Tuscany Week Long Road Trip Vlog | Florence, Siena, Pisa, Wine Tasting, Things to Do

By Brian Lemay 93 comments

After a busy time of Rome, Japan and Marrakesh,
we thought we would round the year off taking in the scenic roads of Tuscany. Getting legless on delicious wines and driving
drunk without a care in the world. Tuscany is a relaxing destination and one
where it is very easy to gain weight. Pizza, pasta, cheese, coffee, calzone, bread,
cheese, pasta, pasta and the best damn mashed potato, I’ve ever had. Seriously. Covering central Italy, Tuscany spreads over
23,000 kilometres with its rich landscapes, winding roads and vineyards. Tucked away beneath those hills are hundreds
of tranquil, traditional Italian towns, almost none of which I can confidently pronounce. Keeping that in mind, we explore the smaller
populated areas such as San Gimignano and Monteriggioni. Next we venture to the larger cities like
Sienna. Driving further north we take in the beauty
that is Florence. And finally we head to Pisa, where never before
had subsidence been such a celebrated occurrence. This is Suitcase Monkey eating over 6 nights
in Tuscany. (MUSIC) My new favourite Italian word, San Gimignano
was conveniently en route to our hotel. San Gimignano is a walled in medieval town,
around an hours drive from Siena and the whole city just wreaks of a time gone by, but but
without being lost in it. I strongly recommend. After a few hours spent in San Gimignano,
we took a 40 minute drive to the Aquaviva Hotel & Spa. Located in the commune of Casole d’Elsa, we
chose the location since it was a pretty central part of Tuscany so most places on our list
were a few hours drive away, in either direction. For us, it was the perfect blend of the conveniences
of a small hotel, whilst still feeling that Tuscany vibe and a room with a view to die
for. It had been a long first day so that evening,
we relaxed with some wine and a well earnt dinner. After over indulging once again, we got some
rest knowing that tomorrow we would be exploring Sienna, which is a must do for every Tuscan
traveller. (Car sounds, clicks, tyres screeching, Horns beeping) On the way to Siena, we made a brief stop
at my new favourite Italian word, Monteriggioni. Its main attraction is this medieval wall
which circled the entire commune and offered up some more stunning views. The couple of Euros it costs to ascend the
wall also includes what might goes down in history as the quaintest museum in the world. Containing 4 rooms, the museum allows the
chance to step back to an age gone by when people wanted to take back control and make
Tuscany great again. Whilst you only need a couple of hours in
Monteriggioni, its unique enough to warrant a visit if you are in the area. As you would expect, we ended our time here,
eating too many carbs. (Car sounds, clicks, tyres screeching, Horns beeping) (UPBEAT JAZZ MUSIC) To help anyone who is planning a Tuscany driving
holiday I have a very important message for you: Parking anywhere near a populated zone
in Tuscany is a big fat pain in the ****hole. Looking back on the footage we have from this
trip, I really wish we had captured the stress, pain, and anxiety it takes to find a suitable
resting place for your temporary vehicle. Instead, lets show you some tranquil shots
taken of better times whilst I explain. First of all, coming from merry ol’ England,
the gear stick being on my right hand side kind of made me wish we’d have got automatic
transmission. Second, Italian drivers either just know EVERY
single road by Osmosis, or they are born with the innate ability to see round corners. I can’t tell you how many times I crept
around a bend while a 10 foot wide HGV came at me, almost in a post Brexit outrage. Yet, Italian drivers seem quite happy taking
this bend, at great speed, in the middle of the road, without any consequence. But mainly, its that there are almost never
any available parking spaces where you want them to be: Remember San Gimignano? 30 minutes to find a space. Siena? 20 minutes. Along with a spot of driving the wrong way
down a one way street. Great times. Usually the solution was parking somewhere
a good walk away, but all I’m saying, is work that INTO your schedule or take a good
look at all possible parking options before you start driving… And just be prepared from an expectation point
of view and all will be well. With that mind, following a tip off from,
the internet, we were super ready for some Florence parking action. We parked near the Co-Op of all places, situated
right in front of my new favourite Italian words the Nenni – Torregalli Tram stop, making
the journey into central Florence a breeze. I’ve linked a Trip Advisor discussion about
this below. The tram takes around 15 minutes and gives
a nice view as you cross the Arno River arriving at Alammani Station. (UPBEAT MUSIC) Florence is the capital city of the Tuscany
region and is considered the birth place of the Renaissance. Packed with cathedrals, town squares, a bustling
energy, magnificent architecture, shopping, culture, museums and much more, you could
easily spend days here. For us, we were more than happy to wander
the streets aimlessly and see where we ended up (SAT NAV: In 200 meters, your destination is on the right.) If you’re going to Tuscany for more than
a few days, I would really recommend splitting your hotels over 2 locations. By the last few days of the trip we did feel
stuck to one area, without wanting to endure 10 hours of round trip driving. Some of the best highlights in the last few
days included the time we visited Volterre, a medium sized town, with plenty of shops
and climbable high towers with rewarding views. Or the time we visited the nearby tiny town
in Casole D’elsa. A picture postcard collection of sunny streets
and alleyways. Or even the time we actually listened to some
advice given to us during our stay, and we drove all the way to the “coastal town”
of Livorno. We heard canals and thought Venice. But this video here literally is the only
nice shot taken after this 3 hour journey. Not wanting to be beaten, having got all the
way to the west coast, we took the scenic drive south to Cecina. Here, we found a calm, quiet area where trees
and water and beach and rocks all combined for a relaxing break in the afternoon. Then, of course, throughout all this, there
were all the times we enjoyed the amazing Italian food. Finally, on our last day, we had a few hours
to spare before boarding our flight. After dropping off the car at the airport,
the Pisa Mover takes you to a 30 minute walk way from the Leaning Tower itself. Due to the time constraints we had, we pretty
much made a bee line towards the famous landmark but I reckon you couldn’t go far wrong spending
a whole day here. If we had the luxury of time, I would have
enjoyed heading inside the tower to feel the slant under my own feet. Still, the Leaning Tower of Pisa itself is
a great sight to behold. Even after seeing so many photos of it, witnessing
that iconic lean with your own eyes is really impressive and was a great way for us to round
of another Suitcase Monkey adventure. If you’ve enjoyed this vlog, you really
will be doing us a big favour by liking this video, along with subscribing for all future
trips and clicking that notification bell as we maybe only post once a month on average. In the meantime, why not watch our recent
travels to Rome, Japan, Kenya and Marrakesh to name a few. And keep up to date with all the behind the
scenes stuff on Facebook, Instagram and Twitter. Thanks for watching Suitcase Monkey.


