Help with Italy Itinerary, first Europe trip!!

OK, staying 2 days in Rome (one with a day trip to Naples/Pompei) then going to Amalfi, then going back to Rome wastes time and money.
When you land in Rome, go straight to the Amalfi coast, relax, take day trip to Pompei, then go back to Rome and spend time there. That will save 2 days almost. 2 nights in Venice should be a minimum.

Since you haven't purchased your tickets, fly into Naples (NAP) and out of Venice (VCE)
This way you are not doing a lot of backtracking
1 Travel
2 Arrive Naples Bus to Sorrento http://www.curreriviaggi.it/inglese/E_index.html
3 nites Sorrento
3 Amalfi Coast
4 Pompeii
5 Train http://www.trenitalia.com Napoli Centrale-Roma Termini 1H10m 29 euro
3 nites Rome
6 Rome
7 Rome
8 Train Roma Termini-Firenze SMN 2H51m 29 euro
2 nites Florence
9 Florence
10 Train Firenze SMN-Venezia S. Lucia
2 nites Venice
11 Venice
12 Travel

With only 9 full days you are planning way too much - unless you enjoy train stations since that is about all you will see based on this itinerary. For each change of location, you need to plan on 1/2 to 3/4 of a day for packing/checking out, travel to the train station, train travel and then finding your new hotel.
So, here is what I'd recommend
Day 1 - fly into Rome - check into hotel and acquaint yourself with the neighborhood - depending upon your interests you could check out the Pantheon, Piazza Navona and the Trevi fountain - have an early dinner and get some sleep.
Day 2, day 3 and day 4 - Tour Rome
Day 5 - train to Florence
day 6 and 7 in Florence - depending upon your appetite for shopping and art, you could do a day trip to Siena.
Day 8 - train to Venice -
Day 9 Venice
Day 10 Venice
Day 11 - you could take the train to Milan if you want to see the Last Supper and then fly home from Milan. If the Last Supper isn't high on your "to do" list, then I would add that day to either Rome or Florence. If adding to Rome, you could do a day trip to Pompeii from there or if adding to Florence, you could do a day trip to Pisa and Lucca. I would save the Amalfi coast for another trip - you simply don't have enough time to make the travel there worthwhile.

Or, fly into Milan, train to Venice, train to Florence, train to Sorrento (daytrip to Pompeii from Sorrento), bus to Amalfi Coast, train to Rome, fly back. How many days in each place is up to you.

I checked flight prices, and it's an extra $1000 to fly open jaw...looks like I'll have to fly roundtrip to Rome. That complicates things. I may have to make some cuts. If I went direct to Amalfi Coast when I land and day trip to Pompeii from Amalfi (3 days), then go straight to Florence and day trip to Tuscany (2 days), then Venice (2 days), then Rome (3 days), would that work? Or too much travel time? I hate to cut Amalfi Coast. I'd probably cut Pompeii first.

Curious about where you are flying from and which airlines charges more for open jaw?

We are flying into Venice then out of Rome- either way we did it the cost was the same- 1200 RT direct flights to/from Philly on USAir.

I'll also add that I think you are trying to fit in too much.
We have 17 nights and I am still slightly concerned about our 2 nite stays!
Venice- 2
Florence- 3
Tuscany- 4
Assisi-2
Orvieto-2
Rome 4

$1K more for open jaw? That doesn't sound right. Try again using different dates. You might be surprised to find how much the price can change based on the days of the week you travel. Tuesday thru Thursday are typically the cheapest, then Fridays and Sundays are often the most expensive.

You might consider trying to extend your travels an extra day or two. 12 days really isn't long at all for Italy, and you'll certainly be wishing you had stayed longer! 12 nights is exactly how long my first trip to Italy was 2 years ago, and this year I'm going back for 3 weeks!

If you eliminate the first two days (flight from US/jet lag recovery) and your last day from your travel plans (flight home) you really only have nine days of sightseeing. I would keep it to 3 locations, maximum. I would even argue for 2. Everyone has a different travel speed preference but I prefer not to be rushed. Train travel, even if the cities are relatively close, can take half a day off your sightseeing if you figure in transfer to/from train stations. And navigating a new city upon arrival can be a little stressful, especially when it will be your first time in Europe. If you decide to do two locations, it sounds like you have your heart set on the Amalfi coast and Rome. Some people choose to do Florence as a day trip from Rome. That would be too rushed for me but others have done it and say it worked for them. Happy travels!

