Planning a trip to Italy can feel like a lot, but it doesn’t have to be. These nine steps will help you get everything organized, book on time, and avoid common mistakes so you can focus on enjoying the trip.
Let’s start planning your dream itinerary!
1. Decide your travel dates
6 – 12 months before
There’s no right or wrong time to visit Italy—it all depends on your travel style, budget, and what you want to experience:
- Sightseeing: April, May, June, September, October
- Beaches, boat trips & hiking: July, August, September
- Skiing: December–March
- Budget travel: January, February, November, early December (except mountain resorts)
- Food & wine: September–November
- Fewest crowds: January–March, November–early December
How much time you should spend in Italy depends on what you want to see, but 10 days is a great starting point, and two weeks or more is ideal.
👉 Check out my detailed guide on the best time to visit Italy for all my tips
2. Make a budget
6 – 12 months before
Before planning your itinerary, it’s a good idea to have a rough idea of your budget. If you’re anything like me, it’s easy to plan an epic trip and then realize too many costs added up and you have to start all over again.
So, to have clear expectations, let me give you an idea on weekly budget costs.
Weekly budget for 2 people
Budget: $1,000 – $1,500
Mid-Range: $2,000 – $4,000
Luxury: from $4,000
Main expenses
3. Plan your itinerary
6 – 12 months before
Start by deciding what you want to see in Italy. Some places, like Rome, Florence, and Venice, are considered must-sees, but your itinerary should match your interests—whether it’s history, food, nature, or beaches.
👉 If you need inspiration, check out my guide to the best places to visit in Italy.
Once you know where you want to go, it’s time to plan your itinerary. Avoid cramming in too many destinations: Italy has a lot to see, and rushing through places isn’t ideal if you want to experience la dolce vita.
A 10-day trip lets you see about three destinations (e.g., Rome, Florence, and Venice or the Amalfi Coast), but two weeks or more gives you time to slow down and explore beyond the main cities.
Sample itineraries
Classic Italy
7 days
Rome, Florence and Bologna or Siena
10 days
Rome, Florence, Venice
14 days or more
Rome, Florence, Venice, Amalfi Coast, Milan and Lake Como
Food and wine
7 days
Florence, Chianti, Bologna and Modena
10/14 days
Rome, Florence, Chianti, Bologna and Modena, Barolo and Alba (Piedmont)
Nature and landscapes
10 days
Dolomites, Chianti, Val d’Orcia, Amalfi Coast
14 days or more
Lake Como, Dolomites, Chianti and Val d’Orcia, Amalfi Coast
Not sure how to fit everything into your itinerary?
I can create a custom itinerary tailored to your travel style, budget, and pace—so you don’t have to worry about logistics.
Let me do the work and focus on enjoying your trip!
4. Check travel requirements
6 – 12 months before
Before booking anything, make sure your passport is valid for at least 3 months after departure and that you meet visa requirements.
EU travelers don’t need a visa and can enter with a valid ID or passport. Non-EU travelers may need a visa, but many countries—including the U.S., UK, Canada, and Australia—can visit visa-free for up to 90 days in a 180-day period.
To check your exact, use the Italian Visa Tool and double-check with your country’s official site, for example: USA – UK – Australia – Canada.
From mid-2025, travellers from visa-exempt countries will need an ETIAS travel authorization to enter Italy. It’s not required yet, so for now, there’s nothing you need to do.
5. Book flights
6 – 12 months before
Flights are one of the biggest trip expenses, so book early. I always use Skyscanner to compare dates and find the best deals—it’s the easiest way to check flights to Italy.
If your itinerary covers multiple regions, consider flying into one airport and out of another to save time. Also, check different destinations with Skyscanner: flights to one city might be cheaper than to another on the same day.
Italy’s best airports are:
- Rome (FCO – Fiumicino): Best for first-time visitors and central Italy.
- Milan (MXP – Malpensa): Best for Northern Italy, the Dolomites, and Lake Como.
- Venice (VCE – Marco Polo): Best for Venice and the Veneto region.
- Naples (NAP – Capodichino): Best for the Amalfi Coast and Southern Italy.
- Florence (FLR) & Bologna (BLQ): Smaller airports for Tuscany and Emilia-Romagna.
