Planning your perfect Tuscany itinerary

Imagine strolling through the vineyards with a glass of Chianti in hand, savoring the rich flavors and soaking up the timeless beauty of Tuscany. It's not just a vacation - it's an immersion in centuries-old traditions, world-class wines and unforgettable cuisine. Tuscany is a region where every hill, every village and every vineyard has a story to tell. Here’s our guide to crafting the perfect Tuscany itinerary.

See our itineraries below, or get inspired by duration and regions: 5 days - 7 days - 10 days - 14 days - North Italy - South Italy - Amalfi coast

Why visit Tuscany?

Tuscany draws travelers with its perfect mix of history, natural beauty, and culinary delights.

From the charm of medieval hilltop villages to the artistic treasures of Florence, it’s easy to see why this region is so beloved. Tuscany is a paradise for wine lovers, offering vineyard tours and tastings of world-famous wines like Chianti and Brunello di Montalcino, set against stunning landscapes of rolling hills and cypress trees.

Any Tuscany promises a heady blend of culture, breathtaking scenery, and unforgettable flavors—making it a destination that lives up to its reputation.

Best places to see in Tuscany

In Tuscany, every town and city offers something unique and unforgettable. Whether you’re marveling at Renaissance art in Florence or tasting world-class wine in Chianti, Tuscany is a region filled with beauty and history at every turn.

Florence

The capital of Tuscany, Florence is a must for art and history lovers. Highlights include the Florence Cathedral (Duomo), the Uffizi Gallery, the Accademia Gallery (home to Michelangelo's David), and the iconic Ponte Vecchio bridge.

San Gimignano

Known as “medieval Manhattan” for its striking towers, San Gimignano is a well-preserved city where you can be transported back in time. Wander its cobbled streets, sample award-winning gelato and admire the breathtaking view of the surrounding countryside from one of the towers.

Pienza

A UNESCO World Heritage site, Pienza is celebrated for its Renaissance architecture and harmonious urban design. Visit the beautiful Piazza Pio II, explore the cathedral, and sample the town’s famous pecorino cheese. Pienza is a gem in the Val d’Orcia valley with a distinctive charm.

Chianti Region

For wine lovers, the Chianti region is paradise. Famous for its Chianti Classico wines, this area is dotted with vineyards, wineries, and rustic villages. Take a leisurely wine tour to savor the region’s finest wines and soak in the breathtaking countryside views.

Lucca

This walled city is known for its Renaissance fortifications and charming atmosphere. Take a stroll or bike ride along the top of the walls for panoramic views, explore the historic center, and enjoy authentic Tuscan cuisine in one of Lucca’s cozy trattorias.

Want to explore Europe even more? We have prepared the most convenient European itineraries for you to explore the continent.

How to get to Tuscany

Starting your Tuscan adventure is easy, with several convenient travel options available.

By air

Fly into Florence or Pisa, both of which offer regular connections to major European cities. Florence Airport is close to the heart of Tuscany, while Pisa Airport provides access to the western coast and nearby attractions.

By train

Italy’s extensive rail network makes it simple to reach Tuscany by train. High-speed trains connect major cities like Rome and Milan to Florence, allowing you to enjoy scenic countryside views as you travel.

By road: rental car

For maximum flexibility, consider renting a car. Tuscany’s well-maintained highways make it easy to explore the region at your own pace, giving you the freedom to visit charming hilltop towns, vineyards, and hidden gems along the way.

7-day Tuscany itinerary

Explore the enchanting heart of Tuscany with our meticulously designed Tuscany wine & food itinerary created by our local travel experts. In just one week, delve into the heart of this iconic Italian region, celebrated for its vibrant culture and awe-inspiring scenery.

You’ll begin this 7-day Tuscany itinerary in Florence with a tour of the Oltrarno district and the next day you will be transferred to the hotel in San Gimignano.

Take a scenic hike, visit an olive oil mill, and enjoy a boutique winery tour with a traditional Tuscan lunch. Discover wine-making secrets during a Vertical Wine Tasting.

Explore Montepulciano's vineyards, savor regional foods, and conclude with a Chianti Food and Wine Pairing. Depart from Florence Airport on day seven. Read more.

Want to skip the hassle of planning? Have us create your trip for you.

Itinerary overview

Day 1

• Arrival in Florence.
• Immerse yourself in the local culture with a guided tour of the Oltrarno district, visiting the workshops of skilled artisans.

Day 2

• Transfer to San Gimignano.
• Take this day to explore the surrounding area at your own leisure.

Day 3

• Morning hike through the Tuscan countryside.
• Visit an olive oil mill, followed by a guided exploration of a boutique winery.
• Traditional Tuscan lunch.

Day 4

• Lunch at a Tuscan vineyard.
• Dive into a Vertical wine-tasting experience featuring 15 distinct Tuscan wine products.
• Delve into the art of winemaking with an educational lesson.

Day 5

• Wine Tour in Montepulciano.
• Explanation of winery history and philosophy, as well as fermentation and aging process insights.
• Explore the vineyards.
• Winetasting with regional foods.

Day 6

• Chianti Food and Wine Pairing.
• Venture into the depths of the cellars for a tasting of wines and regional products.
• Balsamic vinegar tasting.

Day 7

• Departure from Tuscany.
• Transfer to Florence Airport.

Create your Tuscany itinerary with us

Ready to explore the beauty of Tuscany? Our Italy experts are ready to design a trip just for you. Work with us to create a customized itinerary that reflects everything you're looking for - vineyard tours, culinary workshops, historic sites or scenic hikes.

Browse our selection of Italy itineraries for inspiration, and remember that each one can be tailored to your unique preferences. Contact us when you're ready, and let's bring your dream Tuscany adventure to life.