Travel Itinerary help please! (Leaving in 5 weeks)

If it were me, I would go straight to the furthest away place (in this case Venice), and then work my way south and spend several nights in Rome before you depart. You certainly have enough destinations on your list that you really should not add more. In fact, you might want to remove some, to allow some time to relax and to really get to know the places you visit rather than checking off something that you've seen as you speed thru it.

Thanks Angela! That's a great suggestion. I might switch the order to: Rome - Venice - CT - Florence - Siena - Rome
Earlier today I booked my stay in Rome for when I arrive so I won't be able to leave for Venice right away.

If you had to remove one place / city what which one would it be?

Thanks again!

You say that you are not touristy types and like places off the beaten path, yet you have listed all of the most touristy places in Italy. As far as your itinerary it looks fine, a bit rushed, but probably doable. If you truly want to have some unique and non touristy experiences you might want to pick a few obscure towns or villages , rent a car, and find some of your own 'off the beaten path' locations. It's especially easy to do that in Italy, but given your itinerary you will probably end up going to all the tourist highlights (not necessarily bad...just not what you said you wanted)

Thanks Terry. I should have clarified, that we like off-the-beaten path in the sense that we're not looking to see all of the major tourist attractions in those cities. We're not rushing to 'check box sightsee.' Since it's our first time in Italy, we were advised that we shouldn't skip the big 3 and to explore on our own time . If you have other suggestions that would be great.

My original idea was to see Puglia region, but I will have to visit it on my next trip ;)

None of the places you mentioned are off the beaten path. However there are really no places in Italy that are off the beaten path. Tourist destinations in Italy come in two varieties:
1- places overrun by Italian and/or European tourists but not known to North Americans
2- places overrun by both European and also tons of American tourists.
The places you mentioned belong all to category number 2.
The ideal for you would have been an open jaw plane ticket, landing in Venice and returning from Rome.that would have saved time and money.
Since I imagine you already have your plane tickets, I also suggest to go to the farthest place first, Venice.
my order:
5/24 arrive Rome (morning). Take immediately train to Venice (4hr trip)
Venice: 3 nights
Train back down to Florence (2hr trip)
Florence: 4 nights (day trip to Siena)
Train to 5 Terre (3hr)
5 Terre: 2 nights
Train to Rome
Rome: 4 nights
The total is 13 nights.
If you are not interested in big cities like Rome, you could reduce one night there and add it to the Cinque Terre. Also from Florence you can visit other small villages in Tuscany on day trips.

Thanks Roberto. I've actually already booked accommodation at the beginning of the trip in Rome.
This is what I've got now with everyone's input:

24-May 1 Rome (arrive)
25-May 2 Rome
26-May 3 Rome
27-May 4 Rome-Venice
28-May 5 Venice
29-May 6 Venice
30-May 7 Venice to Florence
31-May 8 Florence
1-Jun 9 Florence (Siena day trip)
2-Jun 10 Florence
3-Jun 11 Florence - Cinque Terre
4-Jun 12 Cinque Terre
5-Jun 13 Cinque Terre - Rome
6-Jun 14 Rome (depart)

Let me know what you think!

OF,

Given that you've already booked hotels in Rome, the last Itinerary you posted is the most reasonable and should work fine. A few thoughts to add.....

• I'd suggest pre-booking accommodations in as many locations as possible. You'll be travelling in "spring shoulder season" and it could be very busy in Italy.
• I would ESPECIALLY recommend getting accommodations booked in the Cinque Terre SOON! Have you decided which of the five towns you might like to stay in. Monterosso is the largest so also has the most hotels, restaurants and other tourist facilities, so that might be a good place to start.
• For your trip from the C.T. to Rome, there are several direct (no changes) trains from La Spezia Centrale to Roma Termini. It's very easy to get from any of the five towns to La Spezia. I'd suggest using one of the direct trains rather than one of the others that has multiple changes. You can see all the departure times and other details on the Trenitalia website.
• It would help to know whether you've been to Italy before, as there are some potentially expensive "caveats" to be aware of when using the trains.
• When you use the Bus to Siena, don't forget to validate your tickets!

Happy travels!

Thank you, Ken! So very helpful. It's my first time in Italy so I'd love to know of these potentially expensive "caveats" when using trains. I have not booked accommodations in each city as I was truly hoping to do this on the fly. I.E. Start in Rome and go with the wind. Thanks for the advice. I will start looking at some accommodations now in the other cities.
What about trains and buses? Can I book that while there?

You can buy train and bus tickets until just before departure time, but you need to leave time for possible ticket lines and time to get to the track (binario). RoninRome.com has excellent detailed suggestions on transportation in Rome (good elsewhere in Italy as well), including photos. Ticket validation boxes may be green/grey rather than yellow.

See my reply on your later itinerary revision.