Florence and Tuscany, a perfect 4-day pre- or post cruise adventure

Rich in history, art, and timeless charm, this region deserves more than just a quick visit. Ideally, spend a few days here—more if you can—to truly soak in its beauty and culture.

In this article, we’ll guide you through a four-day itinerary that blends the best of Florence with unforgettable countryside escapes, designed to help you make the most of every moment.

Why Florence deserves more than just one day

While visiting Florence on a cruise shore excursion is possible, be aware that the city is several hours from major ports like Livorno and La Spezia. That means your time in Florence will be limited, and the experience can feel rushed.

That’s why we recommend extending your vacation by booking a hotel and spending a few extra days in Florence and the Tuscan countryside before or after your cruise. It’s the perfect way to dive deeper into the region and enjoy the sights, food, and culture at a relaxed pace.

When you purchase through links on our site, we may earn a commission. Here’s how it works.

If you’re planning a Mediterranean or Greek Isles cruise starting from a cruise port in Italy. This is a fantastic opportunity to explore inland Italy and make the most of your journey.

🚗 Renting a car is the best way to explore Tuscany’s hilltop villages and vineyards at your own pace. Use the tool below to search offers from top rental companies—just enter your destination, travel dates, and number of passengers, then click “Car Rentals.”

Start your Tuscan adventure in Florence

Florence is the perfect base for exploring Tuscany. As the region’s capital, it offers a rich mix of Renaissance art, historic landmarks, and a vibrant local culture.

From Michelangelo’s David at the Accademia Gallery to the grandeur of the Duomo and the masterpieces inside the Uffizi, there’s no shortage of things to see.

Beyond the city, the Tuscan countryside awaits—rolling vineyards, charming hilltop towns, and world-class wineries. To explore at your own pace, we recommend renting a car (you’ll find rental offices conveniently located near the central train station).

But if you prefer to sit back and relax, we recommend plenty of excellent day trips, excursions, and transfers through trusted partners like Viator.

Ready to explore? Here’s our perfect 4-day itinerary to help you make the most of your time in Florence and the Tuscan countryside.

Day 1: Arrival in Florence

Your adventure in Tuscany begins with your arrival in Florence. This beautiful city is the capital of the Tuscany region and is known for its art, architecture, and history.

After checking into your hotel, take some time to explore the city and its many attractions. Visit the iconic Duomo di Firenze, a stunning cathedral masterpiece of Renaissance architecture. Make time to climb inside the dome, but only if you feel comfortable in tight spaces. The view from the top is fantastic.

Afterward, stroll through the city via the best-known food market in Florence, the Mercato Centrale, also known as the San Lorenzo Market.

This historic market is known for its vibrant atmosphere and wide selection of fresh, locally sourced produce, meats, cheeses, and other food products. The market is spread over two floors, with the ground floor dedicated to fresh produce and the upper floor housing a variety of food stalls and restaurants.

Visitors can sample a variety of local specialties, including panini, pasta, pizza, and gelato, or purchase ingredients to prepare their own meals. The Mercato Centrale is a must-visit destination for anyone interested in food and is a great place to experience the flavors and traditions of Tuscany.

Leave the market to visit the original David statue by Michelangelo at the Accademia Gallery. You will need to pre-book entrance tickets to ensure entrance on the day you want.

The statue is considered one of the greatest masterpieces ever and a must-see for anyone visiting Florence. The Accademia Gallery is also home to a collection of important works of art, including other sculptures by Michelangelo.

Authentic Tuscan restaurants we recommend

Finally, end your day with a delicious dinner of traditional Tuscan cuisine at a local restaurant. Here are two that we love:

1. Osteria dell’Enoteca – This charming osteria is located near the Ponte Vecchio and offers a selection of traditional Tuscan dishes and local wines.
   You’ll find dishes such as pici with wild boar ragù, roasted pork with fennel, and pappa al pomodoro. The wine list includes a variety of local wines, including Chianti Classico and Vernaccia di San Gimignano.
   
