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
Gettysburg PA
8860 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
9339 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.
Posted by
119 posts
Hi Fran,
My first trip to Italy was a rush job. It was also for 5 weeks. My husband has some mobility issues and we were traveling only by train/taxi/private driver. It was for Sept/Oct, so still busy. This was right before Covid. I had 4 1/2 months to plan. It all worked out and was perfect, in our minds. We often stayed in lodging that I may not have considered and ended up with wonderful experiences. We had to be flexible and adjust our preferred itinerary a bit, but that led to less crowded locations that were still fabulous! For example, we spent 4 nights in Montova, which I would not have initially thought to do, but we enjoyed greatly. I would say act quickly first and then refine. Go to Booking. and pick 2 hotels in each desired location in your price range and check availability. You will quickly see how feasible that part may be. If so, book then cancel where need be. That way you are not longer down the road when you try to find places. Flights are not going to vary that much... but lodging is where your needs need to be evaluated. We will be back again this April/May for only 16 nights. I have had months now to plan, reading all I can, and I am set. But I don't think it's any better of a trip plan. Just more expensive since I can get nicer rooms. I hope it works for you!
Posted by
Chicago
2296 posts
Fran--
You're right at the edge of the ticking clock to book. As stated upthread, as long as you book air within the next 3-4 weeks you should get a competitive rate. I didn't say cheap. But you had better figure out a semblance of an itinerary right now.
Your destination desires pretty much require an 'open-jaw' series of flights, and that means probably a couple legs each way. If your seniors are fairly ambulatory, what I would do is fly into Naples, out of Milan. From personal experience (I fly out of Chicago) I know Lufthansa does Chicago/Munich/Naples--at least I've done that the opposite way! And you may be able to find a nonstop Milan/Chicago. Leave yourself on the layovers at least 2 hours so you aren't scrambling, which is no fun in an unfamiliar airport. FYI, multiple legs is how I prefer to fly, rather than 9-10 hours on one seemingly interminable flight!
That being said...how do you get from Naples to eventually Milan? No doubt it's Trenitalia. I believe you can start to book your rail about 4 months out, meaning about a month from now. Download the Trenitalia mobile app and start fooling around with it now. Early bookings are not changeable but have deep discounts of 60-70% sometimes--incredible value. And don't hesitate to book 1st class if it's only marginally more expensive than 2nd class--well worth it especially for the seniors.
One more thing--implore on your travel companions now to individually pack all their worldly possessions for 18 days into one carry-on (22"x14"x9"). It can be done, and will cause major heartache--especially on trains--if there is too much baggage. You can still check your bags through on the plane--at a cost--but it's the intra-Italy moving around that can really be a PITA with too much stuff...again, keeping the seniors in mind!
Now...lodging. I think first choice on all your stops--and that to me would be in this order, south to north...
A) Sorrento/Salerno (4 nights)
B) Rome (5 nights)
C) Florence (4 nights)
D) Como area (4 nights)
...would be to find a minimum 3 BR, 2 bath AirBnBs (preferably larger) in all these places, must be centrally located, walking distance to most everything, including a grocery or open-air markets to stock up in each place. And I would get right on that now! Usually cancellation timelines are reasonable, maybe a week or two before arrival, so you can tweak a little bit on that as you go along. But some of the good places for these destinations have no doubt already been booked. Oh--with everyone only taking one carryon, find AirBnBs with washers, and only take 2nd floor or higher if there's a lift (elevator)!
That should be good for starters. Others have different ideas on how to attack this, and as tour director--having done this more than once--just realize upfront it's a thankless job. But this is how I'd do it. Keep us posted, and--really--enjoy your planning!