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Italy itinerary with Lovely Friends - the perfect combination.

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My husband and I will be traveling to Italy end of June/beginning of July 2014. We are very excited and have done at lot of planning, taking many ideas from fodorites and other forums, books, etc. This will be the 6th visit for my DH and I. Friends have not been there before. Age range from 50's to 60's. All in good physical shape. Air arrangements: tried to fly into Florence and out of Naples - this was a no go related to frequent flyer miles. Also realize there are some tight timelines but we are ok with them. Our likes: honestly, we are open to all types of experiences. Following is the itinerary along with some questions that I know the experts will be able to answer or lead me to it.

Friday, June 27 Arrive Venice @ 9:15 am
Pick up at airport by Consorzio Motoscafi and taken to hotel - Hilton Molino Stucky. Cost - 100€ for 4 (I realize we could take the regular water taxi but I do not do well with time change and want to get to hotel as quick as possible).
Saturday, June 28 train to Florence @ 10:25 am arrive 12:30 pm. Pay for rental car (hertz) load luggage and walk around Florence (we did this a few years ago and all we needed to
do was pay for parking- made it easy). After lunch and walk, we head to Fattoria La
Loggia. (our 6th stay there- dh favorite place).
June 28- July 2 (4 nights) - during this time, we will take a day trip to Sant'Antimo Abbey -
monk chant, crypt (Pieta fresco carvings), and fresco by Giovanni di Asciano - this is on my
"must do" list as we have missed it on prior trips. Question: What else, if anything, do you
recommend we see along the way?
A few of the Tuscany towns we have visited in the past: pisa, lucca, greve, pienza,
montoriggioni (loved it), montepulicano, San giamano, siena.
Any other hidden gems you found?
July 2 - drop off car in Florence and train to Naples. One night in Naples. I know some of
you are going to frown at the one night. We were going to bypass Naples but I read many
good things about it on this forum so we decided to stay and see check it out for our next
July 3 take local train to Herculaneum (been to Pompeii). I hired a driver (Lentino) that will
pick us up at Herculaneum and take us to our hotel in Praiano (200€ round trip - back to
Naples). Question: we would like to have lunch at the winery at the foot of Mt versuvius.
What is the best way to get there? I read somewhere that they started a new bus service.
Afterwards, we head to Praiano on the Amalfi Coast. For 3 nights (July 3 - 6). We are
staying at Villa Marggie. Any suggestions about the town from those who have stayed in
Praiano would be appreciated. I have read that there are ferries that can be taken directly
from Praiano? We were planning on visiting Laurito Beach (red fish boat).
July 6 we are headed Rome -with - 2pm pick up by the driver who will take us to Naples for
our 4:30 pm train to Rome.
Overnight Rome July 6 & 7 - dh and I have been here 6 times - we are going for the
convenience of the plane and for friends to visit Colosseo, forum and Vatican (or whatever
they want to do with the day)
Depart for US on July 8.

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