Anyone want to help me with my 2 week trip to the Tuscan region of Italy? I have a few conditions that make my trip a little limited? Can anyone offer advice or experience?

In Summer 2021, (given the world can travel again) a family member is renting a house in Florence for 4 weeks. They said anyone who wants to come stay there can do so for however long they want and for free! So my wife and I are going for 2 weeks in the middle of June. The only catch is that for the 2nd week that we are there (M-F) my wife will have to work remotely from 15:00-23:00 local time. So we will need to purchase a strong, reliable wifi source (if that's possible) and figure out how best to explore the surrounding areas of Tuscany while still being able to enjoy Florence.

Here is the "itinerary" we've come up with but this is very loose and very flexible. We are also very well seasoned travelers and love traditional aspects of cultures, history, museums, art, nature, wine, walking/discovering cities, and any and all food. Dislikes include touristy spots (cant necessarily avoid them but were not the hectic crowd types), scams/ripoffs/being treated like a sucker. We have both spent time working overseas and traveling at both a very fast pace and a leisurely "take it all in how we want" pace. We will fly out on a Friday night and land on our first official day of time off.

Day 1 - land in Italy and go to our house in Florence. Meet family and get settled.

Day 2 - Take the day to get acclimated to the time change. Explore Florence a little grabbing food and walking around. Not a big day for us.

Day 3 - Take the train to Cinque Terre and spend the day exploring. We would ultimately like to make our way from Levanto to Riomaggiore with stops at each of the villages in-between. End our night in Riomaggiore and leave the next morning.

Day 4 - Take the train from Cinque Terre to Pisa and check out Pisa for the afternoon before going back to the house in Florence.

Day 5 - Wine tour. We would love to do a wine tour, but given there are so many countless options to choose from we might find some sort of travel company to rent us a car and book us a tour or two. I haven't looked too much into this yet but am up for any and all suggestions!

Day 6 - Day trip from Florence - Lucca/Siena/San Gimignano/Volterra.

Day 7 - Day trip from Florence - Lucca/Siena/San Gimignano/Volterra.

Day 8 - Day trip from Florence - Lucca/Siena/San Gimignano/Volterra.

Day 9 - Day trip from Florence - Lucca/Siena/San Gimignano/Volterra.

Days 10-14 - This is our 5 days of "half vacation". My wife has to work 3pm-11pm local time so we will be exploring Florence on these days starting early in the morning and getting home around 2pm so that she can be available to do what she has to do. I will figure out things to do with family during the rest of the time and try my hardest not to make her feel too bad about having to work.

We will obviously need to purchase some sort of wifi source that will guarantee she can work from home, otherwise we have a completely different trip on our hands. Is this doable? I've been able to do this for work in other countries but never in Europe and never in Italy.

Also, we would love to find a way to mix in Venice but were not sure if it's worth the travel time and cost (we would want to stay overnight similar to Cinque Terre).

Any and all recommendations/advice/critiques or input will be greatly appreciated and taken into consideration. If I missed any must-see surrounding areas I would love to hear about them! Hope to hear any and all anecdotes or experiences!!

Submitted October 28, 2020 at 08:14PM by thrwthisout https://ift.tt/31QFwR7