Itinerary help - first timers

I see that you have already purchased your flights. Do they happen to be refundable/exchangeable? If so, you may be way ahead to change them to multi-city flights where you fly into the airport you want to be and leave from the airport that is your last destination. As an example, flying into Naples from your home instead of Milan and then taking another flight on another ticket to Naples. That can give you an additional half day and save some money on extra transportation, if possible.

If you want to go with Option 1, you might want to add another day to Sorrento and Tuscany if you drop Venice. Your arrival day and next day will be affected by some jet lag, and the transportation time will cut into your actual “on the go” time in Tuscany.

I like to have some of my favorite locations in the middle portion of my trips, so that I’m well over jet lag and not in the winding down stage of the trip. Sometimes that first location is just a blur because it goes so fast, so that might determine whether you like Option 1 or 2 better.

Trains are a great transportation method in Italy. If you purchase the tickets on-line a few months ahead, you can save a lot of money - especially since you have 5 on your trip. Enjoy your time!

I know you said you don't mind a fast pace, but I want you to sit down with these itineraries and a calendar. Option one: you're only allowing 2 days in Florence, and 2 days in Rome. Then one full day in Cinque Terre, and one full day in Venice. Option two allows only 2 days in Sorrento, not much time for Sorrento, Pompeii, and Capri.

Please bear in mind that traveling from one town to another will take up a full day, by the time you consider checking out of your hotel, getting to the train station, getting to the new town, finding your hotel, checking in and unpacking, getting oriented, eating on both ends of the journey ... If I were you I would seriously consider dropping at least one of your destinations on each itinerary.

Jean's suggestion of a multi-city (open jaw) flight is a good one, if your flight allows free or inexpensive changes.

But I like your attitude, and I like that you're taking the boys' wants into account. They need to be invested in the trip.

That's a very nice trip! A bit fast paced, perhaps 1 too many locations in a 14 night trip. The 2 night stays you have are in locations that take a good bit of effort to get to- giving you just 1 day really there.

I like Option 2 better.
Option 1 is a LOT of travel on one day. Won't be at your lodgings in Sorrento til midnite? Next day you will still be quite jet lagged and you only have 2 full days in Sorrento- Capri 1 day, Pompeii the other. Those 2 places are high priority for your kids.
If Venice is just not a priority it is OK to skip- and we do love Venice. You'd arrive evening and have just 1 full day. Not sure it's worth it and you may leave not liking it so much cuz you didn't have enough time to enjoy.

With Venice
Venice 2 nights
Florence 3 nights
CT 2 nights
Rome 3 nights
Sorrento 3 nights
Milan 1

Without Venice- add a day to Rome and a day to Florence. Go to Florence on arrival. (3 hr train vs close to 4 for Venice)
Florence 4- w/day trips
CT 2
Rome 4
Sorrento 3
Milan 1

If you want to keep Venice then I would drop CT.
Venice 3
Florence 3
Rome 4
Sorrento 3
Milan 1

I dislike option one due to the fact you are changing airports that will require a trip of 2+ hrs after you clear immigration.

"early afternoon' arrival--- presumably no later than 2PM?

Arriving in Naples at 930PM and then making your way to Sorrento will make for a a really late arrival. Be sure your lodging has late night check in. If you are in bed by midnight that would be doing well. I suspect you will resemble road kill the next AM

On the back end, what is 'late afternoon'? Having to be at airport 3 hrs for flight to US, does not leave a lot of time for touring on departure day.

I see option two as the better choice

Thank you for the feedback. We are able to make changes to the flight but will have to look into your suggestion of flying in and out in different cities. I like this idea and will have to explore our options. My thinking is to cut Cinque Terre from the itinerary. As much as I want to visit this area it seems to be a bit out of the way. If you were to cut one destination, which would you suggest?

If you were to cut one destination, which would you suggest?

Cinque Terre

If you can change flights at a reasonable cost- fly out of Naples- add that Milan night to Sorrento or do a 1 night stay in Naples before departure. Depends on departure time, if early am I'd be in Naples.

Such great advice - thanks! So, looks like option 2 might be better and then drop either Cinque Terre or Venice. Our flight will get in on 6/8 @ 12:25 pm and departs on 6/22 @4:10pm. I did not realize the flight on Rhynnair would be from a different airport so thank you for sharing that information! That is not a realistic option considering what you all have shared.

I think Easy Jets flies Malpensa-Naples- but I still would not do that on arrival day.

Hi nzauke!

How exciting to take your kids to Italy! It's a wonderful country and you will have a great trip.

First, I can't stress enough how jet lagged you will be on Day One. My kids were so excited to be going to Europe, they didn't sleep on the flight over; instead they watched movies. Consequently, they were dead tired on the first day, and not much better on the second. Just a heads up.

Second, IMHO, I would drop Cinque Terre for sure. The beaches there are rocky and while it's beautiful, there's not much for kids to do other than the hiking between the cities. And shopping and eating.

For young adults, I love Rome. So much to see and do. There's art and history around every corner. Watch the da Vince code movies (for the scenery). A few days in Sorrento to visit Pompeii and Capri would also be wonderful.

Enjoy your trip!

DD