Where to stay between arrival and cruise?

It looks like you really only have 3 days, since it will take you several hours on Friday morning to get to your cruise ship. The CT is remote enough that you use too much time getting there and back to go for a day trip or to use as a base for Tuscany. You could train directly from Milan to the CT for a night, then to Florence for a couple of days and on to Venice. That's liable to be a lot of rushing around after your long flight. I recommend you drop the CT, and concentrate on Tuscany.

season? car? train? interests? prior visits to...? budget issues?
places/sites/experiences that attract you? What would you say to an Italian who posted: "arriving Seattle on a Monday and are leaving on a cruise from Vancouver CAN the Friday of that week. I would really like to explore Seattle, Portland, the San Juans and the Olympics. Where would be a good place to stay so that we can easily take day trips to both regions?"

To answer your question directly, you have sufficient time to spend a four nights in Florence as a base for day trips or even to stay in CT. Save Tuscany for another trip. An easy AM high speed train to Venice would be there by noon and easily board your ship that PM. Or you could spend a day in Ravenna or Bologna on the way to Venice. You have plenty of time but try to keep you travel distances short. Although I have not done it, there appears to be direct trains from the airport to Florence.

It would be a good idea to stay in Venice Thursday night. If the train is delayed or there is a strike, you have a better chance of being in Venice when you need to be. I think you can take a day trip to Florence from Milan by fast train in a reasonable amount of time. Lake Como (Varenna) is only an hour or so by train from Milan. I wouldn't try for a day trip to CT from Milan. It would take too long. You might go directly to Florence on Monday, then have two days to daytrip from there-Siena, etc. Thursday take the train to Venice. There are numerous trains Florence to Venice throughout the day. It would be possible to day trip to CT from Florence with a couple of train changes. I did it once, but don't recommend it.

Hey folks-let's be nice here, remember what the Webmaster said? GIve the gal a break!!

It's okay! In my excitement from purchasing the plane tickets, I totally forgot to add in some of the pertinent information that may help in making this decision. :) We will be traveling in Italy during the first week of July in 2012. We will most likely be traveling by train, though I wouldn't be opposed to renting a car for a few day trips. I've been to Italy twice before (in particular Rome, Venice, and Cortona), but this will be the first time for my fiance. He and I are not generally interested in major touristy things. Honestly, we love eating and good wine, so that's why I figure we'd be happy no matter where we are in Tuscany. We also enjoy going to places where you have the opportunity to interact with locals and get the feel of the culture. We don't have a set budget yet and are willing to splurge a bit, since it's our honeymoon. However, we definitely don't want to go overboard!

Siena will get a lot of votes as a destination/base camp. For good reason. It's got everything a major hill town/city should have: atmosphere, sites, history and food. With a car, days trips to little hill towns in central Tuscany are very do-able. I've never tried to do the CT from Siena or vice verse.

I'm with Swan. I'd plan to get to Venice the night before the cruise. Except if you rent a car . . . which is a great way to explore Tuscany. Get the DK Eyewitness "Back Roads Tuscany" guide book. Then, if there's a problem with the train on Friday morning, you can keep the car to drive to Venice.

We're doing a similar trip in October but we will have six days before the cruise starts. We plan on riding the train to Bellagio in the Lake Como area. It's not far from Milan and on the way to Venice. So that would be my suggestion. Our cruise leaves from Rome. So we will also do the Cinque Terre on the way down to Rome. Have a great time!

FWIW, Bellagio, though lovely, is not on the way from Milan to Venice. It's due north of Milan and a little tricky to get to since no trains go there. Travelers generally train to Varenna or the town of Como, and ferry across to Bellagio. Even trickier is going from Bellagio to Venice - you have to backtrack through Milan. Perhaps I'm misunderstanding Les's post?