Tuscany – Renaissance Towns and Chianti Wine Country

Nature
The wow factor for nature - does it show nature at its best? Doesn't need to be the wildebeest migration or diving with hundreds of hammerheads. Rather make you pause as you realise just how awesome the natural world can be
7
Culture
How much does this experience showcase some of the better and finer things that us humans can offer? Sure, it can be ancient ruins and renaissance churches, but it can also be festivals or soaking up some of the great modern cities of the world
10
Fun factor/activity
Very simple - was it fun? This is usually linked in with doing some kind of activity - i mean, walking along some cliffs is nice, but paragliding from them, now that is fun. Its a vastly underrated factor in a truly great experience
6
Avoid the crowds
Big tour groups and being surrounded by loud fellow tourists can sap the life out of even the greatest of travel experiences. This score is to reflect just how much you can avoid this. But. . . The score also takes into account if the crowds actually add to the experience, such as with a party town or a bustling local market
5
World famous
How world famous is the experience?
10
unique
How hard is it to have a similar experience in other places round the world?
10
Overall TE Score
The overall travel experiences score:  fun factor + avoid the crowds + (best of nature or culture) + (best of world famous or unique). Then convert into a score out of 100
77 *What the scores mean and where do they come from
RANKING
How this travel experience ranks compared to all the other experiences on this site, based on the travel experience (te) score
71st/454
Top 20%
continent
Europe
country
Italy
Length of time
3-4 days
Typical daily price
This gives you a rough idea of the daily price based on 2 people travelling where they can split costs like accommodation. It excludes travel there and back, and factors in inflation the numbers in brackets show the price range for the full time of the experience (so not necessarily daily). It is a range to reflect different budget vs higher end
$210 (typically $120 - $300)
Time of year visited
September
Primary Tags
Click on any of the tags to see all travel experiences with the same tag
Christian site Old town Vineyards
All Tags
Bustling restaurants City Walls Driving Hilltop towns Local villages Museums Restaurant recommendations Romans UNESCO world heritage site Wine
Wow Factor
The wow factor reflects just how much you’re likely to say “wow”. As there’s a lot of experiences in the world, and a lot of wows, i’ve gone with a simple ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ to ⭐️ score, and a separate category for the truly "gash"
⭐⭐⭐⭐

Summary

Tuscany – Florence, Pisa, Sienna, Lucca, Chianti Wine Country, cypress-lined roads of the Val d’Orcia, stone-built hamlets surrounded by perfect countryside . . . they are all just such wow experiences and justify travel entries on their own (some do – see Two days in Florence, The Leaning Tower of Pisa and Sienna).  But, I’ve grouped them together because most people’s Tuscany visits are min 3 days / typically a week and naturally want to see it all.  Doing so makes Tuscany a truly world class experience . . . its only major downside is the sheer crowds, which especially for spots like Florence do take a bit of the gloss away and mean this wonderful place only just misses out on the top score of wow wow wow.

 

Tuscany - Renaissance Towns and Chianti Wine Country

 

Table of Contents

Highlights of Tuscany

Tuscany - #1 Florence's mega cultural attractions - the Duomo, its many art galleries and museums and, in particular, Michelangelo's David in the Piazza della Signoria (it's not just this one either, there are HEAPS of them there and all spectacular)

#1 Florence's mega cultural attractions - the Duomo, its many art galleries and museums and, in particular, Michelangelo's David in the Piazza della Signoria (it's not just this one either, there are HEAPS of them there and all spectacular)

Tuscany - #2 Sienna's Piazza del Campo - stunning (what an incredible experience it must be to be there for the horse racing)

#2 Sienna's Piazza del Campo - stunning (what an incredible experience it must be to be there for the horse racing)

Tuscany - #3 Staying in one of the many farmhouses in the Chianti wine country just south of Florence and enjoying good wine and food out in the sun

#3 Staying in one of the many farmhouses in the Chianti wine country just south of Florence and enjoying good wine and food out in the sun

Tuscany - #4 Driving through Val d'Orcia - a photographers dream.  Setting for Gladiator scenes, cypress-lined roads everywhere and finished off with pecorino cheese and lunch in Pienza.  It was terrible weather when we visited, hence the photo, but still beautiful spot

#4 Driving through Val d'Orcia - a photographers dream.  Setting for Gladiator scenes, cypress-lined roads everywhere and finished off with pecorino cheese and lunch in Pienza.  It was terrible weather when we visited, hence the photo, but still beautiful spot

Tuscany - #5 Exploring the Chianti Wine Country and tasting world-famous wine with a view across the glorious vineyards, in this case the Castello di Brolio

#5 Exploring the Chianti Wine Country and tasting world-famous wine with a view across the glorious vineyards, in this case the Castello di Brolio

