Italy Best Things to Do: 11 Insider Tips

After traveling to Italy four separate times in my life (and giving my kids Italian names!), you could say it’s amore. With that, I’ve curated a list of my favorite experiences and top tips for the best things to do in Italy!

⇒Read also: My 10-14 day itinerary ideas for Italy 

Some links in this post are affiliate links, meaning if you book or buy something through one of these, I may earn a small commission (at no additional cost to you!).

Tip #1: Venice – Ride a Gondola by Night

Everyone who goes to Italy wants to ride a gondola, and why not? It can be fun, romantic, and a great way to beat the heat. Going in the peak of the day off of the main canal though is a bad idea! The gondoliers will hike up prices, making it almost outrageous.
Venice, Evening, Gondola, Italy
If you wait until sunset or early nightfall, and find a gondola in the back waterways, you will pay almost 60% less! In addition to saving money, it will be more quiet, isolated, and peaceful.
Yes, you will still be able to see everything you want, but you don’t have to worry about bumping into 100 of your best friends on the water.
Venice, Evening, Italy, Gondola, italy best things to do


Tip #2: Capri –Visit the Blue Grotto

The Island of Capri itself is a heaven on Earth, and taking a boat out to the famed Blue Grotto will make you feel as though you are truly there.
Sitting in your small boat, you wait for the tide to drop, and then enter a tiny hole in the rock face. Once inside the grotto, the outside sunlight magically illuminates the cavern water to make it shine in the darkness like something out of a dream.
The beautifully eerie singing of the boaters, combined with the glowing water, is a true Italy bucket-list experience. Brave travelers can even jump out for a swim inside this mystical cave!


Tip #3: Assisi – Get a True Taste of Perugia

Assisi is an Italian countryside gem! Whether you are interested in the life and legacy of the Catholic Saint Francis, or just want to see what small town Italy can be like, this place is definitely worth a visit!
You can take a scenic hike above the city, visit one of two medieval castles, and then come back to town for a delicious meal. Essentially everywhere you stand has a postcard perfect view!
Assisi, Italy, Perugia
I took this photo back in 2007- I was a trendsetter with my digital camera 🙂

Tip #4: Siena – Relax with Gelato

If you make it to the Tuscany region, you should certainly take an iconic Tuscan vineyard tour. Beyond that, you really must consider stopping by this character-filled medieval city.Siena, Campanele, Bell Tower, Italy, Tuscany
Sit in the main square, look up at the campaneli (church tower), and take a moment to relax and people-watch. It will be a memory you won’t soon forget- and grabbing a fresh cone of gelato from one of the nearby parlors can only help make this memory sweeter!
Siena, Gelato, Tuscany, italy best things to do

Tip #5: Florence – Find “Real” Italian Food

Many tourists visit Italy expecting that all the food will be AMAZING. They come with a dream of homemade pasta made by a little old Italian Opa ,and just know each bite will taste phenomenal. For many visitors however, this is nothing but a myth.
If you stay near the main tourist areas during your trip, you will see bland microwaved pizza, canned pasta sauce, and disappointing glasses of wine.
Taking the time to research restaurants, and making the effort to leave the tourist circle and explore will be worth it tenfold. In Florence, if you leave the Ponte-Vecchio central area and head to the hills, you will find the most flavorful homemade Italian food in the country.
If you have a distant view of the duomo (rather than closeup!) while you are dining, you can be assured that the food on your fork is better too!

Photo Credit: Rachel Taylor (my little sister!)


Tip #6: RomeVisit the Catacombs & The Appian Way

If you come to Rome, it is of course necessary to visit the iconic sights such as the Forum, the Colosseum, the Pantheon,Trevi Fountain, and the Spanish Steps. Once you have done this, take some time to explore the lesser known parts of Rome too.
A visit to the Christian Catacombs is one idea! You can descend a dark staircase into an underground world of intrigue, murder, and history. When you’re finished with that, take some time to explore the Appian Way.
Religious or not, it is truly humbling to know you are walking on the same cobbled stones that Saint Peter did. Italy best things to do

appian way, rome, italy best things to do


Tip #7: Chianti/Tuscany – Do a Wine Tasting and Vineyard Visit

While there are innumerable wineries you can visit in these regions, each offering vineyard tours and free samples, some are better than others.
One place I can vouch for is Castello di Meleto, in the Chianti region. Here you can tour the grounds, enjoy the frescoes in this historic building, explore a subterranean wine cellar, sample some drinks, and roam a medieval castle!Castello di Meleto, Chianti, Italy, Tuscany
Castello di Meleto, Chianti, Italy, Tuscany
Castello di Meleto, Chianti, Italy, Tuscany

Photo Credits: Rachel Taylor (my little sister!)

