Roamin’ Around Tuscany

Italy has a lot of amazing places to visit, but Tuscany is in a league of its own. Here is a road map of some must see cities and towns to visit while you explore this gorgeous region.

When most people think of Italy, they tend to think of pizza, pasta, vino, and of course the many landmarks from the canals of Venice to the colosseum in Rome. For me, there is no better place than the rolling views and sunsets of Tuscany. I may be biased since I was born in Pisa, but every time I return, I find more hidden gems all throughout this region.

Visiting the larger cities allows you to capture the rich history of Tuscany, but the beauty of Tuscany lies in its small towns on your way from one city to the next. I’ve put together a little road map to get you started on your trip throughout Tuscany.

Map of Tuscany
(All time allotments are driving times from Vicopisano)

Where to start? Vicopisano!

A short 30 minute drive east of Pisa you will find the adorable little medieval town of Vicopisano. I would recommend that you stay here while spending a few days (or weeks even) exploring Tuscany. It is a quiet town with lots to do from hiking, wine and olive oil tasting, cooking classes, and tons of markets on the weekends. You can find the most authentic, chic, and charismatic rooms or even houses to stay in that makes it feel like you are returning home after a day of exploring. Stay in a tower house at Casa Colomba or the little 1 bedroom studio at Nido Bianco – you can’t go wrong! During your stay in Vico, learn about the history of its once many towers and the ancient books that still remain in the tower house or take a stroll in the Tuscan countryside as you pass cyprus trees and poppy flowers.

View of Vicopisano
View of Vicopisano from winery and olive oil makers

Iconic Pisa

(25 min drive)

Pisa is a quaint city with the river Arno flowing through it dividing the city into east and west. On the west side lies Miracle Square or Piazza dei Miracoli. Imagine walking under a thick century old stone wall where on the other side you encounter an immense pearly white marble tower (that just so happens to lean), with lush green grass and a massive marble cathedral – it will appear as if you have stepped into a painting. The square, especially the tower, never ceases to amaze me. The grandeur of the white marble is something that takes you by surprise. You cannot leave Pisa without attempting to find the perfect place in this grand square to take your perfect picture with the leaning tower to make everyone back home jealous. Get creative with it!

Leaning Tower of Pisa
What kind of iconic picture can you take?

If you want to wander the city to get a different vibe, walk along the Arno and see where the locals hang out. If you’re lucky enough to plan around it, visit Pisa in June during the Luminara di San Ranieri (June 16-18) to see a century old tradition where every bridge and building along the river is lit up for 2 days by candlelight. It is an evening that you will not forget!

Luminara di San Ranieri
Luminara di San Ranieri along the Arno

Head to the beach – Marina di Pisa

(35 min)

You can’t go wrong with the food in Italy, but for some of the best seafood, head to Marina di Pisa. This is a must for some delectably fresh seafood caught that day. Remember Italy is all about the food, so before you dive into the platters of calamari and anchovies…yes anchovies, head to Sunset Cafe to watch the sunset over the horizon while you enjoy an aperitif and nibbles. Sit on bamboo mats on the sand and watch the golds, pinks, and oranges paint the sky that lead you into the evening.

Bike around Pisa’s old medieval rival, Lucca

(40 min)

Meet Pisa’s medieval rival – Lucca. The unshakable solid wall that once used to protect the city against invaders still stands and provides visitors an above view of the city if one chooses to walk or bike around it – which I highly recommend. Besides the beauty of the trees that line the path and listening to Italians carry on conversations as you pass, the beauty also lies with the city itself. From the red roofed houses to cathedral towers to gardens sprinkled throughout the city, you get a glimpse of how life may have been centuries ago. Once you have biked around the walled city, you have earned yourself a plate of pasta. Venture to the city center square, Piazza dell’Anfiteartro. You will enter through one of four gateways that leads you into the square, actually elliptical in shape, which is surrounded by a ring of buildings that once used to be an old Roman Amphitheatre – an enchanting backdrop while eating a lovely Italian meal in the open piazza.

