Christine - you are AMAZING! I just can't believe all the valuable information I am getting! I do have Rick Steve's guidebook. I feel okay with most of the tours. We are going to pass on Uffizi because none of us are art fans and we feel like we will see a lot of other art in Rome and Accademia. The actual tour of Tuscany is the one that I can't decide. I contacted Roberto's tours, but saw some negative reviews about his personality. I also wasn't sure about going to a family vineyard. It seems like we would only see some small vineyard and not the experiences we would want for our first time in Tuscany. I will check out your other links.
I am going to give up on Perillo. There are just too many things they couldn't do for me. If I have to do a bunch myself, why bother paying the premium!
As far as insurance, I have to pay the Airbnb and hotels in advance, so they would be a loss. The tours also would need to be booked, but not sure of cancellation costs. For a family of 4, I figure about $10K of coverage is needed since we aren't paying for flights.
Here is my Itinerary BTW....
SATURDAY, JUNE 20, 2020 DEPARTURE JFK AIRPORT
SUNDAY, JUNE 21, 2020 10:50 - ARRIVAL – ROME-FIUMICINO AIRPORT
Transfer to Rome Termini.
Transfer to Florence via Frecce train (1.5 hours)
Local taxi pick up at Train station in Florence to Airbnb (or walk 5 min)
Airbnb June 21 – June 26, 2020. ( 5 nights )
Arrive appx. 2:30 pm
MONDAY, JUNE 22, 2020 GROUP TOUR - TUSCANY WINE AND OLIVE OIL TRAIL
TUESDAY, JUNE 23, 2020 Best of Florence Tour with Accademia
WEDNESDAY, JUNE 24, 2020 Relax a.m. FLORENCE COOKING CLASS WITH OLTRARNO FOOD TOUR
THURSDAY, JUNE 25, 2020 Pisa Private 3 Hour Tour followed by Frescu Mozzarella Experience
FRIDAY, JUNE 26, 2020 Late morning transfer to Sorrento
--- ACCOMMODATIONS--- Hotel Regina Sorrento – June 26 – June 30, 2020 (4 Nights)
SATURDAY, JUNE 27, 2020 Capri Excursion in Private Boat
SUNDAY, JUNE 28, 2020 Pompeii tour or free day
MONDAY, JUNE 29, 2020 Private Amalfi Coast drive - 8 Hours
TUESDAY, JUNE 30, 2020 Afternoon/Evening transfer from Sorrento to Rome
-----ACCOMMODATIONS--- Trastevere Airbnb June 30 –July 4, 2020. (4 nights)
WEDNESDAY, JULY 1, 2020 Colosseum/Segway Tour?
THURSDAY, JULY 2, 2020 Vatican Museums
FRIDAY, JULY 3, 2020 Trastevere Food Tour – 10:45 a.m. departure – 4 hours
SATURDAY, JULY 4, 202O Departure to New York