Ina Austria Galo

Nov 11, 2017, 1:51 pm Reply

I just enjoy watching your videos. You can visit Philippines next. 🙂 Check out Boracay, Palawan and Cebu.


Nov 11, 2017, 9:45 am Reply

"Pisa, when never before has subsidence been such a celebrated occurrence."
That is a phenomenal line and totally English of you.

Robert Lamas

Jan 1, 2018, 6:23 pm Reply

Nice job bro, keep it up

Life of Brighton

Jan 1, 2018, 7:27 pm Reply

Hi Paul. Love your editing, that's hard work! My daughter and I have a channel and as someone who spends a lot of time editing I had a couple q's. I also use FCPX and love it. 1. your intro, how'd you make it, any special software? 2. Music. I mostly use Kevin MacLeod. Where do you source your great music? Are you monetized? 3. How did you manage the hand drawing on the italy map? I'm creating a video now on the fastest way to Pandora's Flight of Passage, without the long waits, thus the map question. 4 Sound FX source? I find stuff free online but find the libraries lacking what i need often. Thanks for any help, and again amazing work!


Feb 2, 2018, 10:24 am Reply

That was really helpful and entertaining presented. I am planning a few-days-trip to Tuscany in September this year, being on my own and looked for some recommendations. Since I spent many years ago a university semester in Siena, I would like this time so see some more spots in the countryside. So, considering a temporary car and take maybe two different hotels, might be a good way to choose. Mabye, to safe money for food and other things to see, I might take an unexpensive overnight accomodation somwhere in the countryside but still looking for addresses. 
Anyway, thanks for that nice video.


Feb 2, 2018, 8:32 pm Reply

Oh my God, Monteriggioni's museum is probably the most embarassing museum that we have in Italy! It worths the visit just because it's included in the ticket ! 😀 It is so useless and awkward that actually becomes an essential stop! The dummies…Jesus…pure uneasiness! 😀
"Pisa, when never before has subsidence been such a celebrated occurrence." And with this sentence I subscribed!

Hector Nunez

Feb 2, 2018, 8:38 pm Reply

Awesome video!!

canadian cpap supply

Feb 2, 2018, 3:56 pm Reply

which two regions in Tuscany do you recommend staying overnight ?


Mar 3, 2018, 2:39 am Reply

love your editing so much!! check out my videos to siena as well!!

