Hooray! You’re headed to Italy.

Life is all rose-colored through your glasses, right?

Visions of zero alarm clocks, Tuscan terracotta and neverending creamy cappuccino have you firmly in the yay-phase.

The bad news: the yay-phase typically wears off.

Right around the 30-minutes-into-planning-your-trip mark.

That’s because planning a trip to Italy is a crap ton of work.

Sure, it can be fun work. Interesting work. And we’ll tell you the things you should be thinking about.

But it’s still endless hours of work. Hope you like your new full-time gig!

My prediction:

1) You’ll fall into the Tab Abyss, which resembles this:

how to plan italy trip makes you have 50 tabs

That’s right. Only 50 tabs open.

2) You’ll spiral into a wormhole of information overload.

3) You’ll hopefully find this page, come up for air, and get back on track.

In the next 3000 words, we’re going back to the BASICS.

The things you need to do and think about before a single hotel is booked.

At the time of writing, we have 2941 comments posted to the blog. In other words, a lot of you feel a little lost about how to plan a trip to Italy.

Read this and you’ll know 99% more than most, and you’ll lay the foundation for the kind of trip you’re craving.

How to Plan A Trip To Italy: The Top 5 Buzzkills (Most Beginners Make These Mistakes)

  1. Not knowing practical distances you can travel in a day.
  2. Not understanding how your mode of transport (train or a car) will dictate your trip.
  3. Not understanding how long getting from Point A-B in Italy can take (even if on paper it sounds reasonable).
  4. Not using simple, free tools to design your itinerary.
  5. Relying on outdated info found online.

How to Plan Your Italy Itinerary: The Right Way.

In this Zero-Fluff Guide, you’ll learn:

  1. How to reverse engineer your trip.
  2. How to avoid the common mistakes people make.
  3. How to use the constraints you’re working with to your benefit.
  4. About simple, free tools to get you started.

If you already have a solid plan and itinerary, you should skip to the bottom of this page where you’ll find links to tools and resources we love.

If you have not planned out your basic route, bookmark this page and reference it as you plan.

Step 1: Reverse Engineer Your Trip

When you’re in the “dream up” stage, this is a great opportunity to highlight all the things you know you want to do while on your vacation.

You’ll use these ideas to reverse engineer your trip (another way of saying work backwards). Your “big and exciting” ideas act as a starting point so that you can make sure the practical details (flights, hotel bookings) don’t douse the flames of all the dreamy stuff that’s actually motivating your vacay in the first place.

The first thing you should do is brainstorm all the things you visualize yourself doing in your mind’s eye.

Things that you’re really looking forward to! What do you see yourself doing? What have you been thinking about for ages? You need to write those random things down at the top of your page so you can work them into your plan. It’s also great to just do a brain dump and get them off your mind.

Here are few examples:

1) “I would love to learn how to make pizza in Italy.”

If that’s on your mind, make sure you enroll in a cooking class or stay at a farmstay or agriturismo that has a pizza-making class.

2) “I really want to see famous art, like Botticelli’s Venus and Michelangelo’s David.”

In that case, you need to schedule an entire day in Florence. Or two half-days. And you should also investigate getting skip-the-line tickets. (Oh, and The Birth of Venus lives in the Uffizi and David lives at Galleria dell’Accademia.)

3) “I just want to lay on the beach for two days and read all the books I never get a chance to read.”

If that’s you, prioritize three nights minimum in a beachy place (like the Cinque Terre or the Amalfi Coast). Better yet, choose a hotel based on its proximity to the beach and don’t settle. That relaxation time is what will make you feel recharged upon your return home, so don’t let it fall to the bottom of the priority list.

4) Do you have a particular hotel in mind that you’ve read or heard about? For example, Villa Lena, in Tuscany, was recently covered in Porter Magazine. That’s an example of something you may have seen in the past. Where do you “save” all these things. Go look there, now.

I’ve planned an entire getaway around staying in one destination hotel. I also know that hoteliers can be ahead of the curve, introducing you to a town you would never even have heard of were it not for the hotel that captured your imagination. (We list our fave hotel sites below.)

At the end of this brainstorming process you should have a list of “wants”. This list will help you plan the route and the number of nights you need to spend in each place. In the end, of course, you may need to sacrifice some of your wants for practical or other reasons, but getting them out of your head and onto a list is the first step in creating your dream trip.

aeolian islands plan italy trip

Step 2: Why Constraints Are Your Friend

I also wanted to talk about constraints. We all have constraints, but we should treat them as friends because without them we would languish in the “what should I do stage” for way too long — the opportunities would be endless. That’s way too confusing.

Constraints generally fall into three categories: the time category, the money category, and the transportation category.

One of the biggest mistakes I see travelers make is not managing time constraints well. They simply pack too many destinations into their trip.

In the end, you know yourself best.

It’s all very personal, but if it’s your first time planning a big trip abroad and you want my straight-up advice, I want to share it with you.

My ideal is that your hotel stays are a minimum of two nights. Three nights (or more!) is best.

On a ten-day vacation, that’s a maximum of three or four hotel choices.


