How to plan a trip to Italy, Rome, Florence, Venice, planning guide
Amalfi Coast, Europe, Florence, Italy, Places to Visit in Italy, Read About Can't Miss Places, Rome, Travel Tips, Venice

How to Plan a Trip to Italy

Amy French the Roaming Historian

There’s something magical about planning a trip to Italy. Ever since our first trip there in 2013, I get the same excited feeling and anticipation. Since we go there annually, I don’t get the nervousness when planning and just get to completely enjoy it. But for a first-timer or someone who hasn’t gone to Italy a lot, you might be feeling a bit overwhelmed. I love helping my friends plan their European trips, so I thought I would put some of my advice in a blog–along with a checklist similar to what I use when doing my planning.

You might be wondering–where do I start? How many cities are too many? When should I book tickets? Are trains easy? How much will it cost?

If those are some of questions you’re asking, you’re in the right place. After well over a decade of planning Italy trips, I can say that Italy is not hard — but it does reward smart structure. Here’s how I approach planning an Italy trip — in a way that feels exciting, not overwhelming.

1. Start With the Big Picture (Before You Book Anything)

Before diving into hotel tabs and flight comparisons, zoom out.

Ask yourself:

  • When do I want to go?
  • How many nights do I realistically have?
  • Do I prefer slower travel or fast-paced sightseeing?
  • What would I regret missing?

When thinking about when you want to go, you might be limited by when you take your vacation usually. If you’re not, know that Italy changes dramatically by season. Summer is hot, crowded, expensive, but has lots of hours of daylight. Winter is cheaper and quieter, but colder and with shorter days. Spring and Fall are still crowded (Italy is always busy) but a little more manageable, prices aren’t at a peak and there is lovely weather. There’s no wrong answer — but knowing the tradeoffs helps you plan smarter.

2. Build a Realistic Budget (With Breathing Room)

Italy doesn’t have to be wildly expensive — but surprises add up quickly. I like breaking budgets into six simple categories:

  • Flights–start looking for them far out, so you know what a good deal looks like. Here is a blog on how I book: https://roaminghistorian.com/2025/12/07/use-ai-google-flights-flight-deals/
  • Accommodations–I use Booking.com and VRBO to get ideas about what places offer what, where they’re located, etc. Make sure you’re comparing apples to apples with cancellation, breakfast inclusion, etc. Expect mid-range hotels to be around €200-300 per night in Rome. Booking.com: https://www.awin1.com/cread.php?awinmid=6776&awinaffid=1985445 and VRBO: https://vrbo.com/affiliate/KvF3nms
  • Food–this too can vary widely but plan around €30-50 per day per person for budget eating in any major city, €50-75 for mid-range, and €100+ for fine dining. Smaller cities are less expensive but even Rome can have great deals. Street food is generally tasty and fairly inexpensive, as are pizzas and pasta dishes.
  • Transportation within Italy (trains, taxis, water taxis, buses, private cars)–this varies widely with buses being the cheapest. Some routes (like Rome airport to city center) have fixed prices for taxis. Regional/local trains are very inexpensive.
  • Attractions, tours, experiences–I find tickets in Italy to be much cheaper than their counterparts in North America. Even the biggest attractions, like the Colosseum, aren’t that pricey. Look at prices through our trusted partners to get an idea of prices (listed under #4).
  • Miscellaneous (travel insurance, souvenirs)–even though I have medical insurance that covers globally and some travel insurance through my credit card, I still take out a policy each time to cover the gaps. I use Travel Insurance dot com because I can view multiple policies at one time and buy directly from the insurer through their website. https://www.travelinsurance.com/?utm_source=pap&a_aid=65590b3a60c44

Then I always suggest adding a 5–10% cushion. There is always something unexpected. A few gentle planning reminders:

  • Stay in a central hotel or apartment. Yes, a city-center hotel is more expensive than one on the outskirts of town but you save money in time transportation costs. In the end, it’s often only a little more when all things are included and you’re right in the center of the city you want to see–a late night stroll through a piazza is worth a little more to me.
  • High-speed trains are usually cheaper than you think. The further out you book a train, the cheaper it is. There are two main train companies–Italo (private) and Trenitalia (state system). Trenitalia also has regional/local trains. Italo only has high-speed. Compare prices with both of them and book as soon as you can since the cheapest tickets sell out first. I always book straight from the company itself–Italo or Trenitalia.
  • Major attractions almost always require advance tickets. Do not leave this up to chance. These days even smaller attractions are selling out, so if there is something you want to see you will need to book it. Get a good estimation of ticket prices for your budget.