Suitcase Monkey

Mar 3, 2018, 1:50 pm Reply

Please support us by giving this video a big LIKE! It really helps us and is appreciated. I post around every 6 weeks so please enjoy our back catalogue of travels until the next movie, SUBSCRIBE above ? and hit the NOTIFICATION BELL to become part of our Notification squad and not miss out when we post something new! (I won't Spam you!)

Rosbelys Grullon

Apr 4, 2018, 1:18 pm Reply

Perfect vlog just what I needed before going to Tuscany

Stephanie Ortiz-Minami

Apr 4, 2018, 5:40 pm Reply

How was driving in Italy? We are going in June. Flying into Naples from Amsterdam and want to explore Pompeii, Amalfi, Coast and then head to Rome. I've read a lot about car break-ins and attempted car jackings at red lights. Is this accurate? Thank you!

Emmy B

Apr 4, 2018, 10:37 pm Reply

Best video I've seen on visiting the region. Thank you!

ECJ Vlogs

Apr 4, 2018, 10:59 pm Reply

Thanks for all the tips. I like how you give tips to help viewers by giving us the good and the bad on each places. Rather than making everything look good and perfect you give us a good idea of what to expect and help us save time incase we visit these places. Thank you and i hope you channel blows up as it will help alot of travellers out there.


May 5, 2018, 11:49 am Reply

Wonderful video!!! 🙂

Lala Sloney

May 5, 2018, 12:11 am Reply

LOVE THIS ! I miss it so much ! Check my Italy vlog out too !! ????


Jul 7, 2018, 11:54 am Reply

This is such a helpful video! Thank you!

Shashank Shrivastava

Jul 7, 2018, 3:14 pm Reply

I am hungry now?

Miguel G.

Jul 7, 2018, 12:35 am Reply

Yes, that was “a” statue of David but not “the” Statue of David. It might have been useful to clarify that. And who would pick up their wine glass like that?

Gvøðny Miriam Gunnarsson

Aug 8, 2018, 2:29 pm Reply

This was very helpful, thank you! 🙂

ice la honk

Aug 8, 2018, 11:32 pm Reply

pretty cool except that bit about 'driving drunk, without a care in the world'. thats pretty appalling

peter barber

Aug 8, 2018, 11:26 am Reply

finally a real travel vlog without basic girls showing off their shopping and dresses, subbed and liked great content 🙂

Jarinya Sriprayoon

Aug 8, 2018, 4:39 pm Reply

Very nice and informatove clip
How long did you spend for this whole trip?

The Cuban

Sep 9, 2018, 7:19 pm Reply

was your trip in November? I wonder if the end of November or December is a good time in regard to the weather conditions to visit the area.

Jenny Marie Molina

Sep 9, 2018, 11:55 am Reply

I loved your Video and your humour. New subbie ?

Niamh Leonard

Sep 9, 2018, 1:39 pm Reply


Low Waste Oasis

Sep 9, 2018, 5:20 pm Reply

is this friggin' rick Steve's Europe????


Sep 9, 2018, 5:26 pm Reply

If you visit Volterra, pay a visit to the Etruscan museum.


Oct 10, 2018, 4:39 pm Reply

Hey, everytime I drive to Florence I also park at the Coop and take the "tramvia"! Smart move & good tip. They also sell super cheap Daily Family tickets for max 4 persons, good all day for the tram and buses too.

School Developers

Oct 10, 2018, 2:08 am Reply

horrible song . . . had tostop watching.

Mr Gunslinger

Oct 10, 2018, 8:55 pm Reply

THe parking is 100% you fault. We never had any problem. Use gps and local forums. Also if you are just stopping for 1 hour, do what every brainy tourist do…stop in a shopping center parking lot.

Alessandro M

Oct 10, 2018, 6:22 pm Reply

Actually compared to what you eat in AngloSaxon countries, the Tuscan cuisine should make you lose weight because it's far more healthy.

Michele Matthews

Nov 11, 2018, 2:41 pm Reply

Very helpful!


Nov 11, 2018, 8:39 am Reply

What time of the year is this video shot? Does anyone know?


Nov 11, 2018, 7:37 pm Reply

The British are always the best at explaining things.

Anurag Priyadarshi

Nov 11, 2018, 10:11 am Reply

I really loved the fact that you gave candid review with tips. You clearly expressed what you did NOT like. This honesty is missing in most travel blogs/vlogs. Most of them just praise every darn place… Liked and Subbed :)… looking for more reviews with tips.

Guy Werbrouck

Dec 12, 2018, 6:53 pm Reply

Trouble finding a parking spot? Well, what would you expect in this heavily touristic region! Is it any easier to find one in London or Manchester? As for the driving, frankly, the Italians drive quite civilized and mostly abide by the speed limits. I've travelled in Tuscany by car countless times during the last 20 to 25 years, never had the feeling it was scary by any means! So, sorry, but a lot of BS here, although your videos are quite nice overall!

