72 Hours in Tuscany | Family Road Trip Through Italy’s Hidden Gems

72 Hours in Tuscany | Family Road Trip Through Italy’s Hidden Gems

our Italian road trip continues as we spend the next three days touring Tuscanyany checking out wineries medieval small towns the incredible rolling hills meeting wonderful people and of course taking a pasta cooking class there is honestly nothing like the rolling hills and the roads through Tuscanyany we are continuing our Italian road trip and have stopped now in Medina we’re going to walk around maybe grab a snack grab some lunch and see what the city has to offer [Music] we just grabbed lunch in the market chris and I both got something that was called a Medina burger and would not it be exactly what you would say a burger would taste like in the US it kind of tasted like a cross between ground meat and sausage yeah and it was pretty raw so they must have been fresh meat and the bacteria on it so it was still good in its own way yeah just totally different and um also had balsamic vinegar on it but going to wander around hopefully get an espresso because this mama is tired and head back on the road [Music] medina is actually the birthplace of Ferrari and the originator of balsamic vinegar and these cute little streets with all the different colored buildings you could definitely get lost in and we’re passing a square right now that has a carousel we just parked at the Adar Turismo we are staying in in Tuscany and we had to park and then they were going to text us the passcode so we just got it we’re going to go inside as soon as you walk in it is the kitchen there’s a dining room nice area to sit and relax i love the ceilings this is so cute look at that view now this one we found on Airbnb it has two bedrooms and they even have a crib and a high chair for the little guy this room also has two full baths which will be perfect for us so that Chris and I and the little guy and my parents each get our own bathroom make mornings very easy so this evening we are actually going to be doing a cooking class with the hosts of this Airbnb it’s her uh daughter and her son-in-law so we are back in the room we actually stopped at the co-op to grab a couple things for breakfast and for snacks and they let us know they’ll be here any minute we have no idea what we’re cooking yet but they know we know that they’re bringing food and wine and going to give us a little glass and enjoy everything right in our room time to cook from the moment these two stepped into the apartment they just gave off such hug energy they were an absolute joy to be around and to learn from it was almost like learning from family the wine was flowing everybody was laughing and having a good time and it was an incredible moment and memory for our family [Music] with his hands yeah so cuz after you mix the soap with the pasta is not We just found out we get to make tiramisu what what do you see i got it recovered most of them i don’t know i think this is perfect it was so stinking cute the couple is adorable like you can tell my mom’s in her element too mhm you I thought it was so much fun we have We love cooking classes in general something we’ve always done when we travel and this one was even better with the baby um it was in that in our apartment and yeah we’ll see how everything tastes see if we did a good job so good this looks amazing with the hands with the hands the hands [Applause] [Music] was this like scaretta scaretta you’re a beautiful family thank you very much thank you thank you very much so wonderful meeting you that was the most amazing experience our family is honestly over the moon and just so surprised at how sweet and endearing that couple was and we definitely just made some memories that will last a lif see the gnomes now we just had a great experience right there i think Katie summed it up perfectly some memories will last forever we’re all here you can tell almost brought tears to some of the lady’s eyes so it was amazing [Music] what a phenomenal place to be waking up to we are going to be spending the day driving all through Tuscanyany going to San Moo Montterion and we even have a reservation at a winery for later this afternoon and I still can’t get over last night we just have been talking about it all morning and wait until you see this video [Music] all right so we just parked and are walking up the hill to go into Sanjimano and if you are coming here and want to park in P1 you’re going to take the last roundabout before this city take the third exit not the one that it tells you because there’s no entrance up there and then take the keep going and you’ll see a sign for P1 and an area to grab a ticket so that is at least the largest parking lot that we’ve seen we think there is one closer but we couldn’t really see how to get there on the map but I’m very excited this is one of the things I was looking forward to the most so we are just about to the entrance and it took about 5 to 7 minutes walk uh but that was also with a stroller so super easy oh my gosh wow this is so cool it looks like a movie set this is amazing yellow yellow so we are walking around St jim and Yano there are so many markets just in all of the squares and shops on all the roads i guess I just didn’t really expect this to be a big shopping town but if you want to stroll walk through shops and check everything out this is definitely a good stop and I think I’m going to get some treats we are standing in front of the Dwamo right now and there’s a giant tower right above us and they’re actually used to be over 70 towers but there’s only 14 that remain these were actually built by families that were wealthy and to show power we’re just leaving Sanjimano and it was getting really busy it’s about 12:30 now and it felt like the crowds became tenfold like at 11:30 noonish so if you’re going definitely go early also parking when we got there super easy parking to leave was insane that was like a 17 point turn i should have filmed it that was so tight we literally almost thought we were going to be stuck there but we are on the way to Monte Reion okay so we just parked at um Monte Reion sorry I almost forgot the name they all kind of blend together after