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Top 10 Must Visit Italy Vacations

Venice Italy

Have you ever dreamt of going on one of those Italy vacations you see on TV and in the movies? The gondola rides through the waterways of Venice, the ancient ruins of Rome, the fashion scene in Milan, the Leaning Tower of Pisa—Italy seems to have it all, and we didn’t even mention the beautiful churches, awe-inspiring architecture, museums, or the food!

Italy vacations grace the bucket lists of many, with few ever coming to fruition. Don’t let this happen to you. Planning Italy vacations can be daunting. While Italy isn’t a huge country from a geographical standpoint, there is so much to see and do, many would-be enjoyers of Italy vacations get overwhelmed by the possibilities. If this sounds like you, read on. We are here to help you scratch Italy off your bucket list.

We will give a brief beginner’s guide to Italy vacations, helpful travel tips, and then a list of 10 must-see Italian cities.

How to Begin Planning

When planning your trip to Italy, you will first want to establish your budget. If you are working on a tight budget, you may want to look into going to Italy during the low season which would be November through February. Travel and accommodations are usually cheaper for trips to Italy this time of year.

If you have a flexible schedule, you may find some great last-minute package deals, many of which would remove the need for a lot of planning as package deals will include your flights, accommodations, and include tours. Many people will choose cruises for this reason, and cruise lines also offer last-minute deals.

If you don’t have a flexible schedule or don’t like the rigid itineraries of vacation packages, you will need to make your itinerary. Italy has so much to offer that you won’t see it all in one trip. You will need to choose a few destinations, depending on how long your trip will be, that you want to see. Aim for places that offer multiple points of interest in the same region. For example, if you stay in Naples, you will be close to the island of Capri and Pompeii.


Arno River in Florence Italy



If you consider yourself a more independent traveler, see what accommodations Airbnb has available for the cities you will visit. Often you can find amazing properties at a much lower cost than hotels, and they can provide a much more authentic experience.

You may begin researching your trip to Italy with one plan in mind and end up with a whole new plan as you have adequate information. You may find that your original plan doesn’t make sense geographically or financially. Don’t let this stress you out. Be open to changing your mind in the planning phase to save yourself stress during the actual vacation.

Helpful Travel Tips

Learning the Language

Well, maybe not the entire language, but there are a few key Italian phrases that will be helpful to—if for no other reason than to be polite. Below is a list of a few words to learn before setting out on Italy vacations:
Hello: Buongiorno
Goodbye: Arrivederci
May I?: Posso?
Please: Per favore
Thank you: Grazie
How much?: Quanto costa?

It is also helpful to know how to ask the natives if they speak English in cases where you need to have more than just a short interaction. To ask somebody if they speak English, say: Parla inglese?


Italians do not place the same emphasis on tipping as Americans do. However, tipping is a way to show your gratitude for good service, so it is still expected in some situations. When grabbing a coffee, it is customary to leave a small amount of pocket change. In restaurants, the gratuity will often be added, but if not, tip up to 10% in nicer restaurants and one or two euros in places like pizzerias. Bars don’t require tipping at all.

Cash and Credit

Credit cards are widely accepted in Italy, especially in larger establishments, but you can’t count on that everywhere you go. Smaller businesses and some museums will only accept cash, so be sure to carry some with you.


While other vacations, like say a trip to the Caribbean, allow for very lax clothing choices, Italy vacations require a little more fashion effort. Appearance is important in Italy, and you’ll want to make sure you are dressed respectably. For sightseeing, you will want to make sure you have comfortable shoes. Many of the streets in Italy are cobblestoned, and while this is charming, it can be torture in the wrong shoes.

When visiting churches, there are often strictly enforced dress codes—be sure to cover your knees and shoulders. If you are going out for the evening, you’ll want to put a little more thought and effort into getting ready than you normally would.


For more popular tourist attractions like Vatican Museums, the Colosseum or Gallerie dell’Accademia, you will probably have to wait to get in. For any large attraction, check to see if tickets are available online. While you will still have some waiting to do, this will save you time.


Colosseum in Italy



You can also try to arrive during times when these places aren’t as busy, such as first thing in the morning or late in the afternoon. If you want to see the Vatican Museums, try going on a Tuesday or a Thursday.


If you are wondering whether you should rent a car in Italy, the answer to that is—it depends. There is some beautiful scenery once you get out of the city, and if you want to see the Italian countryside, then renting a car makes sense. If that is not in your itinerary, then you’ll probably want to skip it. The traffic in Italy can be crazy, and parking is difficult.

The major cities of Italy are extremely walkable, and for longer journeys, public transportation is available. Tickets for public transport can be purchased from street kiosks, and they are typically valid for a window of time in which you can take as many trams and buses as you need.

