Should one return to Tuscany on a regular basis and if so, how regular should that basis be? This is a question that I also ask myself about Hawaii. Both places are breathtakingly beautiful and are favorites of mine. To be in either place is to experience a great sense of peace and relaxation; but ironically, I get pretty doggone tired when visiting both places. Then again, Bob and I are fairly aggressive travelers, so I should clarify – tired and happy and strangely energized.

To answer the question from the beginning of this post – Yes, one should go to Tuscany on a regular basis or an irregular basis, or just once, if at all possible! That is if you’d like to experience old Italy, great food and wine, classic architecture, great food and wine, timeless art, great food and wine, beautiful rolling hills, great food and wine, spectacular sunrises and sunsets, and great food and wine.

A little backstory for our most recent trip – we have traveled extensively with three other couples, all of whom we’ve enjoyed friendship with for over forty years. It has been over a decade since we have had the privilege of traveling together. When the last of our group retired at the end of 2023 and told us they were considering going to Italy, the door opened for another group trip. Actually, I’m not sure if the door opened or if we kicked it in, but either way, last month the eight of us set off for Italy and Switzerland on an adventure.

Traveling at our current “certain” age is vastly different than it was over a decade ago, even though we would have considered ourselves a “certain” age way back then. Silly us! We are now more “certain” than ever and a bit slower, too, but we managed our trip with friendships and body parts intact. That’s a win.

We chose not to check baggage as we were literally doing a planes, trains, and automobiles type of trip with four different destinations along the way. You may notice striking similarities in our luggage and backpacks as we texted each other with every detail of our trip planning. (Thanks, Amazon.) I’m not sure if it’s a thing, but it may be time to get the tires rotated on our luggage. We gave them a workout on those cobblestone streets.

Six of us began in Orlando on a Saturday morning. We connected with the other two in Charlotte, and from there we headed to Florence via Madrid. I don’t like math, but I’m guessing that it took us about a zillion hours to arrive at our VRBO in Siena. (a zillion = approximately 23, according to my engineer and numbers guy, Bob)

Siena – che bello! These sights eased our travel-weary souls!

These are the views from our VRBO in Siena. (Here is a link in case you’d like to book here yourself. I highly recommend it. https://www.vrbo.com/10788011ha)

There were a few things that were musts for us American certain-agers. First and foremost was our own bedroom with attached bathroom. The bed size must be queen or larger. They don’t designate bed sizes the same way as we do in the states, but we were able to figure it out. This VRBO in Siena checked all the boxes. It even had a washer and dryer, though one should note that a clothes dryer in Europe will likely be a rack on which to hang clothes, which was the case for us. Still, it was bene da noi (fine by us).

We started our visit with a catered dinner at our new Siena home. This was an extravagance suggested by the owner, and it paid off in spades as we were all tired and hungry. This pair of lovely Italian ladies invaded the kitchen and put out a spread worthy of a king. This included an appetizer which included home-made crackers. I didn’t know that was even a thing. Perhaps I’m easily impressed, but they were deliziosa! Home-made bread and charcuterie with fresh vegies and honey were just the beginning. Our main course was ravioli. It was the first time I had eaten it aside from Chef Boyardee. Chef Boyardee has been canned! For dessert – tiramisu. I didn’t even think I liked that, but I do!

The nighttime held a welcome of its own. The blue, blue sky framed our lovely home with warm lights emitting a special glow. The sound of a nightingale, which was a new one for me, was like a lullaby! And this lovely place to lay our weary heads and rest for the journey ahead – so special.

One of the challenges for us was adjusting to the eating times in Italy. We had coffee and breakfast in our Siena home, but for the rest of the meals, we had to wing it. Most restaurants closed around 2:30 and didn’t open again until 7:00. It seemed like we all got hungry sometime close to 2:00 and had to scramble to find someplace to eat or else wait until 7:00.

As we walked into Siena, we quickly came across an osteria, which translates – a place of serving wine and simple food. We asked if the eight of us could be seated but it was not possible. How about two tables of four? Again, no. As we turned to leave, the hostess came to us and asked if we could split into two tables and be finished eating in an hour and a half as she had reservations for that time. I told her, “No problem. We’re Americans. We excel at eating fast.”

So cozy!

As we entered La Taverna di San Giuseppe, we didn’t feel like there was anything “simple” about the place. It was as inviting as a warm hug and a perfect reflection of everything Tuscan. There was a wine cellar downstairs which could be seen from our dining table. It was the perfect photo op. Bob and I ordered lasagna, something I don’t order at home. It was delicious and unlike anything I have tasted our side of the Atlantic. There was no red sauce, and the ricotta cheese was whipped as smooth as Barry White.

The outside of the restaurant was covered in Michelin plaques and the restaurant is featured in their guide, but I couldn’t figure out if it actually achieved star status, so I simply have awarded it 2 stars. After consulting with the other seven of our group and hearing rave reviews, it was the least I could do.