5 Days in Florence & Tuscany Itinerary

Your first day in Florence will be spent exploring the city center with your private guide.

​The city’s Renaissance brilliance will be brought to life as you stroll its streets and enjoy skip-the-line access to some of its most iconic attractions.

​Begin with a guided tour of the magnificent Florence Cathedral, where you can admire its striking façade and climb Brunelleschi’s iconic dome for sweeping views over the city.

​Continue through the historic heart to Piazza della Signoria, an open-air gallery of sculpture and political history, before strolling across the charming Ponte Vecchio old bridge, lined with traditional artisan shops.

​Day 1 culminates with skip-the-line access to the world-renowned Uffizi Gallery, where your guide unveils masterpieces by Botticelli, Leonardo da Vinci, and Michelangelo.

Join your private driver in the lobby of your Florence hotel and set off for a day trip into the heart of Tuscany, where you’ll meet your private guide in Siena.

​Explore its winding streets and hidden corners before arriving at the remarkable Piazza del Campo, a shell-shaped square that has hosted the famous Palio horse race for centuries.

​Continue to Siena Cathedral, a masterpiece of black-and-white marble, where intricate mosaics, sculptures, and artworks reveal the city’s artistic and spiritual legacy.

​In the afternoon, your driver will take you onward through the Tuscan countryside to San Gimignano, often called the “Medieval Manhattan” for its iconic skyline of stone towers.

​As the day draws to a close, relax on the scenic drive back to your Florence accommodation.

On day 3, your private driver-guide brings you into the heart of the Chianti wine region.

​Your first stop is a boutique winery, where you’ll enjoy a private cellar tour and learn about the winemaking process from grape to glass. In an intimate tasting, sample Chianti Classico wines, each reflecting the land’s character, alongside a guided olive oil tasting that highlights the region’s rich culinary heritage.

​Settle in for a leisurely lunch at a vineyard or traditional agriturismo, where seasonal Tuscan dishes are paired with local wines in a relaxed, scenic setting.

​In the afternoon, continue through the countryside to explore charming villages such as Greve-in-Chianti, where quiet piazzas, wine shops, and local artisans offer a glimpse into everyday life in rural Tuscany.

​Return to Florence in the evening with your driver.

Explore the historic city of Pisa and its famous Leaning Tower on day 4.

​Begin at the Square of Miracles, where you’ll see the iconic Leaning Tower, the Cathedral, and the Baptistery, one of Italy’s most recognizable architectural ensembles. You’ll have time to scale to the top of the tower and take in its unique history and design.

​Continue on to Lucca, a well-preserved walled city known for its relaxed atmosphere and Renaissance character. Enjoy lunch in the historic center before spending the afternoon exploring.

You may choose to walk or cycle along Lucca’s city walls, which offer a unique perspective over the rooftops and streets below. Afterward, explore the town’s cobbled lanes, quiet piazzas, and local shops at your own pace.

​Return to Florence with your driver in the evening.

Your final day in Florence begins with a private guided visit to the Accademia Gallery.

​With skip-the-line access, view Michelangelo’s David, one of the most celebrated sculptures in the world. Your guide will provide insight into its creation, artistic significance, and the legacy of Renaissance Florence.

​Following your gallery visit, the remainder of the day is tailored to your interests.

​Our local tour planning specialists can reserve either a private cooking class, where you’ll learn to prepare traditional Tuscan dishes with a local chef, or for you to explore Florence’s artisan heritage through workshops focused on leather craftsmanship or perfume making.

​The day concludes at your leisure, with time to enjoy Florence before your departure.