Italy and the Via Francigena – Days 1 and 2 – May 18th and 19th

This trip will be the first of many father-son trips I hope to take with each of my sons every three years. Davis chose this itinerary based on a trip we took thirteen years ago. That trip, the first my family took to continental Europe, took us to parts of France and Italy before spending time in Tuscany. One of the small towns we explored was Monteriggioni, nestled between the cities of Florence and Siena.  

While in Monteriggioni, Davis and I ventured out and discovered a portion of the famous Via Francigena – a historic, 1,200-mile pilgrimage route stretching from Canterbury, England, to Rome, Italy. Thirteen years ago while on that trail Davis told me that he wanted to go back to Italy and hike a segment of this famous camino.  Well,  it is about to happen…

This particular road was first used by Caesar Augustus when he visited the British Isles to negotiate a trade treaty with the locals. However, not happy with the treaty, Claudius, the 4th Emperor of Rome from 41 to 54 AD, led a huge army on the same road to conquer the British Isles. But it was not until 900 years later that Archbishop of Canterbury Sigeric mapped the route. His journey took him through the Alps, including the Great St. Bernard Pass, and down through central Italy to Rome. Our part of the route includes hiking through the Tuscany and Lazio regions of Italy. 

Day 1 of our trip was uneventful – and believe me, you want that on a travel day!  We did receive an unexpected pass from the nice ticket agent to stay in the Dulles Airport British Airlines Lounge while we waited for our flight to London. We took advantage and ordered Negronis, a drink with gin and compari, at the bar. And because I took a sleep aid before our flight left, I slept most of the flight to London. 

Day 2 – Wow! What a first day in Italy! It was NOT uneventful. After arriving at London Heathrow at 6:20 a.m., we were supposed to take the 8:10 a.m. flight to Florence arriving at 11:30 a.m. Based on that schedule, I had booked trains to Florence city center and then to Siena arriving at 2:40. We would then take a taxi to Monteriggioni, our starting point the next day for our 7-day pilgrimage on the Via Francigena – just your basic Planes, Trains and Automobiles kind of day. 

As we waited to board our flight to Florence, I said to Davis, more as a philosophical muse, “We will encounter a problem at some point on this trip – it just happens. And when it does, we will just roll with it.” And I recalled Elizabeth and my emergency landing last year in the Azores on our way to Rome. Sure enough, due to weather, our flight to Florence kept getting delayed until the airline finally decided to reroute us to Pisa and put us on buses to Florence. So, we had to do some rolling today… 

While waiting in London as our flight got delayed further, I decided to book us on trains from Pisa to Siena, connecting in the town of Empoli, a town I had never heard of until that moment. The only mistake I made in my booking was failing to take into account that we lose another hour from London to Italy. So, when we landed in Pisa, I rebooked because we arrived an hour later than I thought. But everything worked out. 

As we left Empoli heading to Siena (our third train) Davis and I admired a grove of Stone Pines – happy to be on our final travel leg that would take us through the beautiful Chianti region and to Siena, a short taxi ride to our destination for the day – the beautiful hill town of Monteriggioni. 

But as we headed to Siena we realized that the train’s route must pass close to Monteriggioni on its way South to Siena. And maybe, just maybe, it would make a stop not far from Monteriggioni. So, as we looked at the various stops and at our phone maps we realized that the Castellina in Chianti stop was less than 2 miles from Monteriggioni! And even better, there was a greenway with a path that connected the two! So, we hopped off of the train at Castellina and hiked with our luggage to Monteriggioni – and actually entered Monteriggioni walking on the Via Francigena! This unexpected adventure became the highlight of our day.

After arriving in Monteriggioni, the first thing we did was to check into our accommodation – the Hotel Monteriggioni – the same hotel our family stayed in 13 years ago. Parts of the hotel were former horse stables. You would never know it today because the beautiful stone structure is now a four-star hotel in the heart of this stunning medieval fortress town.  

We were determined to take advantage of the hotel’s outdoor swimming pool and garden. So, after checking in and getting settled, I went to a local wine shop and bought a bottle of wine and a charcuterie and brought it back to the hotel garden for a picnic. After some wine and food, Davis and I got up the courage to swim in the frigid waters of the pool. After our picnic and cold swim, we walked around town. Doing so brought back so many wonderful memories from 13 years ago when our family stayed here. Situated between Florence and Siena, this hill town that is totally walled in was a very important strategic fortress in the Middle Ages when Siena and Florence were fierce rivals. 

After an amazing dinner at Ristorante da Remo that included homemade tonnarelli pasta and Etruscan pork roll finished with fresh truffle, we ended the meal with some amazing grappa. Tired from our day of adventures, we walked back to our hotel and retired early.

Because we will be averaging 15 miles a day, we are looking forward to refreshing ourselves further on unique local wines and tasting fresh local Italian cuisine. Wish us a “Buono Camino”!