May Italy Trip Scheduling - overwhelming!

I think you need to decide how important it is to see Venice - IMHO 1 night is not enough! Not knowing where you plan on staying in Tuscany it is hard to give you an idea of how long it will take you to get to Venice - but to give you an idea from Florence on the fast train it is just over two hours. From Orvieto it is four hours with one change.

I am assuming your flights are booked and cannot be changed - otherwise I'd suggest flying into Venice and out of Naples. Then you could do Venice first - its great place to get over jet lag as you will be walking everywhere!

Here is some info from Wikitravel (http://wikitravel.org/en/Praiano) about transportation to Praiano

By bus

Use the SITA bus (http://www.sitabus.it) from Sorrento Circumvesuviana train station (http://www.vesuviana.it) or from Amalfi bus station. From Sorrento the trip takes 1 hour circa, from Amalfi there is a 20 minutes drive.

Here is info from the same site on the ferry service or lack thereof in Praiano - you need to go to Positano for the ferry to Capri.

There is a network of ferries that run along the towns of the Amalfi Coast. The ferry service is run by Coop Sant'Andrea [1]. They provide quicker access to the towns during the summer months, as opposed to the one main Amalfi Coast road which connects Amalfi to Praiano to Positano and onwards to Sorrento. Major ferry stops are Salerno, Sorrento, Positano, and Amalfi. In summer, there are ferry connections from Positano and Amalfi to the pretty towns of Maiori and Minori. Praiano is not serviced by ferry as there is no stable pier to dock and ultimately the marina is very shallow. Positano is the closest point for people staying in Praiano who want the ferry.

Praiano sounds gorgous but you might want to think about staying in Sorrento, Amalfi or Positano for convenience.

Whatever you decide to do - I am sure you will have a wonderful trip and what a great way to celebrate a major milestone!

If you can, fly into Venice and out of Naples.

You can take the Circumvesuviana from Naples cntrale train station to Sorrento, take the bus to Praiano (beautiful town). Or take the ferry from Naples (take an authorized taxi from the train station to the port) to Positano, then a taxi or bus (bus may be crowded) to Praiano. Then there are essy short bus trips to the small towns along the Amalfi Coast. You may want to have a romantic stroll through Ravello (I would stay there if possible), right above Amalfi. Spectacular views and some great food.

Unless the private guide for Pompeii is someone special I would wait until you get to the ruins. There is always a small group of guides hanging around outside the entrance that I assume would be less expensive and they all share the same basic information.

My thoughts are directed at saving you some serious days on your rental car. From Rome, you can take the Leonardo Express into Rome-Termini and then take the train to Orvieto for the night. The next day, take the train to Siena. From the Siena train station, take a taxi to a nearby Agriturismo. I have a specific one in mind (I'll PM you). It's just outside of Siena. I get PMs from my RS Sacramento group when I name this Agriturismo on the website. Many of us have stayed there. My wife and daughter were there this past September. It's fabulous.

The whole idea here is that you haven't rented the car yet because you really haven't needed it yet. From the Agriturismo, you take a taxi to and from Siena for your touring there. Taxi is about 12Euros each way. No worry about parking in Siena as you don't have the rental car yet. About 2 days should do it. Next, you can take a taxi to the bus station and go for your overnight to Venice. Yes, you do need more than 1 day but it's worth it to come out of the train station, stand at the top of the steps and see everything in motion. It's the Grand Canal and I guarantee that it will be everything you expected to see and nothing you understand yet. It simply was one of the places that just stopped my world as I stood there.

Still no car rental yet. Now, you can return to Siena and rent your car and begin your travels around Tuscany. When you are ready to head for Naples, drive to Orvieto and turn in your rental car. Two car rental agencies are within about 100 yards of the train station. Then, off you go to Naples. At Naples Centrale, you go down stairs to the Circumvesuviana train and buy a ticket to Sorrento (about 5Euro). It's a crowded local train so just keep a good eye on your luggage. The trip takes just over an hour. From Sorrento, you take the SITAsud bus to Praiano. Two stops there. The first one is high up in the town. The second one much lower. You may need to get off at the second stop and take a taxi to your hotel. The hills are steep.

For flying out of Naples, just be sure that you are aware of your departure time. As with Venice and Rome, many flights depart really early to get you to a larger hub to pick up your flight back to the U.S. Very wise to have your last night in Naples as you would not make an early flight from Praiano on any public transportation.

Unless you can do as one of the other posters suggested and fly into Venice, I'd scratch from the itinerary. Too far for a one- day trip. There is so much to see and do in Tuscany, that I'd just focus my energy for the week there. We liked Capri a lot. Go as early as you can, because the last ferries back leave pretty early. btw, be sure you know what time the last departure is, and allow yourself adequate time to get down to the dock.The towns are up above; and depending on where you are, you'll need the funicular or a bus or taxi to get back down. Our favorite part of Capri was the town of Anacapri. There's a villa with lovely gardens that you can tour and a church with a fantastic tile floor depicting the expulsion of Adam and Eve from Eden.