How to Plan a Perfect Vacation to Italy

For cultural attractions and breathtaking scenery, Italy is tough to beat. The country that nurtured the talents of Leonardo, Michelangelo, Puccini and Galileo still inspires people around the world today – and you can tour Italy’s most famous sights while on vacation.

If you’re looking for the perfect place to vacation, head to Italy. From traveling through different cities and visiting sites that date back centuries, here’s how to plan the perfect vacation to Italy.

Where to Begin and When to Go

Italy’s resemblance to a boot makes it especially easy to navigate. Just start unlacing, so to speak, at the top and work your way down the coast or central regions of the country city by city. Many first-time travelers pick an itinerary that offers a well-rounded experience: Start in Venice, then visit Bologna and Florence, and wrap up your travels in Rome and Naples.

If you plan a longer vacation of 12 to 14 days, you’ll also be able to fit in some intriguing side trips. Lucca, Umbria, Pisa and Parma, the birthplace of everyone’s favorite cheese, are well worth exploring if you have the time.

When it comes to weather, Italy isn’t sunny and pleasant year-round. Some regions can be oppressively hot and humid or cold and foggy depending on the season. May, June, and October are ideal months to see the country at its best.

August, on the other hand, is not preferable. Ferragosto, a national holiday on August 15, coincides with the Roman Catholic Feast of the Assumption. Museums in the large cities remain open, but shopkeepers and restaurant owners tend to shut down for the entire month and head to the beach. Quaint villages often become ghost towns.

Make Sure to Stop in Bologna

Bologna doesn’t automatically spring to most tourists’ minds, but it’s a fascinating stop on the way to Florence. The bustling capital of the Emilia-Romagna region boasts some of the finest examples of medieval and Renaissance architecture in Europe.

The Fountain of Neptune is the crown jewel in the sprawling main plaza of Bologna, which is lined with arched colonnades and dotted with outdoor cafes for people-watching. You can view this stunning and storied fountain from a number of different angles to take in its full beauty.

Come hungry to this Italian city. Open-air markets feature artisanal pastas and cheeses, and the restaurants are generous with ragu alla Bolognese, a robust meat and tomato sauce. It’s a great place to get your fill of some of the world’s best-known pasta dishes.

Spend at Least Two Days in Tuscany

Tuscany’s diverse landscape, which includes pristine beaches, rolling hills, olive groves, and rugged mountains, has inspired artists for centuries – and you’ll want to take your time touring its many sights. Its famous structures hark to the Roman age. Tuscany is rich with historic medieval towns, rural churches, and imposing castles.

In addition to all of that, there’s the wine. When it comes to winemaking, few regions in the world can compare to Tuscany. The Etruscans began cultivating grapes around 3,000 years ago, and there’s been a bumper crop year after year ever since.

The versatile local Sangiovese grape is most common. Different winemaking methods result in distinctive qualities such as cherry-like tartness or peppery notes. You could visit several wineries and not experience the same flavor twice. If you love red wine, don’t skip the Chianti in Tuscany. Only reds made from one specific Tuscan grape can be called Chiantis.

Don’t Miss Out on Florence

The cradle of culture and fine art is Florence, which is a city that’s compact and easy to navigate on foot, so bring comfortable walking shoes. You’ll no doubt stand before some of the most recognizable buildings and works of art in history.

In the Uffizi Gallery, among many other masterpieces, look for Botticelli’s “The Birth of Venus” and Rembrandt’s “Self-Portrait as a Young Man.” Michelangelo’s splendid “St. Matthew” and “David” sculptures are housed in the Gallerie dell’Accademia. You can also see dozens of additional sculptures in Loggia dei Lanzi, a free outdoor museum founded in the 14th century. The Duomo, an enormous Gothic cathedral featuring Giotto’s magnificent bell tower, is also a must-see when in Florence.

Look Into Cruises

If you want to see as much of Italy as you possibly can, consider taking a cruise along the country’s coast. Trying to pack in your own sightseeing and travels can be difficult – from Florence, depending on whether you travel by car or by train, the trip to Rome could take anywhere from 90 minutes to three hours or more. The trek to Naples might consume another three hours.

That’s why many vacationers opt for an Italian cruise. Cruises provide access to all the cities on this tour plus gorgeous coastal towns like Bari, Cagliari, Portofino, Genoa and Livorno, the gateway port to Pisa and Florence. Cruises save the time and hassle of overland travel. The trip from the cruise port Civitavecchia to Rome, for instance, is just a little over an hour.

How to Find the Best Deals

You never have to pay full price to see Italy in all its splendor. Here are some tips for saving on travel and hotels:

  • With the exception of August, travel just before or after peak seasons.
  • Call airlines, cruise lines and hotels directly to ask for the lowest fares.
  • Be flexible with travel dates and days of the week.
  • Look for money-saving package deals.
  • Enlist the help of a travel agent.
  • Use your travel credit card rewards.

Finally, take advantage of internet resources. Many sites are devoted to finding discounts and promotions. Some will even send an email when there are cheap fares to your destination. Often, searching for travel deals online – whether you’re looking for a cruise along Italy’s coast or cheap hotels and travel packages to visit different Italian cities – you can find lower prices and special deals just for first-time travelers or those who want to work with a website’s bundles or touring company.

If you’re interested in vacationing in Italy, start planning your trip with a search today.

Featured Tip

Don’t let your vacation days go to waste – make sure you travel! Only 23% of full-time employees use all of their days off each year, Forbes reports.