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Four nights in Florence

So we will have a little extra time in Florence and I would love to see some of the countryside… does it make sense to do one of those day tours to Siena and Cinque Terre? Are there interesting Florence-based activities in the evening that we could tap into? If there’s a tour company or specific suggestion please share the name of the company that provides it! Thanks in advance!

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4 nights is only 3 full days.
I would consider 2 full days the minimum for Florence. You can probably devote a day to a day trip to the countryside. The most efficient way to visit country locations is probably with an organized excursion with a small group or a private driver since country locations are not well served by transit. Siena is really a small city not really countryside, although it's a popular day trip (by bus on your own or private tour).
The Cinque Terre is best done by train, but takes too long either way. I'd look into small villages between Florence and Siena, maybe the Chianti road and/or San Gimignano, Monteriggioni, etc. Siena can be part of that tour, but to see Siena it takes at least half day, since it has a lot to offer.