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Second guessing Italy over Christmas trip

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My husband and I (early 30s) have never been to Europe mostly due to work schedules which prevent us from taking more than a week or so off at a time. The Christmas holiday lines up well this year so we are booked for a roundtrip flight from Southern U.S. to Florence, Italy, December 21 to 30.

That means we have 8 nights. We are currently scheduled to spend the first 5 nights with rental car near Siena at Castello di Casole which recently opened, and last 3 nights at Four Seasons in Florence. For countryside portion of the trip we plan on doing day trips to Siena, San G., Volterra, 2 Chianti Classico wineries, and 1 Brunello winery.

The inspiration for the trip was a 2010 NY Times article, "Tuscany in Winter," which made it sound fantastic with few crowds.

Now, I'm getting worried about a few things which are causing me to second guess the destination choice:

(1) should we have picked somewhere easier for first trip to Europe like maybe Paris?
(2) have we allotted too much time in countryside versus Florence?
(3) should we try to do a day trip to Rome?

I usually go through buyers' remorse after I book a trip but it's been particularly strong this time with all of the awesome recent Paris TRs here.

As to the countryside versus Florence allocation issue, we tend to prefer the countryside versus cities but I worry that the earlier darkness in the winter may make it hard to be in the countryside though it will be at a luxury resort with many amenities.

The Rome day trip idea is 80% a bad idea, checklist type of traveler thing which we are not. But, it seems very easy to get there. I was thinking if we did Rome we would add a day to Florence and subtract from countryside.

Would it be insane to change the schedule and do the first 3 nights in Rome (immediately take train from FLR to ROM) then come back and base ourselves at the FS Florence for 5 nights and do a few day trips into countryside from there?

Florence seems more interesting and relaxing to me personally than Rome which is why we booked it. We like great food, wine, scenery, and relaxation. We enjoy art and history but are more interested in the experience so don't want a frantic, harried type of trip.

Thanks very much in advance for everyone's wise input.

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