Venice vs Umbria...

Aubrey:
I love Venice (it is NOT Disneyland!) but I think your 2nd itinerary is better for the time you have in Italy. For your Fri-Mon 4 nights, I woudl personally suggest you pick a base and take daytrips, rather then trying to stay in multiple towns. Personally I hate moving every night or two, and you will already have has a 1-nighter and a 3-nighter. If you stay 3 or 4 nights, you get more of a sense-of-place and culture. I think you will also be glad to have 4 nights in Rome. Pompeii is doable in a VERY long daytrip, but Paestum is too far to do in a day. I think you'll find there is more than enough in Rome to fill what will be 3 1/2 days.

There's a reason Venice is so popular. It's stunningly beautiful and it's loaded with art, history and architecture. Yes, there are parts of it that make you feel like you're in an amusement park, but you can easily also see the parts that are still the authentic Venice (e.g. Dorsoduro, Cannaregio and Sant'Elena). Having been to all the places you've listed (except Pompeii and Paestum), I'd put Venice and Rome at the very top. As for daytripping to Pompeii, if you don't want the hassle of the looooong travel time each way, consider Ostia Antica instead.

If you go into Venice on a bus and spend an afternoon wandering with the tourists...you will be impressed...but, if you spend the night there and stay up late and wander the streets after the daytrippers leave and get up early and watch the sunrise...that is truly a remarkable experience. I had done the first one and thought I didn't need to go back, but now I have done the other and there is really no place I have visited that is comparable. Not that there aren't other cities and villages that I love, but Venice is quite unique. (Just left Epcot a few weeks ago and Vegas last week and saw 'fake Venice' at both.... and I couldn't believe it, neither one of them copied those beautiful rose-colored street lights correctly... they used white bulbs) Maybe its energy efficiency but they could have tinted the glass pink...small detail, but I am a photographer and notice these things. You'll have a great time no matter what you do, but Venice can be magical.

Wow. I'm sorry, but Cinque Terre is an "amusement park" compared to to the other places you want to see. The towns are colorfully painted houses with little cultural or historical significance. And the local population has become accustomed to deriving their incomes from catering to enormous numbers of German and NPR-listening Americans during warm weather. Venice is a city of enormous historical and cultural significance. While its own native population is tourist-oriented, they've been at the game for centuries. But the buildings, the art, and the setting make Venice a destination you need to see at least once in your life. I love the CT. But they're a confection best visited on a much longer visit to Italy. Rick Steves made the towns popular because they show up so well on TV. But, Aubrey, you're from Oregon. If someone said you couldn't visit Oregon without seeing Cannon Beach, would you believe them? The CT are Italy's equivalent of Cannon Beach.

Ironically, I have never been to Cannon Beach. Still want more opinions on the matter before I comment.

For the record...I love both Venice and CT and would not give up one for the other... I love the Mediterranean Sea so a trip to Italy without it doesn't feel quite right.
( I also have a friend who lives on the Oregon Coast in Arch Cape just south of Cannon Beach and it is beautiful)

Is there a night train from Venice to CT?

Regretably, you cannot take a night train to the CT. It's 2 changes of train (minimum): Florence & La Spezia, about a 6 hour trip. Believe me, I love Venice and would highly recommend you go there for at least 2 nights, preferably 3, but you will be hard-pressed to do everything in your first itinerary in 12 days. Your OP said "Venice vs Umbria" so I thought that was your trade off and the CT was a "must." If this is your first trip to Italy, consider Venice/Tuscany/Rome as your trifecta. Transportation is more efficient, you can make Lucca a Tuscany stop, and give perhaps 3 nights to Venice and 4 to Rome, with 5 remaining for Tuscany.

I have a solution!!!! Quit my job and move there....problem solved! Do you think I would get healthcare and a 401k as a dental hygienist in Italy??? ;) Ok, how about this one... Mon 12- Arrive in Venice in the evening. Night in Venice Tues13- Venice. Night in Venice Wed 14- Spend most the day traveling to CT. Night in CT Thurs 15- CT. Night in CT Fri 16- Pisa/Lucca Sat 17- Hill Town Sun 18- Hill Town Mon 19- Orvieto. Night train to Sorrento Tues 20- Pompeii. Night in Rome Wed 21- Rome Thurs 22- Rome Fri 23- Rome
Saturday morning leave for home.

