Italy Vacation Ideas

Colosseum in Rome

Planning a trip to Italy? Need some Italy vacation ideas? Italy is a beautiful country full of delicious pasta to eat, beautiful piazzas to sit in and Roman ruins to wander. And of course, some of the world’s best wines! From the peaceful shores of Lake Como in the north to the busy food markets of Sicily in the south, there is so much to explore! You will want to return many times to experience everything Italy has to offer. Keep reading for ideas to get you thinking about your next trip to Italy, whether it is your first or your fifth!

Italy Travel: First Trip to Italy?

If this is your first trip to Italy, consider exploring the history of ancient Rome, the treasures of Renaissance Florence, and the watery wonders of Venice.   Must-sees are:

Florence-View from Piazzale Michelangelo, Italy Travel
Florence-View from Piazzale Michelangelo
  • Gazing at the Sistine Chapel
  • Wandering the ruins of Ancient Rome
  • Shopping the famous leather shops and markets of Florence
  • Seeing Florence from Piazzale Michelangelo, the best viewpoint in the city
  • Taking a gondola ride on the most scenic route through the canals of Venice
  • Taking a cooking class in Tuscany using fresh, local ingredients

Italy Travel: Ready to Leave the Crowds Behind?

While there are many top sights to see in Italy, make sure to take some time to see some less popular, equally appealing, and far less crowded parts of these beautiful places.

Wandering Through the Locals Side of Florence

Most people visit Florence and never set foot on the other side of the Arno River.  There are truly “two Florences” separated by the Arno and both worth visiting. Head over any of the bridges and explore the neighborhoods the locals enjoy with some of the best restaurants and a casual vibe. Don’t miss my favorite gelato spot, La Carraia. 

Want to learn some secrets of Florence? Click here to read more in my blog post.

*Tis’s Favorite Experiences: I love having a beer or two in a pub while watching the local football (soccer) team play. While the Italians love their vino, they will grab a pint when it is game time and cheer on their team. In Florence, the local team is Fiorentina. Check the schedule and head to the Friends Pub in the Oltrarno neighborhood to cheer them on. Grab a seat and watch the locals pile in at game time.

Montepulciano with San Biagio, Italy Travel
Montepulciano with San Biagio

Siena and San Gimignano have their charms and are worth a visit, but some of the less-traveled towns such as Montepulciano and Montalcino are well worth the trip. They are less packed and you may explore them at a more leisurely pace, all while taking breaks to taste some of the best wines in the world for much lower prices than you can get back home.

Eat Like a Local in Venice

Oddly enough, you may find it hard to get a truly tasty meal in Venice.  Many Italians will confirm this problem.  Instead, spend an evening wandering Venice eating the famous “cicchetti” or small bites for your dinner that are readily available if you just step out of the main streets and peak in the small wine bars, called “bacari”.  These are traditionally eaten standing at the bar while ordering a drink.

Italy Travel: Need more trip ideas? I have many!

Italy has so much to offer beyond the usual cities visited.  When making your Italy travel plans, consider jumping off the Rome-Florence-Venice trail and adding something different to your trip. Below are just a few options. Don’t hesitate to contact me if you want even more ideas! There is nothing I love more than talking about Italy, especially the less-traveled areas!

Blue Grotto, Capri
Blue Grotto, Capri

Naples and the Amalfi Coast

Make a quick stop in Naples to experience authentic pizza here in its birthplace.  Then head down toward Sorrento and base there or in lovely Positano.  From either, you can explore Capri home of the famous Blue Grotto, and historic Pompeii where you can walk amongst the ruins.

*Tis’s FAVORITE Experiences: Naples has somewhat of a bad reputation and in my opinion, not a deserved one. I love Naples. Naples gave the world pizza! What is not to love about that? I highly recommend spending at least a night in Naples. Yes, it is a big city and you do have to be careful but don’t miss some great experiences. I love walking around Via San Gregorio Armeno, or “Presepe Street”. “Presepe” is the Italian word for nativity scenes. Some of the merchants on this old street have been making the now world-famous presepes for generations.

After you finish shopping on Via San Gregorio Armeno, you must eat pizza in its birthplace! There are many options so don’t feel you must stick with the famous “Da Michele“. If you do choose Da Michele, just prepare for a wait and a simple choice, “Margherita or Marinara”! Neapolitans rarely order anything but a Margherita (cheese and sauce) or Marinara (sauce garlic and oregano) and those are your only options at Da Michele. I recommend getting both!

Riomaggiore View from the Sea- Tis Travels
Riomaggiore, Cinque Terre

Cinque Terre

In Italian “Cinque Terre” means “five lands”.  In this case the five towns are Monterosso, Vernazza, Corniglia, Manarola, and Riomaggiore. These are five fishing villages that were only accessible by boat when first inhabited.  All five remain traffic-free with the exception of the new part of Monterosso.  You may hike between the five towns or simply take the local train.

*Tis’s Favorite Experiences: I adore Cinque Terre…well when the massive crowds are not adoring it as well. When I first fell in love with the area people looked at me strangely when I mentioned it. Now that everyone knows about it, it is insanely packed in the peak months. It’s hard to enjoy the picturesque towns when you can barely walk down the street. Go in the offseason and you will have a much better experience.

