One week is enough time to experience three destinations in Tuscany. Art and architecture enthusiasts will appreciate Siena's medieval towers and Florence's piazzas and galleries. Aspiring chefs will enjoy making pasta in Lucca, and wine lovers can sample reds in the Chianti Hills, Sassicaia in Bolgheri, and white wines in the Cinque Terre. Active travelers can cycle the Eroica route or hike through Radda's vineyards and the Val d'Orcia—visiting historic sites and tasting Tuscan fare along the way.

Itinerary #1: Explore Tuscany: Florence, Siena, Pisa & Lucca

This classic itinerary is well-suited for first-time visitors to Tuscany, and those there enjoy a blend of art, architecture, culture, history, and cuisine. You'll sample regional specialties, such as pecorino cheese and Vino Nobile di Montepulciano, visit popular sites like the Leaning Tower of Pisa, Siena's Duomo, and the Renaissance masterpieces of Florence, and learn the art of pasta making with a masterclass in Lucca. 

The Piazza di Anfiteatro in Lucca
The Piazza di Anfiteatro in Lucca
Day Highlights Overnight
Day 1 Arrive in Florence, Tuscany's Renaissance Capital Florence
Day 2 Visit Pisa & Tour the Leaning Tower Florence
Day 3 Transfer to UNESCO-Listed Siena, Explore Siena
Day 4 Day Trip to the Hilltop Towns of Montepulciano & Pienza Siena
Day 5 Transfer to Lucca, Afternoon City Tour Lucca
Day 6 Pasta-Making Masterclass, Free Afternoon Lucca
Day 7 Depart Lucca  

Your journey begins in Florence, the capital of Tuscany, renowned for its Renaissance art and architecture. You'll explore the city's top sights, including the Piazza del Duomo, and see the works of Michelangelo and other Renaissance artists at the Uffizi Gallery and the Galleria dell'Academia. Next, you'll visit the curious Leaning Tower of Pisa before heading to the UNESCO-listed medieval city of Siena, where you'll soak in the atmosphere of the Piazza del Campo and tour the city's landmarks, including the green and white striped Duomo and its Piccolomini Library.

Set out on a guided tour of the picturesque hilltop towns of Montepulciano and Pienza, where you'll sample regional specialties, such as pecorino cheese and Vino Nobile di Montepulciano wine. Afterward, your driver will transfer you to Lucca to experience its laid-back bohemian atmosphere and well-preserved Renaissance-era structures. On your final full day, try your hand at pasta making in a culinary workshop, then feast on the fruits of your labor before enjoying free time to wander the Old Town and fit in one last Italian aperitivo (an aperitif, often served with small bites) and dinner. Learn more

Itinerary #2: Highlights of Florence

Based in Florence, this highlights itinerary is a great choice for travelers who prefer only to unpack once, dive deeper into Florence's art and architecture, and take day trips to the countryside, medieval villages, and coast. In addition to guided tours of the top sites in Florence, you'll have time to see the works of Michelangelo and other artists with a full day at the city's museums and galleries, check out the medieval architecture in San Gimignano, and hike the Lover's Pathway in the Cinque Terre. 

The unmistakable sight of Florence's terracotta-tiled Duomo
The unmistakable sight of Florence's terracotta-tiled Duomo
Day Highlights Overnight
Day 1 Arrive in Florence, Tuscany's Renaissance Capital Florence
Day 2 Historic Walking Tour of Florence Florence
Day 3 Visit the Uffizi & Galleria dell'Accademia Florence
Day 4 Day Trip to the Medieval Towns of Siena & San Gimignano Florence
Day 5 Explore the Villages of the Cinque Terre Florence
Day 6 Italian Cooking Masterclass, Free Afternoon  Florence
Day 7 Depart Florence  

Get acquainted with Florence on a guided tour that includes stops at the iconic Duomo and Michelangelo's "David" sculpture. Then, dive deeper with a full day dedicated to two of Europe's most renowned museums, the Uffizi Gallery and Galleria dell'Accademia, where you can view masterpieces by Leonardo da Vinci, Michelangelo, and other artists at your own pace. Take a day trip to the medieval towns of Siena and San Gimignano to explore their medieval architecture and towers before visiting the fortress of Monteriggioni and capping the day off with wine tasting in the Chianti Hills.