6. Decide how to get around in Italy
4 – 6 months before
Italy has great public transport, but in some areas, renting a car makes more sense—it all depends on where you’re going.
When to take the train
High-speed trains (Frecciarossa, Italo) connect major cities, while regional trains reach smaller towns too. If you’re only visiting cities like Rome, Florence, Venice, or Milan, you don’t need a car—trains are fast, affordable, and way less stressful than driving in cities.
Book high-speed train tickets in advance on Trainline—they sell out quickly, and prices are much lower when booked early.
When to rent a car
If you’re exploring Tuscany, the Dolomites, Sardinia, or Sicily, renting a car gives you more flexibility and saves a lot of travel time.
Just watch out for ZTL zones (restricted areas with automatic fines) and keep in mind that non-EU travelers need an International Driving Permit (IDP).
You’ll usually find the best deals to rent a car on rentalcars.com—I use it all the time, and it’s been great.
When to take a flight
I usually avoid internal flights in Italy unless I have to—they’re rarely worth it if high-speed trains are available. The only time they make sense is for long distances or reaching Sardinia and Sicily.
Love traveling, hate logistics? Let me do the work!
I’ll create a custom Italy itinerary so you see and do exactly what you want—without the stress.
Just need advice while planning on your own? Let’s hop on a call, and I’ll help you plan like a pro!
7. Book accommodations
4 – 6 months before
Italy has tons of accommodation options, from hotels and boutique stays to Airbnbs, B&Bs, and agriturismos.
Prices vary by type and season, but budget hotels typically cost €70–€100 per night for two people, while mid-range options—including boutique hotels, agriturismos, and well-rated Airbnbs—range from €150–€250 per night. For a luxury experience, expect to pay anywhere from €300 to over €1,000 per night, especially in high-end resorts or five-star boutique hotels.
My favorite website for booking hotels and rentals is Booking.com, though Airbnb has good options too. The earlier you book, the better the prices—especially in high season!
How to choose where to stay
- Love nature and authentic stays? Agriturismos are a fantastic option.
You’ll find everything from simple farm stays to luxury retreats, but all offer a local, countryside experience. - Want a unique city stay? Boutique hotels often feel more personal and local than big chains.
- Need more space and a kitchen? Vacation rentals give you more flexibility and can help you save on food.
8. Book tours and activities
2 – 3 months before
Many popular attractions in Italy sell out weeks in advance, so booking early is key—especially for must-see spots with limited daily admissions.
Some attractions always require advance booking: Colosseum, Vatican Museums, Last Supper, Doge’s Palace, Uffizi Gallery, and St. Mark’s Basilica.
The best private experiences like boat tours, guided day trips, cooking classes, and wine tastings also fill up fast!
Most attractions have different ticket types:
- Standard entry tickets: the cheapest, but expect long lines.
- Skip-the-line tickets: 100% worth it, the lines can be brutal.
- Guided tours: The best way to actually understand what you’re seeing. Group tours are budget-friendly, private tours are more personalized but cost more.
I strongly recommend booking skip-the-line tickets or a guided tour—especially a private one if it fits your budget.
For fewer crowds, aim for entry times near opening or closing.
You can book directly from official attraction websites, but I usually book through GetYourGuide, Viator, or Tiqets as they often offer free cancellation, and I love having flexibility when I travel.
9. Get travel insurance
As soon as you book
You know, life happens, and you never think you’ll need insurance until you do.
Travel insurance covers unexpected costs and emergencies, from medical expenses and trip cancellations to lost baggage.
For full coverage, book within 1–2 weeks of booking your flights, especially if you want cancellation benefits. Some policies let you buy it a few days before departure, so it’s never too late!
I recommend checking out Allianz Travel or SafetyWing.
You’re all set
So, now you know how to plan a trip to Italy!
Planning your first trip to Italy takes time, but breaking it down into clear steps makes everything easier. With the right itinerary, smart bookings, and a little preparation, you’ll have an unforgettable experience—without the stress.
No time to plan?
Let me do it for you!
I create custom Italy itineraries and offer one-on-one consultations to help you plan the perfect trip—without the stress. Whether you need help choosing destinations, planning an itinerary or finding hidden gems to visit, I’ve got you covered.