Because it takes an epic amount of effort and agility to be able to travel throughout Italy only staying a night or two in each spot. It’s not that travel times are long — it’s that traveling from Point A to Point B requires a bunch of fiddly steps. Pack. Check out. Find transportation. Get on transportation. Travel time. Arrive. Find hotel. Check into hotel. Unpack. You get the drift. That’s all the work of a vacation. It’s not really the fun or relaxing part. When we’re designing tours for our trips to Italy for women, we stay a minimum of two or three nights in all hotels — sometimes up to seven nights in one. Don’t stay one night anywhere if you can help it (unless it’s because you need to catch an early flight in that city — that’s another story).

If three nights seems like a long time, remember that three nights is only two full days in one place.

Because Italy is so dense you could spend four or five nights in one hotel, but plan day trips to all the surrounding places. For example, if you stayed in Florence for four nights, one day you could day-trip it to the gorgeous Chianti countryside via a cycling or wine tour. The next day you could travel to a local village like Fiesole, which is right near Florence. That actually just leaves you with one full day in Florence. Then you would check out. See how four nights is only three days and it really whips by?

Another constraint you could be working with is money! Moolah! Cashflow!

If you know you only have X amount of dollars (or pounds or euros) to spend on your entire trip, divide that final amount by the number of nights you want to stay (minus your plane ticket cost if that’s applicable). If your total amount is looking skinny, consider upping your budget by staying for a shorter amount of time or by spending less on accommodation. Accommodation in Italy will be your biggest expense. Renting cars can also be expensive. The chapter “What You’ll Spend & How You’ll Spend It” section of Gigi Guides explains all that.

Another constraint could be transportation. Are you driving or taking the train? This will highly influence your itinerary. As will taking a flight or long-haul ferry within Italy. Read that sentence above again and let that sink in. Your transportation choices are a critical and don’t plan a day of your trip until you have a solid idea what you’re doing.


If you’re renting a car, then you can visit places in the countryside not reachable by train — many towns in Tuscany fall under this category, for example. If you’re not driving, that means your itinerary is reliant on train schedules and train-accessible destinations and you’ll need to consult Trenitalia (who operates the Italian state trains) and get very good at reading those schedules. We give you the deep dive on car rental and train travel issues in Gigi Guides.

Step 3: Tools and Resources to Plan Your Trip to Italy

Now, I’m a big fan of setting yourself up with the right tools before you even get started.

If you’re planning this trip with other people who don’t live in your household, consider scratching out your initial ideas on a “sharing platform” like Google Docs or Google spreadsheets (called Google Sheets). Or inside of a tool most people associate with managing projects, like Trello. I love and use all these tools for planning my trips.

Bonus: they’re all free and simple. Links are below.

What’s nice about these tools also is that they live in “the cloud,” which means your travel partners can edit your document and you can all have access to it as it’s updated in real time. No more searching through email threads!

Pro tip: If you use your phone for everything, try downloading the apps for Trello or Google Sheets or Google Drive. The changes you make on your phone will be updated to the cloud and accessible anywhere you have internet.

If this kind of tech freaks you out, don’t worry! A simple notebook will work too. You can always sketch out preliminary ideas with a pen a paper and then add them to a paper calendar after.

Now, once you’ve figured out which tools you’re using to track and plan your trip, you’ll need to get your distances worked out.

For this nothing beats Google Maps, which is a quick way to check distances between places and get a handle on the geography. If you’re driving, the maps at Via Michelin are even better for calculating distances. If you’re taking public transport, like trains, you’ll need to use the Trenitalia website.

Of course, you’re not limited to just land-travel options for your Italy vacation. You can also fly or ferry within Italy. If you’ve never considered this before, it could seriously shake up your preconceived notions of what your trip can look like! Adding ferries and flights might not be right for everyone, but click on the links below if you’re up for investigating just how your Italy trip can be shaped by these options. For example, knowing you could take the ferry from Genoa to the Amalfi coast might mean you can scrap your driving plans. Or knowing that flights can cost under 50 euro might seriously make you reconsider taking a ferry, which is usually more expensive — and takes sooo much longer.

What I love about this part of planning is throwing a lot of ideas down and not worrying about self-editing. Enjoy this “dream stage.”

By playing with these new-to-you tools, your trip could turn out to be a lot different than you originally thought.

That’s what traveling with insider info can do — expand your horizons and help you think of innovative ways of doing things. We’re innovators and we’ve been in the trenches helping hundreds of customers via our tours to Italy and DIY guide. Oh, and over a hundred free blog posts.

Ok, you’re getting closer!

After you’ve listed your a) “must do” ideas b) investigated distances c) decided on limitations and d) transportation, it’s time to start laying all your dates and details. Use your paper calendar, Google Doc, spreadsheet or Trello board.

This way you won’t waste your time looking for hotels on dates you don’t even have firmed up. Once you have those dates decided, start your hotel search.

The city guides inside of Gigi Guides list our best recommendations.

Also check out the links we share below for general accommodation websites that have some ooh la la Italy options.

You’ll want to book hotels as soon as you know you’re going, as hotels in Italy get booked up quickly. (For example, we book our hotels a year in advance, so our tour guests get the best stuff.)