Grab your hiking shoes on Day 5 for a trip to the Cinque Terre, where you'll enjoy coastal views on a walk along the Via dell' Amore (Lover's Pathway). Then, continue to Monterosso al Mare for some gelato and free time to wander the historic city center before refueling with a seafood lunch in Vernazza. Finally, learn the secrets of pasta making in a masterclass Back in Florence with a local chef and a glass of Prosecco, then sit down together to feast on your creations and toast your Italian adventure. Learn more

Itinerary #3: Tuscany Road Trip: Florence, Siena & Montepulciano

This self-drive road trip is best suited to wine lovers and travelers who enjoy getting behind the wheel. After a guided walking tour of Florence and some free time to peruse the stalls of Mercato Centrale or learn about fresco painting at Studio Artemisia, you'll partake in a wine tasting in Siena, check out the medieval towns of San Gimignano and Monteriggioni, and wrap up your trip with a tour and tasting at an ancient wine cellar in Montepulciano.

Wind your way through wine country on your way to San Gimignano
Wind your way through wine country on your way to San Gimignano
Day Highlights Overnight
Day 1 Arrive in Florence, Explore Florence
Day 2 Historic Walking Tour of Florence Florence
Day 3 Pick Up Rental Car, Drive to Siena & Afternoon Wine Tasting Siena
Day 4 Day Trip to San Gimignano & Monteriggioni  Siena
Day 5 Drive to Montepulciano via Pienza Montepulciano
Day 6 Wine Tasting in Montepulciano Montepulciano
Day 7 Return to Florence, Depart  

Upon arrival in Florence, you'll have free time to explore on your own, perhaps attending a class in ancient fresco painting techniques at Studio Artemisia or sampling local flavors at the Mercato Centrale open-air market. The following day, you'll embark on a guided walking tour of the city, taking in Florence's most significant squares and monuments, including the Piazza della Repubblica and Giotto's Bell Tower. On Day 3, you'll pick up your rental car and begin your road trip.

Your first stop is Siena, a medieval town where you can check out the frescoes at the Piccolomini Library and sip Tuscan wines in a tasting experience. Next, head to San Gimignano to see medieval plazas and churches and try Vernaccia di San Gimignano, a local white wine. Continue to Montepulciano, where you'll visit the Palazzo Piccolomini, famous for its hanging gardens and as a shooting location for Franco Zeffirelli's film "Romeo and Juliet." Toast your journey at an ancient wine cellar in Montepulciano, where you'll learn about winemaking and enjoy a lunch and wine pairing. Learn more

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Itinerary #4: Italian Wine Journey Through Tuscany & Cinque Terre

Wine connoisseurs and travelers eager to imbibe regional wines will appreciate this food and wine-focused getaway. In addition to touring Florence's famous sites and visiting medieval villages like Siena and Monteriggioni, you'll enjoy a homecooked meal paired with local wine at a farmhouse in Colle di Val D'Elsa, sip reds at renowned vineyards in Montalcino and the Chianti Hills, sample the "Super Tuscan" Sassicaia in Bolgheri, and indulge in Ligurian cuisine and local white wines in the Cinque Terre.

Wine tasting in Chianti
Wine tasting in Chianti
Day Highlights Overnight
Day 1 Arrive in Florence, Transfer to Colle di Val D'Elsa Colle di Val D'Elsa
Day 2 Private Tour of Florence  Colle di Val D'Elsa
Day 3 Wine Tasting in Montalcino, Visit Siena  Colle di Val D'Elsa
Day 4 Day Trip to Volterra & San Gimignano, Chianti Winery Visit & Tasting Colle di Val D'Elsa
Day 5 Transfer to the Cinque Terre via Bolgheri & Pisa La Spezia
Day 6 Visit Portovenere & Riomaggiore La Spezia
Day 7 Depart La Spezia  

Your Italian wine journey begins in Florence, where your driver will meet you and transfer you to a farmhouse in Colle di Val D'Elsa for a home-cooked dinner paired with local wines. The following day, you'll take a private tour of Florence, including the Il Ponte Vecchio stone bridge and the 13th-century palace, Palazzo Vecchio, and enjoy the city's best steak and wine. Next, you'll sip regional red wines at the vineyards of Brunello di Montalcino, then experience the medieval fortress in Monteriggioni, the cobbled streets and medieval towers of San Gimignano, and the famous red wines of the Chianti Hills. 

Continue to Bolgheri, where you'll taste the renowned "Super Tuscan" Sassicaia wine, and stop to see the Leaning Tower of Pisa on your way to Cinque Terre. Here, you'll tour the colorful coastal villages with your guide, stopping in Riomaggiore to sample the region's dry and aromatic white wines and savor Ligurian flavors and homemade pasta dishes. Finally, your journey comes to a close with a seaside dinner (and, of course, more wine!) in La Spezia, Liguria's bustling port city, and try ravioli alla Genovese. Learn more

Itinerary #5: Cycle the Eroica Among Tuscany's Famous Vineyards

Cyclists will enjoy this alternative tour that follows the Eroica race route, taking you through the region's vineyards and olive groves and to hilltop towns like Montalcino and Siena, all while staying in traditional farmhouses. Highlights include feasting on farm-fresh meals, tasting Tuscan wines, and admiring the natural beauty and medieval architecture of the region.