Tuscany - #6 Lunch in the very unusual but stunning oval square of Piazza dell'Anfiteatro (I'd recommend L'Angolo Tondo) was wow

#6 Lunch in the very unusual but stunning oval square of Piazza dell'Anfiteatro (I'd recommend L'Angolo Tondo) was wow

Tuscany - #7 Pisa's Piazza dei Miracoli - not just the famous tower but also the gobsmackingly beautiful Cathedral di Santa Maria Assunta and Battistero di San Giovanni (the world’s largest baptistery)

#7 Pisa's Piazza dei Miracoli - not just the famous tower but also the gobsmackingly beautiful Cathedral di Santa Maria Assunta and Battistero di San Giovanni (the world’s largest baptistery)

Tuscany - #8 Getting lost in Sienna's higgledy piggledy lanes and wandering zig zag through its 17 historical districts called Contrade, each with their own proud flags and symbols

#8 Getting lost in Sienna's higgledy piggledy lanes and wandering zig zag through its 17 historical districts called Contrade, each with their own proud flags and symbols

Tuscany - #9 Wandering Florences' streets and bridges, in this case the world-famous Ponte Vecchio

#9 Wandering Florences' streets and bridges, in this case the world-famous Ponte Vecchio

Tuscany - #10 The views out across the Tuscany countryside from just about any of the towers in the main towns, in this case from Sienna's Palazzo delle Papesse

#10 The views out across the Tuscany countryside from just about any of the towers in the main towns, in this case from Sienna's Palazzo delle Papesse

Tuscany - #11 Wandering Lucca's so well-preserved medieval Old Town, surrounded by the city walls and looking up at the various towers littering the skyline

#11 Wandering Lucca's so well-preserved medieval Old Town, surrounded by the city walls and looking up at the various towers littering the skyline

Tuscany - #12 Craning your neck by so often looking up at, well . . . ridiculousness

#12 Craning your neck by so often looking up at, well . . . ridiculousness

Tuscany - #13 The little things, like noticing hoops on all the walls for the horses back in the day

#13 The little things, like noticing hoops on all the walls for the horses back in the day

Tuscany #14 The mosaics - again, I don't usually get that bothered by them, but in Tuscany they're genuinely captivating

#14 The mosaics - again, I don't usually get that bothered by them, but in Tuscany they're genuinely captivating

Tuscany The Cathedrals - I can get churched / templed out very quickly, but the 4 main Cathedrals in the 4 cities are just so wow that they arguably need an entry on their own. Utterly blown away. Cathedral #1 - Sienna's Duomo for the insane interior

The Cathedrals - I can get churched / templed out very quickly, but the 4 main Cathedrals in the 4 cities are just so wow that they arguably need an entry on their own. Utterly blown away. Cathedral #1 - Sienna's Duomo for the insane interior

Tuscany - Cathedral #2 - Florence's Cathedral of Santa Maria del Fiore for its facade, Giotto's Bell Tower, Baptistery and sheer size

Cathedral #2 - Florence's Cathedral of Santa Maria del Fiore for its facade, Giotto's Bell Tower, Baptistery and sheer size

Tuscany - Cathedral #3 - Pisa's Cathedral di Santa Maria Assunta and its incredible roof and surrounding paintings

Cathedral #3 - Pisa's Cathedral di Santa Maria Assunta and its incredible roof and surrounding paintings

Tuscany - Cathedral #4 - Lucca's Duomo di San Martino for the fascinating stories around the making of its facade

Cathedral #4 - Lucca's Duomo di San Martino for the fascinating stories around the making of its facade

Tuscany – what to prioritise for wow factor

 

  • Florence – a must, with sensationally famous items, but wow the crowds are silly.  Florence has 3 mega wow sites of the Duomo, the statues like Michelangelo’s David on Piazza della Signoria and the Ponte Vecchio – mind blown wow levels, sheer stunning.  But the sheer volume of crowds can diminish the whole experience.  I’ve been 3 times – winter midday, summer afternoon and even 7am summer morning – heaving everytime.  The other issue is that whilst it does have lots of small alleyways to get slightly lost, it misses the cute vibe of the other towns.  Is dirty (especially in the early morning when they are cleaning) and at times commercialised.  As I say – you’re not going to visit Tuscany without going to Florence and those 3 items are worth the visit alone, but I’ve now been 3 times and not in a rush to go back.  Wow Factor: ⭐️⭐️⭐️

 

