Italy 11-Day Thanksgiving Week Itinerary

This Italy Itinerary pretty much hit the typical tourist route covering Rome, Tuscany, Florence, and Venice, which marked the second time that Julie and I did such a route (and our first time in 10 years since our first trip to Italy in 2013).

However, this was also our daughter’s first time visiting this part of classical Italy (we’ve done the Dolomites with her before), which was very relevant to her studies of European history in school.

As a matter of fact, this trip wasn’t even supposed to happen as we had debated about visiting Portugal in the off-season or even Jordan (before another Palestinian-Israeli war broke out and killed those plans).

I’m generally bearish about doing repeats in our travels, but I think in this particular itinerary, we did things quite a bit differently, and the end result was a pleasant (albeit short) trip where we definitely got a lot out of our experiences this time around compared to our first time.

And that’s what we’ll detail in this itinerary write-up, which you can delve right into down below…

Trip Map

Trip Highlights

Castello di Sant’Angelo – Although this wasn’t the first time that Julie and I went to Rome, we did seek out doing things that we hadn’t done that first time around. And this fort was one of them! In addition to Roman history coupled with history from the Middle Ages and onwards, we also got some nice views over the Tiber River as well as views towards Vatican City. Our late afternoon visit also coincided with the sunset so we got some twilight ambience to boot!

Rome Walking Tour – While in the same vain of sightseeing Rome in ways that we hadn’t done the first time around, Julie actually spend the money to do a guided walking tour of Rome. And since we only really had one full day to sightsee the city, this was actually a very good idea because it was a very efficient way of spending precious time in the historical city. To further add to how this tour made efficient use of our limited time, for crowded places like the Vatican and the Colosseum, we had skip-the-line queues so we didn’t have to waste precious time just to go through airport-like security in addition to getting tickets.

Speaking of famous sights, this tour was like the greatest hits of Rome hitting places like the aforementioned Vatican and the Sistine Chapel, St Peter’s Basilica, a quick walk-by of city landmarks (e.g. Piazza Navona, Pantheon, and Trevi Fountain), the Roman Forum, and the Colosseum. The tour guide we had was pretty good with her English, but she also did a great job explaining the things we were seeing in real-time, which definitely helped us to get much more out of our sightseeing than how we did it the first time around when we wandered about on our own and randomly took photos along the way.

Heck, even though this was a long day (where the guide smartly gave us a lunch break near the Trevi Fountain), Tahia thought this was a highlight of the trip, which is saying something for a young adult with a short attention span! Indeed, I could have itemized each of these sights as a highlight, but the tour itself helped to fill in the gaps, so to speak, and that’s why I’m calling this excursion was a highlight in and of itself.

Cascate del Mulino di Saturnia – In all the years that we’ve been chasing waterfalls, there are few places that actually live up to the hype, and there’s even fewer still that actually “WoW’ed” us. Well, this turned out to be one of those places, where we had a good time enjoying the scenic while also bathing in the warm waters of the cascading hot spring. Sure this place was a bit out of the way, but despite that, this place gets quite a few visitors, and now we fully understand why!

Bagno Vignoni – Experiencing thermal spas was something Julie and I didn’t get to do on our first time in Italy. So we really looked forward to these types of experiences, and this compact village was where we based ourselves. What made this place unique among the Tuscan towns that we had visited was that there was a thermal pool right in its historical center! Sure it wasn’t a pool that you could bathe in, but its hot waters fed all the resorts around it, and it also fed a waterfall of its own beneath the town. Indeed, if we needed a place to stay in Tuscany on a return trip, we wouldn’t hesitate to come back here again!