Budget clarity reduces stress. Once you have rough dates and cities, I usually recommend checking flight prices early—not necessarily to book immediately, but to understand the range. If you see something that fits your budget and timing, that’s when I’d lock it in. I personally prefer comparing options in one place so I can weigh timing, layovers, and price side by side before booking directly with the airline. You can use Expedia, Google Flights, or Booking.com for ideas.

Expedia: https://expedia.com/affiliate/p7ZcFsz

Booking.com Flights: https://www.awin1.com/cread.php?awinmid=6776&awinaffid=1985445&campaign=flights&ued=https%3A%2F%2Fwww.booking.com%2Fflights%2Findex.html

3. Choose Fewer Base Cities Than You Think

One of the biggest mistakes first-time visitors make is trying to “do all of Italy.” Italy is not a checklist country. Instead of bouncing hotels every night, select 2–4 base cities that align with your interests and explore them more deeply rather than trying to see everything. I recommend staying in each city for 3-4 nights at a time. Use day trips to visit other places rather than moving hotels. Moving hotels wastes time and day trips are a lot easier than repacking, checking out, and checking back in. For instance, you can stay in Rome and still easily see Naples or Pompeii in a day. Similarly, Siena, Pisa, Bologna, and many other cities are a day trip away from Florence. A lot of the tour companies we have used offer neatly packaged day trips with transportation included, so you can sit back and relax while you gaze at the Italian countryside while going wine tasting in Tuscany, take in the archaeological ruins at Pompeii, or go hiking in the Cinque Terre.

What cities have you always dreamed of seeing? Create a wish list of those places and use that list to create your dream Italian vacation. Here is a simple framework that seems to work for a lot of tastes based on how long you have.

7–8 Days: Two cities (Rome for four-five nights + Florence for three)

10–12 Days: Rome, Florence, Venice (at least four nights Rome, three-four Florence, and three-four Venice)

13+ Days: Rome, Florence, Venice plus add one to two regions (use the same format as above and add a region or two like a coastal area, northern lakes, a countryside place)

When mapping out the final itinerary, visit your base cities in order of the rail line and try to get fast train tickets if possible, rather than regional.

When choosing accommodations, location matters more than star rating. Staying central saves time and energy — and in Italy, that’s everything. I always filter for properties within walking distance of major sites. You want to experience the city at all its finest. Flexible cancellation policies are worth prioritizing, especially if you’re booking months in advance. I look for city-center locations in any city. Also, accessibility varies greatly. It is not uncommon for an elevator to start on Italy’s first floor, which is North America’s second floor. If you don’t want a flight of stairs before your elevator, check the hotel’s details. Most hotels have in-room bathrooms but it’s still good to check. It’s also good to check if air conditioning is included; you might find budget hotels that lack it. I like Booking.com to compare and contrast the various hotels, their locations, and their amenities/accessibility. Also, be cognizant of the terrain–Rome is built on 7 hills, so your hotel location might be tiresome to get to if you’re at the top of one. Other Italian cities are hilly or have other idiosyncrasies (like canals), so beware when picking a place.

Booking.com: https://www.awin1.com/cread.php?awinmid=6776&awinaffid=1985445

4. Plan Your Days Gently (Not Like a Marathon)

Italy has so many amazing things to do that it’s easy to try to pack a lot in…but that is where burnout happens. You will be so busy racing from place to place that you won’t be able to really enjoy the sites you see. Nor will you have time for leisurely meals, gelato breaks, and aperitivos on piazzas. To figure out what to see, pick your non-negotiables. What will you be devastated if you miss? Those need to be on your itinerary. But they don’t have to all be in one day.

I usually recommend:

  • 1 major attraction in the morning
  • 1 major attraction in the afternoon
  • Open time for wandering, visiting markets, having coffee, seeing churches and smaller sites, getting lost

Cluster sites in the same neighborhood, if possible, to cut down on time wasted going back and forth. Here’s an example of how I would plan three days in Florence: https://roaminghistorian.com/2025/03/09/top-attractions-in-florence-a-3-day-itinerary/

And yes—book major sites in advance. Italy is more crowded than ever and even sites that didn’t use to sell out are difficult to get tickets for. On top of it, many sites have gone to requiring pre-booking, so if you don’t book them in advance you won’t get in.

Showing up without tickets can mean long lines — or complete sellouts. Here are some of our favorite tour companies and online marketplaces to help you get an idea of what options are out there.

