How to plan a trip to Italy

Your ultimate guide to Italy

Planning a trip to Italy is like opening a door to a world of rich history, stunning landscapes, and culinary delights. From the romantic canals of Venice to the ancient ruins of Rome and the rolling hills of Tuscany, Italy offers something for every traveler. If you’re dreaming of experiencing la dolce vita, here’s your friendly, relatable guide to planning the perfect Italian adventure.

1. Decide When to Go

Best Time to Visit

Italy is beautiful year-round, but the best time to visit depends on what you want to experience.

  • Spring (April to June): Spring is perfect for pleasant weather, blooming flowers, and fewer tourists. It’s an ideal time for exploring cities and countryside alike.
  • Summer (July to August): Summer is peak tourist season, especially in July and August. Expect warm weather, bustling streets, and higher prices. It’s great for beach destinations but be prepared for crowds.
  • Autumn (September to October): Autumn offers cooler temperatures, harvest festivals, and stunning fall foliage. It’s a fantastic time for food and wine enthusiasts.
  • Winter (November to March): Winter is off-peak, with fewer tourists and lower prices. It’s perfect for visiting cities and enjoying winter sports in the Alps.

2. Choose Your Destinations

Must-Visit Cities

Italy is a treasure trove of iconic cities, each with its own unique charm.

  • Rome: The capital city is a blend of ancient history and vibrant modern life. Don’t miss the Colosseum, the Vatican, and the charming streets of Trastevere.
  • Florence: The heart of the Renaissance, Florence is a haven for art lovers. Visit the Uffizi Gallery, the Duomo, and the Ponte Vecchio.
  • Venice: With its romantic canals and historic architecture, Venice is unlike any other city. Explore St. Mark’s Basilica, the Grand Canal, and take a gondola ride.
  • Milan: Known for its fashion and design, Milan also boasts impressive landmarks like the Duomo and Leonardo da Vinci’s The Last Supper.
  • Naples: This bustling city is the gateway to the Amalfi Coast and Pompeii. Enjoy the vibrant street life and the best pizza in the world.
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Hidden Gems

Beyond the famous cities, Italy has countless hidden gems worth exploring.

  • Cinque Terre: These five picturesque coastal villages offer stunning views, hiking trails, and charming streets.
  • Tuscany: Renowned for its rolling hills, vineyards, and medieval towns like Siena and San Gimignano, Tuscany is perfect for a countryside escape.
  • Puglia: Located in the heel of Italy’s boot, Puglia boasts beautiful beaches, whitewashed towns, and delicious cuisine.
  • Sicily: This island offers a unique blend of cultures, with ancient Greek ruins, Baroque architecture, and vibrant street markets.

3. Plan Your Itinerary

Mix of Cities and Countryside

To get the full Italian experience, mix bustling cities with relaxing countryside or coastal destinations.

  • Start in Rome: Spend 3-4 days exploring the historic sites, museums, and vibrant neighborhoods.
  • Head to Florence: Spend 2-3 days in Florence, with a day trip to Pisa or the Chianti wine region.
  • Visit Venice: Spend 2-3 days soaking up the romantic atmosphere and exploring the islands of Murano and Burano.
  • Relax in Tuscany: Spend a few days in the Tuscan countryside, visiting vineyards and hilltop towns.
  • End in Amalfi Coast or Cinque Terre: Spend 2-3 days enjoying the stunning coastal views and charming villages.

Flexible Schedule

While it’s good to have a plan, leave some room for spontaneity. You might discover a charming village or a fantastic restaurant that you hadn’t planned for.

4. Book Your Flights and Accommodation


Book your flights early to get the best deals. Major cities like Rome, Milan, and Venice have international airports with numerous flight options.


Italy offers a wide range of accommodations to suit every budget.

  • Hotels: From luxury hotels to budget-friendly options, you’ll find a variety of choices in every city.
  • Airbnb: Renting an apartment or a villa can give you a more authentic experience, especially in smaller towns and rural areas.
  • Agriturismo: For a unique experience, stay at an agriturismo (farm stay) in the countryside, where you can enjoy home-cooked meals and learn about local farming.
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5. Getting Around

Train Travel

Italy’s extensive train network makes it easy to travel between cities. High-speed trains connect major cities, while regional trains reach smaller towns.

  • Trenitalia: The national railway service offers high-speed Frecciarossa trains and regional services.
  • Italo: A private high-speed train service that connects major cities like Rome, Milan, Florence, and Venice.

Car Rental

Renting a car is ideal for exploring the countryside and smaller towns at your own pace. Be prepared for narrow streets and Italian driving styles!

Public Transport

Cities like Rome, Milan, and Florence have efficient public transport systems, including buses, trams, and metros.

6. Embrace the Culture

Learn Basic Italian Phrases

While many Italians speak English, learning a few basic phrases can enhance your experience.

  • Ciao (Hello/Goodbye)
  • Grazie (Thank you)
  • Per favore (Please)
  • Dov’è…? (Where is…?)
  • Quanto costa? (How much does it cost?)

Dress Appropriately

Italians take pride in their appearance, so dress smartly, especially when visiting churches or upscale restaurants.

Respect Local Customs

Be aware of local customs, such as the afternoon siesta when shops may close, and tipping etiquette (it’s usually included in the bill, but rounding up is appreciated).

7. Indulge in Italian Cuisine

Must-Try Dishes

Italian cuisine is diverse and delicious. Here are some must-try dishes:

  • Pizza in Naples: The birthplace of pizza, Naples offers the best Margherita and Marinara pizzas.
  • Pasta in Rome: Try classic Roman dishes like Carbonara, Cacio e Pepe, and Amatriciana.
  • Gelato Everywhere: Treat yourself to authentic gelato in every city you visit.
  • Seafood in Sicily: Enjoy fresh seafood dishes like pasta alle vongole (clams) and arancini (stuffed rice balls).
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Wine Tasting

Italy is famous for its wine, with regions like Tuscany, Piedmont, and Veneto producing world-class wines. Visit local wineries for tastings and tours.

8. Enjoy the Attractions

Iconic Landmarks

Don’t miss these iconic landmarks:

  • Colosseum in Rome: Walk through the ancient amphitheater where gladiators once fought.
  • Leaning Tower of Pisa: Climb the famous leaning tower for a unique view.
  • Florence’s Duomo: Admire the stunning architecture and climb to the top for panoramic views.
  • Venice’s St. Mark’s Basilica: Marvel at the intricate mosaics and opulent design.

Hidden Gems

Seek out lesser-known attractions:

  • Trastevere in Rome: Wander the charming streets of this vibrant neighborhood.
  • Boboli Gardens in Florence: Escape the crowds with a peaceful stroll through these beautiful gardens.
  • Rialto Market in Venice: Experience the local flavors and vibrant atmosphere of this historic market.