Help plan our trip 3 oct to oct18

Suggestions for luncheons, dinner and nightlife suggestions? Everytime I try to plan ahead on restaurants, I never seem to go there. I do better getting suggestions from my hotel desk.
Places to hang out where people watching is fun. Most would be looking to the area around the Duomo in Florence
Which hill towns to visit? Sienna, Volterra, San Gimignano
suggestions of places to wine tasting, lunch and dinner? Montalcino
To back to florence for nightlife? Italians eat so late that meals are their nightlife.
We will have a car
Umbria Region? Orvieto is a very popular stop to turn in rental cars and take a train into Rome. It's a great hilltown with great B&B's and hotels.
2 villages a day to visit is that possible? Absolutely, as 3-4 villiages would be possible if they're close together in Tuscany.
Overnight in Lucca 2 nights with day trip to Pisa. Lucca's pretty quiet, and many feel Pisa's not worth going out fo the way to see.
Train to Cinque Terre? Yes. Best towns for easiest hike between 2 for the experience and views. I've not been there.
Fast train or car to Venice? Turn in the rental car and take the fast train.
Venice restaurant suggestions appreciated. Just wing it, as restaurants are everywhere--mostly run by non-Italians.
If you're flying out of Rome, I'd suggest you start in the north and work your way south.

You have 4 days listed for Florence with 8 different cities to visit outside of Florence. You've set aside no time to visit Florence so why not pick a town centrally located to all the other ones you plan to visit and do day trips from there?

Two nights in Lucca means a single full day there. It's almost a waste of time to combine Pisa and Lucca with just a single full day.

Personally, with this itinerary I would skip Venice. It's out of the way. It's a 6 hour train ride from the CT to Venice and a 4+ hour train ride from Venice to Rome. With only a single full day in Venice and almost two full days lost to travel to get to/from Venice it makes more sense to add those days to Tuscany and give yourself more time to see the cities there.

Basically, I would suggest an entire week in Tuscany, 2 full days in the CT and the rest of the week in Rome.

Donna

The other suggestions are good so I was going to comment on your question about hiking in Cinque Terre. The easiest hike is between Manarola and Riomaggiore. However that trail was closed after a rock slide a few years ago and there are no announcements of when it may open. The trails that everyone talks about generally get more difficult as you go north between the towns, but there are trails all over the area of varying difficulty. Trails can also close unexpectedly so a trail that is open today may be closed tomorrow if a heavy storm blows through.

Djciv,

In Florence, my favorite restaurant (near the Duomo) is Sasso di Dante on Piazza delle Pallotte. It has wonderful Tagliata di manzo con rucola e pomodorini. The best gelato in Florence is at Edoardo's, right around the corner...

For lunch, you should give the Mercato Centrale a try.

There is no problem finding a place to hang out... Just look and listen for the action. The best seems to be on the south side of the river.

A couple things to remember while in Italy (or any other city for that matter), restaurants on the main piazzas and within view of major sites are more expensive (location, location, location) and the food generally isn't all that great. The best food at the best prices are several blocks away from the tourist attractions.

Pisa and Lucca can be easily be seen as a day trip from Florence. Although I can see spending a night or two in Lucca, you have to factor in the hassle of changing hotels... I did Pisa in the morning and Lucca in the afternoon via the train (from Florence). IMHO, Pisa can be skipped entirely unless you absolutely MUST see a bazillion tourists yielding selfy sticks all competing to get the best "holding up the tower" picture.

October is a great time of year to go on a Chianti wine tasting tour. (Google Walkabout Florence.) You get to stop at multiple wineries to taste wine while leaving the driving to someone else.

Umbria - Perugia, Assissi, Spoleto, Deruta (ceramics), Orvieto, Montefalco (wine road).

Venice - De mamo's, great pizza.

Tuscany - Siena, Volterra, San Gimi, Cortona, but on the other side of A1, Panzano and the crazy butcher.

We stayed at al porta di lucca B&B in Lucca and it ws nice, good meal, just outside the walled city south wall across the tracks from the train station. we also made the good choice to hire Wanda Martinelli for a tour the first day we were there, she gave a half day walking tour and it was great. I had not done tours before but she helped us with what we were seeing and why things are the way they are in Lucca, money well spent. wandamartinelli@gmail.com for her link. We also went to the Puccini music show in Lucca and it was pretty cool and I'm not an opera guy. We got there early (rained in Lucca 2 days!) and sat in the front row! Also a nice trip in the Cinque Terre is to take the ferry down to Portovenere , if you get on the ferry at the north village Monterosso and ride south to Portovenere you get to see all the villages from the sea, pretty cool. We were there during the same time period last year and the weather was great in the CT. We took the train the whole time, Pisa, Lucca, CT, it ws a breeze, this website is useful to learn of Italian train travel.
http://www.seat61.com/Italy-trains.htm#.VR1X5st0wfg give it a look. We loved the CT and hiked most of the main trails, they were taxing but you can pick and choose, you will need to be ready for some steps, up and down, we did some stair climbing to prepare and it was very helpful. I'd love to go back!!