Starting out in Venice...help :)

Venice VCE is the 3rd or 4th largest airport in Italy and has many flight options, including non stops from both JFK (Delta) and PHL (US air). From Venice you can reach Florence very easily with a high speed train (about 2 hours south). Florence is Tuscany's regional capital and from there you can reach many hill towns in Tuscany. Most are accessible from Florence by bus or train, however a car rental is more efficient to visit Tuscany's small towns and countryside, which tend to have only sporadic bus service. If you don't rent a car, Florence should be your base for Tuscany, since it's the public transportation hub for the region. You don't need a car for Florence itself. Siena, Lucca, Arezzo and Pisa, also in Tuscany, can be accessed easily by bus or train and you don't need a car to visit them. They are 4 of the 10 provincial capitals in Tuscany. Rome is only 90 min. south of Florence via high speed rail. You don't need a car in Rome. Rome can also be used as a base for day trips to Orvieto, for example.
Capri is an island in the Gulf of Naples. Naples is about 1 hour further south of Rome via high speed train. In the area, besides the beautiful city of Naples and Capri, you can visit also Pompeii, Sorrento and the Amalfi Coast (Positano, Praiano, Amalfi, etc.). Many prefer to use Sorrento as a base, rather than Naples, primarily due to Naples' reputation of chaotic city famous for its thieves. It's probably an exaggerated reputation, but nevertheless. If you would like an itinerary like that, I suggest you buy an open jaw air ticket (multi-city) with arrival in Venice (in the North) and return to the US from Naples (southernmost) or Rome. Naples however doesn't have non stops to the US (except for a weekly with Meridiana)

Marisol, Could you clarify your travel time? Is that 14 days for actual touring? Keep in mind that you'll require two days for flight times. With only a very short 14 days and given the destinations you listed, you'll need to plan very carefully. You won't be able to see it all, so I don't think meandering through hill towns in Tuscany will be an option, unless you skip something else. I'd recommend open-jaw flights, inbound Venice and outbound Rome. Those will likely provide you with the greatest number of flight choices. On this first trip, you could (for example) spend 3 days in Venice, 3 days in Florence (possibly with a day trip by Bus to Siena), 4 days in Sorrento (to see Capri and other places in that area), and 4 days in Rome. You'll need to allow for adequate travel times between locations, which will generally require a minimum of four hours in each case (and sometimes more time). I suggested Sorrento as it's a good "home base" for touring that area and has rail access. You don't have to spend all your time there. You might find it very helpful to have a look at the Italy 2013 Guidebook (available now), as there's LOTS of good information there on hotels, restaurants, sightseeing, transportation, etc. If this is your first trip to Europe, you may also want to read Europe Through The Back Door. All of the places you want to visit are easily accessible by train (except Capri of course). There are a few potentially expensive "caveats" to be aware of when travelling by train in Italy. If you need more information, post another note. Be sure to wear Money Belts! There WILL be scammers in Italian cities, and they're VERY proficient in their "craft"! Happy travels!

Just one more note. You live very close to JFK and as I mentioned Delta has a non stop from JFK to VCE. That would be your best option. However if that option is not available or if too expensive, you could also arrive to Milan MXP (which has non stops from JFK) and take the train from the airport to Milan Central Station and from there to Venice. The train trip is about 4 hours, all inclusive, and it will cost you at least $60 per person o/w, therefore consider that option only if flying into Venice is significantly more expensive. You can fly to Venice from JFK also via many European gateway cities, like Paris (with AirFrance), Frankfurt (with Lufthansa), Rome (with Alitalia), Amsterdam (KLM) and many others. Consider those options as well before considering flying into Milan and taking the train from there, as they might be cheaper and faster options.

I'm in the process of planning a mother/daughter trip to Italy for 14 days next fall. I don't get to go. We already have the tickets. They will be arriving in Venice-Marco Polo and depating Rome-FC0. They will be visiting the same places your are describing except for Capri. I already have an Excel spreadsheet showing where they will be each night. I would suggest to you that Capri will make your visits to Florence, Tuscany and Rome go a bit faster. Capri is a slight travel reach from Rome. But, it can be done at the expense of the time in the other places.

Marisol, as others have said, everything is easily accessible by fast train (Capri can be reached from Naples or Sorrento by ferry or hydrofoil). I suggest you start looking at places to stay on Venere.com or Booking.com, you can search by price range. Venice is not inexpensive, and since you're starting there, you might want to book those 3 nights as soon as you know your travel dates. You can get to the major hill towns by bus or train (trains usually have a station at the base of the hill, with city buses or taxis to take you into town). Have you considered Assisi?

