Travelling through Italy for 2 months

I would recommend looking at the high-speed train route maps of Trenitalia and Italotreno. You can save some money by buying your high-speed Trenitalia train tix up to two months in advance of the train’s departure date. Italotreno, a private train company, sells its high-speed train tix up to six months in advance. Tickets for trains beyond December 13 can not be bought until the revised train timetables are made official on that date.
Regional trains for other destinations can just be bought at the train stations right before departing as there is no discount for buying them in advance and trains can not sell out.
www.Trenitalia.com
www.Italotreno.com

You could buy multi-city airline tickets to fly into Venice and fly out of Palermo, Catania or Syracuse.
www.Skyscanner.com for flight schedules and fares.

First, pick your rough dates.
Second, pick your entrance/exit cities.
We do this because we are using airline points and avoiding peak days.
Buy your plane tickets.

Third, pick some places in between.
Now, analyze each place and collect things to do.
I use [free] Planapple for collection, but you can use a simple document.

Fourth, choose AirBnBs.

The app Rome2rio is great for planning train trips.

If you are asking a generic travel planning tips, start with this page on this website:

https://www.ricksteves.com/travel-tips.

You will need to figure out where you want to go, what you want to see, where you want to stay (type of accomodations), how to travel between destinations and flghts to and from Italy. (Think open jaw rather than round trip. Open jaw is when you use the multi-city function to fly into one city and out of another. Not two one way tickets as they will be more expensive.)

Rick gives some good tips of putting together a basic itinerary. My suggestion, try to continue moving in one direction and not too much backtracking.

Figure out your basic itinerary then come back with specific questions.

BTW, Rome2Rio is one of the worst sites for planning anything. It is quite often wrong and doesn't always show all of your options. Use the Trenitalia and Italo websites mentioned in earlier postings to this thread for train travel information. There are also buses for travel to smaller towns where there might not be a train.

My last suggestion is to learn a little Italian.

To get an idea of schedules, ticket prices and travel times, download the TrenItalia app. You can then look at possible trips. You must enter the Italian names for locations. If you can purchase tickets in advance, they can be substantially discounted but they are neither refundable nor changeable. High speed trains have assigned seating and variable pricing. Regionale (think local vs. express) are always the same price and have no reserved seating. I find it easiest to purchase any rail tickets on line from the app and the conductor then scans the download on my phone. In Italy it does not pay to purchase any type of rail pass. Buy all tickets point to point.

Where rail service is unavailable, you might be able to travel by bus. I have used buses on a limited basis and it has worked out well for me. I found which buses to take from the front desk hotel clerks.

Thank you so much for all your suggestions. I shall start doing my homework.

My experience last summer was better with the TrenIT! app than with the usual Trenitalia app. But I think either one will be more accurate than Rome2Rio if you're looking solely at train travel. Rome2Rio does give you bus information also, which could be very helpful for some travelers.

What an amazing plan! Use as many transportations as possible -train, buses, ferries- so that you can see the most things! If you start from sicily, go to coastal cities (like Catania or Siracusa), then take a ferry to mainland Italy (e.x., via Messina). From there, travel north by train through regions like Calabria, Campania, Tuscany, and up to Venice. I would suggest to check trenitalia for the trains and ferryhopper for the ferries.

If you have free choice about which two months to spend in Italy, I would sure pick two months from October to April rather than when it is hot and crowded. My favorite times are November/December and March/April, but I've never tried mid-January to mid-March and I know that despite the weather (and shorter hours of daylight) some people like that time because the heavily touristed places are the least touristed.

I could name cities/towns I've enjoyed that are on train routes for you, but they would be according to my own interests (art, food) and not your interests (scenery? hiking? beaches? small towns? cooking? people-watching? learning Italian? history? photography? etc., etc.)

Some don't miss cities are, as follows:
Venice
Bologna
Ravenna
Pisa
Lucca
Siena
Florence
Assisi
Spoleto
Orvieto
Rome
Naples
Sorrento (visit Pompeii)
Capri
Amalfi Coast
Salerno
End in Sicily

I spent two months in Italy in 2024 - if a little differently - and I have some thoughts.

