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

Florence and the surrounding Tuscan countryside is a place that deserves to be savored slowly, over at least a few days. While it may be tempting to try and see everything in a day on a shore excursion during your cruise vacation, this approach may leave you disappointed, with a distinct feeling that you have missed out on all there is to experience. Plan, instead, to visit Florence and Tuscany either before or after your cruise.

A Mediterranean or Greek Isles cruise starting from one of Italy’s main cruise ports is an ideal opportunity to extend your vacation. Here we have a perfect 4-day adventure in this fantastic region that is high on everyone’s bucket list.

Tuscany and its Renaissance capital Florence is unique, and breathtakingly beautiful. It is also far from all major cruise ports and, therefore, an ideal place to book a hotel and stay longer and see at a leisurely pace before or after your cruise.

Your starting point is Florence

Florence is home to some of the world’s most iconic art and architecture, including the Uffizi Gallery, the Accademia Gallery, and the Duomo di Firenze.

Rushing through these attractions in a day is not only exhausting, but it also means you miss out on the many other charms of the city, such as its beautiful parks, cosy neighborhoods, and delicious food.

Instead, we recommend taking the time to explore Florence on a leisurely pre- or post-cruise adventure. Book a hotel in the town center and this way, you’ll have plenty of time to see the sights, savor the local cuisine, and soak up the city’s unique atmosphere without feeling rushed or overwhelmed.

Tuscany is a region in central Italy known for its beautiful landscapes, historic cities, and world-renowned wines. We suggest renting a car (rental offices are close to the main train station in the center), but if you prefer, there are many day trips and tours to choose from with our trusted travel partners, such as Viator or Tours by Locals.

In this article, we’ll outline the perfect itinerary for exploring Tuscany, including the city of Florence and wine tasting at some of the region’s best vineyards.

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 that is a masterpiece of Renaissance architecture. Make time to do the climb up 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 tickets to be sure of 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. The menu features 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 dishes such as 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 and heading out to the countryside to discover some of Tuscany’s best wineries. In this article, we’ll provide tips on pre-booking a car, where to collect it, and what to think of when driving in Italy.

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

Before you arrive 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.

You can book your car rental online, for example, with rentalcars.com, and we recommend comparing prices and reading reviews to find the best deal. 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. A good car rental company will be able to provide all this information to you.

Collecting your rental car in Florence

We recommend that you 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. Be sure to check the opening hours of the rental office and plan your pick-up accordingly.

General tips for driving in Italy

Driving in Italy can be an exciting but also a rather 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.
  • If you’re driving on the highways, you’ll need to pay tolls.

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

Exploring Tuscany’s vineyards

Once you’ve collected your rental car, it’s time to hit the road and explore Tuscany’s stunning countryside. There are many vineyards to choose from, 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.

Ternuta Torciana is another popular vineyard that offers wine tastings as well as cooking classes and truffle hunting experiences.

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

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

As you drive through the countryside, be sure to 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.

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 located about an hour’s drive south of Florence. If you’re renting a car, simply 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 take a local bus to San Gimignano.

For those of you not wanting to drive, there are many fantastic guided bus tour to Siena and San Gimignano from Florence. Expect a long day, however the experience will most likely stay with you forever. This is an exceptionally beautiful part of Italy. Some tours also include the medival town of Lucca.


Siena is a beautiful medieval town that is 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 that is now home to the Civic Museum. Be sure to climb the Torre del Mangia, a tower that offers stunning views of the city and the surrounding countryside. Another must-see attraction in Siena is the Siena Cathedral, a stunning Gothic cathedral that is home to works by Donatello and Michelangelo.

San Gimignano

San Gimignano is a beautiful hilltop town that is 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 that is surrounded by medieval buildings. From here, you can explore the town’s many narrow alleys and historic buildings, including the Collegiate Church of Santa Maria Assunta and the Palazzo del Popolo.

Remember to stop for authentic gelato at Gelateria Dondoli.

For stunning views of the town, be sure to climb the Torre Grossa, the tallest tower in San Gimignano.

History of Siena and San Gimignano

Siena and San Gimignano are both steeped in history and have played important roles in the regions development and culture. Rivaling Florence in its importance, Siena was founded by the Etruscans in the 6th century BC.

The city is known for its beautiful Gothic architecture, including the Siena Cathedral, from the 13th century.

Siena is also known for its famous, bi-annual Palio di Siena horse race held in the Piazza del Campo.

San Gimignano, on the other hand, was a small medieval town that was founded in the 3rd century BC. The town is known for its well-preserved medieval architecture. Famous, of course, are the soaring towers, that were built by wealthy families in the 12th and 13th centuries.

At the height of its power, San Gimignano had 72 towers, but today only 14 remain. The town is also known for its Vernaccia di San Gimignano. This white wine is produced in the region and considered one of the best wines in Italy.

Visiting Siena and San Gimignano in one day is a great way to experience the beauty and history of Tuscany. Whether you’re interested in art, architecture, or wine, these two towns have something for everyone. And with a rental car, you can explore the region at your own pace and take in the stunning views of the Tuscan countryside along the way.


Lucca is a charming city 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 take a leisurely 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.

With its rich history, beautiful architecture, and delicious cuisine, Lucca is certainly worth including in your itinerary.

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 for a private transfer or hire a car to get you to your port of departure. Just be sure to 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.

Meet the author: Sarah has created and booked hundreds of travel itineraries for thousands of customers during a career in the travel industry that spans 20 years. Having worked hand in hand with cruise lines, hotels, airlines and tour operators worldwide, she offers inspiring & detailed insights in the world of travel and tourism.

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