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Need help with 2-weeks Italy itinerary

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We are a family of 4 (2 kids- ages 8 & 4) , avid independent travelers, planning our first trip to Italy in July 2015. We like architecture, scenery, food and culture.

We will have a total of 14 nights in Italy. Plan to fly into Milan (cheaper tickets), and fly out of Naples. Considering our interests, we were thinking of the following rough itinerary :
Thursday, July 2nd - Fly from JFK@ 10:00 PM
MILAN- 2 NIGHTS
Friday, July 3rd- Reach Milan at 12:15 PM; check-in and half-day sight-seeing (The Last Supper)
Saturday, July 4th – Day Trip to Lake Como, Bellagio (Own or by private tour)
VENICE- 3 NIGHTS (Take 72 hours Vaporetto pass)
Sunday, July 5th – Check out and take train to Venice; Hotel Check-in, some sightseeing out of the following attractions - Accademia, Ca' d'oro – from outside is enough, Piazza San Marco, The Doge's Palace Secret Itineraries tour, St. Mark's Basilica & Torre Dell 'Orologio, Frari Chruch (wooden screen), San Giorgio Maggiore, Rialto Market)
Monday, July 6 – Day trip to Murano, Burano & Torcello (a short 40 minute trip by vaporetti)
Tuesday, July 7 – Continue sight-seeing &/or half-day trip to Padua
FLORENCE- 3 NIGHTS
Wednesday, July 8th - Reach Florence by afternoon; check-in and see Uffizi Museum (advance Reservations)
Thursday, July 9th – Day trip to Sienna &/or San Gimignano (best by bus or private tour)
Friday, July 10th – Half-Day trip to Pisa & Lucca & local signt-seeing
ROME- 3 NIGHTS (–buy 3 day Roma pass – include free entry to Colosseum and one other gallery)
Saturday, July 11th - Reach Rome by afternoon; and half-day sight-seeing (Colosseum, Roman Forum, Sistine Chapel, St. Peter's, and walking tours of the Jewish Ghetto and Trastevere. (Download Rick Steve’s audio guides)
Sunday, July 12th - Local sight-seeing
Monday, July 13th - Vatican Tour - Book a tour in advance
SORRENTO -3 NIGHTS - Not much into swimming or beaches. Interested in Amalfi Coast only for the charm and scenic beauty.
Tuesday, July 14 – Reach Sorrento by afternoon; local Sorrento
Wednesday, July 15th –Day trip to ‘Pompiee &Herculaneum’ OR ‘Pompeii & Vesuvius’ (Take train from Sorrento to Pompiee)
Thursday, July 16th - Day trip to Amalfi (Positano - Amalfi - Ravello) – Hire a Taxi
Take bus from Sorrento to Positano – explore the village and take the boat from the harbor in Positano to Amalfi, explore Amalfi, take the bus from there to Ravello, then bus back to Amalfi from Ravello and either the bus or ferry from Amalfi to Sorrento.
Friday, July 17th - Day trip to Capri -
Ferry from Sorrento at 9 AM; once is Capri- take a boat trip to Blue Grotto; catch a bus to Anacapri; bus down to Capri Town; lastly funicular back to marina
Check-out and reach Naples at night – airport hotel
NAPLES- 1 NIGHT
Saturday, July 18th - Fly to JFK @ 8:15 am; Reach JFK @1 PM

Does the above sound doable ? Any suggestions would be helpful - anywhere where driving makes more sense - please let us know. This will probably be our first and last trip to Italy, so yes we do want to fit in as much as would be possible. We are used to a slightly fast paced travel.

Look forward to your guidance.

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