Top 10 Must Visit Italy Vacations

1. Naples

In Southern Italy, you will find Naples, the capital of the Campania region. Naples is a great place for foodies as pizza, spaghetti, and parmigiana originated in this city, and you will find these dishes made with fresh and locally grown ingredients. Naples is a great base for exploring the Bay of Naples, the ruins of Pompeii, Mount Vesuvius, and the San Gennaro Catacombs. Besides sightseeing, you can enjoy great shopping and nightlife.

aerial view of Naples Italy



2. Sicily

In Sicily, you will find Europe’s tallest active volcano, Mount Etna. Sicily is the largest island in the Mediterranean Sea and is separated from the mainland by the Straits of Messina. Because it is an island, its beaches are popular, especially those on the north and northwest coasts. If you tire of the beaches, visit ancient ruins such as the Valley of the Temples or Segesta Temple. At night you can party at a beachside club or visit Italy’s largest opera house, Teatro Massimo.


Alley Road in Sicily, Italy



3. Milan

Milan is known for being one of the wealthiest cities in Europe and a global fashion hub. Visitors of Milan can view Leonardo DaVinci’s “The Last Supper,” visit the famous opera theater Teatro alla Scala, or have a night out in the Navigli District which is a series of bars, restaurants, and cafes along the interconnected canals in Milan. Sports fans might want to check out San Siro Stadium, the largest stadium in Italy, and one of the largest in all of Europe. The stadium has a capacity of about 80,000 people, and many great concerts are played there.


Duomo Square in Milan



4. Pompeii

You may remember learning about Pompeii in middle school. This famous Roman city was covered by several feet of volcanic ash for almost 1700 years after Mt. Vesuvius erupted until 1748 when excavation began. To this day, Pompeii is not unearthed. Walk through the ancient stone streets and history comes alive before your very eyes.


Street in Pompeii



5. Venice

Venice is an amazingly unique city built on a lagoon encompassed by the Adriatic Sea. Venice comprises 118 islands connected by bridges and canals that you have undoubtedly seen on television. Venice is known for being a city of romance, with its gondola rides through the canals attracting many couples—but try a gondola ride with or without a romantic partner; you won’t regret it.


Canal in Venice Italy



In Venice, you can also visit Saint Mark’s Basilica, catch a show at Teatro La Fenice opera house, or visit the Doge’s Palace, a balance in Venetian Gothic style and once home to the Doge of Venice.

6. Tuscany

Tuscany may be one of Italy’s most famous regions. The picturesque countryside with rolling hills, vineyards, and olive groves can bring on an instant feeling of serenity. While you could have a wonderful time indulging in local wine and eating bread dipped in freshly pressed olive oil, there are many other things to do.

aerial view of Montepulciano Tuscany


You can visit Tuscany’s capital, Florence, where you will find red rooftops, cobblestone streets, and quaint shops, restaurants, and hotels. Tuscany is also where you would go to get one of those pictures that looks like you’re holding up the Leaning Tower of Pisa.

7. Rome

Where to begin with Rome—there is so much to do. When one thinks of Italy vacations, Rome always comes to mind. The ancient heritage of Rome is unmatched. The Colosseo district is where you would find the most ancient attractions such as the Colosseum, Capitoline Hill, and the Roman Forum.

night view of Vatican City in Rome


Old Rome holds the Pantheon, amazing Renaissance architecture, and breathtaking cathedrals. The number of museums, historical sites, and attractions in Rome are too numerous to list, and realistically, any traveler would have to narrow down the top few things they want to see because without living there, you could never see it all.

8. Amalfi Coast

This cliffside coast hosts 13 colorful seaside towns on the Mediterranean, the two most popular being Positano and Amalfi, where you will have no trouble finding hotels and restaurants. This region is known for an abundance of Michelin-starred restaurants. Lay on the beach, hike, or walk along the streets and admire the colorful homes and ancient villas.


amalfi coast italy



9. Cinque Terre

Cinque Terre is located on Italy’s Ligurian Cost and consists of five seaside towns which used to be remote fishing villages. These charming seaside towns are connected by a train. While the beaches are not as numerous as on the Amalfi Coast, boat tours and hiking will keep you busy. The oceanfront Footpath Monterosso hike is a must-do while you’re here.


Cinque Terre italy



10. Capri

The island of Capri is a short ferry ride away from Naples, and a place so serene Charles Dickens once wrote about its “delicious peace and quiet.” In Capri, you can visit the Piazzetta, or La Piazzetta, a tiny, bustling square you will find right when you step off the ferry. It consists of four bars and is great for those who love to socialize.

capri italy


But for those who go to Capri for the delicious peace Dickens wrote about, take a boat tour around the regal rock formations jutting out of the sea, or visit the iridescent waters of the Blue Grotto. The coastal hikes are also an amazing way to experience the natural beauty of Capri.


Italy is a country rich in history, culture, and natural beauty. Regardless of your vacation style—a cruise, a pre-planned package deal, or a DIY itinerary—you will have a wonderful time drinking local wines, eating amazing food, exploring ancient ruins, and gazing upon breathtaking architectural feats. There is a reason Italy is on many bucket lists, but now is the time to get it off of yours.