that parking excursion that Katie just mentioned i mean I probably bumped the first car a little bit but love tap is never a bad thing right so we are learning that blue paint means that it is a paid spot and white means that they are free parking spots yeah that’s good to know it’s simple it’s been pretty much everywhere from the Dolommites to Tuskany right now so let’s see got free parking here there’s like maybe 20 spots that are free someone just pulled out and I pulled right in so hopefully we have a better situation here and we’ll see as much as we can here in the next 20 minutes so let’s speedun through this so we walked in and seen you can walk on top of the castle wall so we split up katie is going to conquer the bottom side so just a couple steps up the stairs you can see this beautiful view [Music] montreioni is a walled medieval city built in the 13th century to defend from the Florentine attacks we were able to walk on just a short section up here and then Chris and my dad walked on another one so you can see the view of Tuskin picked up gelato i got tiramisu i got pistachio look good [Music] they got some fields there [Music] we are on a back road on the way to a winery and those goats would not move an inch they They had no fear of a car but we made it through safely no goats were harmed in the making of this video we are in the middle of nowhere surrounded by this beautiful forest we found this is a little zoom on the turoscan region and here we got two stones these stones right here is representing the most beautiful city in the world which is Fin as you understood I consider myself from Florence then this is the other city Sienna it doesn’t really doesn’t really matter i’m joking anyway this little teeny tiny area which is in between the two cities is considered Keianti classicalico area we were adding in the past with the fit obviously we do not use any of the fit much heavier nose much what is the difference when you do the comparison let’s try i was getting shocked it’s really good though at the same time what can I pair with this wine well depending on the season everything in the summer time a very heavy fat fish in the winter time the person I don’t want to drink a red wine i want to drink something like this but needs to have same thing for sushi okay [Music] what do you think like the best spirit we produce 1,00 400 1,500 bottles a year and actually I tell you a funny story about this this wine is hours under the rain and we had to bottle quite good i like rosé because the machine has to close the middle which is this side of the time please next approach the nose you go from one nostr to the other you will feel you will feel this intensity it’s dark fruit you are by the acidity so at first at the first sip you will have this bite of the will clean up your palette now enjoy i want to bring out a 2013 beautiful it’s [Music] vinegary what was it this one was Keianti classicalico i typically like red wine i don’t know that I like this though but it’s what 12 years old so maybe she don’t have the acquired taste yet ah yes my taste is more like under $7 bottles of wine beautiful talent here guys that was lavated by the time so passage of oxygen inside the wine it was evolving very soon then beautiful musk beautiful musk muskiness yes yes i would say muskiness that’s right all the other things he said I don’t know what he said oh I’m sorry why is that so funny massive tiny but very round precious that will invite you to see this is crazy dangerous oh this is the dance at top of the table so we just finished the wine tasting we actually only paid for three when we booked online and ended up giving seven I think um but the last one we had actually put our camera away and it was graa which is essentially tasted like whiskey um I don’t mind whiskey it’s not my favorite thing but this one I could only touch my lips and that was enough for me um but dad how did you describe it well they called it a wine but they served it in a glass and it seemed like a whi I’m not a whiskey drinker but it gave you that sinus rush that you would get from a whiskey and uh yeah that stuff was strong i’d like to know what the proof was we’ll look it up later there you go good morning from Sienna today is the last day of our Italian road trip from here on out we will be on trains or transfers and I just had the cutest barista make me a soy cappuccino and he taught me how to say cappuccino de soya and we are walking over to the duo in Italy it is respectful to cover your shoulders shoulders and have outfits on when you’re going to religious places all right the ticket office is on the left side of the Duomo and costs €5 per person we are inside the Duomo in Sienna the black and white marble you see behind me represents their civic colors and the building is actually known to be one of Italy’s greatest examples of Gothic architecture it’s absolutely stunning and the ceiling is covered with all of these little gold stars that I they look 3D i don’t know if they’re metal but on like a navy background it looks like the night sky [Music] also in Sienna I’m pretty sure that everything is considered a road like even standing in front of the tollo there were um cars coming past i don’t know if there’s a way to tell if it’s just pedestrian but we’ve seen cars pretty much everywhere we are currently walking around the delo which is one of their medieval squares it’s what they’re most known for in Sienna but twice a year they actually hold a bearback horse race um through one of the town squares between the districts but I’m not exactly sure what square it is yet [Music] we stopped and had a little snack at a cafe gelataria i thought I was ordering an avocado and it definitely came out more as a parfait this is not what I wanted i messed up and I immediately panicked cuz that’s just the person that I am and we’re going straight and it was really good and I shouldn’t have panicked i think that’s just kind of part of what travel is and then you have an idea in your head of one thing and when it’s not that it’s kind of hard to adjust but we are headed here comes a car we’re headed back to the car so we can head on over to a winery reservation that we have at 100 