Please Help! 1st time in Italy, round ticket

I would do option B but take the train straight thru to Venice. Then Florence , CT, Rome. I would not do well with a long train ride anywhere after the flight. I remember my first trip to Europe at 14 when my grandfather took me and my 13 yr old cousin back to his home country of Spain. From Madrid, we went right onto a very scenic train to Barcelona, which my cousin and I sleep thru. The only time we woke up was to spend his money on snacks from the cart. LOL, Plan gone awry- poor grandpa kept trying to point out the scenery.
I have not been to CT - others can weigh in on that.
Why are you going to factory outlet, just curious.

I am one of the few...who is not necessarily a fan of open jaws...when staying so close to the arrival city, as you are. I also don't consider a train ride through the countryside a waste of time. I enjoy spending a couple of days in my arrival city to acclimate to the new country. I then head for my second destination and so forth. When I return to my arrival city, it is already familiar and I know what is left for me to see, etc. and in a way it is like coming home. I find my trip more relaxing this way. Personally, I'd dump CT for your first trip (or any trip), but, hold harmless, I have never been there after several trips to Italy, as it sounds horrible to me. I like to hike where there aren't crowds...or 'hike' around the city. Florence is my favorite and not because of its museums (although wonderful), but because of it's ambiance.

I also would not take the train ride to Venice immediately after arriving in Rome. I would consider having only 3 stops on your trip. We spent 10 days in Rome on our first trip to Italy, and 10 days in Florence on our second trip.

How are you getting to Venice? I would suggest that you fly to Venice the same say you get to Rome since you are already packed and are at the airport. If you do train you are talking about 3+ hours (I think).

Hi. Everybody will have different opinions - here are mine:
- you will have an awesome trip
- do NOT skip CT. If good weather, it is awesome hiking with spectacular views and gives you six small towns (with Levanto) to explore and enjoy very easily.
- good order of travel is Rome / Venice / Florence / CT / Rome.
- my suggestion ( I am biased toward CT, and I found Florence only so-so) would be night 1 Rome, nights 2,3,4 Venice, nights 5,6 Florence, nights 7-10 CT (stop in Pisa briefly to see the tower if interested, and/or stop in Lucca?), nights 11,12 Rome. (Don't know where the factory outlet is you refer to)
- once you settle on exact itinerary, buy your train tix in advance (but not Florence to CT) at trenitalia.com to get discount fares.
- enjoy your trip!!!

Good suggestion Nestor, flying to Venice on day of arrival (if possible).

Unlike Diane, I do not consider the train ride between Madrid and Barcelona to be very scenic and would be happy to nap through it following flight arrival. The same goes for the scenery on the main transport corridor between Rome and Venice. You'll see it on the way back, anyway.

Her is one reason to stay in Rome first. Advance purchase nonrefundable tickets can be got for way less than spur-of-the-moment tickets. If you go to Venice straight from Rome airport, you will have to pay the spur-of-the-moment price because you cannot guarantee that your flight will arrive on time or you will get through immigration quickly. Those cheap nonrefundable tickets become worthless if you miss your train.
So option B would be my preference. You can then buy all of your tickets in advance and save a bit of money. Florence to CT can be done with Regionale trains, so that is the exception to buying ahead of time. Regionale trains are always the same price and have no reservation.
Example, spur-of-the-moment tickets Rome airport to Venice are 78 EUR per person, bought 90 days ahead, 40 EUR per person.

I'd go to Venice straight upon landing. That way you save yourself one hotel change.

There are trains every hour from Rome main stations (Termini and Tiburtina, the trains stop in both) and 2 that actually depart from the Airport station (at 11:08 and 15:08).
www.trenitalia.com
station names: Fiumicino Aeroporto, Venezia Santa Lucia, Firenze Santa Maria Novella, Roma Termini or Roma Tiburtina.

You have 12 nights on the ground. I'd allocate as follows
Arrive Rome in the morning. Train straight to Venice (4 hour trip).
Venice: 3 nights (that's 2 full days: you can do both Venice, or one in Venice and one visiting the lagoon islands of Murano and Burano)
Florence: 3 nights (that's 2 full days: you can do both in Florence or one in Florence+one day trip to Siena or Pisa/Lucca or the outlets)
Cinque Terre: 2-3 nights
Rome: 3-4 nights.

I wouldn't waste time to go to the outlets, although my wife drags me to "The Mall" in Incisa and to "Prada outlet" in Figline all the time (but that is not our first time to Florence either). There are also outlets in Barberino and in Foiano della Chiana (been there done that, boring! they look like the outlets here in California).

I think in the end you save by buying those designer clothes on http://www.yoox.com/us, based in Bologna (ships worldwide) and not just because I have a cousin who works for them.

Wow.. Thank you guys so much! You have no idea how much help is that. I posted this before I went to bed, and woke up with so many useful and good tips! Magic of time difference :)

Now I do have a clearer picture of the sequence. I would follow the sequence of Rome / Venice / Florence / CT / Rome. I think we would stay one night in Rome before proceeding to Venice. Though the packing and unpacking is abit of a hassle, but I think it will be less stressful and tiring. Yeah, think I will still go CT, that place looks really charming and is the first destination (besides Rome) that caught my attention.

For those wondering the outlet store I'm referring, it is like what Roberto mentions, it is to the "The Mall". Branded goods in Singapore are unfortunately much more expensive. Yeah, I did read some reviews that it is not worth the trip down. We might cancel that and add a day trip or just stay in Florence if we liked it there.

Yay, now I have the destinations decided. Finally I can proceed to research on the places to go and start making reservations and bookings.

Once again, thank you so much! You guys have made my day!