tips for budget travelers:
- Visit during quieter or off season (April to May or October to November)
- Stay in agriturismi or smaller family run hotels
- Enjoy lunch as your main meal (lunch menus are often less expensive)
- Visit free attractions like churches, markets and public squares
- Purchase a Firenze Card if planning to visit multiple museums in Florence.
Is Tuscany suitable for family travel?
Yes, absolutely. Children will enjoy medieval castles, gelato shops and outdoor activities. Many agriturismi are family friendly with swimming pools and animals. Balance museum visits with outdoor time in parks and gardens.
What should I pack for Tuscany?
Pack comfortable walking shoes for cobblestone streets, layers for variable weather, modest clothing for church visits, sunscreen and a hat. A small daypack is useful for excursions.
How do I book wine tastings in Tuscany?
Many larger wineries accept online reservations through their websites. For smaller, family run vineyards, email or call ahead. Your accommodation can often help arrange visits. Most tastings require reservation at least 24 to 48 hours in advance.
Can I take day trips to Cinque Terre or Rome from Tuscany?
While possible, these would be very long days. Cinque Terre is best reached from northern Tuscany (3 to 4 hour journey from Florence). Consider adding an overnight stay for these destinations.