p.m and then after that we are going to be headed to Montiano today is Mayday and there’s supposed to be a festival in Montipuchiano if we can get in and get parking so um weatherwise though it is going to be 76° outside it’s right about 12 now and I would say it is pretty warm i am definitely comfortable in a tank top and a skirt so just so you know for packing wise if you plan to come in May so if you’re coming to Sienna and you’re driving I definitely suggest checking checking out the Elmpo garage there was multiple levels lots of spots and you are pretty close to town we just got to our wine tasting in Malta and they have us set up at this little outdoor gazebo they brought a chair for the little guy they let us know that they are on their seventh generation of wine makers they both live here and work here it’s all local grapes everything was started by their grandfathers and it is stunning they have a little dog I’ll show you in a second named Bobo that came up and kind of greeted us and our little man is absolutely obsessed but they have cats and dogs and horses and it’s so cute but we’re going to get appetizers with all of our wine tastings and they said they also have a chef on hand if we’d like to order anything else is one salami with fellow inside cheese they have their own olive oil and breads and cheeses and fresh marmalade and we’re just sitting cuz the weather is absolutely perfect [Music] so no wine for you crap so they have a private chef here and that prepares a little something different every day and they let us know that today that there was fresh pasta with a bore bolognese and asked us if we wanted to have some of that along our teeth with our wine tasting and of course we said yes it’s so beautiful and it is so good it came out with rosemary and pansies on it you’re going to get one for mama get a flower for mama i I had to take a bite before I took pictures of it so Oh well no delicious and yesterday’s guy was like a sauce pitch and this is like you don’t have to sell it it’s It doesn’t need sold it’s fantastic fantastic environment conditions it was interesting though i I enjoyed the chat we just finished our pasta and we are definitely learning that the family run more personal experiences are much more our vibe and our speed this was just wonderful and honestly a fantastic surprise and just kind of relaxing we’re all just enjoying their daughter came out and brought the little guy a coloring with colored pencils it was very cute yeah it’s definitely middle of the road it’s It’s really good though it’s really refreshing and smooth [Music] so we were just discussing how much it would be to ship bottles back to the US because how wonderful of an experience this was to just be able to bring out a bottle when we were all together and kind of reminisce about this moment and my mom and I were just talking about how perfect it was and I don’t know that I’ve ever cried as much on a trip as I have on this one it’s just making beautiful memories and we’re going to get two bottles to share and relax together and just enjoy each other’s company on our next stop we’ll be in Florence and then we’ll be in STO for several days so it’ll be great i just feel so blessed to share this experience with my parents my husband and our son that’s beautiful we were driving down the road and we saw the sign for Palazzo Masini um and had to take a picture it is just the quintessential Valdorcha view with the cypress trees and as you can see there’s a lot of people that felt the exact same way but it was super easy nice pull off and everybody took turns so everybody must have went to preschool so we finished up the Vora Drive there were some beautiful sites along the way we stopped at a few pulled over and checked them out took a few photos they’ll be right here and we’re just continuing on we took a quick break went home uh fed the little guy and now we stopped by a small town near our Airbnb this has to be maybe three streets maybe four parking lots total but we’re going to check it out for a quick dinner before our last night in Tuscany um so let’s see how it turns out it’s always good to find like little random stops you weren’t expecting so so we’re sitting in the piaza of Babarino we got two pizzas and a fkatcha which the fkatcha kind of looks like pizza too but one has a decon feet and honey and mozzarella and the other one is more of a bacon and parmesan and then our fkatcha is a um kache and everything’s really good um we took pictures but we did not take a video before we started diving in so there’s only a couple pieces left and little man is also diving into how did you choose this place so we there’s one road that is seems like the main road in Barbarino and there’s three restaurants back to back and then like another store and a restaurant down the road and this one had the most people at it so we figured why not let’s try it and when we sat down we found out that they only had pizza which I mean you’re in Italy eat pizza so um but we did find out that there are two other restaurants kind of down the road that have a view of Tuscany so we did walk down and look at the view cool enjoying some pizza so we just finished up the dinner um the pizzeria was delicious the pizza is actually really good everything was pretty unique there a lot of different flavors but we’re walking through this small town at night and it’s so empty but the walls you can see behind us are small it’s walking paths only and it’s kind of nice being in like a town like this where we were so busy in San Jim Majano and all the other places and now we’re here totally by ourselves i literally feel like we’re walking through a movie set and this was not something that was on our list at all but we were actually like at the Airbnb packing and we’re like you know what this is our last night in Tuscanyany like let’s go out and do something and this just happened to be the town that was closest yeah and it ended up being almost perfect picture perfect there was a hillside you can look at um and everything you want out of a Tuskanyany scenery so that’ll be it for Tuskanyany so I hope that you guys like subscribe and follow along for more of our Italian adventures ciao ciao

