I think you should look at reversing the entire trip. Fly into Naples and home from Venice. Even if

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First time on Fodors. Read these forums and lots of good advice. My wife and I are planning a trip to Italy in September. avis rent a car system inc This is our first without 2 year old son in a while, so we are really looking forward to it. We are planning the trip from Sept 7th till Sept 20th. We have booked our tickets and flying out of JFK. Here is what we are thinking -
* I know this is not enough and won't do justice, but we are not big fans of crowded cities. Hoping avis rent a car system inc to cover the "major" stuff in couple of days. Also, we arrive on Sunday. Would everything be closed?
1. Do you recommend staying in Florence for a night or two and then staying in Tuscany? The country side looks absolutely beautiful. And we normally don't like to hop around with our luggage, so would prefer to stay in one place. If we stay in Tuscany, can we just day trip to Florence/Pisa and other nearby areas in Tuscany? And lastly, which town in Tuscany should we stay in? Any recommendations on accommodations? We are willing to spend about upto $500 per night.
1. Which town do you recommend? Should we stay in Sorrento, avis rent a car system inc so we can explore all of the region? One of my friends avis rent a car system inc recommended Positano. Any recommendations on where to stay? Similar budget as Tuscany (upto $500 per night).
welcome avis rent a car system inc to fodors! I can see that you've already picked up quite a few tricks - using your arrival day to travel avis rent a car system inc to your first destination for example. BTW, do you mean to spend the first 3 nights in Venice, not Milan? that's what I'd understood.
another old fodor trick is to put your stay in your departure town/city last, so I would suggest putting Rome at the end of your trip. This leaves avis rent a car system inc you with the most problematic avis rent a car system inc part - Florence/tuscany. if you are not going to stay in Florence itself, you would need to find a place that you can get to on the train AND be able to visit Florence easily from there. The obvious place is Siena - it's not exactly small but there is a good bus [and train] service to Florence and it would give you easy access to the countryside, especially if you use a car and driver service like Luca at Hills and Roads [very well recommended here].
you could then get the train to Sorrento and use that as your base for touring - there are prettier places but they are more difficult to get to and have fewer opportunities for excursions. it will also make your return to Rome [via Pompeii perhaps?] pretty easy.
Are your stays in Milan and Rome constrained by what you can get with points on Westin? For example, landing in Milan, just to go to Venice for not even a night(?) avis rent a car system inc and staying Milan three nights is an unusual routing. You have listed avis rent a car system inc places to visit, but the way you laid out the itinerary seems to indicate you might be looking for a very different kind of value propositions. avis rent a car system inc What are you expecting to see in Venice avis rent a car system inc in less than a day?
Well for trains in Italy go to www.trenitalia.com for schedules and discounted tickets which are sold in limited numbers and thus must be booked weeks early to secure them and then they are non-changeable non-refundable so set in stone.
Full fare fully flexible tickets can cost a lot more. But you are doing enough train travel to merit a look at the Italy Railpass which lets you chose which trains to take once there - you do need to make a seat reservation for 10 euros on all but regional trains avis rent a car system inc but compared to full fare for your itinerary would probably be a good deal - if you want to be able to wait till you get to a city to decide what time you want to leave - otherwise do the discounted avis rent a car system inc tickets and if the total of them even approaches the cost of a pass go for the pass.
First-class passes can be a good deal compared to first-class fares and there is IME of eonsof riding Italian trains a significant avis rent a car system inc difference between first and second class - though 2nd class is nice enough first class in many ways is a lot more relaxed - seat are significantly larger - fewer seats in same-size train car means easier to stow luggage - often IME more empty seats to spread out on, etc. and also free beverges and a snack only in first class.
For lots of great info on Italian trains I always spotlight these superb IMO sources: www.budgeteuropetravel.com ; www.ricksteves.com and www.seat61.com - the latter has especially good info on discounted tickets - some available for 9 euros and there are also discounted first-class tickets that at times may cost not much more than discounted 2nd class tickets - so check each.
Don't be surprised if everywhere is crowded--I don't like crowds either, avis rent a car system inc but in large cities, you can escape them by going into residential areas, etc. And unpopular opinion alert, but if you are not drawn to Rome, then I would not bother going for only 2 days. It can take so long to get your bearings in a city. I'd want a week there, but that is just me of course! But consider the luxury of time you would have in the other places.