• You're probably looking at 5-8 locations given your description so I would work from a list of places that have "must see" on them. It sounds like you have 2 already so figure out the others starting from a too long list and editing down.
• Set a budget. Two months in the touristy areas of Italy will be expensive so you may want to balance staying in more rural places mixed with places like Rome, Florence and Venice to keep expenses under control.
• Set a time of year. Summer is very hot and tourism is rampant in Italy so planning two months in your sweet spot is going to take some doing. Do you have any "must sees" that involve a time of year or an event? That may make planning easier. Watch for events in specific places that might make them extra-expensive if that's not why you're going.

In general I would advocate going North to South since the northern parts of Italy are more orderly and as you head further south the forces of chaos seem to get stronger and more pronounced. Travelling this direction will ease you in more to Italy than starting in Palermo. However, if you go in Spring you might want to go South to North chasing the warming weather.

Not ever place is going to be interesting for a whole week. You should also plan to visit places based on their proximity and how connected they are to other places to visit and plan to branch out. I also think you should stay flexible and think about staying someplace a night or two on the way between places to see more places. Orvieto is a lovely little town but I think a week would be way too much with Rome on one side and Florence on the other, but it could make a nice rural break between those two big cities.

How's your Italian? The more rural and less touristy you go the faster English proficiency drops off. It's entirely possible to operate daily life with only a few words of Italian, but if you're hoping to get to know people and the country on a deeper level you will need to know a certain amount of Italian. Italians love to talk, but if you run out of things to say after "Che bel tempo oggi, vero?" this will limit your ability to engage.

At this point I would check all the guides to critical cities, sights and activities and make a list which is too long and start to whittle it down. Look at how cities and sights can tied to together and relative time in places and work out when it would be best and go from there. Ask questions here about specific areas, regions or places you're wondering about.

Once you have a start on an itinerary swing back by and get some feedback on it from the forums, but always remember it is your trip not anyone else's. The final decision is yours and follow your dreams.

Happy planning, sounds awesome,
=Tod

If it’s you first time to Italy look at where the major tour companies go (including Rick Steve’s’ tours). That will give you the idea of the main destinations for a first time traveler. Some of those destinations will be easily reachable by train, others only by bus. Decide how many nights you want to spend at each location. Try to spend at least 2 nights at each location, but if a place is a good central hub for transportation in an area, use it as a base and take day trips from there, so that you minimize hotel changes, which are time consuming.

Here’s some general ideas from my experience, staying at 45 Italian cities:

I love attending festivals, so I would be looking up “festivals in Italy” to see what’s of interest and which month they occur. I also love cooking classes & music concerts. Do searches on hobbies that interest you.

I look at the “Italian Train Map” diagram to see which cities are covered on routes. I don’t like to go more than two hours on trains between locations, so I look up cities along the routes on TripAdvisor to get a quick “yes/no” feel for them after seeing “Things to Do”. I draw up a network web diagram on paper to see which cities are practical for transportation. I avoid buses when possible. Also, don’t plan to travel by train or bus on a Sunday; it’s less reliable.

Absolutely start learning as much Italian as possible - both to be respectful & also because you will want to be staying in places where it’s essential.

Have a great time!

Thank you so very much for your suggestions and tips. There is a lot to work on and it is daunting but it’s my dream. Thank you all. These are very helpful in my planning.

I don't know if you are from the Sydney in Australia, or Sydney, Nova Scotia, Canada, or Sydney, North Dakota, USA or Sydney, Vanuatu. But if you are from Sydney Australia, you know what hot and muggy weather means (July and August are particularly unbearably hot). If you want the hot and somewhat muggy weather in Italy, mid June through mid September will be like Sydney in December through January. Mid June through Mid Sept is also the most expensive time to vacation in Italy.

If you prefer milder, less scorching hot, I recommend to avoid mid-June through mid-September and opt for Spring (April to mid-June) or Autumn (mid-Sept through October).

Intercity bus service on Sundays is very scant to non existent. So avoid to travel on Sundays. Train service doesn't change much on Sundays, but trains tend to be crowded with vacationers on Sundays afternoons and evenings.