Tip #8: Sorrento – Swim, Relax, & See Pompeii

If the distant view of Mount Vesuvius looming over the doomed town of Pompeii does not intrigue you enough to pay a visit here, then maybe the beach will. If you like sunshine, ocean water, being surrounded by beautiful people, or sipping wine while sunbathing… this town may be for you!
Mount Vesuvius, Sorrento, Italy
The beautiful Mount Vesuvius
Hotels with ocean-views can be pricey, but they offer ridiculously amazing views. If you’re on a budget, you can still make it to the many beaches nestled under steep cliffs.
You can also hop a ferry or rent a car to take you to the ruins of Pompeii for a half or full day trip from this location. The ruins in the summer will make you very hot and sweaty, but coming back to the ocean breezes of Sorrento will be a huge relief. || ♠PS- Stay at my favorite hotel in Sorrento ♠|| 
Sorrento, Sunset, Italy best things to do
Sunset in Sorrento


Tip #9: Pisa – See the tower, then head on

Most visitors to Italy make it a point to visit the city of Pisa and that one tower, and with good reason. However, after about an hour in the town of Pisa, many travelers are disenchanted by the sub-par, overpriced food, and want something fun to do.
This is when you take a local train to the nearby town of Lucca, rent bikes for the day from a local vendor, and explore a charming old Italian town on two wheels. Stop for some gelato and a picnic on the way, and you’ll be set!

Tip #10: Value the Small Towns!

Anyone who visits Italy will want to see the famed and historical cities within its borders. However, the quaint small towns of this beautiful country cannot be ignored.
No matter what kind of tour or schedule you have arranged for your Italian visit, be absolutely sure that it includes a visit to at least one small town. Some suggestions include Levanto and Bonassola (near Cinque Terre), and Tuscan towns of Montepulciano, San Gimignano, or Radda.

Photo Credits: Rachel Taylor (my little sister!)


Tip #11: Learn a bit of Italian

Most TESOL-certified teachers and tourists visiting Italy, unfortunately, seem to make minimal effort to learn the language. While it is easy to get by relying on English, taking the initiative to try using Italian will make for a better experience overall. Locals will react better, and may even go out of their way to help.
Asking a small town artist “cuanto costa cuesta?”, or saying “bellisima” while pointing at their painting, will lead to a far better interaction then a slow and loud “HOW. MANY. EUROS?”.
Good places to start are the Lonely Planet Conversational Italian Guide, or the language learning app DuoLingo.

More Helpful Links:

♥ Get yourself some travel insurance! I honestly never travel abroad without it
♥ Browse my Amazon storefront to see my favorite travel products
♥ Book your hotel in Italy
♥ Follow me on Instagram, and send me a DM with any questions
♥ Find a fun local Italy tour or activity to book

Pin it for later!


  • Reply Mary Muntel May 3, 2016 at 11:42 pm

    Wonderful insights and tips! Delightful photos! Thank you!

  • Reply Christine | The Traveloguer May 25, 2016 at 7:27 am

    Great tips here! I would love to visit the cave in Capri, it looks so cool. That is so true about needing to research restaurants. I was so disappointed when I was in Florence as I expected the food to be amazing, but because we were going to cheap tourist restaurants, the food was really bland.

  • Reply Anabel March 9, 2022 at 6:13 am

    Great tip for Venice! Heading there shortly and will def try to save some €€ on the gondola ride!

    • Reply Michelle W. March 9, 2022 at 2:12 pm

      You will love it!! Yes hopefully you can save a few!

      • Reply Michelle W. March 9, 2022 at 2:13 pm

        Yes it’s very easy to go as a US citizen of course, but definitely understandable if you’re based in Europe 🙂

    Leave a Reply