Gaming God

Dec 12, 2018, 11:53 pm Reply

Don't drive in Italy, the government are scumbags. They have cameras all over, and they specifically go after rental cars once verified. What this means if that you can be driving with the speed of traffic, and no one else would get a ticket, except non residents like yourself that are driving a rental car.

In the end, do what you want, research as much as you want, but I guarantee that if you drive in Italy for at least a week and a half, you're getting a ticket for sure, because that's the way the Italian Government has it setup, they collect money from tourists to fund their failing economy….

That being said, it still is one of the most beautiful countries in the world, so if you CAN afford $250 (per ticket) average tickets, then by all means, drive and enjoy….

CrisMelo DotCom

Dec 12, 2018, 4:37 pm Reply

When in Europe, maybe don't say "the whole city just reaks" lol


Jan 1, 2019, 1:16 am Reply

You are my new favourite channel, thanks for all the great content and charming personality of course.!!

D Walker

Jan 1, 2019, 5:58 pm Reply

Beautiful And informative as always thank you


Jan 1, 2019, 2:20 am Reply

Very well made video ?. The places you went are all quite away from each other like Malta to Tuscany to Greece. How do you manage to travel so much , yet staying at good properties?

Jamila Parvez

Jan 1, 2019, 6:48 am Reply

It's very beautiful lovely place my grandson is studying in florance I have bee twice here

Jamila Parvez

Jan 1, 2019, 6:49 am Reply

Lovely beautiful place


Jan 1, 2019, 7:21 pm Reply

Use some tuscan music/ classic italian music.

Teodor Peníze

Jan 1, 2019, 2:28 am Reply

inspiring, thank you 😉


Feb 2, 2019, 4:11 pm Reply

Thank you so much for this wonderful video. Incredibly helpful for our trip to the Tuscan countryside

Fiordalina Rodriguez

Feb 2, 2019, 3:57 am Reply

Precious nature and good food everything place god bless you


Feb 2, 2019, 1:11 pm Reply

Take a train or bus. Hop on or off to see the countryside in between your destination towns.

Mr. McPhee

Feb 2, 2019, 9:30 pm Reply

Lots of great stuff in a short amount of time. You've a good eye for composing within the frame and for color and use of natural lighting. Because there's so much to see in your quality cityscapes, panoramas and food, may I suggest leaving 1 second more in those scenes. I had to stop the video a few times for all that was there to see. Still 6 days in one video, all in all, quite worthy.

Neha Rai

Feb 2, 2019, 2:21 pm Reply

What time of year( month) did you go there? Thanks


Feb 2, 2019, 8:09 pm Reply

That statue of David you showed is a copy not the original Michelangelo.

Cristina Pintucci

Feb 2, 2019, 12:04 pm Reply

As a girl born and raised in Florence and the hills surrounding it (but now living in beautiful Gent, Belgium), I just adored the description of Italian driving customs, so true. I'm a very diligent driver here in Belgium, but my Italian blood never fails to bring back my killing driving skills every time I set foot in my home country

Welcome 2 Prato

Feb 2, 2019, 1:14 pm Reply



Mar 3, 2019, 6:27 pm Reply

My Tuscany ❤


Mar 3, 2019, 10:29 am Reply

Would be a great video without the annoying loud soundtrack!

Favian Mayora

Mar 3, 2019, 12:57 am Reply

Was thinking about renting a car there , is it worth It or should I just do trains? I’m doing Rome, Florence Verona and Venice

Aliaksandr Anikovich

Mar 3, 2019, 1:55 pm Reply

very good video. A good overview about Italy. Thank you.

i’m cool

Mar 3, 2019, 5:26 am Reply

I want to go there because its so pretty but also the food looks good

Snowbirds Mexico

Mar 3, 2019, 12:06 am Reply

Europecar – did they rip you off when you arrived? Some car rental places do that and we would like to rent a car but i think it can get a little pricey?

Marney Cohen

Mar 3, 2019, 7:38 pm Reply

Really great video….My daughter and me are going we have never been to Italy or Europe we don't know where to start, driving looks fun but not so sure about those crazy Italian drivers. 🙂 …Tuscany looks beautiful and Volterra…my daughter loves to shop…me I like the wine!

Alba Nasoni

Mar 3, 2019, 1:10 am Reply

Only 20 minutes to park in Siena? You have been lucky my friend! =D

Cinque Terra

Mar 3, 2019, 5:01 am Reply

Great but annoying music makes it unwatchable.

