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  • Writer's pictureTiffany Eastham


Italy is one of the most incredible countries in Europe... and probably the world. I may be biased because I am Italian, I've lived and studied abroad there, and have traveled there more than any other country.

But, Italy has it all - an extensive food and wine culture, rugged northern mountains, rolling tuscan hills, cliff-side towns, golden beaches, tropical islands, and the list could go on. Not to mention some of the most iconic landmarks and cities in the world (ahem, see my earlier blog on Rome). Italy is so diverse, both in its landscapes and cultures. What you find in southern Italy is far from what you'll experience in the north. Due to the significant amount of diversity within Italy alone, this blog will focus on the amazing region of Tuscany (with a few little extras thrown in).

1 | FLORENCE (Firenze)

Florence is the capital city of the Tuscany region and is often called the "Cradle of the Renaissance" for its important role in that time period. It was home to many prominent Renaissance artists including Leonardo da Vinci, Michelangelo, and Raphael; as well as the great astronomer Galileo.

So where should you eat? What to see and experience? How do I even begin? I guess the real question is, how much time do you have?? I would recommend at least two to three full days in Florence.

The city's iconic red roofed dome (il duomo), Santa Maria del Fiore, was completed in 1436, and is still the world's largest brick and mortar dome today. There will undoubtedly be a long line to get inside, but to save you some time, the outside looks better than the inside. Get your pictures of the exterior, and forego the more bare interior.

Check out the Uffizi Gallery. It is one of the greatest museums in the world, displaying works by Leonardo da Vinci and Michelangelo, among many others. Definitely buy tickets in advance to get a time slot. Depending how much you want to see, this could easily take several hours up to a full half day, so just keep that in mind. Visit their website here.

And of course, there's not a statue more famous than Michelangelo's David in the Accademia Gallery. When I was there, no pictures were allowed, and the security guards prowling around made sure to yell, "NO PHOTO" as loud as they possibly could into the echoing gallery. Probably just to extra shame any tourists attempting to be sneaky. But you know who was sneaky and didn't get caught?

And again, reserve tickets in advance with a time slot. It'll be worth it once you see the line of tourists waiting outside to get in. Book tickets here.

Something else to see that isn't a major tourist attraction, is the Santa Croce church. This modest cathedral is a little off the main path, but not by much, and it holds the actual tombs of Michelangelo, Galileo, Machiavelli, and many other illustrious Italians. Dante's tomb is also here, though it is empty because he was exiled from Florence.

Michelangelo's tomb is shown here with beautiful, but interesting purple marble tones.

For the absolute best view of Florence, head to Piazzale Michelangelo. The panoramic shot as the cover photo is also taken from this lookout.

The stairs to get there really aren't too bad. It takes a little work, but it's well worth it. There are a couple cafe's at the top if you need a refresher, but there are also plenty of gelataria's on your way back down :)

Another reason to climb to this piazza is for La Loggia, the absolute best restaurant in Florence, in my opinion - and obviously with the best view in town, too. Make reservations here.

Where to stay? I prefer the area along the Arno River and near the Ponte Vecchio. We stayed at the incredible and quirky Hotel Torre Guelfa, just a corner away from the Ponte Vecchio. We were able to get the exclusive suite with a terrace at the very, very top of this old tower hotel. You can't avoid stairs when it comes to Italy, but it really just adds to the old world charm.

Book a room directly with them here.

A few other things to see include walking across the Ponte Vecchio (literally meaning old bridge), taking a trip to the Boboli Gardens to learn all about the Medici family and see some of the prettiest grottos and gardens around, and wander through Italy's oldest pharmacy, the Santa Maria Novella Farmacia.


Siena is my favorite Tuscan town. It's where I lived and studied for a summer many years ago, and I have gone back to visit almost every time I pass through Italy.

Siena has many charming qualities and landmarks to see that you may find in larger towns or even cities, but it's clean, quiet, and has that "just right" amount of small city bustle without being obnoxious or overwhelming. No cars are allowed inside the old city walls, which I think really makes a difference. It's very much a walking town.

Head to Piazza del Campo (shown above) for one of the most famous town squares in all of Tuscany. Be sure to climb the tower for breath taking views of the surrounding Tuscan countryside.

