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First Time International Traveler

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Well we are finally doing this!! This is my first post after a very long time lurking. I want to thank you all for not only helping me get ideas for my trip, but most importantly, the courage to plan my own trip. Me and my wife (late 40s), have been discussing going to Italy for well over several years. Our original plan was to go to Positano and Venice for our 5th anniversary for a romantic trip. Well, of course things never go to plan and our 5th anniversary has come and gone.

First, as I didn’t know where to begin, I found this site back a long time ago. We were looking at going with a tour group as neither of us really have any experience with international travel (and at the time, my wife had never flown before) and was looking for ideas. Boy, was I like a kid in a candy store. The more trip reports I read, the more places I wanted to go and visit. However, I have learned that it wasn’t possible to see it all on our first trip.

The more I read, the more I was learning that, hey, I think I can plan this trip myself. Of course, the wife was a little reluctant and we talked her sister and brother in-law (active/early 60s) to join us (strength in numbers she felt). Well, this could become a long story, but my wife’s oldest brother and his wife (active mid 60s) are also joining us. So there is a total of six of us. I have taken a lot of advice from you guys and trying to keep my itinerary simple and hope I can go back and visit again as there are so many places I want to visit.

So the first part was finding a time we could all get away from work. Next was finding 3 bedroom apartments and 3 bathrooms as I am taking 3 women that could be late for their own funerals and need these bathrooms. So I have booked our vacation around the apartments and we already have put deposits down for them.

I have some questions below, but first here is our itinerary.
We have 13 nights in Italy for Sept/Oct 2017. We have an overnight flight from US to Venice. Planning on landing early in Venice Sunday AM.
Venice 4 Nights (staying here https://www.vrbo.com/1227248ha# )
Florence 4 Nights (staying here https://www.vrbo.com/128031# )
Rome 5 Nights (staying here https://www.vrbo.com/6400223ha# )

In Venice, we are looking at doing two tours with Walks of Italy. St Marks after dark tour and the VIP Secret Passage tour.

In Florence, we want to do a day trip to Tuscany. Looking at Walks of Italy’s Tuscany day trip to Chianti, Siena and San Gimignano.

In Rome, we are looking at doing 3 tours with Walks of Italy (Pristine Sistine, VIP Colosseum and A Day tour to Pompeii and Positano). Of course I am going to try and get reservations for the Scavi Tour as well if possible.

Museums are not the highest priority (other than my one brother in-law), but do plan on seeing a few of them. We are interested in seeing the main sites, churches and enjoying the local culture.
1. Am I looking at doing too many tours? As anyone had any experience with Walks of Italy Tours?
2. We plan on not doing many expensive meals, but would like to have one really nice meal in each Venice, Florence and Rome. Looking at around 150 Euros per couple. Any recommendations?
3. For Wifi/Hotspot, I was looking at Glocalme. Anyone have experience with this or should I just look at getting a SIM card once I get to Italy?

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