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Tuscany, Rome or Florence base for kids' first Italy trip?

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My husband and I used to take long (2-3 week) vacations to Italy, France and Greece before The Kids. We used this site extensively planning our honeymoon and later trips! Good times (sigh). Anyway... Now, 10 years later, we are ready to attempt travel abroad with our 3 small kids (next summer when we travel they will be 4, 6 and 8). I have been devouring past posts on where to stay with kids in Tuscany, but I'm afraid I have confused myself. I am beginning to wonder if the countryside is the best idea, or if an extended visit in a city would be better. What typically works for us on vacation is a "morning activity", lunch, then back home to nap, swim or rest in the afternoon. The evening could be out or in, depending on our moods. I love the idea of taking the kids around the cities, but I also know that a pool and some green space is going to be essential at their ages. We are hoping to visit for 3 weeks in the summer (probably June).

My initial questions are: Is it best to find a countryside base which is close enough to visit Florence and/or Rome for day trips (any suggestions on which town this would be)? Or, if we plan to visit the cities for more than one day, is it preferable just to base ourselves there (even without a pool or garden) rather than making multiple day trips? If so, is Rome or Florence best at this age? Originally, I thought we'd choose a Tuscan town, rent a villa with a pool, make morning excursions, and venture into the village for dinners in the evenings. Now, I'm having trouble figuring out which location provides relatively quick access to the city (either one), and also a village to visit for dinners in the evening. Perhaps Siena would be better, offering both countryside and town?

Since we are planning an extended trip, we really want to settle in and have a relaxing time, but I also want the kids to be entertained and engaged, so the "morning activity" options are of top priority. :-) Sorry for the lengthy post, but I'd appreciate any insight in setting our itinerary in terms of location. Thanks so much!

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