Your First Trip to Italy: A Planning Guide

Thank you for downloading our guide! Here's what we share with every first-time traveler to Italy, from when to go to how to order coffee like a local.

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1. When to go

  • Best overall: April to early June, and September to October. Pleasant weather, fewer crowds than summer, and everything is open.
  • Summer (late June to August) is hot and busy in the cities, but perfect for the coast and the lakes. Book early.
  • Mid-August: around the Ferragosto holiday on August 15, many Italians go on vacation and some local shops and restaurants close.
  • Winter (November to March) brings the lowest prices and shortest lines in Rome, Florence and Venice. Many coastal hotels on the Amalfi Coast and Cinque Terre close for the season.

2. How long to stay

  • 7 to 10 days is ideal for two or three cities, such as Rome, Florence and Venice.
  • Plan at least 2 to 3 nights in each place. Every hotel change costs you half a day.
  • Leave free time. Some of the best moments in Italy happen over a long lunch or a slow walk.

3. Getting around

  • High-speed trains connect the major cities quickly and comfortably: Rome to Florence takes about 1.5 hours, and Florence to Venice about 2 hours.
  • Regional trains reach smaller towns. If you have a paper ticket, validate it in the machine on the platform before you board, or you may be fined.
  • Driving is wonderful in the countryside, like Tuscany, but avoid driving in cities. Most historic centers are restricted traffic zones (ZTL) with cameras and fines.
  • Venice has no cars at all. You'll walk and use water buses (vaporetti) and water taxis.

4. What to book ahead

Popular sights sell out, especially from spring through fall. Reserve these in advance:

  • Rome: the Vatican Museums and Sistine Chapel, and the Colosseum
  • Florence: the Accademia (Michelangelo's David), the Uffizi Gallery and the Duomo climb
  • Milan: Leonardo's The Last Supper, often weeks or months ahead
  • Special experiences: cooking classes, wine tastings and private tours

We can book all of these for you, along with skip-the-line and early-access options.

5. Money and tipping

  • Italy uses the euro. Cards and contactless payments are widely accepted, but carry some cash for small cafés, markets and tips.
  • Many restaurants add a small cover charge (coperto) per person for bread and table service. This is normal and not a tip.
  • Tipping is appreciated but not expected the way it is in the U.S. Rounding up or leaving a few euros for good service is plenty.
  • Most cities charge a small hotel city tax per person, per night, usually paid at the hotel.
  • Venice charges day-trippers an access fee on peak days. Overnight hotel guests are exempt but may need to register.

6. Dining like a local

  • Breakfast is light: a cappuccino and a pastry at the bar. Italians usually order cappuccino only in the morning.
  • Coffee costs less if you drink it standing at the counter rather than sitting at a table.
  • Lunch runs from about 1 to 3 pm, and dinner rarely starts before 7:30 or 8 pm.
  • Look for restaurants with short, seasonal menus in Italian, away from the main squares.
  • Try the regional specialties: carbonara in Rome, bistecca alla fiorentina in Florence, cicchetti in Venice, pesto in Liguria and pizza in Naples.

7. Practical tips

  • Churches require covered shoulders and knees. Carry a light scarf.
  • Comfortable shoes are a must. You'll walk a lot, often on cobblestones and stairs.
  • Pack light. Trains, stairs and bridges are easier with a small suitcase.
  • Outlets are 230V with type C, F or L plugs, so bring an adapter.
  • Watch for pickpockets in crowded places like train stations, buses and busy squares.
  • Learn a few words: buongiorno (good morning), grazie (thank you), per favore (please) and il conto (the check). They go a long way.

8. Before you go

  • Your passport should be valid for at least 3 months beyond your return date, and ideally 6.
  • The EU is rolling out new entry systems, including the ETIAS travel authorization for U.S. travelers, scheduled to begin in late 2026. Check the official requirements before you travel.
  • Consider travel insurance that covers cancellation and medical care.
  • Let your bank know you're traveling, and check for foreign transaction fees.

Ready to plan your trip?

Every journey we plan is designed around you: your pace, your interests and your budget. We handle the hotels, trains, tours and details, so you can simply enjoy Italy.

We plan in English and Spanish. Hablamos español.

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