Leaning Tower of Pisa – It’s a bit out of the way to get to this historic landmark, but to be honest, what made this place a highlight was witnessing our daughter’s reaction to actually seeing this place in real-life. After all, she was the reason why we prioritized coming here, and upon witnessing with her own eyes this place that she had only seen in textbooks and on a computer screen was priceless. Anyways, on this go around, we actually spent a bit more time here than when Julie and I first came here 10 years ago, and we even spent a little time checking out one of the walking streets as well as going all the way around the complex. The only thing we didn’t do was walk the city walls for a bit of a more elevated perspective.

Bagni San Filippo – While Saturnia impressed us, the sleeper hit of Tuscany had to have been this series of travertine formations and hot springs. It yielded a bit of a different experience in that this place wasn’t as well-visited (though it’s by no means a secret anymore), but it was great for taking pictures as well as for bathing under warm waters (even if it’s a bit more constrained compared to Saturnia). Perhaps for Julie and Tahia, the best part of this place was that there were no little red worms to bring about that ick factor while bathing here.

San Gimignano – Even though Rick Steves had some less than flattering things to say about this place, on its own merits, seeing all these medieval towers where the rich tried out one-up each other was definitely something we didn’t get to see on our first trip to Italy. But this theme of one-upping each other seemed to be prevalent throughout Italy, and perhaps this was the lightbulb moment that made us realize that the country has so many sights to see because of this tendency of each region trying to one-up and outdo each other. So in a way, this place kind of made us realize the why behind all the rich history and cultural sights in Italy!

Florence Walking Tour – Leveraging the successful Rome Walking Tour, we decided to do a walking tour of the Renaissance City to see if we could get more out of this visit as compared to our first visit, where we just walked about and randomly took photos as we went. Sure enough, with another guide with a pretty good command of English as well as a good concept of keeping the audience’s attention, we toured the famous spots like the Accademia Galleria di Firenze (hello, David), Il Duomo di Firenze, Piazza della Repubblica, Piazza della Signoria, and the exterior of the Uffizi.

We did go an a separate excursion later in the day covering the paintings within the Uffizi Gallery (which is not part of this walking tour), but the main takeaway of this tour was understanding the transition from democracy to a dictatorship by the Medici Family, which managed to gain their wealth and power essentially as loan sharks. It helped to explain the lone copper statue that we saw in the Piazza della Signoria facing David (i.e. the Florentine version of the Statue of Liberty), and it also helped us understand the degree of wealth and power on display by the Medici’s, which essentially dictated a lot of what we saw around us. Indeed, this experience was way more fulfilling than on our first visit, and we even got some good restaurant recommendations concerning where to find the elusive brasato (i.e. the mysterious dish we had for our wedding and our first time in Florence)!

Walk to Piazzale Michelangelo – Even though we had missed an opportunity to stop at this square and overlook of Florence when the sun was setting (when we went on a bit of a self-driving misadventure trying to return the car near the Florence Airport), we had an opportunity to walk up here from the Ponte Vecchio where we were staying. While the morning views and threatening rain made for a less dramatic view, we were surprised by encountering what’s remaining of the old city walls still standing in the Centro Storico (historical center) of Florence.

In addition to experiencing the views, we also got a better understanding of the neighborhood of the other side of the Arno River, which was real easy to overlook. And to think that we weren’t going to do this (we only did it because going inside the Duomo was not happening until it got too close to our train ride to Venice), it was another instance of how even accidental encounters could be every bit as rewarding compared to those we had preconceived and planned on visiting going into Florence!

Burano – Unlike the first time when Julie and I visited this island off Venice 10 years ago (when it was a sunny day and not terribly busy), this time around, we were forced into making a last-minute visit in the late afternoon and into sunset. The experience ended up being magical, and we once again experienced the charm of this colorful island in a way that contrasted with our first time around despite being a repeat. Moreover, we got to see the familiar leaning tower of Burano as well as more of the island than we did on our first time around!