2. Trattoria da Giorgio – This family-run trattoria is located near the Duomo and offers a selection of classic Tuscan dishes and local wines.
   The menu features ribollita, pappardelle with wild boar ragù, and grilled meats, all made with fresh, locally sourced ingredients. The wine list includes a variety of local wines, including Chianti and Brunello di Montalcino, and the prices are reasonable.

Day 2: Discover Florence

On your second day in Tuscany, it’s time to explore more of Florence. Start your day by visiting the Uffizi Gallery, one of the world’s most famous art museums – book entrance tickets from home before you travel to skip the line.

Here you can see masterpieces by Michelangelo, Leonardo da Vinci, and Botticelli.

Next, continue walking to Ponte Vecchio and cross the famous bridge to the Palazzo Pitti, a stunning palace once the home of the powerful Medici family.

The Medici family was one of the most powerful and influential families in Florence during the Renaissance period. They were patrons of the arts, supporting artists such as Michelangelo, Leonardo da Vinci, and Botticelli, and played a significant role in the political and economic development of the city. 

The family's wealth and influence allowed them to build magnificent palaces and homes throughout Florence, many of which can still be seen today. 

Some of the most notable Medici palaces include the Palazzo Medici Riccardi, the Palazzo Pitti, and the Palazzo Vecchio. These palaces are not only architectural masterpieces, but also house some of the most important art collections in the world, including works by Raphael, Titian, and Caravaggio. 

The Medici family's legacy can still be seen throughout Florence today.

Finally, end your day with a stroll through the Boboli Gardens behind the Palazzo Pitti. The gardens offer stunning views of the city and the surrounding countryside. With its fountains, sculptures, and manicured lawns, the Boboli Gardens are the perfect place to relax and enjoy the beauty of Florence.

Day 3: Exploring Tuscany’s Vineyards

Renting a car is an excellent way to explore the region’s stunning landscapes and world-renowned vineyards. We recommend renting a car in Florence to explore the countryside. Book in advance and pick up your vehicle at the rental offices near the train station.

If you prefer to pre-book a guided tour with transporation, there are many excellent tours to consider with pickup at your hotel in Florence.

Pre-booking a car for pick up in Florence

We recommend pre-booking a car rental to ensure you get the type of car you want at a reasonable price. There are several car rental companies in Florence, including Avis, Hertz, and Europcar, so you’ll have plenty of options.

Book online before you leave home. Remember to check the small print on your agreement, ensure you have adequate insurance, and find out if you need an international driver’s license or if your license from your home country is sufficient in Italy.

Arrange to collect your rental car at one of the car rental offices close to the train station. They are easy to walk to from the center of Florence. Check the rental office’s opening hours and plan your pick-up accordingly.

General tips for driving in Italy

Driving in Italy can be an exciting but eye-opening experience, and it’s important to be prepared and know what to expect. Here are some things to keep in mind when driving in Italy:

• Drive on the right-hand side of the road.
• Speed limits are kilometers per hour, typically lower than in the US or UK.
• Italian drivers can be aggressive, so be prepared for fast lane changes and sudden stops.
• Parking can be difficult in cities, so research parking options in advance.
• You’ll need to pay tolls if you’re driving on the highways.

It's a good idea to check with your embassy or consulate to see if an international driving license is required.

The Tuscan countryside

Once you’ve collected your rental car, it’s time to hit the road and explore Tuscany’s stunning countryside. There are many vineyards, but some of our favorites include Cesani Winery, Ternuta Torciana, and San Donato:

Cesani Winery is a family-owned vineyard that has been producing high-quality wines for generations and offers a variety of wine tours and tastings.

Tenuta Torciana is another popular vineyard that offers wine tastings, cooking classes, and truffle hunting experiences.

Finally, San Donato is a beautiful vineyard known for its Chianti Classico. It offers guided tours of the vineyard and winery.

You can pre-book a tour on the winery’s website. Or, if you prefer more freedom and do not want to pre-plan your day too much, just turn up to do some wine tasting and take a tour if space is available. Just remember to have your designated driver!