Friends cycling along the famous L'Eroica
Friends cycling along the famous L'Eroica
Day Highlights Overnight
Day 1 Arrive in Siena, Explore Siena
Day 2 Cycle to Buonconvento, One of Italy's "Most Beautiful Villages" Buonconvento
Day 3 Cycling Loop to Medieval Montalcino Buonconvento
Day 4 Cycle through the Crete Senesi to Castelnuovo Berardenga Castelnuovo
Day 5 Cycle to the Ninth-Century Village of Radda in Chianti Radda in Chianti
Day 6 Cycle Back to Siena Siena
Day 7 Depart Siena  

Your cycling trip begins in Siena, a UNESCO World Heritage Site renowned for its Gothic architecture and the Palio horserace. Explore the Piazza del Campo and the city's medieval architecture before hopping on your bike and heading to Buonconvento. Cruise along unpaved strade bianche (white roads), passing vineyards and olive groves before reaching your destination: a farmhouse where you'll refuel with a dinner made of farm-fresh produce and olive oil. After breakfast, bike the 37-mile (60 km) loop, beginning and ending in Buonconvento, with a stop in Montalcino, where the Eroica cycle race culminates.

Celebrate the loop ride with some Vino di Brunello di Montalcino, then head back to the farmhouse for a dip in the pool and a home-cooked Tuscan dinner. The following day, cycle through the Crete Senesi to Castelnuovo Berardenga, taking in the Chianti Hills scenery and the UNESCO-listed Abbey of Monte Oliveto Maggiore, a redbrick Benedictine monastery. On Day 5, set off for a challenging climb to the ninth-century hilltop village of Radda. The final leg of your cycling tour brings you back to where it all started: Siena. Here, you'll visit the Duomo di Siena and then celebrate with a bottle of Chianti. Learn more

Itinerary #6: Active Italy: Trekking & Tuscan Heritage

Opt for this active trip, an excellent option for outdoor enthusiasts and history buffs who enjoy a leisurely pace. This tour takes you to historic cities like Florence and Siena, hiking the landscapes of Val d'Orcia and exploring the medieval towns of Pienza and Montepulciano. Along the way, you'll experience locally sourced foods, world-renowned wines, historic sites, and the dramatic views Italy is famous for.

Hike along the famous "white roads" of the Val D'Orcia landscape
Hike along the famous "white roads" of the Val D'Orcia landscape
Day Highlights Overnight
Day 1 Arrive in Florence, Tuscany's Renaissance Gem Florence
Day 2 Transfer to Radda in Chianti, the "Village of the Vineyards" Radda-in-Chianti
Day 3 Transfer to Panzano, Return Hike to Radda in Chianti via Volpaia Radda-in-Chianti
Day 4 Visit Siena, Transfer to San Quirico d'Orcia San Quirico
Day 5 Trekking in the Val d'Orcia San Quirico
Day 6 Hike to Pienza, Return Transfer to San Quirico San Quirico
Day 7 Hike to Monticchiello & Montepulciano, Return Transfer to San Quirico  

Ease into your adventure with free time to see the sites in Florence, such as the Cattedrale di Santa Maria del Fiore, before your driver transfers you to Radda, the "Village of the Vineyards." Here, you'll spend 4-5 hours hiking among the vines and olive groves. Then, your driver will bring you to Panzano, where you can wander the cobbled streets before making your way back to Radda on foot, stopping in Volpaia, a small charming village, for prosciutto with pecorino and honey and a glass of Chianti.

Take a break from the trails and spend a day sightseeing in Siena. Day 5 is dedicated to hiking in the Val d'Orcia countryside to San Quirico d'Orcia (if you have time, take a dip in the Roman pool in Bagno Vignoni). The next leg of the journey takes you to Pienza, where you'll enjoy Renaissance architecture and views of the Val d'Orcia. Finally, end on a high note with a hike to the fortified village of Monticchiello followed by a hike to Montepulciano, where you can grab a coffee or spritz and take in the views from the Piazza Grande that include landmark architecture like the city's Duomo, before departure. Learn more

More Great 1-Week Italy Itineraries

Looking for more inspiration for your trip to Italy? Check out these other one-week Italy itineraries, with outdoor adventures, cultural trips, and best-of tours to hit the highlights.


Map of 1 Week in Tuscany - 6 Unique Itinerary Ideas
Map of 1 Week in Tuscany - 6 Unique Itinerary Ideas