Venice Walking Tour – Keeping to the theme of trying to get the most of our limited time in the cities, we did a 6.5-hour walking tour of the city complete with background information of what we were seeing, including getting to go into St Mark’s Basilica and the Doge’s Palace as well as getting a half-hour gondola ride! Our guide Alessandro was very good about keeping the audience’s attention, and he even kept a four-year-old entertained throughout, which goes to show you how good he was at not losing the audience (couldn’t say the same about our Uffizi Gallery tour).

In addition, we were pretty efficient about touring Venice in this one greatest hits day experiencing things like the Piazza Rialto, Mercato del Pesce al Minuto, Campo Santi Giovanni e Paolo, Piazza San Marco, and of course the interiors of the Basilica di San Marco and Palazzo Doge, where the latter involved skipping the lines. I think we walked away from this experience with a much deeper understanding of how and why Venice came to be, and it really shed a light on the difference between winging it on our own the first time and doing this guided tour the second time around!

Watching the Sunset over the Grand Canal – It’s not often that staying in our room would be a highlight of the trip, but it just so happened that our unit had a commanding view over the Rialto Bridge and the Grand Canal, and it was a great place to not only watch the sun set over the Grand Canal as well as all the colors that come with it, but also see what the sunrise does to the colors as well. We were also getting a kick out of how crowded the Rialto Bridge became during the sunset, which made us better appreciate our unique experience that much more!

Trip Advice

During our 11 days in Italy, we still had lessons to learn despite being seasoned veterans of visiting Italy and travel in general. It just goes to show you that no matter how well-traveled you think you are, there are always things that happen and experiences to be had to demonstrate to us that you can never know it all. So here are some of those humbling lessons that we took away from this trip…

Low Season: It’s said that November is the low season in Italy because it’s the wettest month, and it’s in those doldrums between the Summer and when things pick up again for Christmas. Well, on this trip, it seemed like we were still seeing some high season-type headaches in terms of crowds and things booking out quickly (especially restaurants) because apparently there was some revenge travel going on and some vouchers and delayed tours affected by COVID-19 were expiring. So that created a surge in an otherwise typically quieter time of Italy, and the end result was a mixed bag of peace and quiet in some moments while quite the busy times at other times, especially in the cities. I have to believe that this is probably a one-off due to outbreak of COVID being hopefully a one-off kind of event, but with people following whatever they see on the socials and AI exacerbating the lemmings effect, who knows?

Returning the Rental Car: It took a two-hour misadventure trying to follow GoogleMaps to the rental car center (only to be trolled and be misled into the city center of Florence through ZTLs) did we finally remember that we should have used the car’s inherent navigation to go back to the rental car center! That would have saved those two hours of misadventure followed by the inevitable fines for driving through ZTLs that I’m expecting will happen in the coming months. Well, whatever the case, that was a big lesson learned and a bit of boneheaded misstep on our part, and I’m sure this isn’t going to happen again on our next self-drive in Europe or anywhere else.

Accommodations and Taxis: Unlike the first time that Julie and I visited Italy where we stayed near train stations and were more efficient with our money in terms of sticking with mass transit, on this trip, we stayed more in the heart of the cities and thus we actually took more taxis than I can ever remember. The end result was around $700 USD of cash expenditures (as most of them are cash only as far as foreigners are concerned), and we even got ripped off in Venice by a porter who took our bags without asking and charged $10 euros just to get from the train station to the water taxis. Speaking of water taxis, it was 50 euros to get to the Rialto Bridge and 70 euros to get back! And going from hotel to train stations costed on average 20-40 euros while the airports costed 40-50 euros per ride. I guess time is money, and in a short trip like this, I guess we made out on time in some respects while in others, we just got ripped off. So that’s something to consider, when weighing the balance between cost and precious time!

Cell Coverage: Apparently, we were pretty spoiled in Asia where cell coverage in Korea, Taiwan, and Japan were all fast and reliable (especially in Korea). However, on this trip in Italy, the SIM card kept dropping out, which made using the phone with that foreign SIM as a hotspot less reliable. And that made navigating a bit trickier, especially when it came to self-driving as well as self-walking! I’m not sure if we got the raw end of the deal with our SIM card that we procured at the Fiumicino Airport, but that’s definitely something we weren’t expecting to have difficulty with on this trip.