Open Jaw is the only way to go! I traveled this way 4 years ago.... and again this May on a return trip. My flight wasn't much more than a regular flight. I am flying into Venice (2 days), train to Cinque Terre (2 days), train to Florence (4 days), train to Rome (3 days) then train down to Amalfi(4 days). We then took a cab from our hotel in Amalfi to the Naples airport to head home. It was perfect!!!! And if you're staying in the Amalfi area don't miss a boat ride out to Capri!

One more thing.... flying into Venice to start your tour is a great idea! Venice is slower paced and easier to get acquainted for your first day. I used this blog when planning my first trip to Italy and added a few extra days for the Amalfi coast. http://www.italylogue.com/planning-a-trip/italy-itinerary-the-perfect-two-weeks.html

Don't confuse an open-jaw ticket with two one-way tickets. Open-jaw is flying into one city and out of another, all on one ticket. Another term for open-jaw is multi-city. Two one-way tickets can be VERY expensive - that may be where the $1,000 is coming from.

Are you planning to book your hotels when you arrive in each city, or in advance before your trip begins? I'd recommend booking in advance (like, now), since June is a busy travel month.

Wow, thanks so much everyone. I've been looking up 2 one-way tickets...not multi-city. I'm sure that's the problem. I've been using skyscanner and there's no option for multi-city. Where is the best place to check prices?

Most sites like travelocity/expedia have a multicity option. You may have to go under Advanced Search. Since you live in Dallas, I think American Airlines will offer the most flights for you. Try their website.

Kayak and Orbitz also have the "multi-city" option. I use these sites to get a feel for prices/airlines, but I always book directly on the airline's website.

With NINE days on the ground, please, please only do three cities! My first trip to Europe was so exhausting, I spent
one or two nights in each location and when I got home, felt like I'd seen a slide show rather than a country!.

Every time you change locations you lose a half day. Think: check out of hotel, taxi to train, ride train, taxi to hotel,
check into hotel. You will fall in love with Italy and will want to come back so badly that you WILL do it.

My advice is to do the "big three" for a first trip: Venice, Florence, Rome. If you can arrive from the U.S. in Venice,
do it! It's an easier place to land and be "Italianized!" Then Venice to Florence, three nights in Florence -- there's
so much to see in Florence, but if you MUST, day-trip to Siena or take a one day "wine tour" of Tuscany from there.
This will give you a chance to see the countryside and also enjoy the fabulous wines of the region. While in Florence,
make sure you spend some time at night, sitting in a piazza and drinking some wine and just enjoy 'being.' Must
see sites would be the Academia - for the Statue of David, and the very ancient musical instruments! This is much
less time consuming than the Ufuzzi, but you can work in a half day there -- and walk across the bridge and see the
world's most beautiful collection of gold and sparkles at the Ponte Vecchio.......lunch at "Golden View Open Bar"
get a table at the window for a lovely view of the Arno River. I won't go on. You can PM me if you want more info!

Rome is certainly worth at least three days as well. The sites are so well known, but as many times as I've been
there, I am superstitious and ALWAYS throw my coins into the Trevi Fountain to ensure I will return! Walk towards
the Campo Di Fioro, Piazza Navonna....then cross the bridge to Trastevere! Again, I won't go on. It took three trips
to Rome before I discovered these beautiful piazzas. The Vatican Museum and St. Peters will take a half day, and you
do NOT have to be a Roman Catholic to love these. I was amazed at the pre-Christian artifacts, paintings, statues that
have been lovingly preserved here.
First two trips to Italy had family obligations, requiring us to land in Milan. I've never "gotten" Milan, other than the
Last Supper, and it seems a wasted stop on a 9 day trip, In My Opinion.

Amalfi is a destination in and of itself, and if you go there, I'd just split my time between Rome and Amalfi, and swear
to return and see Venice and Florence on the next trip, again, that's just my opinion. (And I'd let the time of year
decide that for me.) Again, feel free to PM me.

You will fall in love with Italy!! Now, reading my post, I'm ready to go again!