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Italy planning advice...

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We are in the beginning stages of a trip with our 16 year old daughter. We were going to take a cruise but for a variety of reasons have decided on two weeks in Italy instead.. We csn go in the beginning of may and I can get us there & back on 150,000 plus fees(600.00 .. Sort of annoying...)
our daughter will be 17 at time of travel... It is a high school graduation/16 bday gift (ayers late!) combo gift...
This is what we have planned thus far:
We are using miles to fly so have pretty cruddy flights...:( dfw to Frankfort - Frankfort to Berlin & Berlin to Rome... Trying to focus on the 20,000 miles per ticket instead of the flights... We will have carry on only fortunately.
May 5 - depart dfw
May 6 arrive Rome - thinking of spending 3 nights in Rome .., I can stay at either the Marriott Grand Hotel Flora(two rooms on points) or boscolo palace Roma - (leaning towards this property) - would love any feedback ... Staying on points for free... So that is why those two..
Train to Florence .
May 9- 14 - Florence - renting an apartment for 5 nights -thinking of casetta Bonsi from Italy perfect- would like to do day trips from here... Dd wants to take a cooking class would love recommendations.. Want to see some of the surrounding area..
May 14-16 ... Flexible ... Dd would like to hike in cinque terre (maybe?)
May 16 -19 venice... Staying here on points.. Boscolo Venezia - any feedback on hotel?
May 19 flight back to dfw (pretty cruddy due to miles)
Arrives into lgw @ 12:10 am ... Will need a hotel
May 20 Flight from Lhr @ 3:00 pm
Arrive into dfw 7:10 pm...

How is the weather in may? From "reports" seems to be a nice time of the year..
Any recommendations on car tours for the day in Florence or cooking classes?
Dd wants to see catacombs in Rome..

Thoughts on transportation from Florence to cinque terre? Cinque terre to venice?
The othe option is 3 nights in Lake District and 2 venice... ?

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