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May 2026 trip report - Italy: Part 1 Siena

Part 1 - Arrival in Florence and first city - Siena

3 posts for our trip to Italy - one for each city we stayed in, 4 nights, 3 full days each.
I should also note that this was my ninth trip to Italy and my husbands seventh. Having already hit the big 3 and their major sights in the past, this trip our intentions were mostly focused on relaxing, day trips, lesser known sites and of course enjoying the food.

Our flights were booked through Delta our preferred operator, and we were able to use an ecredit received last year due to a drop in price of our flights, which was a nice way to offset the cost of some initial seating upgrades to comfort and preferred. After the credits our initial cost of booking the flights was about $1,100/each. The flights there were operated through AirFrance and we were able to upgrade the first leg to CDG to first class when we checked in online through AF, at $935/each. We enjoyed use of the lounge at LAX before our departure. So in the end, our flights in total were about $2,000/each after the business class upgrade.

On Sunday, 5/3, we arrived in Florence just after 5:30pm slightly delayed but made up time not having checked luggage. And having connected in Paris, already completing immigration there meant within minutes we could be on our way to the city center. So we quickly made our way toward the exit where before leaving we stopped for a quick, first caffe crema (surprised at this hour they were even serving them). Yum!

We caught a taxi to FSM train station and decided to take the 8pm train to Siena so we could have a chance to pop into one of our favorite spots, the amazing Gilli to grab a few cookies for the hubby and for me, a tasty turkey sandwich on their seeded cornetto. Back at the train station, the hubby got a quick piece of pizza while I sought to purchase our tickets for the regional train. For some reason I had difficulty purchasing online AND through the app, with internet connection spotty. I was about to purchase tickets from the ticket machine when I thought to check my email in the odd event our online purchase completed, and sure enough one of the attempts was successful even though the ticketing system indicated the payment timed out.
Once we boarded the regional train it was the smallest we have rode with only 3 cars and an unusual seating configuration. It was a packed train that we were barely able to get seats together. One and a half hours later we arrived in Siena, just after 9:30pm. Quick taxi to our hotel on the far end of the city put us back €15. It was a long day of travel so we went to bed immediately after checking into the lovely Palazzo Ravizza, the same hotel we stayed in last year.

The next morning, we managed to wake up on time, had a quick breakfast at our hotel, enjoyed the views from the hotel terrace and located the resident turtles in the garden (we counted 5 this year and even saw the mama turtle appearing to possibly be burying eggs) before we headed out for a full day tour of Brunello di Montalcino wineries in the beautiful Val d’Orcia area, arranged through Tuscan Escapes. We walked 15 minutes to our tour meeting point where we joined what would be a small group of 7 plus the guide, Matia. It was an overcast day, fortunately the rain held off and it wasn’t too chilly so we were able to have lunch at one of the wineries outside, a short visit to Montalcino to explore the city, as well as the Abbey of Sant’Antimo. That evening we were back to our hotel by 7pm, so we decided to go for dinner at Vivace, after we had a great experience and meal there last year. Another lovely meal with a less crowded terrace this time. Also to note they added a “robot greeter” at the restaurant entrance that guides you to the terrace. First time I’ve seen this anywhere.

Continued in comments…

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On our second full day we strolled around town in the morning with our only real objective being to get cash from an ATM (to pay our hotel which offers a 15% discount for cash payment!). Along the way the hubby opted for his first affogato of the trip, for a reasonable €4,50 at Grom (whereas we noted only two blocks away on Piazza Campo they were going for €12 - I guess you pay for the view of the Campo). I located and attempted to get cash from 4 different bank ATMs, trying 2 different accounts and was not successful with either card. I finally checked our capitalone account online to determine exactly which ATMs I could use and finally was successful; I don’t recall having issues with using bank ATMs on previous trips, and this was our first time using the account since their switch to the discover network.
In the afternoon we had a food and wine tour of the city, also arranged by Tuscan Escapes, which turned out to be 75% wine tasting at the Tuscan Wine School where we tried several different wines, paired with charcuterie of various pecorino cheeses (the best we have had to date), meats and a balsamic tasting, followed by classic bruschetta. We then went for a walk around a few streets where our guide took us to try an unsual type of pizza: ciaccino - at a ciaccineria, which was fantastic. We returned to the wine school for a final cheers of dessert wine and cantucci. Although not exactly what we expected, a good 2 hour+ tour for the price of €60 each. That evening we returned to the same pizza place, this time ordering a classic piccola pizza of mozzarella and prosciutto to share. That and a beer for the hubby only put us back €12,50 so we were happy with essentially a $15 dinner; it was delicious.

On our last full day in Siena we had a bike tour of Tuscany booked, also through Tuscan Escapes. Our group was another small group of 6 plus the guide, Enrico. I was a little nervous with rain in the forecast but the rain held off and turns out with overcast the day was perfect for a long bike ride. Although the views of Tuscany may have been nicer with clear weather, it was much more comfortable than a warm day would have been for all that biking. Because our group included an older couple with some mobility issues, Enrico modified our route and instead of stopping in Monteroggioni we stopped at an agriturismo for a tasting before we stopped at the planned farmhouse for additional tastings, tour of their production facility and a small lunch, ending with the best cantucci I have ever had with pistachio and hints of chocolate. I would have bought some to take with us but sadly that was not for sale. We returned to Siena just around 4pm, where we had enough time to do a laundry run, some souvenir shopping and have an aperitivo at the hotel but otherwise skipped dinner due to a need to get to bed early in order to check out early the next morning to catch the train to the next location of our trip.

In all, we had a wonderful time in Siena this year, with great tours and another great stay at Palazzo Ravizza. I was happy we also found a unique boutique where we purchased some small hand painted ornaments for gifts and our customary “annual trip ornament” for our Christmas tree.

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Final notes and observations for this leg of the trip:

-Palazzo Ravizza did not disappoint. Our room was slightly smaller this year but still larger than most other accomodations we have had in Italy. The included breakfast was a nice addition with a good spread offered.

-strange to have such a difficult time purchasing train tickets both through the app and online. And with getting cash from multiple ATMs, I don’t recall such issues previously.

-on our bike tour, the modified route to include the agriturismo was at an added cost of €25/person. That was not disclosed to us until after we completed the tasting.

Next update I will recap our time in the next location, the tiny village of Monterosso Al Mare in the Cinque Terre.