This is also where the famous Palio takes place twice a year in July and August. It's a two minute long race (at the most) around the piazza where jockeys and horses from the different contrade (districts) compete for the title. It is a crazy site to see. People travel from all over to watch it and go NUTS with celebrations. I waited eight hours out in the August heat to secure a spot right along the fence. At 20 years old, I thought it was a great idea! Not so much now :D

Be sure to visit il duomo di Siena. The marble detail on the exterior (and interior) is unmatched. My husband and I actually got married in Siena, and waking up at 5am for a photo shoot around the town before the streets and squares were flooded with people is a great idea (and at any destination you visit to get those serene shots).

Thanks Angela, at Angela Kelly Design for the stunner shots.

Other things to explore in Siena include finding the 12 original gates to the walled city, walking around the perimeter of the ancient fort protecting the city (Fortezza Medicea), and listening for the bells of Santa Maria della Scala (and take a stroll inside for some amazing stained glass windows). Siena also has some of the best shopping. The main walkways (and plenty of side streets) host local galleries with art for sale, olive wood kitchen utensils, linens, leather purses and shoes (OMG), ceramics, and plenty more. For some additional fun, visit their local torture museum (seriously, it's interesting), and go down into the crypts of a former Renaissance hospital, Percorso Antico Ospedale.

For the best Tuscan dinner with the best view of the duomo lit up at night, eat at Pizzeria Ristorante di Nonno Mede. You won't be disappointed. I've had everything from their pizzas, to pici cacio e pepe (a local, signature pasta dish of Siena), and gnocchi. It has all been exceptional.

We have stayed at Hotel Chiusarelli each year we return to Siena. It is within a 5 minute walk from the central bus station (Piazza Gramsci) where you will likely arrive, and is also within a 5 minute walk to Piazza del Campo. The rooms are good, they have a great restaurant, and their prices have always been very reasonable. See their website here.

Siena is also a great, budget-friendly home base location for day trips to other nearby towns, including many of the following recommendations you'll see further down the blog.


This medieval, walled town was strategically built on a natural hillock by the Sienese in the early 1200's as a front line defensive fortification during their war against Florence in the Middle Ages. Monteriggioni was also famously mentioned in Dante Alighieri's Divine Comedy.

Monteriggioni is a perfect day trip from Siena, being only a 20 minute drive and easily accessible. The town inside is so quaint with some simple restaurants and cafes, a few piazze (town squares), and miles and miles of Tuscan countryside views. The highlight of visiting is definitely climbing up and walking the perimeter of the walls. You get a glimpse of just how perfectly placed this medieval fortress was in securing the surrounding areas from attacks.

4 | PISA

The city of Pisa is also a great day trip. This gives you plenty of time to see the iconic landmarks, without having to commit to booking a hotel for an overnight stay.

Of course, Pisa's most famous structure is the leaning bell tower. In the 12th century during its construction, it was meant to be the tallest tower of the age, but due to some structural and architectural mishaps, it didn't quite reach that. The city is known, now, for its soft subsoil, which ultimately led to the tower's increasing lean over the years.

And yes, you can still climb to the top despite its unstable appearance! The tower is closely and constantly monitored, and has been fortified for stability as much as possible. Still slightly unsettling, though...?

Don't forget to see the Cathedral, Baptistry, and prestigious cemetery that also share the "Field of Miracles" where the leaning tower... leans.


Carrara is a small town in Tuscany known for its white and blue-gray marble that has been quarried here for centuries. It has a few churches and cafes, but the prime site seeing location has to be the mountain with which the town sits.

We got to don some hard hats and take an off road vehicle into the center of the mountain where marble is being excised and exported daily all over the world. This location is, in fact, where Michelangelo sourced much of his marble for sculptures.

Carrara marble has also been used since Ancient Rome. Just look at the Pantheon, and many other sculptures and structures of the Renaissance period. In addition to its marble quarries, Carrara also hosts a handful of academies of sculpture and fine arts.

It's such a unique experience, and not a town on most tourists' radar. I would highly recommend a day trip here in addition to your other Tuscany experiences.