LivTours (high-quality semi-private and private European tours led by expert guides)
Save 10% with code AMYRH10 (valid on two or more tours).
https://livtours.com?af_code=E1DDN61

The Tour Guy (engaging small group & private European tours)
https://tidd.ly/3J78sNi

Viator (compare thousands of tours, day trips, and experiences worldwide)
https://www.viator.com/?pid=P00161535&mcid=42383&medium=link&medium_version=selector

GetYourGuide (flexible booking options for tours, attractions, and local experiences)
https://www.getyourguide.com/?partner_id=CMSFGKK&utm_medium=online_publisher

Shore Excursions Group (high-quality shore excursions with lower prices and return-to-ship guarantees.)
https://www.shoreexcursionsgroup.com/?id=1634209&data=roaminghistorian@gmail.com

5. Transportation Is Easier Than You Think

Between cities? Take the train. It’s fast, efficient, and city-center to city-center.

Within cities?

  • Walk as much as possible.
  • Use metro/tram or buses where available.
  • Use taxis (look for taxi stands). In Venice, use the vaporetto (water bus).
  • Skip rental cars in major cities.
  • Regular Uber doesn’t operate in Italy—they have Uber Black in some cities but I wouldn’t count on it as much as I would public transportation.

Italy’s transport system is far less intimidating once you understand the rhythm. As I mentioned above, look at the two train companies—Trenitalia and Italo—to get ideas of routes and prices. Early bookings often mean lower fares and better seat selection.

6. Lock in the Important Things Early

Once your structure feels right:

  1. Book flights
  2. Book accommodations
  3. Secure tickets for attractions, tours, and experiences.
  4. Purchase train tickets
  5. Make reservations for the restaurants you can’t miss

If something is a dream moment—book it before you leave home. That one decision alone eliminates so much stress. Think back to those non-negotiables and lock them in. Get those tickets ahead of time or risk disappointment. Even secondary attractions are selling out these days. For those things you’ve always wanted to see or do, I strongly recommend securing timed-entry tickets before you leave home. It’s one of the simplest ways to avoid long lines and sold-out disappointments. I usually compare official tickets and small-group tour options to see what offers the best balance of value and access. Here are my preferred companies.

See our favorite tour companies in section #4 to book now.

One final thing that often gets overlooked: protecting the trip itself. Italy is wonderful — but flights get delayed, luggage gets misplaced, and unexpected things happen. Travel insurance isn’t exciting, but it’s one of the smartest bookings you’ll make. I always compare policies side by side, so I know exactly what’s covered before departure. I use Travel Insurance.com: https://www.travelinsurance.com/?utm_source=pap&a_aid=65590b3a60c44

I know that this is probably a lot to take it, so I created a downloadable “Italy Trip Planning Checklist” that you can print to help with your journey.

Italy Trip Planning Checklist: https://roaminghistorian.com/wp-content/uploads/2026/03/Italy-Trip-Planning-Checklist.pdf

Happy travels!

FAQs About Planning a Trip to Italy

How far in advance should I plan a trip to Italy?

For summer travel, start planning 7–10 months in advance. For shoulder or winter seasons, 5–7 months is often sufficient.

How many days do I need in Italy?

For a first trip, 10–12 days allows you to visit Rome, Florence, and Venice comfortably. With 7–8 days, focus on two cities only.

Is it better to rent a car in Italy?

In major cities, no. Trains are faster and easier. Rental cars are helpful only in rural regions that don’t have ample public transportation. I recommend not renting a car your first time. I spend a lot of time in Italy and I still have not rented a car. It’s too easy to end up in a ZTL zone and to get a hefty fine. If you really feel you just must drive, make sure you have an International Driver’s Permit and learn about where you can and can’t drive in Italy.

Are trains in Italy easy to use?

Yes. High-speed trains are efficient, comfortable, and connect major cities directly. Booking in advance often saves money.

Do I need to book attractions in advance in Italy?

For major sites — absolutely. Attractions like the Colosseum and Vatican Museums regularly sell out days (or weeks) ahead.

Check out my YouTube video for more tips on how to plan a trip to Italy: https://youtu.be/5IGB9Hu-uts

Amy French, Ph.D., is the voice behind Roaming Historian. A professional historian and seasoned traveler, she shares stories that blend history and travel to give readers a deeper understanding of the places they explore.

A Favorite Italy Tour Partner: LivTours

LivTours is a boutique, family-owned company specializing in high-quality, semi-private (maximum 6 people) and private tours, primarily in Italy, as well as Spain, France, England, Austria, and other parts of Europe. They are highly regarded for skip-the-line access to major sites, expert, English-speaking guides, and curated, immersive experiences designed to avoid “cookie-cutter” travel. We’ve had amazing experiences with them and enjoy that they hire local guides exclusively.

LivTours offers Roaming Historian readers 10% off two or more tours! Save on your next favorite European memory by using our coupon code “AMYRH10.” We highly recommend this company; they offer topnotch tours, tickets, and experiences and you can save money with Roaming Historian!