Weather: As mentioned earlier, November is typically the low season in Italy because it’s the rainiest month. However, on our trip, we must have gotten lucky with the weather because the only “bad” weather we got was in Florence, and you could argue that the weather wasn’t even that bad at the time (it was certainly not like the flooding that the Tuscany Region got two weeks prior to our arrival, which might have beaten up the roads). Like with anything, the weather is a roll of the dice that you can’t predict when you’re booking your trip. The only defense is to be prepared and to be flexible to changes because sometimes trying to force the issue when the weather makes certain excursions or being in certain places dangerous is just not worth it.

If anything, we found that the temperatures were actually quite chilly, especially overnight where it often got cold enough to freeze water, especially in Tuscany! So we were certainly glad to have packed some warm clothes on this go around!

Travel Itinerary

Days 0-1: Flight from LAX to Fiumicino and then briefly exploring Rome

Overnight: Boutique Hotel Campo dei Fiori (Rome, Italy)

This was a basically brutally long travel day where we flew out in the mid-afternoon and eventually made it to the city center of Rome near the Campo dei Fiori at around 2pm. Then, we explored a bit on our own checking out the Piazza Navona before spending the rest of the afternoon within the Castello di Sant’Angelo. Afterwards, we went on a foodie tour in the Trastevere District at around 6pm, where we got to try a variety of Roman cuisine, including a very smooth porchetta as well as a Maiale di Mazzio (a couple of things we had never tried before). Despite being jetlagged, we were beat when we returned to our room at 10pm!

Day 2: Touring Rome

Overnight: Boutique Hotel Campo dei Fiori (Rome, Italy)

On this day, we did a full day tour that started off in the Vatican City, then spent the better part of the midday exploring Rome before capping off the tour going through the Roman Forum and ending up inside the Colosseum. Not only did we do stuff that we never did the first time we were in Rome, but we also had less time than we did the first time around so this tour made very efficient use of time while also giving us a deeper understanding and appreciation of what was around us. In the evening, we spent some time going to the Spanish Steps and then having dinner for Julie’s b-day.

Day 3: Transit from Rome to Florence, then drive to Bagno Vignoni via Saturnia

Overnight: Albergo Le Terme (Bagno Vignoni, Italy)

On this day, we got a very early start going to the Roma Termini Station to catch a bullet train to Florence Santa Maria Novella Station. Then, we took a taxi to the rental car center near the Florence Airport, where we picked up our rental car and promptly drove to Cascate del Mulino di Saturnia before finally settling in at Bagno Vignoni.

Day 4: Diborrato and Pisa

Overnight: Albergo Le Terme (Bagno Vignoni, Italy)

Because of Tahia’s desire to see the Leaning Tower of Pisa, we prioritized going out of our way to visit the iconic tower, but we spent the better part of the morning driving to Colle di Val d’Elsa to visit the Cascata del Diborrato, which was another waterfall in the Tuscany Region. These excursions took the entire day, and it wasn’t until after 5pm when we finally returned to Bagno Vignoni and called it a day

Day 5: Transit from Bagno Vignoni to Florence

Overnight: Hotel degli Orafi (Florence, Italy)

On this day, we started off by exploring the Bagno Vignoni Waterfall beneath the town we were staying in. Then, we went to Bagni San Filippo to explore the White Whale and hot springs over there. Then, we made the drive to San Gimignano for a quick exploration of the impressive towers and medieval architecture in this popular town. Finally, after returning the rental car and checking into our hotel near the Ponte Vecchio, we then did some exploring on our own of Florence’s centro storico (historical center), where we managed to catch an opera singer busking in the streets under the cause “Opera in the Streets”. Needless to say, this guy attracted quite a crowd right in front of Florence’s Duomo.