Hi Aubrey, I first visited Italy in the 1990's and was not impressed (but I was so much older then, I'm younger than that now.) The first visit did not include Venice and only 2 nights in Rome. This past year, I spent time in Florence and the CT. I found the CT to be stunningly beautiful. Spending time there is restful. The trail system from village to village is not to be missed. Florence is also worth a visit. All of Italy can be considered a tourist trap if that is your expectation. Having spent time in Italy last year, I am thinking of visiting Venice this year, something I never thought I would do. I am not a traveler who wants to constantly be on the go, so your hill town visit does not resonate with me. I would go to Florence from either Venice or the CT. Take a train from there a town or 2. I may be missing something in not driving to the hill towns, but to me I'd rather stay put in one area. Really depends on if your goal is to relax or to get everything done.
Claudette

Aubrey:
Your latest plan can be done, but the question is whether you would really enjoy your trip. It's 6 places in 12 nights, That is a LOT of transfer and travel time. Every time you change locations you have to pack, move, check-in, unpack. It is exhausting and detracts from your enjoyment. Plus, every time you go to a new place you are spending time orienting yourselves. It takes more time and energy than you might imagine. There is no "night train" from Orvieto to Naples (you get to Sorrento on a separate train, the Circumvesuviana). The latest you can leave Orvieto to get to Naples is 20:13, arriving at 23:00. If the CT is a "must" then I'd recommend dropping Sorrento/Pompeii. Add that regained night to the CT. Since you really seem to want to see it, and are traveling all the way across Northern Itlay to get there, take time to enjoy it! Remember you will be back! Sorrento can be "next time" when you take a proper amoutn of time to experience Naples, Pompeii, Sorrento and the Amalfi Coast.

I admit, I am putting too much in the plan. It is so hard to "be just a train away" and not go! I think Venice to CT (via Milan to Genoa) to Lucca to a couple hill towns to Rome is for us. We are only bringing a backpack, so packing and repacking isn't this huge deal. We are young (29...although that 30 is coming quicker than we anticipated!) very healthy and trying to get a dream trip before we have some babies.
Thanks for your help. Opinions are still welcome if anyone would like to add to the discussion!

Regardless of your age or level of activity, you still only have one full day in Venice and one full day in the Cinque Terre. Also regardless of your age, consider the number of hours you'll spending traveling from location to location vs. being IN the location and enjoying it, whether you're visiting a museum or sitting at a cafe people-watching. I think you'll enjoy Venice and the Cinque Terre more than Pisa/Lucca and/or Orvieto, as delightful as those places are. Consider dropping one or both of those destinations, and adding that "extra" time to Venice and/or the Cinque Terre. Also, it looks like you'll be travelling by train; no rental cars. If that's the case, keep in mind that visiting Tuscan hill towns is a little more difficult and time-consuming by public transportation. So factor that into your travel plans and times.

Laura has planned the perfect itinerary, IMHO. Great job!

I agree with Lauren, your second plan is better. As beautiful as Venice is, perhaps you should leave it for your next trip, especially in view of a whole day spent travelling from Venice to CT. You will also need more than one day to see Venice properly, so better to put those days to better use by adding them to the rest of your trip. Italy is just gorgeous so it doesn't matter what you choose and what you leave out, you will enjoy it, but the simpler the plan the better.

Hi Aubrey, My husband and I are also in our late twenties, and planning a trip to Italy for the fall before having children. In all the research I've done, here is our plan: Venice- 3 nights Cinque Terre- 3 nights Florence- 3 nights
Rome 5 nights We are planning on stopping in Pisa between Cinque Terre and Florence (the train actually stops there). We are also debating a day trip to Lucca or Siena from Florence, and Pompeii from Rone, but are undecided. From all the research I've done, I felt the quietness of Cinque Terre will be a welcome break, and balance the intensity of the big cities. For us, we didn't want to be traveling all the time, so we chose the open jaw flight and a minimum of 3 night stays. Happy Planning! Laura

What does IMHO mean? Call me techo-challenged.

In My Humble Opinion.