I just completed a trip similar to what you are considering. We started out in Venice and spent 3 nights there. Our itinerary was this: Day 1 Depart the US Day 2 Arrive in VCE and walk around to get oriented Days 3-5 Venice; afternoon train to Florence Days 6-8 Florence; afternoon train to Rome Days 9-12 Rome
Day 13 Fly home We bought our train tickets in advance and got them for 9 euros each person per leg. This is very cheap! the only drawback is that you must take a specific train or lose your money if you change. This wasn't a big issue for me though. Hotels: This really depends on what time of year you are going and what you consider cheap. We stayed at the Hotel Accademia in Florence and Hotel Smeraldo in Rome. I thought these were a good value. Restaurants: In Venice, we had the best risotto at Ae Botti on Giudecca island. You can get there by vaporetto. It's located right on the Guidecca canal. In Florence, get a crepe at the Bermuda Triangle and a steak Florentine at Trattoria lo Stracotto. For Rome, pick a spot on Campo De Fiore and watch the show.

Marisol, Congrats on your Italy trip. Here is some info on Vicenza, the military base. For housing, stay on base. The rates are excepitional for the area!! http://www.vicenzamwr.com/lodging.html The city itself is unbelievable, especially if your into Pallidan architecture. It is about 1 hour from Venezia (venice) by train,cost, 5-9Euro The website for train travel thru Italy is Trenitalia.com Have done this trip several years ago, and should be very doable as far as Venice (3) Florence (2) Tuscany (3) and Rome (4). If you were to add Capri, my suggestion would be to take a day from Tuscany and a day from Rome. Head to Naples directly from Tuscany use your remaining days in Rome. This would give you a taste of some great areas. For lodging try looking at cross-pollinate.com They have some great rental apartments in most of the areas at some very reasonavle prices. Any questions? Just Pm me
Gerri

You'll probably have difficulty finding a room at the Ederle Inn in May, that's prime PCS season. And you have to be ID card holders.

Marisol: All of the above postings are giving you great advice. After running your same itinerary in April, I can tell you'll really enjoy your trip. We stayed in Zagarolo, 20 miles south of Rome, on an agriturismo. We found as many sites to see outside of Rome as there is in the city center. Have a great time.

Thank You thank you. Wayyyy excited. I posted a reply yesterday but I see it didn't go through. You have all given me AMAZING information. I'm counting down the days. For one, I just can't wait to see my son. Holiday will be hard without him. So yeah mama misses him. In the post that didn't go through Irmtionr that I had been to Rome back in 2009 (I won Lufthansa tickets) my hubby dint hve his passport so I went with my BFF. So I know here to go there and how to get around. I definitely want to do a wine tour. Also, was told we could ONLY bring 4 bottles of wine per person. Has anyone shipped wine back home? Seriously 8 bottles is just not enough for me lol. I also mentioned we can fly out of Rome. I'm a flight attendant so I'm open to any airport. I just want to arrive in Venice.

Hello Marisol: AIR TRAVEL. If you are a flight attendant you might be able to get body passes or some other perks with an airline that is partner with the airline you work for. As I mentioned the only non stop from JFK to VCE is with Delta. However you can reach Venice VCE with many airlines with just one stop somewhere else in Europe. VCE is the 4th busiest airport in Italy and, together with Milan MXP and Rome FCO, is one of the only 3 airports that are classified as Major Intercontinental by the Italian Civil Aviation Authority. Just do a search with Kayak.com to find the best deals. Since you are traveling south, search the multicity option arriving to Venice and departing back to the US from either Naples (NAP) or Rome (FCO) in the south (Rome will probably give you the most options at the best prices with the fastest times, since there are several non stop from FCO to JFK). ALCOHOL: You are right, 8 bottles of wine are not enough. You can ship wine to the US. It has to be done through a courier (not postal service). Wineries and wine stores generally will do so for you. The US customs has no limits for importing alcohol for personal use, but there is no tax duty exemption if you ship it (so you have to pay tax duty on the entire shipment). There may be importation limits set by your State however. Check for your State of NY. (Advice: don't ship to a Utah address). If you bring alcohol back with you on board, you need to check it in as liquids aren't allowed as carry on (buy a wine bottle container). In that case the first liter (per person) is tax free. Anything above you need to declare and pay customs duty when you arrive to JFK.

I did basically that exact trip back in April. We flow into Venice spent 2 days, Florence 2 days, Rome for 6, then Sorrento(day trip to Capri) for 4 and flying out of Naples. We based our days on how many things we wanted to see in each place. In Florence we went on a winery tour through slow days, they brought us to a small family run winery were the owner cooked us a homemade lunch(best meal of our trip). It was by far one of my favorite memories of our trip and the owner would actually ship wine home for you so you wouldn't have to worry about it(I saw you were worried about bring home wine). Here is there website if you wanted to look into it http://www.slowdays.com/index.html They are also on tripadvisor so you can read the reviews. I hope you enjoy your trip!