While a small country, Italy punches well over its weight class and is undeniably one of the most known cultures in the free (and not so free…ahem China) world. Chances are high you’ll find Italian cuisine, along with Ferraris, in most countries, including Shanghai.
One of my favorite things about Italian culture is the Italian style.
Italian is to style, and Bureaucracy is to government.
It’s everywhere. The clothes, architecture, food, and product design. And certainly, you won’t find yoga pants at the dinner table in Milan unless you’re sitting next to a sunburned tourist from the midwest.
I’ve been coming to Italy for seven-ish years ever since I decided to start exploring greater Europe. So I committed myself to an annual summer pilgrimage from America to the continent where everything is beautiful, and the food quality is arguably the best in the World.
I’ve sipped wine in Verona, flown seaplanes over lake Como, sipped espresso in Milano Centrale train station, swam off the coast of Positano, and toured the canals of Venice. This is not to brag but to let you know I have some idea of how to get around.
Rather than have an extra car in the garage or an airplane in the hangar, I prefer to spend on travel and experiences with my friends and family.
If someone wants a bit more out of Italy for their next trip or this is your first, I wanted to share my experience traveling within the boot and give you my top pro-Italy travel tips and recommendations.
So hop into the Gondola and get your camera ready.
Time of Year
If you are one of the lucky few, who can choose when and where on your own terms, then I would say May or September are the best times to visit. It’s not as hot, and more importantly, you’ll avoid the droves of covid carriers that spill into the country during June, July, and August.
August in Italy is to be avoided like a New York subway car with no air conditioning in July. Not comfortable, packed, and hot as rats having s*x in a wool sock (ugh on that visual). Point made.
Top Travel Spots
There is much to Italy, but the cities below will give you a great introduction to the country and showcase how diverse Italy really is. I hope you enjoy them as much as I did.
Milan
I’d recommend flying to Milan, Italy’s center for design and fashion. Milano is located north at the base of the Alps and a great hopping-off point for the rest of the country by train.
Trains in Italy are incredibly reliable and nice and a much more enjoyable experience than fighting for arm space on a crowded budget airline with long security lines and crying children.
If you want to travel to Italy like a professional, then go by train.
There are so many great boutique hotels in Milan, and I’d recommend the site Mr. & Mrs. Smith for the best boutique hotel recommendations.
I recently stayed at Aethos Milano and had a great and affordable stay.
Personally, I prefer the boutiques over the big soulless chains because the service and stay are much better.
Start off by sightseeing in Milan in and around the Duomo cathedral and shopping district.
Indulge in a rooftop drink at the Aperol bar and have dinner in the trendy arts district.
The following day, hop on a train from Milano Centrale to Como for a quick walk on the lake and in and around the historic Como city center.
I also highly recommend booking a seaplane tour at my favorite flying club, Aero Club Como. Book a flight over the lake in the club’s Cessna 206 but do it well in advance because tours sell out fast. You can see the entire lake in twenty minutes, including the incredible Bellagio and the many famous hotels and villas Como is known for, like the Clooney and Star Wars villas.
I learned how to fly seaplanes here in 2018, and the magic of the flying experience has captured my soul ever since. I go back and fly a few times a year.
The club is also the oldest seaplane club and base in the world and runs like a Swiss watch.
Tell Francisco or Matteo I sent you.
After the flight, you can walk around the lake with a casual stroll back to the train for the 40-minute ride back to Milan and a late dinner.
Stay a third night and visit the famous Garage Italia to look at Italy’s iconic car designs by this incredible restoration company.
Milan, check. Now we head east to the coast across from Croatia to the land of the Gondola.
Venice
Venice I put off visiting for many years. Perhaps I was waiting for the planets to align with my romantic interests because I’ve always imagined the city to be like Paris, a place for lovers. After visiting, I was right to think this way.
I finally went this year with my girlfriend, and Venezia did not disappoint.
It’s one of the most romantic and unique cities I’ve ever been to, and I’ve been to over 100 countries and maxed out several passport books.
From Milano Centrale, we took the train and arrived at the main station in Venezia in just over two hours.
Book your hotel in advance and get instructions from the station from concierge before arrival.
The water taxi system in Venice is incredible and less expensive than the private taxis.
Buy a multi-day taxi pass, and if you’re traveling light, I’d recommend taking the public water taxi from the train station to your hotel. However, if you have large bags, arrange for a private water taxi ahead of time for about 60 Euros. Take a right out of the train station and head to the blue taxi pier or public taxi stand to the left.