As you drive through the countryside, take in the stunning views of rolling hills, vineyards, and olive groves. And don’t forget to stop for a leisurely lunch at a local trattoria or agriturismo to savor some of the region’s delicious cuisine.

Find your perfect excursion or guided tour to the Tuscan countryside here if you prefer not to drive yourself.

Day 4: Visit Siena and San Gimignano

The historic towns of Siena and San Gimignano are a must. These beautiful towns are located in the heart of Tuscany and are known for their rich history, stunning architecture, and delicious cuisine. In this article, we’ll provide some tips on how to visit Siena and San Gimignano in one day, including how to get there from Florence, what to see and do in each town, and a little bit of history about each place.

Getting there

Siena and San Gimignano are about an hour’s drive south of Florence. If you’re renting a car, head south on the A1 highway and take the exit for Siena or San Gimignano. Alternatively, you can take a bus or train from Florence to Siena and then a local bus to San Gimignano.

For those who don’t want to drive, there are many fantastic guided bus tours to Siena and San Gimignano from Florence. Expect a long day, but the experience will most likely stay with you forever. This is an exceptionally beautiful part of Italy. Some tours also include the medieval town of Lucca.

Find your perfect guided tour or excursion from Florence to Siena, San Gimignano, or Lucca here.

Siena

Siena is a beautiful medieval town known for its stunning Gothic architecture, historic palaces, and beautiful piazzas. When you arrive in Siena, head straight to the Piazza del Campo, one of the most famous squares in Italy.

This beautiful square is home to the Palazzo Pubblico, a stunning palace now home to the Civic Museum. Be sure to climb the Torre del Mangia, a tower that offers spectacular views of the city and the surrounding countryside.

Another must-see attraction in Siena is the Gothic Siena Cathedral, home to works by Donatello and Michelangelo.

San Gimignano

San Gimignano is a hilltop town known for its well-preserved medieval architecture, including its famous towers.

When you arrive in San Gimignano, head straight to the Piazza della Cisterna, a beautiful square surrounded by medieval buildings. You can explore the town’s many narrow alleys and historic buildings from here, including the Collegiate Church of Santa Maria Assunta and the Palazzo del Popolo.

Remember to stop for authentic gelato at Gelateria Dondoli.

Be sure to climb the Torre Grossa, San Gimignano’s tallest tower, for stunning town views.

A glimpse into the history of Siena and San Gimignano

Both Siena and San Gimignano are rich in history and have helped shape the cultural identity of Tuscany.

Once a powerful rival to Florence, Siena dates back to the Etruscans in the 6th century BC. The city is famous for its striking Gothic architecture, notably the 13th-century Siena Cathedral, and for the Palio di Siena—a thrilling horse race held twice a year in the shell-shaped Piazza del Campo.

San Gimignano, often called “Medieval Manhattan,” was founded in the 3rd century BC. Its skyline was once dotted with 72 tower houses—symbols of wealth and power built by noble families during the 12th and 13th centuries. Today, 14 towers remain, giving the town its iconic silhouette.

The area is also known for Vernaccia di San Gimignano, a crisp white wine celebrated since the Renaissance.

Lucca

Lucca is known for its beautiful medieval architecture, historic city walls, and delicious cuisine. Visitors to Lucca can explore the city’s many narrow streets and alleys, visit its churches and palaces, and stroll along the city walls.

One of the most popular attractions in Lucca is the Torre Guinigi. This tower offers stunning views of the city and the surrounding countryside.

Lucca is also known for its delicious food, including its famous buccellato, a sweet bread made with anise and raisins.

Onwards to your cruise port

Leave Tuscany behind, as it’s time to head to your port of departure. Whether you’re joining a cruise from Ravenna, Venice, Trieste, Rome, or another port, there are several transportation options to get you there. If you travel by train, Florence has excellent connections to major cities throughout Italy.

Alternatively, you can arrange a private transfer or hire a car to get you to your port of departure. Just allow plenty of time to get there and check in for your cruise.

And don’t forget to savor your last moments in Tuscany by enjoying a leisurely breakfast or taking one last stroll through the city before you depart.