Thanksgiving in Tuscany: Why You Should Travel for the Holidays

Trick-or-treating is over for another year, cotton cobwebs and jack-o-lanterns are out by the curb, the last few colorful leaves are tumbling out of the trees, and the clouds and rain have shrouded Seattle in gloom. At times like this, I’m glad to have some happy memories of past travels.

A few years ago at this time, I was getting ready to head to Tuscany for Thanksgiving with my wife’s family. (I wrote a series of blog posts about the agriturismo we stayed at just outside of Pienza, and the many culturally enriching activities they arranged for us.) It was, without a doubt, the most memorable Thanksgiving of my life — and a reminder of why, much as we love our traditions, it’s important to break free from them every so often and spend the holidays in a new place.

When I tell people I was in Tuscany for Thanksgiving, their first question is — with a note of concern — “Did you have turkey?”

Americans love their Thanksgiving dinner. And many of us simply can’t fathom counting our blessings without an oversized portion of turkey, stuffing, mashed potatoes, and gravy. Our agriturismo host, Isabella, understands this, so very early in the planning stages she reassured her nervous American guests: “And of course we will celebrate Thanksgiving with a special Thanksgiving meal — one with a Tuscan twist.” Well, phew!

In typically thoughtful fashion, Isabella had arranged a fantastic feast, which happened to be at one of my favorite restaurants in the region (Ristorante Daria, in the tiny hill town of Monticchiello). Months before, Isabella had conspired with the owner/chef, Daria, over a list of traditional Thanksgiving dishes. And the gang at the restaurant had come up with a delicious mashup of American and Tuscan.

The first two courses were the most Tuscan, but cleverly informed by “our” Thanksgiving ingredients: a delicate pumpkin soufflé, topped with creamy pecorino cheese sauce and fresh-grated truffle. And a dish of pillowy sweet potato gnocchi, gently nestled in a subtle citrus cream. Both dishes were, at once, explosively flavorful and intensely comforting. I would not mind seeing either of these on my Thanksgiving table for many years to come.

Then it was time for the main event. The waitstaff loaded all of the turkey onto a tray and ceremonially paraded it through the restaurant, like proud hunters with their kill. Then they took it back into the kitchen and re-emerged with beautiful — and very traditional — plates of turkey, green beans, Brussels sprouts, and mashed potatoes…with, in a delicious Italian twist, a trickle of fresh-pressed olive oil.

They also brought out some fantastic gravy and surprisingly traditional cranberry sauce. Daria explained that she’d asked some American friends to ship her some cranberries, which are completely unknown in Italy. (Pretend for a moment you’re an acclaimed Italian chef. And imagine your shock — and maybe disgust — upon taking your first-ever bite into a raw cranberry: an explosion of sour and astringent, wrapped in a tough little shell and infused with a blood-red dye. How on earth do Americans eat this stuff? The answer: Lots and lots and lots of sugar. Even on her first try, Daria nailed it.)

Sitting around the dinner table, watching Isabella’s family, and my family, enjoying an American-Italian hybrid dinner, was poignant. But it made me sad to think that people might pass up an idyllic week in off-season Tuscany with their families, just because of a fear that they may not get their turkey fix. Even if we’d missed out on the turkey, this week would have been totally worth it.

Holiday traditions are powerful. But keep open the option of busting out of your rut every so often. Risk not having turkey at Thanksgiving. Spend Christmas at a radish festival in Oaxaca instead of singing carols around a fir tree. Skip trick-or-treating in order to be in Slovenia the day after Halloween, when everybody in the country goes to the cemetery to decorate their family graves — in a touching celebration of generations past and present. Instead of dozing off watching another Detroit Lions blowout, drive around the French Quarter of New Orleans, handing out Thanksgiving leftovers to homeless people.

I’ve been fortunate enough to experience all of those magical holidays, and never regretted what I was “missing out on.” If holidays are fundamentally about surrounding yourself with the people you care about, you can do that anywhere. Your traditions will always be there, back home, waiting for you…next year.

If you’d like some inspiration for experiencing Europe for the holidays — or anytime off-season — here’s a recap of some of the other wonderful experiences we enjoyed during Thanksgiving week in Tuscany:

We stayed a full week at Agriturismo Cretaiole, perched on a ridge just outside of Pienza and wonderfully run by Isabella and Carlo. Carlo’s dad, Luciano, kept us well-lubricated with nightly doses of grappa and Vin Santo.

We experienced three entirely different — and equally enjoyable — cooking classes: preparing a blowout feast in an Italian mama’s house; shadowing a Michelin chef in his restaurant’s kitchen; and rolling our own pasta back home at our agriturismo.

We explored Montepulciano — my favorite Tuscan hill town — with its colorful cast of craftsmen.

We followed a talented dog as she sniffed out truffles in a primeval forest.

And, in general, we fully enjoyed being in the foodie paradise of Tuscany.

Finally, at the end of the week, we did a little “Black Friday” shopping in Tuscan hill towns, and enjoyed the first of Italy’s holiday lights.

All in all, we found that off-season is a wonderful time to travel in Italy. It’s mild but not cold, it’s less crowded than peak season, and it’s a great time to sample seasonal specialties most tourists never taste.

While you’re digesting your turkey this year, why not do a little daydreaming for next year? A cross-cultural holiday is something worth trying for anybody. Sure, you could miss the turkey, or the Santa suits…but you might just discover something even better.

Or maybe you already have. If you’ve enjoyed holiday experiences on the road, share your favorite memories in the Comments.