  • Sienna – gobsmacked, stunning square and cuter than I expected.  Sienna is probably my favourite because it’s so higgledy piggledy with lanes going in all direction (compared to the more grid layout of the other towns) and just a generally more medieval feel to it – the reason for this is the plague hit Sienna which led to Florence winning their war and the collapse / evacuation of Sienna meant there were very few works done and, so, the city is well preserved.  The Piazza del Campo is stunning (what an incredible experience it must be to be there for the horse racing) and the Duomo has one of the most beautiful interiors of anything I’ve seen anywhere in the world.  Wow factor: ⭐️⭐️⭐️⭐️

 

  • Pisa – super famous, yes it is crowded but the grass square with the Tower, Cathedral and Baptistery are beautifully done.  The combination of the Leaning Tower, Cathedral di Santa Maria Assunta (gobsmackingly beautiful, even considering all the other gobsmackingly beautiful cathedrals in Italy), Battistero di San Giovanni (the world’s largest baptistery), the Camposanto Cemetery building with paintings and the lush green fields with old city walls surrounding make this 100% worth the visit.  Only need a couple of hours.  Wow Factor: ⭐️⭐️⭐️

 

  • Lucca – very cute and the Piazza dell’Anfiteatro is a gorgeous spot for lunch.   Lovely spot to walk around and a touch less busy than the other 3.  The simple walking tour (see photos) within the city walls is a nice one and lunch in the very unusual but stunning oval square of Piazza dell’Anfiteatro (I’d recommend L’Angolo Tondo) was wow.  If at a push though, you’d probably place this down the list compared to the other 3.  Wow Factor: ⭐️⭐️

 

  • Chianti wine country – some of the best wines in the world, stunning vineyard locations and quiet country.  We loved staying here and found just about everywhere we visited gorgeous.  Be sure to visit the Rinuccio 1180 restaurant and vineyard for big architecture, Castello di Brolio for the best views, and everywhere in between those two for the pretty countryside. Wow Factor: ⭐️⭐️

 

  • Val d’Orcia – a photographers dream.  We visited when raining and it was still beautiful.  Setting for Gladiator scenes, cypress-lined roads everywhere and finished off for the pecorino cheese and lunch in Pienza.  Really beautiful drive. Wow Factor: ⭐️⭐️

 

Tuscany – Travel Tips

 

  • How much time – can do in 3-4 days, but a week more civilised.  So two factors: 1.The distances between the places in Tuscany is really quite small at only 250km / 155miles or 4.5 hours of driving so see it all (see the basic google map in the photos for an idea); 2. Unless your a mega history buff or heavily into your renaissance art, you can get a touch bored of the cities after half a day or so – magical at first, for sure, but once you’ve seen the main square / main art, you’re often ready for the next place.  So it isn’t an exaggeration to suggest this can all be done in 3-4 days.  But that would be minimal chill time, especially in the wine country.

Total drive time for all across Tuscany and the 5 major sites: 5 hours

 

  • Base yourself in Florence or Chianti just south of Florence.  As the distances are so short, it makes most sense to base yourself in one place and do day trips, with Florence the most obvious place as you’ll most likely fly in there.   But, its daft busy and expensive and, if you do have a car, its so much nicer to aim for the wine country.  Full farm houses with 4 bedrooms in the vineyards of Chianti are less than €100 a night in areas such as near San Casciano in Val di Pesa and Barberino Val d’Elsa and only 30mins from Florence, plus you avoid the Florence traffic when travelling to the likes of Pisa / Sienna / Lucca etc, so the time balances itself out.

 

  • Have a look for events.  We arrived just after a series of very cool concerts and events, which Tuscany do a lot of (especially in the summer) and which would have been fab to combine with the visit.  Have a quick scan on Tuscany Events from Visit Tuscany.

 

  • Car – if just the cities, you don’t need a car and in fact it may be easier without one.   If you’re aiming for wine country and Val d’Orcia, get a car.

 

  • Context is everything – read up on all things Renaissance and Tuscany beforehand if you can.  It adds a whole new dimension if you can.

 

Experiences Nearby

The below map shows experiences nearby with a colour that reflect the Overall Score of those experiences

Other Incredible Regions to visit

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The Blue Mountains on a train from Sydney
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Exploring Northern Burma by boat and train from Myitkyina to Mandalay
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Bali – in and around Ubud
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Walking the Valley de Cocora, visiting the humming birds and soaking up Salento
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Driving through the White Towns of Parque Natural Sierra de Grazalema
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Summer days in Rural Provence
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Score Detail

The scores above are the real point of this site.

Over 20+ years and 100+ countries, I’ve tried to rank the world’s best travel experiences — from genuinely mind-blowing ⭐⭐⭐⭐⭐ to the properly gash.

Every one of the 500+ places on this site has both a Wow Factor rating and a more analytical Travel Experience (TE) score based on the things that actually make travel memorable.

If you're curious about the thinking behind it, head to the About page.

Otherwise, explore the map above or on the Home page and see which places truly deliver maximum wow.

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