Stay in Monterosso which has the old and new parts of town. You can walk between the two so choose whichever suits you best. At sunset, sit by the water in one of many cafes, facing south. The lights of the other towns will slowly start changing your view, turning the towns into twinkling dots on the horizon. It is magical.


Siena-View of Piazza del Campo, Italy Travel
View of Piazza del Campo, Siena

Tuscany is full of picturesque towns perched high on hills and full of friendly locals.  There is storied Siena, home of the famous Palio horse race, and San Gimignano which is known as the “Manhattan” of Tuscany for its many medieval towers.  There is also Cortona, of “Under the Tuscan Sun” fame which is a charming little town and a very nice choice to spend a night or two.

The region produces some very good red wines. Stop in Montalcino and taste the famous Brunello wine and Montepulciano to sample some Vino Nobile.

Bravio delle Botti, Montepulciano

*Tis’s FAVORITE Experiences: Everyone flocks to Siena for the famous Palio horse race that ends on the Piazza del Campo in the middle of the town. The jockeys are revered until they lose of course. Skip it. Head to Montepulciano for the not famous but much more exciting Bravìo delle Botti, a wine barrel rolling festival! The true test of strength must surely be where one rolls a heavy wine barrel up to the main piazza of a steep hill town instead of simply riding in on a horse.

Perugia Piazza IV Novembre, Italy Travel
Piazza IV Novembre, Perugia


Umbria is Tuscany’s less traveled neighbor and with no good reason.  It is just as picturesque and offers a bit more for your money.  Visit Perugia, a somewhat larger town with a beautiful historic center;  Assisi, where you can walk in the steps of St. Francis and see the famous Giotto frescoes at the Church of San Francesco;  and Orvieto, a quaint hilltop town with an ornately decorated Duomo. Don’t miss tasting the famous Perugina chocolates in their home of Perugia!

*Tis’s FAVORITE Experiences: While I am often a fan of visiting places in the off-season so you can really have them more to yourself, I highly recommend the off-peak month of October when visiting Perugia. In October the town hosts the Eurochocolate Festival. I highly recommend going on the first day of the festival so you can watch artists sculpt huge blocks of chocolate into works of art. How sweet it is!

Lecco View of Bell Tower, Italy Travel
View of the Bell Tower, Lecco

The Lakes Region (i.e. Como, Bellagio)

Ah, the lakes of Italy.  This picture-perfect region is the ideal place to soak up La Dolce Vita.  Enjoy breathtaking views in every direction, explore the beautiful towns and 17th-century villas by boat, and of course, indulge in amazing food and wine. There are plenty of outdoor options for active travelers including biking, hiking, and water sports.

*Tis’s FAVORITE Experiences: While many people flock to Bellagio and Como which are worth a visit, I loved much less crowded and stunningly beautiful, Lecco. Lecco is mostly tourist-free and offers a perfect setting to explore the area while feeling like a part of true Italian life on Lake Como. Visit when the annual race to the top of the mountains is happening in the summer. The town is full of activity that day with everyone coming out to support those brave enough to tackle the challenge.

Matera View from a Cave, Italy Travel
View from a Cave, Matera

Southern Italy Travel

Southern Italy is often this last place travelers choose to visit but holds many treasures.  Visit the Unesco World Heritage towns of Alberobello, with its cone-shaped homes called Trulli; and Matera, with its Sassi dwellings built into the rock. Matera celebrated for a year recently as one of the 2019 European Capitals of Culture. Lecce is quite popular among those familiar with the region for its many Baroque buildings. It is often compared to its popular northern neighbor, Florence, in that walking around town feels like walking around an open-air museum.

*Tis’s Favorite Experiences: While many base in Bari or Lecce, spend a couple of nights in a cave home in Matera. Matera was largely a poor area due to the very hard nature of life in such a barren, dry area. Mostly neglected and eventually abandoned after WWII, Matera came back to life in the ’90s, earning a Unesco World Heritage site designation in 1993. Now you can choose from a variety of experiences when choosing your cave-dwelling. There are some that are still quite rustic while others have been converted into luxury hotels.


Taormina at Easter
Easter in Taormina

Sicily has much to offer when it comes to islands! Visit busy and beautiful Palermo, stroll by the sea in Cefalù, enjoy the Mt. Etna views from hilltop Taormina, and wander the characteristic streets of Siracusa. There are many notable Greek and Roman ruins to explore. The food is much lighter compared to the heavier Tuscan fare, usually pulled from the sea that morning.

While every region of Italy has its own atmosphere, Sicily is particularly unique.  If you do it right, you really feel like a part of old-world Italy when you are here. 

*Tis’s Favorite Experiences: Skip the hotel and get an apartment during your visit. Stay in Palermo which, while a big sprawling city by Siciliy standards, has a good local vibe. Head to the open-air food markets to get that morning’s catch for dinner along with some fresh vegetables. Or choose to eat from among the many food stalls and restaurants that serve the street food Sicily is famous for. Need a night out? Get tickets for the opera or enjoy one of the many restaurants with outdoor seating and watch the world go by.