LuvaPlays HD

Apr 4, 2019, 9:19 pm Reply

I am so stoned rn and this is the best shit i‘ve ever seen #lowkey


Apr 4, 2019, 2:26 pm Reply

"Make Tuscany great again" ha ha 🙂

Mundher Al.Askari

Apr 4, 2019, 2:37 pm Reply

Awesome vlog keep on traveling ?

Jan lee Lee Jan

May 5, 2019, 11:45 am Reply

Rick Steves reminds me of being here in his show entitled "Best of Europe". ?

Allan B

May 5, 2019, 9:23 pm Reply

One of the best travel videos I have ever seen on YouTube. Slick, on point, creative, informative and very entertaining. Wish all travel vloggers could see this.

Richard Perkins

May 5, 2019, 1:55 pm Reply

Nice production and great choice of music. Great sense of humor.

Natalie Hadweh

May 5, 2019, 6:55 am Reply

How long did you stay in Florence?

Roger Manley

May 5, 2019, 1:19 am Reply

Enjoyed your video! I didn't visit Sienna when I was in Tuscany; I will have to return;)


Jun 6, 2019, 10:22 am Reply

Great video and very informative. Thanks!???

Si Vis Pacem Para Bellum

Jun 6, 2019, 12:12 pm Reply

Pizza isn't a Tuscan thing. If you'd eat real Tuscan recipes you would not gain weight on the opposite. Tuscan cuisine is very healty.

fahad ghaib

Jun 6, 2019, 6:41 am Reply

do you reccomend driving from Madrid, barcelona , cannes , milan, venice, rome ? or its better to take flights or trains ? thanks !

Smug Smugly

Jun 6, 2019, 5:19 pm Reply

So are you telling me there's not one house to rent in all of Tuscany?

Pearl Soriano

Jul 7, 2019, 2:05 am Reply

Where did you have the best mashed potatoes at?

Ferry Anolin

Jul 7, 2019, 5:27 am Reply

We had a tour of Siena, San Gimignano and Pisa

Joan Lynch

Jul 7, 2019, 6:45 pm Reply

It is so beautiful there, I really want to go!!

Dina Vitullo

Jul 7, 2019, 7:46 pm Reply

Firenze è una bella città dal punto di vista artistico. Ma se si considera la città per il clima la viabilita e il traffico le strade rotte l inquinamento la mancanza della qualità della vita per le famiglie È UNA VERA CITTÀ DI MERDA.

Plan C

Jul 7, 2019, 3:38 pm Reply

Very nice video. Did you really do this with an iPhone only ??


Jul 7, 2019, 7:41 pm Reply

Sangminano in my beautiful town

Athulya Mohan

Jul 7, 2019, 11:05 am Reply

Love your vlogs ❤️


Jul 7, 2019, 1:54 pm Reply

Awesome video! I enjoyed it, thankyou:)

Ga Young Yang

Aug 8, 2019, 12:00 am Reply


Baturay Önbaş

Aug 8, 2019, 8:08 am Reply

Great video! Informative & funny. Thank you very much for the tips!

Crna Puma

Aug 8, 2019, 7:05 pm Reply

Video is good.Music very bad for this video

Ferry Anolin

Aug 8, 2019, 12:51 am Reply

Had a Tuscany tour. Loved the lunch at a winery!

Becky Culbert

Aug 8, 2019, 3:41 am Reply

Very informative. Great info for visiting the Tuscany region, as I will be doing in mid-September. Thanks! I checked out the hotel you mentioned. Unfortunately, no vacancies

Jean-Marc Boussefa

Aug 8, 2019, 4:38 pm Reply

nice video, however there's much more than pizza and pasta in Tuscany

Daniela Rigutini

Aug 8, 2019, 9:03 am Reply

♥️??Toscana…meravigliosa..cibo ottimo..??

Ivan Motta

Aug 8, 2019, 10:18 am Reply

Que merda de lugar é esse chamado de Tuscany ?? Só conheço a Toscana.

Nicole Fanz

Aug 8, 2019, 12:10 pm Reply

man you missed LIVORNO my city! amazing genuine sea-city on the west side coast from 15minutes (by train) from the famous PISA. in Livorno you 'll find fabulous rock coast called calignaia were the landscape is breathtaking, terrazza mascagni plus a district called "venezia". You have to tried the no-commercial tuscany! our proud food? cinque e cinque, cacciucco, baccalà alla livornese.

craig hanlen

Aug 8, 2019, 12:02 pm Reply

Great video, thanks

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