After you’ve made your reservations, you can fill in all the fun details, like day trips and restaurants that might need to be organized ahead of time.

Of course, how much or how little you plan is up to you, but we do advise that at a minimum, you should pre-book cars, flights, ferries and hotels as soon as you can. For the most part, you can just buy your train tickets when you arrive in Italy.

Resources You’ll Love for Vacation Planning

Here’s a sample Trello board for trip planning to give you an idea. Trello is fab for visual learners.

Google Drive
Google Drive is basically word processing “on the cloud”. It’s a tool we use daily — for trip planning for clients and our own personal holidays. Perfect if you are sharing the trip planning with other people you’re traveling with.

Google Sheets
This is spreadsheets on the cloud instead of using Excel spreadsheets and emailing them to your travel partners — it’s just handier. You could map out daily activities in a spreadsheet like this, but I think Trello is more fun for that.

Google Maps
This is the fastest way to map out the distances you’ll be traveling. I like using it to figure out what flow I should be following — according to a north-south route or a west-east route. My best tip is to play in Google Maps for a while, especially if you’re driving.

Via Michelin
This is an excellent resource for drivers in Europe. It calculates gas and toll prices and gives you more driving detail than Google maps does. Link here.

Download our Getting Around on Trains guide for the lowdown on Italian trains. For example, you’ll need to know that to take the train to Venice from the Cinque Terre, you’ll first need to go down to Florence for your connector. While you’re in the “dreaming” stage of your trip planning and mapping out your itinerary, you’ll need to consult Trenitalia. Remember: use Italian names not English names (like Venezia, instead of Venice) when searching for routes.

Here is a schematic map of the state trains.

Here is an overview of where state trains travel (not all routes are listed but real-time updates are posted).

Italo Trains
This a private train company with fancier trains. Not as widely used but worth checking out. Link here.

Best Websites for Finding Italian Accommodation

There are way more options than just looking at Hotels.com. Here are some of our fave ways to sleep outside the box!

Insider Tip: For some good deals on room rentals by locals, try Googling the phrase “affittacamere [name of destination]” An example would be “affittacamere Vernazza.”

All our top picks for accommodation in Rome, Florence Venice and the Cinque Terre are in Gigi Guides.

Taking a Ferry

Since Italy is surrounded by the sea on most sides, taking ferries to various destinations is an interesting option that is worth considering, especially if you like an adventure. Larger routes are listed on aggregate sites like Direct Ferries or Ferry Savers. These sites are not a complete list of every single ferry in Italy — just major routes. There will always be smaller companies running ferries for small routes (like the ones that operate in the Cinque Terre).

Flights within Italy

There are a number of low-cost flights within Italy that can also complement your plans. Low-cost flights tend to fly out of smaller airports, but they can help you travel greater distances faster (read How to Get To Sicily for an example) or to fly to other European countries within your Italy trip. Want to go to Greece for a few days? How about Croatia?

Pro tip: Read baggage restrictions carefully. Low-cost airlines have very strict luggage limits. Consider leaving your luggage in your Rome hotel for a few days and returning to the same hotel while you spend a few days in a neighboring country with just a few days’ worth of clothes in a small bag. Find flights within Italy through aggregate sites like Skyscanner (which is a Kayak-type site but with better European flights). Which Airline can help you get creative with low-cost carriers. Alitalia is not a low-cost carrier, but if you have more than a carry-on, definitely check their site to look for flights. Other airlines that operate in Italy are Volotea, AirItaly, RyanAir, EasyJet or Vueling. Of course, depending on your departure airport (like say, Amsterdam) you could have more options for airlines. This is where the sites Skyscanner or Which Airline can come in handy.

pistachio gelato plan italy trip

Feeling overwhelmed? Just have faith you’ll find the answers.

Faith is taking the first step even when you don’t see the whole staircase.

Martin Luther King, Jr.

Creating a beautiful trip to Italy is completely within your reach. Spend some time on it and when you feel overwhelmed, just step away and come back later.

Remember, this isn’t work. It’s a vacation, so approach it with a lighthearted and playful spirit. Good things will be coming your way, whether you plan for them or not! It’s just the synchronicity of vacations. Which is what’s so great about traveling, right?

I’m excited to hear how you use the new strategies and tools in this guide and I look forward to hearing about how they help as you try and answer the question: How to plan a trip to Italy? A trip that’s an authentic reflection of your best-case scenario.

Please comment! What’s your biggest takeaway from this post? We love to hear from you. <3



Thanks for checking out our blog!

Are you interested in travelling to Italy with us on a day trip?

Check out our Day Tours HERE

We’d love to see you in Italy!



7 Responses

  1. I have been planning our June ’18 trip to Italy for over a year now & purchased the Gigi Guides last year. I LOVE the Trello tool–so handy! That is one of the most helpful suggestions in the GG & this blog. 🙂 Thanks for sharing your helpful tips!
    Can’t wait for June!

    1. Ciao Melanie,
      We are so happy to hear that!

      We love you sharing your feedback with us and other readers, and hope you have an amazing trip with the help of our Gigi Guides 🙂
      We are lucky to count you as one of our Gigi Fam! xo

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