8 Days in May: Itinerary Advice?

With such a short trip, why are you not flying directly into Rome, and out of Venice? Yes, the flights may cost a bit more... But the time and money spent on trains is considerable when time is short.

With only 2 days in Florence you really do not have time for Pisa.

It's a very fast paced trip. You are going to need a vacation from your vacation when you get back.

Ideally flying into Rome and out of Venice would have been best.
We booked flights RT thru Milan and then started planning our trip.
Trying to make the best of what we have to work with.

I think it looks good even though it's fast-paced. Get tickets in advance for the Accademia and Uffizi, buy the vaporetto pass in Venice.

Now I'm going to suggest adding a couple of things: in Florence, take a taxi or bus to San Miniato al Monte and then walk down to Piazzale Michelangelo, a great place for watching the sunset after a long day. In Rome, if you like sculpture by Bernini, go to the Galleria Borghese (advance tickets mandatory, you have 2.5 hours max inside the building including check-in), then walk through the park to the Pincio (folliw signs) for great views from the terrace, then take the footpath down to Piazza del Popolo,

In Florence I would keep Pisa and give up the Pitti Palace if you have to cut something. The Boboli Gardens are nice though, and there's a separate admission fee.

I agree with Zoe, skip Pisa. Since your group seems to be interested in art and sculpture, while in Florence I recommend the Bargello and the Duomo's museum (Museo dell'Opera del Duomo) which is about a block away from the Duomo. There isn't much to see in the Duomo, but the Baptistry has a lovely mosaic domed ceiling.

I like to take evening trains after a full day's sightseeing. Then I can get an early start the next morning. You can have a picnic supper on the way, or a late meal on arrival. You may still be able to buy discounted tickets (with severe limitations on changes) if you hurry up. They go quickly. Only buy them if you are ready to commit to those rides.

In Venice, skip the overpriced gondola ride. Take the vaporetto (water bus) from one end of the grand canal to the other, grabbing seats in the very front, or as a second choice at the very back, for the best views. Do it once during the day and once after dark. One monring, get up really early and go to San Marco to watch the sun rise over the lagoon. Then go back to your hotel to shower, dress and have breakfast. Try to be in the basilica between 11.30 and 12.30, when the wonderful mosaics are floodlit. Pay the entrance fee to visit the museum, there are some interesting artifacts but the best things are the close-up views of the church's mosaics and the view of the piazza from the balcony. The Secret Itinerary tour of the Doge's Palace is very interesting, too.

In Milan, the best part of the Duomo is wandering on the roof.

Hi Christine,

I'm also going in May with 3 others. It will be my third trip. I would advise you skip Pisa ( another time perhaps). Florence has plenty to offer. Also, skip the gondola and just ride the water bus. Unless you are a fan of modern art, skip the Guggenheim. Maybe go over to a couple of the other islands (Murano, Burano). You will love Italy.

MOST IMPORTANT ADVICE: if you haven't purchased plane tickets yet, buy an open jaw (multi-city) ticket. That is landing in a place and flying back from another.
From California you would chose the Multi city function on Kayak and do:
Going: LAX(or SFO, whichever is closest to you) to VCE (or MXP)
Return: FCO to LAX (or SFO)
In either case you'll likely have to stop in some hub somewhere because there are no non stop flights from California to Italy, except for a seasonal Alitalia flight from LAX to Rome (FCO).
It is better to arrive in Northern Italy (Venice or Milan) and depart from Rome. Departing from Rome (FCO) is easier because the airport is close to the city, unlike Milan (MXP) or Venice (VCE) and your departure back to America will be in the early hours of the morning.

Adding a smaller town in the mix would give you a much different experience of Italy than all big cities. My first choice for a daytrip from Florence would be Siena over Pisa. Within the structure you've set, you can be flexible - e.g., decide that day whether or not you feel like leaving the city. Or, Orvieto is a very accessible hilltown on the main train line between Rome and Florence.

The Eurail Italy pass currently offers 4 travel days for the regular price of 3, which is $223 per person in 2nd class. In addition, you'd pay $15 per person, per leg for seat reservations between all the big cities listed (no deadline to reserve), totaling $283 if you do all 4. This is a reasonable value compared to buying tickets on the spot for about $330 per person. But if you're ready to lock in dates and times for the longer train tickets now, then it would be cheapest to buy reserved tickets with advance purchase discounts at www.trenitalia.com. (See also http://www.ricksteves.com/travel-tips/transportation/trains/italy-rail-passes).

I would delete Pisa & go instead to Siena for the day trip out of Florence.

Wow, thanks everyone! We are still trying to book our accommodations in Venice and Milan. Our itinerary is tentative and flexible regarding what our days entail. So, I appreciate all the suggestions! We knew that taking the trains could be costly, but thought it would be a great way to see the country-side - plus it's a great mode of transportation, since we don't travel by train much here in the US.

You will still get to travel on trains with an open jaw ticket. The difference is that you don't have to back track and spend extra money and time you don't need to spend:
Fly to Venice. Visit Venice.
Then high speed train train from Venice to Florence. Visit Florence and Tuscany.
Then high speed train from Florence to Rome. Visit Rome.
Fly back from Rome.
If you want to add Milan to the mix:
Fly to Milan MXP. Visit Milan (one afternoon is enough for what you want to see).
Train from Milan to Venice. Visit Venice.
Then train to Florence etc. (as explained above).

Rome OR Milan, not both. If you fly into Milan, take advantage of the north. If you fly into Rome, the south. In either case I would do Venice, no question.

With so few nights I like Laurel's idea. Since your flights are set in and out of Milan I would think about Lake Como area instead of Rome. You could spend an extra night in Tuscany as well. If you decide to keep Rome I would make sure to try for at least on smaller town/village or you will have a rather narrow perspective of what Italy has to offer. Agree gondola ride can be an extra expense... and may not be worth it. But, often times that comes from someone who has already done it.... I did enjoy the one time I did it (out of many trips) and don't regret it, but don't need a repeat.