First trip to Italy, need help with itinerary
 

18 nights, flying in and out of Milan on airline points:

2 nights Milan
2 nights lake Como, Varenna
2 nights Venice
3 nights Cinquetetra, Monterosso al Mare
2 nights Florence
2 nights Chianti
4 nights Rome
1 night Milan

Thoughts on this itinerary? Thanks

More info.... My husband and I are in our early 50s and hope to combine some hustle bustle tourist site visiting with some calmer, relaxing hanging out days. We like hiking, wine, art, food. Also, would like to visit Jewish quarters.

Our trip is mid to late May.

Here are a few observations and suggestions.

1. lots of short stays which will result in lots of driving/traveling. You didn't say if or when you plan to rent a car.
2.Instead of 2 nights in Milan and 2 nights in Como, do 3 nights in one of them, and do a day trip to the other. I suggest staying in Como, as this will allow you to spend a day on Lake Como to visit Bellagio.
3. 2 nights in Venice will give you 1 day to visit. Venice is not easy to navigate. If you have a car, it will have to be parked in Mestre. If you don't have a car, you will have to spend time on trains and waiting for trains. If you really want to see Venice, make it 3 nights.
4. I am not a big fan of Cinque Terra, and I would not spend 3 nights there. Again, will you have a car? Your itinerary will be affected by your means of transportation.
5. Florence is part of Chianti. My comments on Florence are similar to my comments on Venice. Spend at least 3 nights in Florence, and maybe 4, and do a day trip into Chianti or Sienna.
6. How do you plan to get to Milan from Rome? What time is your flight home?

In short, cut down the number of bases, and try to stay in each place longer and do day trips from each base. With your current itinerary, you will be spending most of your time in your car or an the train.

18 nights, sleeping in 8 different places.

Slow down a little, smell the roses.

You seem to be doing an awful lot of travelling between cities and not always in a logical order. Too much backtracking.

If you have a look at a map of Italy, you'll see that your crisscrossing the country, especially to Cinque Terre from Venice. It would make much more sense to fly open jaw (multi city) into Milan and out of Rome.

As others have said, you have too many stops and not enough time in most places, so IMO you should cut down on destinations. That many places will blur into one at that pace anyway and only you can decide where to prune.

Leave all of your Milan stay until the end and then decide what you leave out, or you won't get any "calmer, relaxing hanging out days."

As others say, less is more

3 nights Venice
3 nights Cinquetetra, Monterosso al Mare
3 nights Florence
3 nights Chianti
4 nights Rome
2 night Milan

makes a bit more sense

I am one of the few who has no problem with a road trip, using trains or by car, and changing hotels is better for me than doing "day trips", especially in Italy, where so much closes in the middle of the afternoon. I think you should figure out how much time you want in each place and not be overly influenced by other people's ideas. For instance, I would spend more time in Florence and less in other places, but I happen to like Florence a great deal. I also live on the Italian Riviera, so I enjoy spending time there as well, and many people don't, so it finally is up to you how much time you want to give to complicated cultural sights like Florence or Venice -- where you could easily spend months and barely scratch the surface of how much art there is to see -- and places like le Cinque Terre, where there is next to nothing to do and that is the point.

But if you want to keep all your destinations, you might consider this:

Fly to Milan, immediately get a taxi to Lago di Como
train to Venice
train to Rome
Train to Florence
pick up rental car, drive to Chianti
Drive to le Cinque Terre (drop off car is Pisa or La Spezia
Train to Milan

I generally like bilbo's plan, which leaves out Lake Como to give you more time in other places. sandra's is OK if you insist on hitting all the places listed in your post (which seems like a lot).

My general recommendation would be to delete either CT or LC and add days elsewhere.

You have to keep in mind that each trip between destinations will kill almost a whole day, taking into account gathering up your stuff, getting to a train station on time, getting from the station to your accommodations, and just generally getting your bearings when you arrive. When you look at it that way, you'll see you are, conservatively, using up 5-6 days just to get from Point A to Point B.

That said, here some random notes:

Florence:
If you're going to the Ufizzi and want to see David, book timed tickets using the international phone service. No service charge, no pay in advance. Take the bus up to Piazzale Michelangelo to have a glass of wine and watch the sun set over the city. Climbing to the top of the Duomo is best done first thing in the a.m., to avoid lines.

Venice:
Yes, see the Ghetto. It's almost like you've stepped out of Venice and are in another place. Try to plot out your itinerary to determine whether a multi-day vaporetto pass is a good value for you. Otherwise, getting around by boat can be expensive. (I, like others, recommend more than 2 days.)

Milan:
Be sure to book ahead if you want to see the Last Supper. Take the elevator to the top of the Duomo and walk around the roof to getting an interesting look at the architecture.

CT:
Use the ferry that stops at all the towns and goes to Porto Venere. I recommend a visit to PV and a walk up to the fort the city's point of entry.

Como:
Ravenna is a pleasant and easy-to-get-to base. The city of Como is a a little too busy for me, especially if you're visiting other cities. Tour the Villa Monastero in Varenna.

Regarding Como, I am pretty sure vicenzo means Varenna on Lago di Como, not Ravenna (several hundred kms away).

ELBALL:

You still haven't told us if you have preferences regarding transportation. There are people who do not want to drive in Europe under any circumstances. What about you?

And Michelangelo's David is in the Galleria dell'Accademia museum in Florence, not the Uffizi (which itself is well-worth seeing for the Renaissance art).