Itinerary help

If you long for Cinque Terre you should stay a couple of nights. Choose Florence as your base and make a day trip only to Siena.

10/8 Venice (3)
10/11 Florence (4) - day trips to Siena, Lucca (??)
10/15 via Pisa to Cinque Terre (2)
10/17 Rome (3)
10/20 Depart

I agree with the previous reply except I would also shave another day off Venice, it is a small, walkable town. Splurge on the three-day vaparetto pass and use it as bus and tour combined (Rick has a great audio guide for this). You can easily see all the highlights in one day but why rush. Plan to stay out late into the evening and get up early to see Venice like a local.
You need two whole days but with the TVG trains, you can easily get to Florence the evening of your second day. Florence is also walkable and mostly safe after dark if staying in the town center.

Siena is small and walkable but very hilly, as is San G. I did the "Siena, San G, small Tuscan vineyard" tour and wished for a little more time in the towns and less at the vineyard. If there are a few of you traveling together rent a car and choose two stops.

10/8 Venice (2-2.5)

10/11 Florence (3-4) - day trip to Siena, San G, Montepulciano, etc. If taking a tour look for English only

10/15 via Pisa to Cinque Terre (2-3) - stop for a few hours in Pisa on your way to Cinque Terre (or skip and do Amalfi Coast instead)

10/17 Rome (3-4) - you could add a day trip from Rome to Naples/Pompeii or Sorrento/Capri

10/20 Depart

I'll be in Rome and Florence at the same time as you but this is my second trip and I'll be spending my cliff-side sunshine days in Sorrento/Amalfi (better weather in October). My biggest piece of advice is avoid shopping. It is such a time sucker and touristy. If you find something unique on your travels pick it up but spend your time and money on experiences rather than things. This time around I am splurging on the "Breakfast with the Pope" tour hosted by Viator. It's a 6am breakfast at the Pinecone Courtyard and early entry to the Vatican museum...totally worth it to avoid the crowds.

I am an EXPERT traveler traveling alone so this rigorous schedule is totally doable for me...not recommended for the novice traveler.

10/5 Portland Flight from PDX to Paris

10/6 PDX/Paris

10/7 Paris

10/8 Paris

10/9 Reims

10/10 Rome

10/11 Rome

10/12 Florence

10/13 Naples/Sorrento

10/14 Positano/Amalfi/Ravello

10/15 Paestum/Sorrento

10/16 Sorrento/Capri

10/17 Pompeii/Sorrento

10/18 FCO/PDX

Happy to offer additional advice.

If you mostly want to see Tuscany, I'd respectfully disagree with the two previous responses about cutting Siena to a day trip from Florence.

Siena and Florence are the two perfect bases for your time in Tuscany. I would suggest doing day trips to small towns from Siena. You could spend one day visiting towns that are south of Siena (Montalcino, Pienza, Montepulciano, and others in that area) and one day visiting towns to the north (Volterra and SG). Be sure to allow for most of a full day in Siena, plus it's especially wonderful in the evening. Hopefully the weather in mid-October will be warm enough to allow you to enjoy dining al fresco.

Florence has enough to see in three days that you don't need to leave. I would personally skip Pisa and the Cinque Terre and spend your days in Florence. It's not that Pisa and CT aren't worth visiting, but on a trip of this length, I think you should allow more time elsewhere.

You could subtract a day from Venice and add it somewhere else, but it depends on what you want to see in Venice. I loved riding out to Murano and Burano, and would have liked more time to explore and maybe visit some of the other islands. Plus you'll be jetlagged when you arrive, so your first day could be a blur.

Enjoy your trip!

I agree with Lane about two Tuscan bases, Firenze and Siena. Lots of history linking these two cities, and good transportation to other places in Toscana.

mandyk01a, very kindly but what does Paris, Reims, Sorrento, Ravello, Paestum and Capri have to do with twg759's itinerary? Yours is a completely different trip than his/hers. This forum is also full of generous, experienced travelers with dozens of trips and months or even years of experience in Italy so take some time to get to know them? They're pretty terrific, and humble me on a daily basis! :O)

That said, I'll throw my vote in with Zoe and Lane: split the time between Siena and Florence. Florence has so much to offer, and the Cinque Terre + Pisa is too much and too far from Florence (you'd take a train, not a taxi) for a reasonably comfortable day trip. Explore some of the other options suggested?

BTW, we've stayed at Giulio Cesare in Rome and it's very nice! The rooms are smaller than you may be used to (unless you've booked a superior or better room) but the enclosed terrace is great for an evening drink from the bar, and breakfast was one of the best we've had in Italian hotels. Prati is a lovely area with a more residential feel than some other parts of the city, and you'll be very close to the tranquil expanse of Villa Borghese. The staff was excellent; hope you enjoy it as much as we did!

Hello
forge the Cinque Terre, you will be surrounded by Rick Steve clutching tourist. Spend the time in Rome or Florence.
John