Join our family as we road trip through the heart of Tuscany for 72 unforgettable hours! From medieval hilltop towns to rolling vineyards, we packed our Italian adventure with history, food, and stunning countryside views.
In this video, we explore:
San Gimignano – The city of towers and gelato dreams
Monteriggioni – A fairytale fortress frozen in time
Siena – With its legendary Piazza del Campo and Gothic charm
Modena – A quick detour for balsamic and motors!
Barberino Val d’Elsa – A quiet Tuscan gem full of local life
Two family-friendly wineries where we learned, tasted, and soaked in the views

This is more than just a travel vlog — it’s a glimpse into what it’s like road-tripping Tuscany with a toddler, discovering hidden corners, and soaking up la dolce vita along the way.

Subscribe for more family travel adventures around the world! 🌍
https://youtube.com/@BayerleinTravels?si=r1lSsneFQvbVLEVt

Chapters:
0:00 Intro
0:36 Modena
2:00 Agriturismo
3:20 Cooking Class
6:40 San Gimignano
9:30 Monteriggioni
11:45 First Winery
17:00 Siena
21:00 Second Winery
25:47 Barberino

#Tuscany #FamilyTravel #ItalyRoadTrip #TravelVlog #WineTasting #TuscanyWithKids

FIRST country as a family of 3•Filmed April 2025• Tuscany, Italy

Where we stayed: https://www.airbnb.com/rooms/50408639?adults=4&infants=1&location=Tuscany%2C%20Italy&search_mode=regular_search&amenities%5B%5D=286&amenities%5B%5D=5&amenities%5B%5D=9&amenities%5B%5D=33&check_in=2025-04-29&check_out=2025-05-02&source_impression_id=p3_1730148162_P3YXkmLmGkW660nm&previous_page_section_name=1001&federated_search_id=b46aa6a1-9dbf-4d8e-b4b1-58c2638256dc

First winery: https://www.montemaggio.com
Second winery: https://tiberiniwine.com

🇮🇹ITALY SERIES
🪂 🪂Paragliding over Lake Garda: https://youtu.be/lFeELsLQbBc?si=2QXAFNKkvfvmAHTP
⛴️ ⛴️Lake Garda in 72 Hours: https://youtu.be/AcKYdyq-1LI
⛰️🏔️48 hours in the Dolomites: https://youtu.be/qiZlNezwLvQ?si=UbFtw3597rSq4U22
✈️✈️TRAVEL DAY: https://youtu.be/ZopD6Y0nt6Q?si=0jIS_fG9IdHPArny
🧳🧳Packing for Italy: Packing for Italy with a Toddler| Family’s First International Trip!

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Who is Bayerlein Travels?
We are Chris and Katie! Both born and raised in Pittsburgh, PA! We fell in love over tne pandemic and took our first trip after knowing each other only 5 weeks! We love traveling and experiencing new things and created this channel after we had our little man to inspire people to get out and see the world!

We travel as much as possible while bot working full time jobs! One of our favorite ways to travel and what allows us to take trips is using miles and points to book flights, rental cars and hotels! We hope that this channel motivates others to utilize points programs out there so that they can continue exploring this beautiful world we are so lucky enough to call home!

We are so grateful to be able to share these adventures with you and hope you follow along for the journey!

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Music: Purple Planet Music