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2 Month Trip to Italy

Hey everyone, new to the board, but I have been a lurker for quite some time. I apologize in advance for the long post. My wife and I have been graced with the opportunity to go to Italy for two months (May 22 - July 27th of this year). We figured we should take advantage of this before we start a family and while we are somewhat younger (both 31). I will preface this by saying that I am unhealthily obsessed with Italy and have watched just about all youtube has to offer on the subject and read countless books. Everything looks great on TV, but I really want to know the places I will regret if I miss. We have roundtrip booked through LHR in London because it was cheaper. We also have a few places booked but have around a full month to fill with places. This is not our first time going, and we were hoping to see places that we have never seen before, but we both are constantly pulled back to Sicily (we are of Sicilian descent). We arrive in London on May 23rd and have nothing booked and no clue what to do until we have to be in Florence on May 30th. We are then in Florence until June 20th and plan on doing some weekend trips (I will have to work during the day, loosely at CST business hours). Once we leave Florence, we will pick up a car in Rome on the 20th and plan to drive to Matera for two days and stay until the 23rd. We then have a Trulli/rustic style stay outside of Ceglie Messapica until June 30th. From there, we have nothing booked but would love to travel around Italy, we both have cousins around Palermo and would like to visit them as well. We have to return the car back to Rome on July 24th and then will somehow get to London to depart on the 27th. Any and all help would be appreciated, it's pretty overwhelming planning a trip for this long. It's a once in a lifetime trip and I keep having to tell myself to pull back because I want to see it all!

Posted by
28249 posts

You're several steps ahead because you've been to Italy before and know how rich a destination it is. You also realize you can't see everything in one trip.

It's going to be really, really hot in the south, especially during the latter part of your trip. If you're in Ceglie Messapica on June 30 and have to be back in Rome on July 24, I would normally not suggest the far north, but two months in central and southern Italy from May 1 till July 24 is going to be physically draining. The voice of experience speaketh; I did Rome-Orvieto-Sicily-Puglia in 2015, beginning on May 25. What was I thinking?

So I'll suggest a mid-trip break in the Dolomites or other mountainous area. I love Sicily, but I don't think this is a good time for you to return.

Posted by
8330 posts

Consider visiting Umbria, SE of Florence and NE of Rome. Recommend Assisi, Perugia and Spoleto.

Posted by
4873 posts

A travel agent mentioned in the WSJ today that Sicily has become very popular because of the White Lotus TV series so be aware

Posted by
3 posts

All very good points and great places to look into. I think we're just a little more drawn to the South, and it is (within reason) usually cheaper. We're getting together tonight to plan a little bit further. I may be posting some updates or questions then. We'll of course also be documenting this adventure, so stay tuned. Thanks again all!