How to Plan a Trip to Italy: Your Ultimate Passport to La Dolce Vita

Beautiful Italy, the very name brings to mind images of cobblestone streets, the smell of pizza wafting through the air, ancient ruins and gorgeous countryside. This European gem of a country has much to offer all who travel to it. Whether you are looking for adventure, romance, luxury or a quiet time in the country, Italy has something for everyone. Planning a trip to this gorgeous country requires more than just merely booking a flight. The trip is also about finding a balance between iconic landmarks and must-see local experiences, all while embracing the local Italian culture. Whether it is your first visit or you are a returning explorer, this Italy travel guide will help you navigate everything from when to go and where to stay, to must-see attractions and insider tips.

Deciding When to Go

Italy can be visited throughout the year, and you’ll still have a great time. However, what you can and can't do during each season may vary.

Image via Anantara Hotels & Resorts

Spring (April to June): 

This season offers mild weather and blooming landscapes, making it ideal for city walking tours and countryside explorations.

Autumn (September to October): 

This is also a favourite for its golden vineyards and harvest festivals.

Summer (July and August): 

This season sees peak tourist numbers, particularly in major cities and coastal towns. While the Amalfi Coast or Cinque Terre are undeniably beautiful in summer, you’ll want to book well in advance to secure a spot at a resort.

Winter (November to February) is the low season for most regions, except the Alps, where ski resorts attract visitors seeking snow-covered charm.

Planning Your Italian Itinerary

Italy’s diversity is one of its strengths. Every region of the area feels like a different country in itself. You could easily spend months exploring and still only scratch the surface. Here are some top regions and cities to consider.

Rome: Start in the capital city of Italy, where ancient history meets colourful modernity. The Colosseum, Roman Forum, Vatican Museums, and St. Peter’s Basilica offer a great starting point for exploration.

Venice: This romantic floating city is like no other. Beyond gondola rides and St. Mark’s Basilica, get lost in its labyrinthine alleys and roads.

Milan & Lake Como: Milan, Italy’s fashion and design capital, is sleek and cosmopolitan. Just a short train ride north, Lake Como offers a peaceful escape with its glassy waters and series of villas.

Sicily & the South: For something more off-the-beaten-path, Sicily is rich in history, cuisine, and rugged landscapes. The same goes for Puglia and Calabria. This area is ideal if you’re looking to delve into Italy’s rustic charm and fewer crowds.

How Long Should You Stay?

If you’re visiting Italy for the first time, aim for at least 10 to 14 days to cover the major highlights without feeling rushed. A classic itinerary might look like:3–4 days in Rome 2–3 days in Venice2-3 days in Milan3–4 days in Sicily & the SouthYou could also explore a single region in depth, such as spending a week in Sicily or a slow-travel escape through the Dolomites.

Getting Around

Italy has an excellent train network, especially between major cities. High-speed trains such as Trenitalia’s Frecciarossa or Italo connect Rome, Florence, Venice, and Milan efficiently. For countryside regions like Tuscany or Umbria, renting a car offers flexibility and the chance to explore lesser-known villages. 

Where to Stay

Your choice of accommodation can make or break your Italian holiday. Italy offers a wide spectrum from agriturismos, which are rural farm stays, and boutique B and Bs to more luxury options. For those seeking a truly refined experience, Italy luxury hotels offer indulgent comfort paired with unique settings. Among the most distinguished brands in this segment is Anantara Hotels & Resorts, which boasts a seamless fusion of local character and modern sophistication.

Practical Travel TipsCurrency: Italy uses the Euro (€). Credit cards are widely accepted, but having some cash is helpful for small shops and cafes.

Language: While English is spoken in tourist areas, learning a few Italian phrases can enhance your experience and interactions.

Packing: Bring comfortable shoes for walking on cobblestones, and consider dress codes for churches and upscale restaurants.