Day 6: Touring Florence

Overnight: Hotel degli Orafi (Florence, Italy)

On this day, we pretty much did another guided tour where the morning was dominated by a walking tour of the historical center of the city along with a visit inside the Academia Gallery to see David. It ended at the exterior of the Uffizi Gallery by the Arno River with a view of the Ponte Vecchio near the Piazza della Signoria. The afternoon was spent on another tour inside the Uffizi Gallery, which was basically a showcase of the personal collection of the Medici’s.

Day 7: Transit from Florence to Venice

Overnight: Hotel Rialto (Venice, Italy)

This was basically a long day where we spent the morning walking to the Piazzale Michelangelo to get our last fix of Florence before taking the train to Venice. After getting settled in our accommodation in Venice, we then promptly took a boat to Burano, where we made it just in time to catch the sunset and some twilight lighting before settling back on the main island.

Day 8: Touring Venice

Overnight: Hotel Rialto (Venice, Italy)

On this day, it was dominated by a 6.5-hour walking tour that pretty much explored as much of the highlights of Venice that one can handle in a day. This tour also included a half-hour gondola ride (a bucket list item) and the interior of the St Mark’s Basilica as well as the Doge’s Palace. The afternoon was spent at leisure watching the sunset over the Grand Canal from our room above the Rialto Bridge.

Day 9: Transit from Venice to Fiumicino

Overnight: Hilton Rome Airport (Fiumicino, Italy)

This was another long day of travel though we did spend the better part of the morning visiting a glass blowing factory in Murano before doing one last bit of exploring Venice from Piazza San Marco through to Rialto Square. Then, we took a train all the way from Venice to Rome Termini Station (there was an airline workers strike that essentially cancelled our flight back to Rome), and then we taxi’d to Fiumicino through some crazy rush hour traffic. By the time we got to our room, it was already pretty late in the evening, and this pretty much concluded all the sightseeing we were doing in Italy.

Day 10: Flying Home

Overnight: Home (Los Angeles, California, USA)

On this day, we pretty much just walked to the airport, spent some time in the Priority Pass Lounge after having gone through a gauntlet of check-in, security, and passport control, and then did a long flight home.

Best Places We’ve Stayed At

Hotel Rialto – We stayed at five different accommodations during our Thanksgiving Week Trip in Italy, and this one was definitely heads and shoulders above the rest though the other accommodations weren’t slouches either.

Of course, we splurged for this place so it had better be good, and it certainly didn’t disappoint as we had an entire top floor, which was a spacious apartment overlooking the Grand Canal above the Rialto Bridge. It was the perfect spot to see the sunset as well as to see how the colors change at both twilight and in the pre-dawn.

Its central location also meant we were never far from the action, and thus as far as being efficient with our limited time in Venice, we probably couldn’t have done it any better.

Perhaps the only gripe with this place was the breakfast, which was not as good as some of the other places we had stayed at like Albergo Le Terme in Bagno Vignoni and Hotel degli Orafi in Florence.

Hotel degli Orafi – Even though our stay in Venice was a splurge and heads and shoulders above the other accommodations, I did want to mention this place as another standout because of its location and its pretty good breakfast, which as you can see from the photo above, its dining room had a very sophisticated decor.

As for the room itself, it featured a high ceiling and a lot of space, which you can’t really ask for much more than that, especially when you’re talking about a place between the Rialto Bridge and the Uffizi Gallery! Indeed, this place did seem quite luxurious, and this place wasn’t even considered a splurge for us! So just imagine how much more benefits we’d get (like the view of the Arno River) if we did splurge here!

And as if that weren’t enough, there was a rooftop bar, where we got some commanding views over the Arno River in one direction as well as views over the rooftops in the direction of the Piazza della Signoria, which was perhaps the most visited square in Florence. Add it all up, and this place certainly deserved to be mentioned as one of our top stays in Italy on this short trip.