Assisi is one of the best-preserved medieval towns in Italy, and the world. In fact, the entire town itself has been deemed as an UNESCO World Heritage site because of the amazing array of frescoes (and art in general), as well as historically significant buildings, such as the Basilica di San Francesco (St. Francis).

As the birth and death place of one of Catholicism's most venerated saints, St. Francis, don't be surprised to see pilgrims making the trek to this location, as well as monks dressed in traditional robes wandering the town.

Construction of the famous Basilica began immediately after St. Francis' death in 1228, but his remains were hidden in an unknown final resting place for 600 years before being discovered in 1818.

Assisi is a postcard-ready town. It can be easily seen in an afternoon, but allowing a full day to wander around all the sites and scenery shouldn't be missed.


You may have heard of Montalcino before, but can't quite place it? Are you a fan of wine? Fine, Italian wines? Then chances are, you've sipped a red and luscious Brunello at some point in your life - the famous vino that comes from only this region in Italy.

Another classic Tuscan town, set on a hilltop and perfectly fortified with a walled, medieval fortress. But don't overlook it! Montalcino is breathtaking with landscapes set in the Val d'Orcia National Park.

Any day in Tuscany is a beautiful day, and Montalcino is no exception.

But back to the wine. This town has been made famous strictly because of the special Sangiovese grapes that are used to make the Brunello, and it is a meticulous process. The Brunello must age for a minimum of five years, with two of those years spent in an oak barrel before even a mere thought of sampling it can take place.

I lean more towards an instant gratification type of person (I'll pass up a baking recipe if I have to wait 60 minutes for something in the oven), so my point being that this wine is thoughtfully crafted with an exceptional amount of patience to uphold its prestigious status.

Step into any wine tasting shop along the small and charming streets, as there are plenty, to get a taste for yourself. And most, if not all, places will ship bottles home for you, so there is no excuse not to buy a couple, or six, bottles of famous Brunello from the heart of where its produced!

And better yet, visit a local family's winery to get that authentic experience. Walk through the rows of grapes, step down underground into the cool cellar stocked full of barrels, and of course, end with a tasting paired with bountiful samples of cheese/olive/prosciutto platters.

Be sure to also visit the dominating Rocco, or fortress, constructed in 1361. The views are unmatched, and it has essentially remained unchanged and intact since those medieval times. In July, it also hosts a Jazz & Wine Festival that should be on your list if you happen to be visiting during that time.

Overall, Montalcino makes for an excellent day trip from Siena, if you choose that as your home base.


I have fond memories of wandering around Castellina. Situated perfectly between Florence and Siena, it's truly an Italian gem to see and experience.

In June, the Tuscan hillsides were in full, lush bloom; and every charming street, doorway, and window in Castellina was covered in ivy vines and vivid flowers in those famous Italian terra-cotta pots. The town was striking, and almost seemed fairytale-ish despite the medieval tunnels throughout the town and imposing fortress.

Perched, of course, on top of a hill, the views of the surrounding Chianti countryside just can't be compared to anywhere else.

Castellina has some interesting history dating back to its Etruscan roots. Be sure to check out the Museo Archeologico del Chianti Senese to learn more about its history.

Additionally, the town is known for Via delle Volte, a tunnel-like medieval passageway that now holds romantic dinner spots, unique wine bars, and electric, handmade art.

The windows throughout that once provided natural light to the darkened street, now provide you with glimpses of the picture perfect surrounding area.

A MUST-DO experience when visiting Castellina is to have lunch and sample wine at Sant'Agnese Farm & Boutique Winery. Check them out here.

Perhaps the best winery tour and tasting experience I've had in Italy, truly. Their farm is stunning, as are their family wines, olive oil, and 30-year-aged balsamic vinegar. It has been six years since I've visited this place, and I still think about it often.


There you have it, eight of my favorite towns in central Italy. I have more exploring of this region to do myself, but so far, each town that I have visited has not disappointed. I mean, come on, it is Italy.

And additionally, honorable mentions to both San Gimignano and Pienza should also be known as great towns to visit in this region as well. Especially if you're into cheese and golden hour glowy viewpoints like this one, check them out.


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