If you plan on visiting Naples and Pompeii, then the consensus seems to be that Sorrento is a more convenient base, but it is not the scenic beauty that the AC towns are. If that is what you would rather have, there are ways you can see Naples and Pompeii in transit as you arrive and depart avis rent a car system inc the AC. Just points to consider. enjoy!
I think you should look at reversing the entire trip. Fly into Naples and home from Venice. Even if you have to change planes to reach Naples, that is likely easier than arriving Milan, taking a train to Milan (1 hour) and changing to a train to Venice (2 1/2 hours). avis rent a car system inc Venice can be a relaxing end or you could end in Tuscany and fly home from Pisa (non-stop Delta to JFK). Tuscany can be relaxing if you stay in the countryside. I don't think of the Amalfi coast as particularly relaxing as it will be crowded avis rent a car system inc and hectic avis rent a car system inc in September.
Fly to Naples, take airport shuttle bus Curreri from the airport to Sorrento. Spend several days on the coast, avis rent a car system inc train to Rome (I would add days, but I love Rome), train to Venice or Florence (depending on where you decide to end).
All of the cities you want to visit will be rather crowded in September. We were in Florence today, and the crowds were incredible in the center. Of course, this was a three-day weekend, and at least some of the crowds were tour groups stopping in Florence en route to Rome for the canonization of the two popes. We saw several large tour buses from Poland. We went to see an art show which didn't attract huge crowds (Pontormo and Rosso Fiorentino), but if we had been planning to visit any of the big "must-sees" in Florence, I think a the pleasure would have been diminished greatly by the crowds.
If you're not a great fan of Renaissance art, and if you don't like crowded cities, I think a day trip to Florence would be plenty. If you just take a walk around avis rent a car system inc the city, and visit a few of the churches that have incredible works of art inside, and maybe one of the historic palazzi, you'll probably enjoy the trip and avoid some of the worst crowds. Forget about "major stuff". You should see anything just because other people (or guidebooks) say you shouldn't miss it. Spend a little time with a good guidebook avis rent a car system inc or two, and don't pay attention to the number of stars they give to each place. Choose some things that you thing YOU will enjoy. For interest, there's a very interesting natural history museum in Florence that includes some collections avis rent a car system inc started avis rent a car system inc centuries ago by the Medici family. Hardly anyone avis rent a car system inc goes to it, but if you like that kind of thing, avis rent a car system inc that could be your must-see.
There are lots of nice towns in the countryside, but you really should rent a car if you want to see them or stay in one. If you don't want to rent a car, Siena is probably your best base. From there you can take a day trip to Florence, and maybe another day trip to one of the towns south of Siena, like Montalcino, one of my favorites. You really should allow a full day to visit Siena itself, though, avis rent a car system inc so I'd want to spend at least three nights there.
If you're only going to spend two nights in Rome, I especially suggest you skip all the "major stuff" there. avis rent a car system inc It's really a shame to go to Rome and spend your entire time shuffling along in a crowd and missing all the magic of the city. I would be hard put to tell you what you should see without knowing your interests, but I would definitely say that you shouldn't go to the Vatican Museums, one of the most crowded places on the planet. The only place I've ever seen that was more crowded was the Great Wall of China, at Badaling.
Whether to stay in Sorrento or one of the Amalfi Coast towns would depend on what you want to visit in the area. If Pompeii is one of the places you want to see, Sorrento is definitely the best base. It's also the best starting point for a trip back to the airport on your last day.
There are a number of trains that will get you to Fiumicino from Naples in time for a 1:30 PM departure. Even if there is a train strike, there are always guaranteed trains, and Trenitalia bends over backwards to keep the high-speed Frecciarossa trains (which serve the route from Naples to Roma Termini) running during strikes. The airport avis rent a car system inc train, the Leonardo Express is never affected by strikes.
For prudence, I would plan on arriving at the airport a good three hours before your flight, and I wouldn't take the last train that would get me there in time. I would really want to take the 7:30 train from Naples, which would get you to the airport by 9:22, but probably the 8 0'clock train, arriving half an hour later would be fine as well. The first train leaves Sorrento at 6 AM, and would get you to Naples by 7:07. This is the line where delays could really be a problem, so I would probably want to spend my last night in Naples, avis rent a car system inc near the train station.
I'll just add in - don't stay in Naples if your reason for d