We are planning an 18-day trip to Italy with our family of five adults (two seniors) and two grandchildren (ages 10 and 12). We plan to fly into Rome, head north to Milan / Lake Como, Tuscany area / Florence, Sorrento / Positano, and Rome. Are we too late to make this happen, starting June 6? Originally, we were going to travel the last week of July and into August, but we are concerned about the crowds and heat. Second, suggestions on other air travel ideas from Chicago to Rome, as there are limited options already. We do appreciate the community sharing their experiences as we continue to research the best options.
Posted by
Seattle, WA, USA ☔️
7537 posts
It's certainly not "too late" to make it happen, but it's generally true that the later one books, the thinner their options are. Plenty of people plan June trips later than the first week of January (though many of us here are pretty obsessive about trip planning and will begin our planning work much earlier). If you want to make it work, you can, and there's no need to panic, but yes you should try to move quickly to start nailing down your itinerary and book things sooner rather than waiting for much later.
You will be challenged to varying degrees by the fact that you are picking very popular places, and also by having a large group (it's much easier to plan a trip for a couple).
One tip: You say you are going to fly in to Rome, go to (a list of places), then go back to Rome and fly home from there. Don't do that (circle back). Fly in to one city, fly home from another (could be Rome + Milan or Rome + Venice, or others). That's much more efficient. But if you're going to do this, roll up your sleeves and start getting things sorted soon.
Posted by
Gettysburg PA
8757 posts
Sure it’s feasible and not too late
Note that June will be crowded too
Consider multi-city flights-fly IN to Milan, out of Naples (or Rome)
Use Google flights to check your options, set up some price alertsa
Once you have settled on itinerary begin looking for lodging-booking.com is a good place to research
Get a good guidebook if you don’t already have
Posted by
Idaho, USA
9219 posts
All of the locations you’ve picked will have some level of crowds.
Maybe fly into Naples & stay in Sorrento/Amalfi Coast for those activities.
Then Rome.
Up into the Tuscany area.
Finish at one of the lakes and fly home from Milan’s Malpensa airport.
The multi-city plane ticket is on one reservation- not two 1-way tickets.