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Trip Report Highs and Lows of a Family Trip to Italy

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In appreciation of all the great tips and advice I received while planning our family trip to Italy, I'm posting my first trip report. We spent a fabulous two weeks in Italy over the holidays. The family trip went far better than I expected (especially with two teens) but it wasn't without its challenges. I'll try to cover the sites and include helpful tips, and try not to veer too deeply into our family's idiosyncrasies. But no promises.

First, a little background. My husband and I met in Rome 32 years ago (yikes!). We were high school sweethearts who got married after college. We have three beautiful daughters. DD1 is 19, DD2 is 17 and DD3 is 8. After a long absence, DH and I finally made it back to Rome 5 years ago for a 2 day visit in between Christmas and New Year’s during a family holiday in England – our last big family trip. We were spending Christmas with relatives and were able to leave the girls for a couple of days. We had always dreamed of taking our girls to Italy and with DD1 now a sophomore in college and DD2 about to graduate, we felt like it might be now or never. So with much angst regarding the cost, we decided to go ahead and plan a trip to Italy for two weeks over Christmas and New Year’s. This was the only time of the year when I could be sure everyone would be able to make it. So after 6 months of wavering, we took the plunge and had about 2 and a half months to plan and dream. And worry. This trip would be different from our trip to England where we stayed with family and much of the point was simply to spend time together. We had a place to stay, a car, and a very relaxed agenda. The girls were older now, and were…how should I put it….less pliable. So it would be a challenge to plan a trip that balanced everyone’s needs and desires, including “together time” and “alone time,” and kept the costs in check, while packing in as many of the charms and gems of Italy that I could manage.

Here was our basic itinerary:
Dec. 21: arrive in Rome from Washington, DC for 5 nights (including Christmas Eve and Day)
Dec. 26: travel to Florence for 4 nights
Dec. 30: travel to Venice for 3 nights (including New Year’s Eve)
Jan 2: travel back to Rome for one night
Jan 3: fly from Rome back to Washington, DC

Now, before folks jump on the obvious weakness in this itinerary, I know it would have made more sense to fly into Rome and out of Venice. What factored into my calculation however was a DH that absolutely hates flying. To the point that he’d rather drive for two days than take a simple two-hour flight. So I had to minimize this stress on him (and more importantly, me) by opting for nonstop flights -- only possible in and out of Rome from DC. And originally, we were going to spend two nights in Venice and a final two nights in Rome, but then my English in-laws decided to join us in Venice. That was a lovely idea (and I figured we’d need new blood by that point in the trip), but it also meant that an apartment was really the only way to go – and that meant a 3-night stay in Venice.

We were also planning 3 possible day trips: one to Pompei from Rome – the kids were really for this, I was a bit ambivalent, and DH thought it was nuts; one to Pisa – can’t take kids to Italy without seeing the leaning tower!; and one to Siena – this was my line in the sand – I had to go to ONE place that I hadn’t been to before, and it was embarrassing to say that I had lived in Italy for two years and never been to Siena.

So that was the basic agenda – not too ambitious, but a reasonable attempt to see the most compelling sites in Italy given a two-week time frame, in the middle of winter, and the height of the holiday season.

Next: pre-trip preparation and our arrival in Rome!

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