Rome, Florence, Venice - sequence of travel

Option 1 has the issue, depending on your hotel, of whether they have check in that late. The other negative is your one full day in Venice is after a long day of travel and late arrival.

I would modify Option 2 to go to Venice from Rome and do Florence last , so you have a shorter trip to reach Rome for your final day.

Presumably you do not have the option to fly into Venice and out of Rome. Hopefully the saving on airfare was substantial enough that it more than covers the round trip train fare, vs having gone just one way.

Option 2 is the safer one, avoiding trouble in case of a late incoming flight or issues with your luggage.

Option 2A:
Head to Venice then Florence.
Be smart with train times to squeeze in more sights.

Day
1. Late arrival in Rome (3 nights)
4. Afternoon train (3hr 45min) to Venice (2 nights)
6. Late train (2hr) to Florence (2 nights)
8. Late train (1hr 30min) to Rome ( 1 night)
9. Morning flight from Rome

I do not know if you have purchased tickets yet nor where you are leaving from but Delta goes direct from New York to Venice. They have what appears to be their own terminal at Marco Polo airport. Flights usually arrive in the morning. If you fly open jaw you can leave from Rome. This will allow you to travel down the country without any backtracking. Good Luck!!!

I vote for open jaw travel. If you have already bought your tickets it may be worth your while to call the airlines and see how much it would cost to make the change - way that amount against the time lost.
You don't want to lose a day - there's too much to see and enjoy! I'd suggest doing some looking at guide books to see what you 'must see and do' in each place. Especially with museums, make sure the ones you want to see will be open on the days you plan to be in that city (usually a Monday problem but not always).

Also, from my experiences (this will be year 15 in a row) I'd give Venice an extra night and take it from Florence. That's a personal preference. I just love wandering through the back alleys in Venice and a late night vaporetto ride around the Grand Canal. August in Florence is going to be extremely hot and humid (it sits in the bottom of a bowl). And crowded! Make sure in Florence to make time specific reservations for the major sites (where available) otherwise you'll be stuck in long lines. Also, you don't say where you are flying from but if you do decide on Option 1, the train (Freccia - high speed) from Rome to Venice is probably shorter than dealing with a connecting flight. Of course, it stops in Florence first . . . . hmmm, maybe start your vacation there? From Rome to Venice (or vice versa) is about 3 3/4 hours. The train station in Venice is right on the Grand Canal so you can walk or vaporetto your way to your hotel.

Thanks everyone for your inputs. Here's some more thoughts on even why I considered Option 1 in the first place.

I have already made flight bookings to and from Rome and changing that is not an option now as its going to cost quite a lot of $$. However, savings in the original booking were significant for me to even consider a flight from Rome to Venice in first place as that was less that 100$. The only reason I was leaning towards option 1 was to get an extra day in Florence even though it might only give me a single day in Venice after a hectic travel.

Joe & Robert, I will be flying in from California and since its just going to be me and my wife, we plan to travel light using only carry-on luggage.

What time is your evening flight?
There are 4 trains departing from the Rome airport station between 7 and 8pm which can get you to Florence the same evening.
So if your flight lands before 6pm, you should be able to take one of those and start your itinerary from Florence, which can be reached in less than 2.5 hours from the airport (one change at Roma Termini or Roma Tiburtina).
If you start from Florence you can avoid splitting your Rome stay:
Florence 3 nights
Venice 2 nights
Rome 3 nights.

If your flight lands after 6pm, then it becomes too tight, even though the airport station is across the Terminal 3 where you arrive, so you might have to book at least the first night in Rome

IMHO I would not try to visit 3 cities in 8 nights. In travel speak, 8 nights = 6 days. With three travel days in the height of tourist season and your arrival and departure days being lost, you will not have an opportunity to experience the charm of any of the cities. Personally, I’d stay in Rome for the whole time and take day trips (Orvieto, Tivoli, Naples/Sorrento?). Otherwise, I’d choose only Rome and one of the other cities. If you are like most visitors, you’ll fall in love with Italy and return often. My 12th Trip is scheduled for September.

Thanks everyone for your inputs. I have finally narrowed down to this option as suggested by David.

Day
1. Late arrival in Rome (3 nights)
4. Late train (3hr 45min) to Venice (2 nights)
6. Late train (2hr) to Florence (2 nights)
8. Late train (1hr 30min) to Rome ( 1 night)
9. Morning flight from Rome