Planning Your Trip to Italy: What to book when

When planning your trip to Italy, you want to work efficiently. It’s easy to get overwhelmed with the amount of online information. It’s a challenge to know what needs to be booked in advance and what can be left open. After all, it’s fun to have some flexibility on the trip. You want to book excursions early enough to have lots of choice, of course. But also not so early that they tell you to call back later!  When planning your trip to Italy, I recommend the approach below, which we use at Italy Beyond the Obvious for our gold and platinum Italy itineraries.

Photo of Lake Garda by Sanjay Jhawar

Planning your trip to Italy: Accommodations

Book accommodations at least 4 months in advance, unless you’re going in August or renting a villa.

When I worked in Milan as an expat, the January espresso machine chat centered almost completely around August vacation planning. Italians book their August vacations in January, and so should you. Villa rental also needs to be done early — it really depends on the villa (and I can always  find something) but for the best selection and the best experience, book 9 months+ in advance. But for hotels, farmhouses, B&Bs, apartments, castles, and other accommodation, aim to book 4-6 months in advance for a good selection (or, if you’re not ready to commit, find your top three, book all three, noting the cancellation window, and then cancel later).

Planning your trip to Italy: Activities and tours

Book classes and short tours about 3 months in advance, unless it’s a rock star teacher.

Often, if you try to book classes or day tours more than 3 months in advance, you’ll be told to call back later. Either the schedule isn’t set, or they just aren’t taking bookings, and it goes in to your must-follow-up-on list. I’m not saying that you won’t be able to book earlier than that, but you’ll have plenty of options 3 months ahead of time and you won’t be told to call back.

Book tickets about 6 weeks in advance.

For small festivals (even ones that happen yearly) or anything that requires a schedule of performances, it’s completely normal for the schedule to be released about 6 weeks beforehand, or less. Major venues like Milan’s La Scala Opera house or comparable venues are released and have tickets available for booking months in advance, but the smaller and more local the festival, the later the schedule will be published.  Even if you don’t need tickets, and are just interested in a local food festival, expect the schedule to be published (most likely only in Italian) 4-ish weeks ahead of time.

Planning your trip to Italy: Logistics

Book car rentals about 2 months in advance. Book train tickets 2-3 months in advance.

Car rental prices change according to some algorithm I don’t understand, but what I do know is that if you book really early, the price is higher compared to about 8 weeks pre-departure (for an automatic transmission). If you can drive a stick shift, you can book 6 or even 5 weeks before departure. At about 4 weeks out, prices start to creep up. I start watching rates starting about 6 months pre-departure and most of the time I confirm the car rental about 8 weeks pre-departure. Driving in Italy stresses out a lot of people, but don’t worry, we have a lot of advice!

Train tickets don’t even go on sale online until a few months in advance, although every now and then I see an exception. But if you’re six months out, and you see that the train ticket you need is “not available”, don’t stress out. It’s not sold out, it’s just too early. That said, train tickets DO sell out in high season, so definitely book a month or so in advance, at least.

Planning your trip to Italy: restaurant reservations

Book restaurants about a week in advance, unless they have Michelin stars.

For the hard-to-get reservation, how far in advance you need to book varies wildly. In general, Michelin-starred restaurants can be booked a month or two in advance. For everything else, there’s no point booking more than about a week to ten days ahead of time. In Rome, Florence, and Venice, restaurants are accustomed to taking reservations from tourists weeks ahead of time, but when I’ve tried to call restaurants in smaller or more remote places that early, they always ask me to please just call back.

We recommend having a dinner reservation that you might cancel, so you avoid the scenario where you’re walking around hungry at dinnertime and all the places in your list are completely booked. It’s also a lot of fun to eat like the Italians and follow the Italian food schedule.

Planning your trip to Italy: Hire Italy Beyond the Obvious!

We know how much work it is to plan your own trip, though. Let us help! We’ve been creating incredible custom vacations since 2008. Just ask our happy travelers.

Let us take it off your plate, make the planning fun and easy, and make sure your trip runs smoothly. We’ve got you.