I still don't really understand the whole unpacking/re-packing thing. I actually never even really did it on long weekend trips of 4 nights or on a 2 month trip abroad staying 1-2 weeks/place. And no, I didn't stay in 1 outfit the entire time. You pack your bag pre-departure so that the things you would use everyday are most accessible and after use get tossed right back in and then if you know the contents of your bag well, you can easily take out the outfit you want to wear, etc.

It seems like some people take out all the contents of their bag, hang up all their clothes, fold them and put them in drawers, etc. Seems unnecessary. The accommodation type also factors in. Staying in hostels, when you unpack the bag where will you put its contents?

Some days simply don't work the way you have it mapped out.

How can you get from Bologna to Cinque Terre, with time to "cycle the blue trail, just wander, eat" and be ready to leave for Florence by the afternoon?

As LR220 pointed out already you've got 7 hours of train travel that day. This isn't about the packing/unpacking, it's about distance and how many hours in a day.

LR220: >>It seems like some people take out all the contents of their bag, hang up all their clothes, fold them and put them in drawers, etc. Seems unnecessary. <<

OK - don't fixate on the unpack/don't unpack. Diverting the thread into a debate about living out of a suitcase or unpacking doesn't address the problem. No matter which you do -- it will still take about 1/2 a day (or several hours minimum) to move from one city center hotel to the next city center hotel.

janisj--I agree with that. But much of that is moving from city to city rather than from hotel to hotel. While emay may be making more changes than I'd make at this stage of my life (but not more than I would have made when I was his or her age), it is very difficult to find just a single base from which to see everything one wants to see in Europe.

There's a HUGE difference between trying to see all of Europe from 1 single central location.... Or going to 20 different places(!!) on a 21-25 day trip as proposed in the original itinerary posted here.

Everyone has given you excellent advice already. I will chime in on one thing in particular. Last year, food was a big priority during my two-week trip to Italy, so I spent 4 nights (3 days) in Bologna. We spent one day doing a food factory tour, another doing a cooking class, the last day relaxing and doing a small amount of sightseeing when most things were closed on Italy's Labor Day. Both the tour and class were spectacular. What was hugely disappointing were the restaurants. With what you have described above, I think that Bologna would be worth skipping on this trip. Then you can add a night to Cinque Terre so that you have time to accomplish what you want (but still at a very fast pace!). If you can't spend the night in Cinque Terre, I suggest skipping it as well.

I realize it's torture trying to trim a trip like this. I did a similar trip when I was in college and really suffered from a lack of planning. I didn't pay attention to when certain sites were closed (no Sistine Chapel on Sunday, no David on Monday, etc) and missed a lot of "must-sees" as a result. I was also so exhausted two weeks in, that I eliminated some destinations so that I could crash at a friend's apartment in Paris and get some sleep! I think at your age, it's fine to do an "overview" trip where you don't see anything very in-depth. But you also have to be realistic on what is possible so that you can actually enjoy sipping a coffee or a night on the town. That usually means a MINIMUM of two nights at each destination, not including day trips.

Best of luck in your continued planning. You have made great strides already!

This may seem rushed, and it is lots of one nighters, but it would work. Looking at Sandralist's very good suggestion to pick your travel times, you might do this.
Day 1 - sleep in Venice.
Arrive in Venice mid-afternoon, walk and explore. This would be the night to enjoy the mystery and quiet of Venice in the dark. Nothing much is happening there at night.
Day 2 - Sleep in Bologna
Sight see in Venice (ask hotel to hold your luggage). Depart venice by train in the late afternoon, 4 or 5 o'clock. Get to Bologna in time for a nice dinner. Food is so much better than in Venice anyway.
Day 3 - sleep in CT. Explore Bologna in the morning. Mid afternoon, head to the CT.
Day 4 - sleep in Florence. Spend morning hiking, etc. late afternoon, head to Florence.
Day 5 - sleep in Rome. Sightsee in Florence all day. Very late head to Rome in time for dinner.
Day 6 - sleep in Rome
Day 7 - sleep in Rome
Day 8 - sleep in Naples, depart Rome early, tour Pompeii.
Day 9 - sleep in Naples, catch a ferry down the coast for exploring

You could spend an extra day anywhere. Your personal interests should dictate.
I would put one in Rome or stop on the way from the CT to Florence for a night in Luca.
You could also add a night in Florence, tour Florence more the next morning and leave around noon for Rome to have late afternoon and evening there, so a bit of extra time in each city. If you are interested in the great art in Florence, that would be perfect.
You could add the day to Naples and ferry to an island for some more hiking if that interests you.
Never too much time in Venice either, IMHO.

Depending on which town you want to go to, the trip to the Cinque Terre can take up to 4 1/2 hours from Bologna, so you can't leave much later than about 3 PM.

The same is true coming back. If you want to hike, you'll have to leave your bags at the hotel and go back to collect them after the hike. You really wouldn't have much time. Most of the lower, more accessible paths are closed due to the risk of landslides. I really wouldn't go there for less than two nights; it's not worth the time it takes to get there if you'll only be there for a few hours.

This is fabulous.

At this stage I'm debating leaving Greece for another holiday when I can do it and Turkey justice.

This will give me more like 15-17days for Italy, and 5+ settled somewhere in Croatia for some wind down time after a fast paced Italy whirlwind!

Thank you Caze for your feedback on Bologna, i had added it with high hopes for a foodie experience and now might devote that time somewhere else!

This is fabulous.

At this stage I'm debating leaving Greece for another holiday when I can do it and Turkey justice.

This will give me more like 15-17days for Italy, and 5+ settled somewhere in Croatia for some wind down time after a fast paced Italy whirlwind!

Thank you Caze for your feedback on Bologna, i had added it with high hopes for a foodie experience and now might devote that time somewhere else!

*15-17 days for Italy, and 5+ settled somewhere in Croati*a

Now THAT is a beautiful plan!!

Much better plan, although you might have the wind-down time in Positano or elsewhere on the AC. Concur with bvalenci on skipping the CT unless you have time to do it right.

Whoops "bvlenci"