Rome, Siena, Florence, Cinque Terre, Venice

2 nights in Siena ought to be plenty, you could move that extra night to Florence. Otherwise looks like an excellent itinerary to me.

You should have very little trouble eating vegetarian in Italy. My husband is vegetarian, so I know what a pain it can be trying to find reasonable meals when dining out together. Avoiding seafood is also easy enough to do. Plenty of chicken, pork, and beef options abound everywhere you go.

Nothing to add as far as your itinerary, but I had no problem eating vegan in Italy last year. It was far easier than I anticipated. We were not in Siena or Venice but in Rome, CT and Florence it was quite easy. We did look at the posted menus before we went in to a restaurant. One time in Rome at lunch a waiter got kind of miffed with me because I ordered a salad and soup and he really wanted me to order an entree. Everywhere else, even when I started off in Italian (I had printed out a card with I am vegan on it), the waiters all switched to English immediately (my Italian is pretty bad, lol!) and were very helpful in pointing out what would work for me. It was actually easier to get a vegan meal there than it sometimes is in the US!

Thank you Angela and Pam for the advice. Sounds like being a vegetarian will not be a problem. I was preparing myself to survive on pasta made with pesto and red wine. Thank you again for taking the time to reply.

You may try Cross-Pollinate.com for lodging in Rome, Florence and Venice. I have used them with great results.

I would also try to avoid flying home to California from Venice. It is a major hassle and expense getting to the airport in time for an early morning flight (unless your flight is NOT super early).

If you can reverse the order, start in Venice and leave from Rome.

You can combine nights in Siena and Florence as they are so close, and avoid the hassle of a "move." Just daytrip from one to the other. I would stay in Florence and daytrip to Siena by bus. I think 3 nights in the CT is a good idea: don't steal a night from there. It's a bit of a trek to get there so make the stay worthwhile. We LOVE October in the CT. Have been 3 times. Enjoy hiking when it is cooler and we've always had plenty of fall sunshine.

In Venice a lot of people clamor for the Campanile in San Marco. We prefer the much less frantic tower at San Giorgio Maggiore, just a 5 minute vaporetto ride across from SM. See San Marco at sunrise before the hoards descend. Watching Venice wake up and get ready for the day is my favorite time to take a stroll.

As Claire said, if you can reverse your itinerary, you will find the flights easier. Getting to Venice airport for an early flight is expensive and/or time consuming. Getting to Rome airport for an early flight is easier, cheaper, and faster.

If you can't reverse your itinerary, do try to find as late a flight as possible out of Venice. When you start investigating the logistics, you'll be glad you did.

If Renaissance art and architecture turn you on, then 3 days in Florence is barely enough. BUT if not, then stay in Siena and in a day trip by bus, you can easily see all the highlights. For me, Florence has a big city vibe, while Siena has small-town ambience.

Maybe someone will chime in with transportation between the CT and Siena. It feels like you are backtracking from the CT to Florence. I'd look for a plan from Rome to the CT, then Siena, Florence and Venice. Or the reverse, because starting in Venice is a much better plan than starting in Rome. Besides the issue with flight times, Venice is easy to enjoy after your really long trip to Italy. You can relax and ride the vaporetto, sit at a cafe, or wander the back canals and just absorb the atmosphere. Rome is big and busy with sights that will wear you out, especially since you'd be starting with little sleep and lots of jetlag.

I keep to a vegetarian menu in Italy and I've never had a problem anywhere. The Italian word for a female vegetarian is vegetariana - not too hard to remember!

The CT in late October is iffy. When the sun is shining, it's wonderful. But if you get rain, it won't be. Try to get reservations that you can cancel close to arrival and keep a close eye on weather forecasts. At that time of year, you shouldn't have trouble getting last-minute accommodations somewhere else, and there are lots of "somewhere-elses" that you'll love. My favorite thing in the CT was taking the ferry from one end to the other in the afternoon when the sun's behind you. The views of the towns are superb.

Wow, I wish I had found this site earlier, everyone is being so helpful and pointing out things I had not considered! Thank you everyone and keep those comments coming! One of my problems is the logistics of getting from one city to another. Perhaps someone can chime in on this, I have not been able to look at a complete train or bus schedule online for Italy. I have been to the recommended site but either it is not working or schedules are unavailable (I think I will start a new thread for this). I do have Rick Steves' Italy 2014 book which is very helpful. I only wish I had purchased it sooner. Basically I got the two reservations in Rome and Cinque Terre (as both B&Bs' were recommended by a friend) and started building from there..not the best idea I know. I see now that Rome-Siena-CT-Florence-Venice OR Rome-CT-Siena/Florence- Venice may be a better route. I read it is 2 hours from Florence to Venice as opposed to 6 hours from CT to Venice. We still like the idea of flying into Rome and out of Venice as we wanted to end the trip relaxed. The flight that I have been considering from Venice leaves a little after 12:00 PM. Would that be late enough? I may have the option of leaving at 3:00 PM also but would prefer the Noon flight if that won't be to stressful. Thank you everyone!

A noon flight is probably ok. Apparently most of the flights leave around 6-8 a.m.

Use the trenitalia.com website - the official train site. Some of the trains are regionals and only appear 7 days in advance. For better results, put in the next date that falls on the day of the week you want to travel to see the schedule.

I believe you will have to get to Florence to get to Venice. The trip from the CT takes so much longer due to the slow trains and connection times to get to the train from Florence to Venice.

A noon flight is definitely OK. The Venice airport pretty much shuts down at night and getting there early is complicated by water transportation from Venice proper. Unless you stay on the mainland for your last night. So noon should be fine.

Regional Italian train schedules are not yet published past June 14, so use an earlier date to get an idea of your options. How to Look Up Train Schedules Online gives you the DB train schedule link and tips for using it.

Bus schedules typically are harder to find, partly because buses are operated by quite a few different private companies. Given the frequency of buses on the routes you mentioned, it's safe enough to just check schedules there. See web addresses and schedule summaries on p. 670 of Rick's Italy book.

Thank you all so very much! I only wish I had posted sooner. I think I am going to go back and see if I can "tweak" the schedule. I already have reservations in Vernazza that I can cancel but I don't want to go back to square one trying to find a B&B again. Wish me luck! And thank you all again!