Exploring Italy from Venice to Florence

Written by Valerie T.

When former Classic Travel group specialist and my former office-mate asked me to visit during her extended backpacking trip, I knew it had to be Italy. After helping to organize so many Italy trips for clients, I was excited to experience it for myself.

I decided to fly into Venice and out of Florence saving Rome and southern Italy for another trip. We managed to visit Venice, Cinque Terre, Pisa, Tuscany, and Florence in 10 days.


Piazza San Marco

As soon as we settled into our accommodation, we headed directly to Piazza San Marco, home to some of Venice’s most well-known landmarks.

Basilica di San Marco lies at the eastern edge of Piazza San Marco. Many mosaics, particularly gold mosaics, cover the interior walls giving the church a nickname of Chiesa d’Oro (Church of Gold).

To its left is the Doge’s Palace, a structure with a surface of pink marble. You can purchase tickets to enter and explore on your own, but I recommend booking the Secret Itineraries Tour. The tour covers the rooms and chambers where the delicate work of some of the most important bodies in the Venetian administration was carried out. This tour should be booked in advance as it sells out weeks in advance.

The prison is connected to the Doge’s Palace by the “Bridge of Sighs”. It is said that as prisoners are being taken to their cells, they catch one last glimpse of Venice and sigh.

Also located in the piazza, the Campanile di San Marco is a bell tower that provides a wonderful view of the city. It costs 8 Euro per person to go up via elevator. There is a plaque up in the tower that roughly translates to, “From here, Galileo Galilei with his telescope on August 21, 1609 widened the horizons of man.”

Among the cafés and shops lining the piazza, Caffé Florian, established in 1720 and still serving, is the oldest café in the world. The café boasts well-known patrons throughout history including Casanova, Lord Byron, and Charles Dickens.

Grand Canal Cruise

A visit to Venice is not complete without a cruise of the Grand Canal. We made our way to Piazzale Roma, which is the bus stop at the entrance to the islands of Venice, and where you catch the No. 1 ACTV vaparetto for a slow, but scenic, cruise of the Grand Canal. Rick Steves offers a free audio tour that you can follow along with and learn more about what you are seeing as you pass by.

If you can, it’s best to sit in the open-air area at the front or back of the boat. We did our cruise after dark, which made for some beautiful views, but I would like to do it again during the day. If you do the cruise after dark, be sure to catch it at Piazzale Roma cruising toward the lagoon versus the other way around to avoid boats crowded with commuters.

Exploring Venice

My favorite thing to do in Venice was to get lost. We took different routes every day (not always on purpose) and were never disappointed with the views we came across from opulent churches to charming residences and beautiful canals. As you walk further and further away from Piazza San Marco, the noise from the square grows faint until it’s completely gone and all you hear is the lapping of water on the walls of the canal and the sound of a gondolier paddling by. This is the Venice I was hoping to experience and it was even better than I expected.

Cinque Terre

From Venice, we took the train to the Cinque Terre. Cinque Terre means five lands. It is a string of five rugged seaside villages on the Ligurian Sea in the Italian Riviera. From south to north, the villages are Riomaggiore, Manarola, Corniglia, Vernazza, and Monterroso. We stayed in Riomaggiore, but visited all five villages via local train and hiking. Hiking is one of the main activities in the Cinque Terre and there are trails between the villages.

We hiked the trail from Monterosso to Vernazza and it was difficult with countless stairs and uneven footing, but the views (and lemon gelato at the end) made up for it. It takes about 2 hours depending on your fitness level. Bring snacks, water, and comfortable shoes!


We decided to stop in Pisa for a couple hours on our way to Florence because why not! The train station offers a baggage holding service for 5 Euro per bag. It’s actually quite a walk from the train station to the Leaning Tower of Pisa, so I’m glad we took advantage of that service. We stopped for pizza before making our way to the infamous landmark. The tower is leaning quite a bit more than I thought from seeing it in photos. We took some obligatory tourist photos with the tower and had a laugh watching everyone else posing for photos too.


We arrived in Florence with only enough time to have dinner before heading to bed to rest up for our full day trip to Tuscany the next day.

Our first stop the next morning was San Gimignano, which offered amazing views of the Tuscan countryside.

We were told we must try the gelato at Gelateria Dondoli, which holds many “world’s best” titles. I had two flavors together, caramel and chocolate, and it was amazing!

The tour included wine tasting and lunch at an 18th-century winery in Chianti, Casafrassi. Lunch included antipasti, bruschetta, spaghetti alla bolognese, and panna cotta.

Next we went to Siena, which is a very interesting town made up of 17 districts, all named after animals or symbols. Our tour started in the she-wolf district where we learned that Siena houses the oldest surviving bank in the world. We made our way to Piazza del Campo, where Palio di Siena, a twice-a-year horserace takes place around the edges of the piazza. After the tour, we had some time to explore before making our way back to the meeting point for the final stop of our tour.

Monteriggioni is a medieval walled town located in the province of Siena. We learned that it is referenced in Dante Alighieri’s Divine Comedy and is featured in the video game Assassin’s Creed.


Galleria dell’Accademia di Firenze

Visiting the Accademia, which houses Michelangelo’s David, is a must. I highly recommend purchasing skip-the-line tickets because the line can be hours long. David is a 17-foot marble statue and is a masterpiece in Renaissance sculpture. It takes your breath away in person.

In the hallway leading up to the David, some of Michelangelo’s unfinished works are featured which was very interesting because it allows you to see the texture of the marble as it is in the process of being sculpted and gives you an idea of how difficult it must be.

Market Tour and Cooking Class

One of the highlights of our trip was a tour of Florence’s Central Market followed by a cooking class with ingredients purchased at the market. We met our chef, Alessandro, at the market and he explained a lot of the ingredients we saw and told stories of growing up collecting, cooking, and eating the ingredients.

We stopped at a shop in the market and tasted oil, butter, and honey infused with white and black truffle. We also tasted different ages of balsamic vinegar, biscotti, wine, and limoncello.

We left the market and followed Alessandro to the cooking school, donned our aprons, and he helped us prepare an amazing meal of bruschetta, handmade pasta with tomato sauce, meatballs, and panna cotta. The food was great and the experience was so much fun!


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