The public taxi stands are very noticeable, and Google Maps tells you exactly when the next taxi leaves. It can be confusing, but there are really only two directions to go on the Grand Canal, so just ask someone or trust Google Maps.
I travel extremely light my girlfriend does not. While she’s not quite British royalty with her luggage capacity, she’s definitely not a backpack and carry-on person like me, so we booked a private water taxi which took us directly to the front door of our hotel.
Again another great find on my favorite boutique hotel site had us stay at the incredible Palazzo Experimental hotel opposite the grand canal and easily accessible to everything Venice offers.
For a first visit, I think two nights is plenty. You can roam most of the city on foot and by water taxi and take a private canal tour for just over 100 Euro (Highly recommend).
Like most of Italy, you can stumble into great food and wine in most places. The hotel concierge arranged amazing dinners on both nights and a private tour. For lunch spots, we just bumped into these daily with great results.
The city is incredible, with buildings dating back to the 1600s. To be honest, I was embarrassed thinking back to the cheesy Italian replicas in Las Vegas and elsewhere in America. It’s like trying to replicate the moon landing in your living room with cardboard boxes. Nothing compares to the real experience.
Venice check.
All roads lead to….
Rome
About four hours south of the Grand Canal by train, you’ll find yourself in the magical city of Rome with its huge squares, gardens, fountains, and Colleseum.
Something about this city moves your soul.
Ever since seeing the movie Gladiator and the series Rome on HBO, I’ve wanted to visit. And the city delivers in every sense of what you’d expect of it.
Food, drink, atmosphere, and museum-quality history are everywhere you look. There are so many artifacts that they are just part of the natural landscape.
Rome also has close to 300 public fountains, an incredibly diverse dining scene, the country’s first shopping mall dating back to around 110 A.D., the incredible Colosseum, the Vatican, and much more.
I’d recommend two nights for a first visit and for a Rome warm-up, you can watch one of my favorite movies of all time, “The Great Beauty,” by Academy award-winning director Paulo Sorrentino.
This incredible film captures Rome’s soul in its entirety.
Rome, check.
Capri Island (off of Naples)
Continue by train south to the city of Naples, where a short taxi ride takes you to the main port where you can catch a ferry to the enchanting Capri island located just off the famous Amalfi coastline, the same one Sinatra sang about.
The island is also the birthplace of the Caprese salad, has a local population of 12,000, and is another one of those magic Italian cities.
I first visited the island with a group of Harvard business school alumni in 2021 and fell in love instantly.
One of my favorite things to do in Europe is to swim in the Mediterranean sea, and plunging into the cool deep blue waters of Capri is medicine for the mind and body.
I’d recommend staying at least a week to really settle into island life and enjoy everything this gem of southern Italy has to offer.
While a boutique hotel now and then is a nice luxury, I actually prefer renting a private home or apartment with amenities like a washer and full kitchen over expensive hotels. I find I get way more value and space renting off sites like AirBnB compared to a hotel.
Photos compliments of the Capri official site. The top is the coast of Capri and the bottom at the famous Paolino restaurant.
Capri is divided into two main cities, Anacapri and Capri center. Most of the island is walkable once you’re in one of the city centers, but occasionally you’ll need to go back by taxi.
The island is incredible for walking with mesmerizing coastal views so bring your hiking shoes.
I’d recommend staying near Capri center on the back side of the island for postcard scenery, and you’re within walking distance of most of the island’s main restaurants, shops, beach clubs, and just a short ride down the Funitel to the main port.
I would highly recommend chartering a private boat in advance for the day. You’ll be able to take in several private swimming spots like the famous Blue Grotto and other hot spots off the island and the Amalfi coast.
Swimming from your private little boat off the coast of Positano is pure magic that will sure to produce FOMO in the hardest of hard-core Instagram travel bloggers.
There are also several lunch options that are only accessible by boat. Your captain will know all the spots, and you can score an all-inclusive boat trip for a small group for less than 1000 Euro, which is reasonably priced when divided by a party of 4-6.
Capri gets tens of thousands of tourists a day by ferry but really quiets down in the evening when everyone returns to the mainland after dark.
Capri, check!
Summary
Italy has so much to offer in terms of diverse landscapes, and if you’re a wine lover, you’ll love exploring some of the wine regions near Verona and Tuscany.
The north is usually more metropolitan and the center of design culture, whereas the southern cities are known to be more relaxed.
If you’re a skier, the north also offers incredible value and expert terrain in the Italian Alps near Chamonix, France.
Whether this is your first trip or not, I hope you find your way to some of my favorite cities in Italy and that you enjoyed my recommendations.
Ciao.
Viaggi Sicuri!
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