This post was contributed by travel blogger, Caitlin Basilio. To learn more about Caitlin and her blog, Caity in Wanderland, see her bio below.
Siena is in the heart of Tuscany, located near numerous destinations and options for fun-filled weekend trips. During my study abroad program through Lewis & Clark College, hosted by Siena Italian Studies, I was not allowed to travel outside of the country during the program. I took this “rule” as a chance to take advantage of my immediate surroundings - the one and only, alluring Italian region of Tuscany.
While in Siena, I saved all of my money by sacrificing going out for drinks with friends during the week, shopping only for necessities, and eating at home with my host family, all in order to travel during the weekends. If you’re currently living in Tuscany or visiting this charming region and are looking for affordable weekend getaways, the following is a list of the best weekend trips in Tuscany to take by train.
Florence
Located only about an hour north of Siena, Florence is a no-brainer. Round trip tickets start at around 8€, and you have an unlimited amount of options once you arrive in Florence. The Uffizi and the Accademia Gallery are great to visit, whether you’re one for art and history or you live with a “you’re only here once” mentality. Both are priced at 6,50€. In the Uffizi, you can admire the famous works of Masaccio and Giotto, while the Academia Gallery is home to the world famous David statue by Michelangelo. Simply strolling through Florence is an experience within itself. If you would rather explore, walk through Ponte Vecchio, check out the most mesmerizing Duomo, shop your way through all of the markets, and eat!
San Gimignano
My classmates started referring to San Gimignano (San Jimmy-ya-no) as “San Jimmy Johns” due to the Italian way of pronouncing the letters “-gn” together. Located about an hour bus ride away from Siena and up high on a mountain top, this town is the perfect epitome of Tuscany and the best place to relax for a while.
Whether you choose to explore its ancient structures, or just sit back and enjoy the view, SG is so great, you might need to visit twice (I did). SG is also home to the world’s best gelato, so you really can’t go wrong. Make sure to try the Vernaccia flavor - made from SG’s very own Vernaccia grape which they also use to make white wine.
Pisa and Lucca
If you’re a first time visitor to Italy, chances are the Leaning Tower is on your list of attractions to see. Other than the Leaning Tower, check out the 11th-century Duomo. Unless you want to deal with the countless tourists at Pisa, venture on over to the nearby town of Lucca. I added Lucca to this trip because this town will make your trip to Pisa worth it. Offering cobblestone streets and elegant palaces, and surrounded by its Renaissance-era walls. Take a bike ride on Lucca’s ancient city walls, roam the piazzas and hangout at a cafe to enjoy the view and talk to the locals.
Cinque Terre
The last two stops on my list are not in Tuscany but they are easily accessible. The weekend I visited Cinque Terre was the weekend that the Italian coast stole my heart. I stayed in Riomaggiore with five friends in an awesome hostel which had its very own balcony! During our time there, we explored as many towns possible and really just loved walking along the coast. We even had lots of time to relax on the beach and read while laying out beneath the sun.
We got to visit four out of the five towns that make up Cinque Terre – Riomaggiore, Monterosso, Corniglia and Vernazza. While in Monterosso, I had the experience of jumping into the freezing cold Mediterranean Sea. We also played frisbee along the shore, searched for sea glass, and climbed rocks. Cinque Terre is the perfect place to visit without a plan and to just take everything in stride.
While in Vernazza, we hiked to Corniglia. You need to go on at least one of the hikes! This was the only open hike while we were there and I’m just grateful to have been able to go on one. Hiking along the Italian coast is an incredible and breathtaking journey and will definitely make you feel small and realize how lucky you are to be in such a beautiful place. Hikes are available for all levels of hikers. Our trip back to Siena was also an adventure! Cinque Terre would not have been completely Italian without a couple of train strikes.
Venice and Verona
A lot of people complain about Venice being too crowded with tourists but that was not the case for me. I visited during February - sure it was pretty cold, but it was definitely worth seeing while close to no one was there. Venice is where I learned to get lost. Even with a map, all of its narrow streets and alleys are bound to confuse you. After stressing out about getting lost, I realized that there was no point to getting upset and that I was better off appreciating my time there.
I also spent way too much money while in Venice - street markets will do that to you. I became obsessed with Venetian glass and wanted to eat everything from Nutella crepes to dinner at fancy restaurants. This is not to say that Venice on a budget is impossible because there are a lot of free things to do there too.
We only had a few hours in Verona so the main attraction we visited was Juliet’s (yes, from Romeo & Juliet) house. My romantic expectations were crushed when I learned that the balcony was made out of part of a sarcophagus. Gross! Other than that there is a pretty wall full of lovers’ locks, similar to Pont des Arts in Paris- but I don’t know why anyone would want a romance like Romeo and Juliet’s.
Have you been to Tuscany? Are you planning on traveling there soon? Share your comments, stories and questions below!
Caitlin is a journalist from Hawaii who is obsessed with travel & food. She is currently based in Indianapolis with plans to move to Chicago this summer in order to begin working toward her master’s degree in journalism. Caitlin’s work has been published in The Midweek, Pink Pangea, Thought Catalog, and more. A collection of her work can be seen on her blog, where she mainly writes about her experiences studying abroad and growing up in Hawaii. She is easily engrossed by culture and is a huge lover of red wine & pizza.
If you are interested in guest blogging for The Pin the Map Project, visit the guest post submissions page here.

Chiara Bond says
Love this post! I’m Italian and I’ve always spent my summers in Tuscany, so it’s really nice to see what a foreigner thinks of the dearest places I keep in my heart!!! I also just wrote about Florence and Pisa (and Rome) in my latest post, the blog is linked in my profile, I’d love for you to check it out 🙂
Thanks for sharing and very cool to get a local’s perspective on this post!
Cheers,
Nikki
I am planning a trip to Europe in June! We are going to Paris, Amsterdam, Venice, Florence, Cinque Terre, Tuscany, Rome, and Greece! I can’t wait! Thanks for the tips!