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Critique 11 day Italy Itinerary - Venice,Florence,Rome,Sorrento

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Hello - my husband and I are planning a trip to Italy at the end of Sept, beginning of Oct and would love some feedback on our itinerary. Yes, we are flying in and out of Milan because of the ridiculously low airfare, so I do have to account for either a train or flight from Naples to Milan. I know the general consensus is not to try and pack too much in, but it's taken me 10 years to get back to Europe and it's hard to leave things out. We are thinking about using Airbnb for this trip - thoughts?
A little about us - we're 40yrs, love history and architecture, appreciate art, but highlights are probably sufficient. I included some of our ideas on sites to see and when to incorporate a tour. Please feel free to give me any advice/feedback/tips. Restaurant suggestions are also welcome!

Fri Day 1 Arrive Milan, train to Venice 2.5hr arrive 3:30pm; Dinner & Gondola ride
Sat Day 2 Venice - St. Marks Square & Basilica; San Marco, Bridge of Sighs, Doge's Palace
Sun Day 3 Depart Venice for Florence 2hrs - Uffizi gallery tour; Palazzo Vecchio; Ponte Vecchio
Mon Day 4 Florence - Duomo; Accademia of Fine Arts; Santa Croce; Giardino di Boboli gardens
Tue Day 5 Depart Florence for Rome 1.5hrs - Viator Ancient Rome and Colosseum Tour: Underground Chambers, Arena and Upper Tier
Wed Day 6 Rome - Vatican 'Skip the Line' tour 3 hrs 9am, including Sistine Chapel, Raphael's Rooms and St Peter's
Thu Day 7 Depart Rome for Pompeii then travel to Sorrento
Fri Day 8 Sorrento - Explore, ferry/hydrofoil down the coast
Sat Day 9 Sorrento - day trip to Isle of Capri
Sun Day 10 Depart Sorrento for Milan train 6.5hrs 8-2pm; 4pm Viator 'The Last Supper' plus Milan Walking Tour
Mon Day 11 Depart Milan at 4:00pm

Thanks in advance for your help!

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