I know you don't plan to drive, however some locations are best visited by car, especially rural and mountain areas where bus service is not frequent. In case you decide to rent a car, in Italy you must drive on the "right" side of the road, not on the "wrong" side of the road, like you do down under. I know how challenging that change of driving habit is, so relying on public transport is not a bad idea. The Italian countryside, the mountains, the forests, the lakes and the sea are great to include in your travel plan. Unlike Australia, where every living creature (big or small) is capable to kill you in seconds, in Italy animals are not dangerous at all. The most dangerous living creatures are the humans, who tend to drive like maniacs.

Which 2 months?

Whether South to North or North to South is better, weather wise, depends on the travel time.

For accommodations I suggest searching for BnBs on https://www.bed-and-breakfast.it/en/
I've used it with great success (excellent lodgings) for several trips.
I concur with the comments about Rome2Rio for train information - in my experience (Italy and Great Britain) it is often incorrect.
My only bus experiences have been the intercity buses (e.g., Catania to Siracusa) but the trains have been great.

Hello,
In Sicily buses are best. There are trains but I have traveled around Sicily and found buses were easier and better schedules. The main Companys are SAIS, Interbus, and AST.
https://www.saisautolinee.it/en/linee-tpl-sicilia

http://www.aziendasicilianatrasporti.it/

https://www.interbus.it/

Enjoy, Sicily is Amazing!!

Just to add — I travelled around Italy in October and November and found it to be a fantastic time to go. The crowds were much smaller, the weather was milder, and there were still plenty of festivals happening in many towns.

Different strokes, for us anyway...

After 4 trips to Italy over 15 years and getting the lay of the land, our next trip will be of the roughly 6-week duration, a true bucket list shot because we are nearing 70 and don't know how many more times there will be for us, ambulatory-wise. And I have reconciled that seeing every part/region of Italy simply just to do it is not in the cards for us. As efficient as we think we are with the RS mantra 'pack light, pack right', frankly it's still a PITA to move your stuff. With a couple of family members that never have been, in April of this year we did Florence 4 nights, Rome 4 nights, Salerno/AC 3 nights, Taormina 4 nights. All by train, wonderful Trenitalia. But re-acclimating was a chore at times...again, that's just us.

Calendar-wise, we are targeting February/March 2027, a time of year we've traveled twice, and loved every minute of it. Few tourists, mostly locals. Yes, one does have to pack more for wider temperature swings, layers & such, but that challenge instead of heat & crowds I'll take any day of the week!

We are thinking of flying in/out of Rome, and weeks 1,2,5,6 will be at an apartment we'll find in Rome near Campo de' Fiori, a neighborhood where we've stayed 3 times and have favorite baristas, vendors, stores, groceries, tabacchi shops...and of course restaurants. Virtually everything and more within a 5 minute walk--amazing! And I will refute anybody that believes that credo of small town=cheaper, big city=expensive. It's simply not true. Where there's competition there is value, period. Those 4 weeks in Rome will cost less--not factoring in airfare, but maybe--than in snowbird-laden Florida, Arizona, California or most other northern European cities over the same length of time. And that delicious routine...getting up and saying over our Lavazza coffee and market breakfast of meats, cheeses & fruit...we're not on any fixed schedule...what shall we do today? As I've said, I could spend six months in Rome seeing local attractions nearly every day and STILL not have seen everything there is to see!

The middle two weeks would be up for grabs. Probably two, no more than three destinations over those 14 days, including Venice or the Swiss Alps on some of those scenic train routes, or western Sicily, or even Sardinia if the logistics make sense. No car, just public trans, meaning wherever we stay must be near the train station. Or using Ryan or Vueling Air puddle-jumpers. Heck, maybe even Vienna, a place I've always wanted to visit.

Many vets on this forum, including my friend Laurel, enjoy this 'setting up shop' way of travel. I've only stayed in one place for a week at a time, at Campo, and felt I was just scratching the surface of possibility.

Regardless, enjoy your planning...I do!

Have you thought about using ChatGTP? I have been traveling to Italy regularly since 2006 but my Daughter wants to go to Portugal and France with me prior to my Italy visit next year. She used it to plan her part of the trip and it mapped it out perfectly. I would have never thought of that myself. Some of the sites suggested in France we have already visited and will change closer to trip but it was helpful and might give you a "draft" for you to plan around.