Greece and Italy

First off, don't try to combine these 2 in one trip with the limited time you have, even in May. With all the travel time required, you won't have enough time actually in all these places. Save the other country for another time.

The earlier in the season you can go, the better will be the prices, weather, and crowds

As for how many days in each place- it depends on what you want to see and do. Get out your guidebooks and make a list of everything that is important. I usually do one or 2 " must sees" per day with an optional "would be nice" if there's time. And I schedule a blank day once a week tallow for any hiccups along the way or just to relax and do laundry. That tells you how many days per city. Every time you move to another place add adequate transportation time (hotel door to hotel door)- a minimum of half a day.

Consider the feasibility of day trips. For instance Pisa is an easy day trip from Florence by train. Or Siena by bus. There are similar possibilities from Rome or Venice, so you could see more places without moving hotels.

If you can go in May/ June choose those dates over summer ones when it will be very hot in all those places. .
August also is when Europeans travel so more crowded.
Choose either Italy or Greece. You don’t have enough time to do them all well.
Your plan for Italy is good but you have chosen the most touristy islands in Greece.
Do Italy this year and come back to the Forum when you are ready to plan your trip to Greece.
You have four wonderful locations in Italy: Rome, Florence, Pisa and Venice. Enjoy your trip!

Thanks for the reply.

I can try and cancel July and add few days in August.
Italy vs Greece - which is cheaper in June?
Italy vs Greece which is cheaper in August?

How many nights to spend in each place in Italy - Rome, Florence, leaning tower of Pisa and Venice and if in any particular order?

How many nights to spend in each place in Greece - Athens, Mykonos and Santorini and if in any particular order? I don’t mind some traveling/distance if Santorini and Mykonos are 2 of best islands to visit as RS says.

Italy vs Greece - which is cheaper in June? Italy vs Greece which is
cheaper in August?

May, June, July or anytime, Mykonos is one of the most expensive places in Europe, incompatible with the word "cheap"

Let me rephrase the question

When is it more expensive June vs July vs August for both Greece and Italy?

JULY thru AUGUST 25 or so is HIgh Season. June is least expensive.

Mykonos is a parody of itself ... hugely expensive... 100s of "highfashion" label shops (Cartier, Hermes, DKNY, et cet cte) Rodeo Drive crammed into a Greek Port. SAntorini has a beautiful "caldera view" --- and up to 5 mega-monster cruise ships dock daily (Island has even resorted to a cut-off limit of 10,000 cruise passengers allowed ashore daily... but that does not limit the huge number ofo tour groups coming in on jumbo jets and large ferries). All advice we give these days is strategy about avoiding worst crowds. I cannot imagine that you have done any research at all if you are suggesting the "cliche twins" promoted by every US tour agency.

If you want someone to plan everything out for you, we are not travel agencies, we are volunteers. When people have done some homwork & have developed a plan, we can assess it, b ased on our experience. For doing the whole thing, I suggest contacting one of the well-regarded GREEK travel agencies that are accustomed to dealing with N. American travelers online. DOlphin-Hellas, Fantasy Travel, and Aegean Thesaurus all have Athens office and are very well reviewed. I suggest you write them with full details - email them all the same time, see who answers first and offers best thoughts and budgets.

Weatherwise the May 27 to June 13 would be the better choice for either location.

If you are determined to do both, then the longer time frame you have in July/August is the better choice to give you time to actual 'be there' versus always being 'on the move'.

I have no research/facts to contradict Janet's comment that June is cheaper than July/Aug, but I do have to wonder if the difference is meaningful.

As for price differences b y month, the Greek tavernas do not charge more for a meal in High season (thank heavens!) but if you favor expensive places ballyhooed for rich folks, in islands like Mykonos/Santorini, it will be much harder to get in or even get reservations. The big zoom in prices is of course for lodgings .. a modest room I could find for €70 or €80 in June would be double that in July - August (and not as enjoyable, due to the huge crowds). Does the OP not realize that most of Europe has 1=month holidays? And that greece is their "Florida"?? And that in addition to foreign visitors, Mch of Greece takes the month of August off, and races off to the islands, and to seashore areas on the mainland. Why fight these crowds if you have an alternative?

If you like late night partying and high prices, then Mykonos is your destination. If not, look at replacing it with another island like Crete.

Prices will be highest in August. May/June slightly lower. For the amount of time you have, choose one country. You will have an easier time getting around Italy.

As many of us have learned, it's okay to disagree with Rick.

I agree with other posters that your trip is very ambitious. We spent 12 days in Rome last May and took day trips to the Amalfi Coast and Tuscany. There was so much to see in Rome, walking around the different neighborhoods. It was the richest experience I've had in 10 trips to Europe.

3 nights is the gold standard for most places, unless super tiny in which case I'd say 2 nights. So your Italy trip is 9 nights automatically, not counting jetlag.

Greece or Italy - which is cheaper?

Depends on airfare

If your goal is to see the highlights, look into a cruise. This way you can spend full days exploring, yes with crowds, both italy and Greece in one trip. The nice part is, you unpack, sleep in a comfortable bed, enjoy beautiful views from the oceans, and the travel happens while you sleep. Plus your child can hang out with young people and enjoy the water slides. From your cruise experience, you can discover if there’s a country or region you would like to explore more at a later date. Finally, travel in late May before the sights get too crowded.

I agree with Noelle. The most efficient way to visit the most places on your wish list is a cruise. The last time we did this we landed in Milan, trained to Lake Como, trained to Venice, then cruised from Venice to Dubrovnik, Crete (scheduled for Ephesus but there was a coup attempt in Istanbul, so they took us to Crete), Santorini, Athens, and back to Venice. Cruise portion was 8 days. Added Italy on so we could do both, as you wish to do.
You are DEFINITELY better off going May 27 -June 13. More time to work with, and less crowded.
You will not be able to go to Greece in August, the cost will be prohibitive, and it may be all booked already.
August 15 is Assumption Day and everyone in Italy goes on holiday, and many go to Greece. Some restaurants and shops in Italy will be closed.
We spent 10 weeks in Rome in the summer of 1996. We could not find a way to get to Greece. Cost was high, and less space available due to aforementioned European travelers. Flying would have been preferred, but flights in summer were too high for us. Driving to east Italy and taking a ferry would have taken a long time, so we didn't do it.
We were in Rome for 9 of the 10 weeks, and still did not see much of what the city has to offer. If you go there, you have to decide how much time to spend there, and see as much as you can. (RS guidebooks will help). You can train to Florence, but if your middle schooler doesn't like museums, I wouldn't do it. Pisa is fun for a couple hours, I wouldn't say it's a must see. When we went you couldn't go inside the tower (it was leaning too far over).