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Italy trip planned for late September 2017

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We have the overall framework planned for a two week trip next year, focusing primarily on the Tuscan countryside. We have 5 nights planned at an agriturismo outside of Siena followed by three nights in Tellaro on the coast. I just booked our airline tickets into FLR, and the schedule will allow for 3 nights on the front end and 1 night on the back end of the trip upon arrival and before departure, respectively. So, here are my questions:

  1. Since this is our first trip to Italy, I'm thinking it might be nice to stay the first three nights in Florence since much of the rest of the time will be spent outside of cities. Are there other options I should look at as well?
  2. I'm investigating accommodation choices in Florence, but are there any 'hidden gems' anyone would like to share? Our budget is pretty flexible.
  3. We know we'll need a car for at least the middle portion of the trip. If we do stay in Florence for the first three nights, should we wait to pick up a rental car until we are ready to head to the agriturismo?
  4. Again, assuming we spend the last night prior to our flight back to the US in Florence, should we turn in the rental car after our return from Tellaro and then just take a taxi to the airport the following day?
  5. (And this is the loaded question) ... Where oh, where, do we begin for planning all the places we want to visit while exploring the countryside?! I can see already that this will just be the first of many trips to Italy. There are so many beautiful spots I want to visit but I didn't want to cram too much into our first trip.

Thanks very much for any feedback!

Posted by
1832 posts

1.) Yes, that is a great idea and the city has plenty to do and see to occupy 3 nights.
2.) Main question is to stay in the main historic center or not ;
Since the main historic center is so small I am not sure it matters where you stay if staying in the center. You are talking about a block to the left or a block to the right. Since the rest of your time will be in more laid back places I think I would opt for someplace in the heart of the city probably near the duomo for the first 3 nights.
3.) Yes, rent the car from the Florence city office and pickup your car when leaving. It is fairly easy to drive out of town.
There are offices for both Hertz and Europcar on Via Borgognissanti which is easy to walk to from center of town and easy to drive out from for Siena.
4.) Depends where you decide to stay, since you can easily reach the Florence airport by car from other areas I might opt to stay in another town this last night at a place with parking and return the car to the Airport. Since you already stayed 3 nights in Florence maybe the last night in Pisa just as an example.
5.) Main thing is to identify which hill towns you want to visit and then try to plan a not too rushed itinerary to visit them. The beautiful countryside ideally you will see while on your travels from town to town. The website discovery Tuscany is a good starting point. I may be biased but think the most beautiful countryside is in the Val D'Orcia which is a fairly small area right near Pienza and San Quirico. This is situated between Montepulciano and Montalcino on a map. So that is 4 towns right there to visit and great countrysides between them this area could take 2 days. Give another full day to Siena and the Crete Sensei countryside which is likely right at your doorstep, maybe one other full day to San Gimignano and Volterra and your whole time is basically spent.

Posted by
22 posts

Perfect! Thanks so much for the response. I like the idea of staying someplace else for that last night so long as it is relatively convenient for getting to the airport for our 10:00 AM flight. And thank you so much for the suggestions of areas to focus on. Although I don't necessarily need to nail down every moment of the trip beforehand, I do enjoy the planning and researching almost as much as the travel itself so it will help me to get a better idea of area to focus on in planning what we want to do. Thanks again!

Posted by
22 posts

I've been looking at possibilities for our last night prior to flying out from Florence. Since we'll be coming from Tellaro, I'd ideally like something convenient to our route, but relatively close to FLR (perhaps a 30 minute drive or so). We'd also probably plan to keep the car unless we stay someplace where it makes sense to drop the car off prior to heading to the airport. Any suggestions (and does this sound like a reasonable plan)? Thanks again.

Posted by
22 posts

One other thought: Perhaps it would make sense to drive to Pisa or Lucca, etc., drop the car off and spend the night there, and hire a driver to take us to FLR in the morning. I just wouldn't want to deal with the drive and dropping the car off early in the morning (trying to keep this trip low stress. :-)

Posted by
1832 posts

If the stress of an early morning drive worries you your most recent thought definitely makes sense.

Your best option in my opinion would be drive to Pisa, carefully avoid any ZTL's, pay to park visit the tower and surrounding piazza which is beautiful and worth going out of your way to see but honestly doesn't need more than a couple of hours and then head to Lucca to drop off the car and spend the night instead of staying overnight in Pisa.

From my experience most Italian rentals do not charge more if picking up and dropping off in another city.

The rental cost is typically less if using non-airport locations for pickup/drop off as well.
Furthermore you will say some time if you don't have to drop off the car in the morning.

if you need a driver from Lucca or Pisa, Elisabetta at Professional Tour Tuscany can provide a professional service at a rate you would likely pay a taxi: [email protected]
She is based out of Pisa so either Lucca or Pisa to FLR would be a normal route for her.

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