Planning a Trip to Italy: 22 Things to Know Before You Go

Thinking about Italy? Start here.
Whether this is your first trip or a return visit, Italy rewards travellers who plan with intention rather than rushing to book places and dates. This guide covers the key things I wish every traveller knew before finalising an Italy itinerary.

If you’d like help planning an Italy trip that fits how you actually want to travel, you can email me directly at:
info@classicvacationrental.com

1. Start with travel style, not hotels

Before choosing where to stay, think about pace, distance, and how often you want to move. This decision shapes the entire trip.

2. Italy is best enjoyed slowly

Trying to see too much usually leads to fatigue. Fewer bases often mean a richer experience.

3. Shoulder seasons are ideal

April–June and September–October typically offer better weather, fewer crowds, and better availability.

4. Flying into secondary airports can help

Rome and Milan are obvious choices, but Venice, Bologna, Florence, or Naples can sometimes make more sense.

5. Trains work well between major cities

Italy’s high-speed trains are efficient and comfortable for city-to-city travel.

6. A car is best for countryside regions

Tuscany, Umbria, Puglia, and parts of Sicily are best explored with a car.

7. Choose your base carefully

A good base makes day trips easy and avoids long daily drives.

8. Town vs countryside matters

Town stays offer walkability and evening atmosphere. Countryside stays offer space and quiet.

9. Accommodation should support your itinerary

The right property complements your travel style — it shouldn’t dictate it.

10. Many great places aren’t online

Some of the best villas, apartments, and small hotels don’t appear on major booking platforms.

11. Book popular sights in advance

The Colosseum, Vatican Museums, and Uffizi often sell out weeks ahead.

12. Museums close weekly

Many museums close one day a week — usually Monday.

13. Sundays are quieter

Smaller towns may have limited shopping and dining on Sundays.

14. Meals follow a different rhythm

Dinner is later, service is slower, and lingering is encouraged.

15. Coffee culture is quick and local

Espresso is usually taken standing at the bar.

16. Cash is still useful

Small cafés, taxis, and markets often prefer cash.

17. Learn a few Italian phrases

Even basic greetings go a long way.

18. Packing light matters

Cobblestones, stairs, and trains are easier with manageable luggage.

19. Local festivals affect travel

Feasts and holidays can be wonderful — or disruptive — depending on timing.

20. August is different

Many Italians take holidays in August, especially around Ferragosto.

21. Planning early gives more choice

For travel in 2026 and beyond, early planning means better options and less compromise.

22. Italy invites repeat visits

You don’t need to see everything at once — Italy rewards returning.

Need help planning your Italy trip?
If you’re thinking about Italy in 2026 or beyond and would like thoughtful guidance — from choosing the right base to finding character-filled places to stay — email me directly at:
info@classicvacationrental.com