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Italy Overview - What Cities You Should Visit in Italy

Italy is bursting with beautiful and interesting cities to visit. That's one of the reasons that planning a trip to Italy can be so overwhelming...all the options!

To help make your itinerary planning a little easier, here's a little overview of some of my favorite Italian cities, regions and great things to do in each region:

See the Duomo in Milan Italy


Milan - Business hub (NYC of Italy) that's modern, mostly on time, home to incredible fashion and a beautiful cathedral. Not too many touristy sites.

Lake Como - Gorgeous serene lakes with sleepy towns and ferries that glide across the water. If you're looking for beauty and peace in Northern Italy, this is it!

Venice - A classic, there's nothing quite like it. Everything happens by bridge or boat. Absolutely worth a visit, unless you go in late July or August.

Amazing Experiences:

*Prosecco tasting, riding a gondola or vaporetto, enjoying the Italian aperitivo (happy hour), soaking in incredible fashion, seafood seafood seafood, seeing live glassblowing in Venice.

Brunelleschi's dome in Florence Italy


Northern Tuscany is the most well-known and tourist-oriented part of Tuscany. Everyone seems to fall in love with it, and you definitely shouldn't skip it!

Florence - beautiful international city that is the heartbeat of the Renaissance + Tuscan art and life, great leather shopping and shopping in general, and...Chianti, need I say more?

San Gimignano - a charming medieval town with lots of towers, a church with beautiful frescos and a delicious wine wine called Vernaccia.

Lucca - a peaceful walled city with delicious food and a slower pace of life, less tourists than Florence but not the same amount of art.

Pisa - Home to the leaning tower of Pisa, hub for flights across Europe, also a great place to eat and enjoy Tuscany without the crowds of Florence

Amazing Experiences:

*Hot air balloon ride, wine tasting in the countryside, cooking class at a private villa, driving through the countryside, visiting inspiring Renaissance art, sunsets, must-see classics like the David statue, Brunelleschi’s dome and the leaning tower of Pisa, sunsets over the Florentine skyline, amazing food

Wine tasting in Pienza Italy


Southern Tuscany is quieter and more natural than Northern Tuscany with adorable hilltop towns to explore like Montalcino and Montepulcinao and closer contact with the local life and culture.

Siena -The small, cuter and less crowded cousin of Florence with an iconic pizza, a famous horse race and cobblestone streets you can wander.

Montalcino - a small town with gorgeous views of the countryside, a little fancier and more geared towards tourists than Montepulciano.

Montepulciano - bigger and more lively than Montalcino, but still with great views and lots of wine to try.


Amazing sunsets with a delicious glass of wine, cute medieval towns, those classic rolling Tuscan hills that stretch for miles, peace + quiet, romantic romantic romantic, Pecorino cheese, the opportunity to speak more Italian, hot springs, amazing food

View of Amalfi Coast from Positano


The Amalfi Coast is a magical combination of breathtaking views, limoncello and Mediterraneansun-and-sea relaxation. Italians invented 'la dolce vita' and this is it!

Positano - The pearl of the Amalfi Coast perched right on the cliffs overlooking the Mediterranean Sea, a little pricey but absolutely gorgeous.

Praiano - A better value option to Positano, great views in a more local area.

Capri - An island with breathtaking views and prices and the famous Blue Grotto. Definitely worth a day visit by ferry.

Sorrento - A good home base, very convenient, but not quite as charming or blessed with views as Positano or Praiano.

Naples - Gritty but colorful and full of life. It has the best pizza as well an amazing underground system of tunnels and caves that were used during World War II.


Amazing orange and pink sunsets overlooking the Mediterranean Sea, exploring the ruins of Pompeii + Herculaneum, taking a ferry to the island of Capri, enjoying anything with lemons, drinking limoncello, eating top notch seafood, best pizza of your life, relaxing to the max!

Sunset in Praiano

P.S. There are also other great areas like Puglia, Sicily, etc. Those are not currently my specialities, but I can recommend an expert to help you plan for those areas!

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