Biking along the wall in Lucca
Biking along the wall in Lucca

Visit some of the most famous landmarks and paintings in Firenze

(1 hour)

No trip to Tuscany would be complete without a visit to the dynamic city of Florence; a major city during the Medici family years. You can take a walking tour of the city that gives you insight to buildings and secret passageways that the family once used to travel unbeknownst to the people and artisans along the Ponte Vecchio. While on Ponte Vecchio stroll by the stalls to gaze at the ornate gold jewelry and lavish gems that line the bridge. Wander and get lost in The Uffizi museum to witness the masterful paintings of da Vinci, Michelangelo, Botticelli, and so many more. The building itself, once a palace, is its own art piece from floor to ceiling. One important statue that is not located inside the Uffizi is the statue of David – perhaps the most famous statue in the world. You can first marvel at this statue just outside of the Uffizi in the piazza; just be aware this not the original David. The real statue is safe in another museum, Galleria dell’Accademia, protected from the elements.

Piazzale Michelangelo
View from Piazzale Michelangelo

Perhaps one of the best views of this city, the center of the Renaissance age, is from the Piazzale Michelangelo, where you can see the Duomo and all the red terracotta roofs that surround it. Best to take this in at sunset, as Italy has some of the most beautiful and divine sunsets I have ever seen.

Walk back in time in Siena

(1 hour and 40 min)

One of my favorite spots to visit is Siena. There is something unique and different about it compared to its neighbor, Florence. No matter which road you take, all roads lead to the Piazza del Campo. This is the famous square where The Palio occurs every year on July 2nd and August 16th. Most of the year you will find the Piazza to be a quiet open space to grab a cappuccino or a pizza and people watch. On the days of the Palio, it is transformed into a medieval race track with sand, as horses race around the square to determine which neighborhood wins the victory bragging rights for the rest of the year. Each neighborhood is represented by a mascot and a distinctive flag, so as you wander the streets of Siena you will see all sorts of mascot memorabilia for sale. What better way to become a part of the festivities than finding the mascot that speaks to you and join in on the fun!

Castellina Chianti

(1 hour and 20 min)

Besides Vicopisano, Castellina is probably the smallest town on this list, but well worth the visit. It’s a sleepy town filled with store fronts selling genuine leather purses and belts, authentic wood cutting boards, and much more. There are unsuspecting tunnels that you can stroll through to go from one end of the town to the other, a museum in a castle, and a church with an early 15th century fresco of Madonna with Child. It’s so small that you can easily combine this visit with Siena while you treat yourself to yet another deliciously creamy gelato.

Visit Roman Ruins in Volterra

(1 hour)

This is my most recent find and one that I would like to explore further. Volterra sits upon a mountaintop and overlooks the wide expanse of the countryside below. It is a city that dates back to 7th century BC and still has evidence of Roman influence from the Roman Theatre ruins and Parco Archeologico. The Roman Theatre is a spectacle in itself as you can still see several rows of seating that lie against the hill for people to watch and listen to music or theatre, while the park still has water basins that look like tubs strewn along various parts of the green lawn. Be sure to bring quality footwear, as there are many steep hills you may be venturing over.

Walking into Volterra

Stroll through the city of towers – San Gimignano

(1 hour and 10 min)

All medieval cities once had a variety of towers to keep the city safe, but due to war or simply urban renewal, many towers have been destroyed over time. Luckily, San Gimignano has been able to safeguard 14 of their towers; hence, its nickname of the City of Towers. Despite the fact that the town is a busy tourist attraction, you can still witness many locals living their day to day life. You will see their laundry hanging to dry or old men sitting on a doorstep together enjoying an espresso and probably talking about the most recent soccer match. I do recommend arriving in town as early as possible though, because once the afternoon arrives, so do all the tour buses. Luckily there are some hidden streets not ventured by many, so you can still get away from the crowds if you’re willing to get lost in adventure a bit. Besides eating at the Gelateria Dondoli which has the claim to fame for having the “Best Gelato in the World” in Piazza della Cisterna, a must see spot is Punto Panoramaico to gaze out over a classic Tuscan view and to watch the sun slowly rise or set over the towers.

Looking out upon the Tuscan countryside from Punto Panoramaico
Laundry in San Gimignano

There is so much to discover in Tuscany that one trip won’t ever be enough. Whether you have a home base, like in Vicopisano, or if you take up a new apartment every few days, the memories and beauty of Tuscany will never fade; if anything, they will only have you coming back for more.

Buon Viaggio!

Author: globetrottingalex

Hi! My home base is Tampa, Florida, but have a passion for traveling. I have been fortunate enough to have traveled from such a young age, and I haven't stopped since. A few years ago I decided to do my first solo trip - it was the best decision ever! Getting to experience new cultures and new cities is when I feel at my ultimate best. This world of ours has so much to offer, we just need to get out there and see it. It's time to share my experiences and stories with YOU! Wander often 💜Always

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