Book with LivTours here: https://livtours.com?af_code=E1DDN61

Liv Tours Tours Save Money with Roaming Historian, Europe Tours, Italy Tours

Viator

Viator offers a vast selection of tours, attraction tickets, and travel experiences around the world, making it easy to find activities that fit different interests and budgets. Travelers can compare itineraries, prices, and detailed reviews to choose from thousands of options ranging from guided city tours and day trips to museum tickets and unique local experiences. Many bookings include free cancellation up to 24 hours in advance and a convenient reserve now, pay later option, providing flexibility while planning your trip. Pro tip: when browsing tours, look for experiences with Viator’s “Badge of Excellence” or listings with a large number of consistently high reviews to help ensure a high-quality experience.

Browse tours and activities with Viator here: https://www.viator.com/?pid=P00161535&mcid=42383&medium=link&medium_version=selector

Get Your Guide

Finding quality tours and experiences while traveling can be overwhelming, especially in popular destinations. Get Your Guide is a global marketplace that makes it easy to discover and book guided tours, skip-the-line tickets, cultural experiences, day trips, and unique local activities in cities around the world. The platform allows travelers to compare reviews, ratings, itineraries, and prices so you can choose experiences that match your interests and schedule, and many bookings include flexible cancellation policies (often up to 24 hours in advance). Because Get Your Guide hosts tours from many different operators, pro tip: always check recent reviews and overall ratings to ensure you’re selecting a high-quality experience. Browse tours and activities here: https://www.getyourguide.com/?partner_id=CMSFGKK&utm_medium=online_publisher

Visiting Italy by Cruise? Check out Shore Excursions Group

If you’re visiting ports during a cruise, Shore Excursions Group is a reliable alternative to booking excursions through the cruise line. Their tours are often smaller, more affordable (sometimes up to 40% less than ship excursions), and led by knowledgeable local guides. They offer carefully designed shore excursions in ports around the world. Even better, they provide a guaranteed on-time return to the ship, giving cruisers peace of mind when exploring independently. Just plug in your cruise ship and sail date and your ports will automatically populate, so you can browse excursions for your cruise ports here:
https://www.shoreexcursionsgroup.com/?id=1634209&data=roaminghistorian@gmail.com

Our Favorite Travel Insurance Site

Protect your vacation with Travel Insurance dot com. This awesome travel site provides quotes from numerous travel insurance agencies and allows you to purchase them with no added increase to you: https://www.travelinsurance.com/?utm_source=pap&a_aid=65590b3a60c44

Travel Insurance dot com, affordable travel insurance

Trusted Booking Resource: Booking.com

When planning a trip, it helps to compare your options in one place. Booking.com allows you to search and compare hotels, apartments, vacation rentals, flights, cruises, and car rentals worldwide, making it easier to organize the key pieces of your trip in a single platform. Travelers can review prices, amenities, guest ratings, and neighborhood locations to find accommodations that match their style and budget, and many listings offer competitive pricing, occasional deals, and flexible cancellation policies. Pro tip: when comparing places to stay, focus on guest reviews, location, and cancellation policies—these factors often matter more than the nightly price alone. Browse and compare travel options here: https://www.awin1.com/cread.php?awinmid=6776&awinaffid=1985445

Plan Your Italy Trip: Helpful Guides to Get You Started

How to plan a trip to Italy: https://roaminghistorian.com/2026/03/08/how-to-plan-a-trip-to-italy/

Packing Light Guide: https://roaminghistorian.com/2025/09/07/the-definitive-guide-to-packing-light/

How to Choose a Hotel: https://roaminghistorian.com/2026/03/17/how-to-choose-a-hotel-when-traveling/

Tipping in Italy: https://roaminghistorian.com/2026/03/03/guide-to-tipping-in-italy/

How to Get to Rome from Airport: https://roaminghistorian.com/2020/02/09/how-to-get-to-the-rome-airport-fco-airport/

Essential Italy Travel Tips: https://roaminghistorian.com/2025/04/06/essential-italy-travel-tips/

When to Buy Travel Insurance: https://roaminghistorian.com/2026/03/13/when-to-buy-travel-insurance/

Travel Insurance: How to Protect Your Trip: https://roaminghistorian.com/2024/02/04/best-travel-insurance/

How I Find the Cheapest Flights: https://roaminghistorian.com/2025/12/07/use-ai-google-flights-flight-deals/

Traveling Soon? Trusted Tour & Travel Partners

Planning your trip? Here are our trusted travel partners — thoughtfully chosen for quality, reliability, and exceptional experiences.

Affiliate Disclosure

Roaming Historian may earn a commission from qualifying purchases made through affiliate links. This comes at no additional cost to you and helps support the research and storytelling that go into every article. All opinions are always our own.

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