4.9/5 rating on Google
Statutory insurance protects you
countryFlags/CZWe are a Czech company
We have your back 24/7
Top Czech media write about us
32,000 followers on Instagram
Show more
4.9/5 rating on Google
Statutory insurance protects you
countryFlags/CZWe are a Czech company
We have your back 24/7
Top Czech media write about us
32,000 followers on Instagram
More
From
Where
Where
Worldee logo
From
Where
Where

The Heart of Tuscany (Florence, Siena and Montalcino) - Medieval Towns, Wines and Landscapes

Worldee logo
From
Where
Where
common/star-emptycommon/star-emptycommon/star-emptycommon/star-emptycommon/star-empty
common/star-filledcommon/star-filledcommon/star-filledcommon/star-filledcommon/star-filled
4.6/ 5
(WorldeeAccommodationPlaces)

The adventure awaits

custom/phone_filled
On my own
without a group, at your own pace
custom/calendar_filled
6 Days
(5 Nights)
custom/location_filled
23 places
visited

Experience Tuscany as you know it from postcards and photographs. Discover the rolling landscape with olive groves and groups of cypresses, stroll through the narrow stone streets of hilltop towns, immerse yourself in hot thermal springs that travel agencies won't take you to. Visit Montepulciano, named the friendliest city in the world by the Time Out travel website. And taste some of the best wines this land has produced: the sparkling Brunello di Montalcino and Nobile di Montepulciano (you'll gladly forget about the Chianti in straw-covered bottles for tourists :-)). And as an added bonus, Siena: a Renaissance pearl of Tuscany, somewhat unfairly in the shadow of the more famous Florence. 

Experience Tuscany as you know it from postcards and photographs. Discover the rolling landscape with olive groves and groups of cypresses, stroll through the narrow stone streets of hilltop towns, immerse yourself in hot thermal springs that travel agencies won't take you to. Visit Montepulciano, named the friendliest city in the world by the Time Out travel website. And taste some of the best wines this land has produced: the sparkling Brunello di Montalcino and Nobile di Montepulciano (you'll gladly forget about the Chianti in straw-covered bottles for tourists :-)). And as an added bonus, Siena: a Renaissance pearl of Tuscany, somewhat unfairly in the shadow of the more famous Florence. 

Included in the price
included
ItineraryPrepared by someone who has actually been to the destination.
Accommodation
Flights
Car
Accommodation
Flights
Car
In-app guideGuides you day by day. Important documents, audio guide, and navigation all in one place.
from11 370 Kč
/ person
Selected date
1. - 6. 11. 20265 Nights
Change date


Total trip price
22 740 Kč
for 2 people
Deposit
6 708 Kč
Your money is protected by our statutory insurance.

Deposit

6 708 Kč
2 people
1. - 6. 11. 2026
Total trip price:22 740 Kč
Worldee Guarantee
Best price guarantee
Option to cancel or modify
100% Satisfaction Guarantee
24/7 Support
Secure payment via Stripe:
custom/visa_chipcustom/mastercard_chipcustom/apple_pay_chipcustom/google_pay_chip

Your itinerary - Easy to personalize
included

Alice
Alice created the itinerary based on personal experience to help you enjoy the trip to the fullest.
No unnecessary transfers
Well-organized days
Top spots and hidden gems
6 days
9 places
Road trip
Worldee logo
The Heart of Tuscany (Florence, Siena and Montalcino) - Medieval Towns, Wines and Landscapes
Day 1–3 / 6
1

Day 1
Florence, the cradle of the Renaissance

1 place
14 km(41 min)

After landing at Florence Airport, pick up your reserved car (according to the instructions you will receive before departure). This will give you freedom of movement and allow you to reach places less accessible by public transport. The program depends on your arrival time. If you arrive in the evening, check in and have a seat in one of the countless bars, either near your hotel or perhaps in Piazza della Signoria with a breathtaking view of Palazzo Vecchio. If you have more time, I have prepared a walking tour of the most important monuments of Florence, where you can admire the palaces, churches and squares of this Renaissance jewel of Tuscany.

2

Day 2
Siena and the most beautiful Italian square

1 place
144 km(2 h 05 min)

Head south to your destination, Montepulciano, the "friendliest city in the world". Before you get there, stop in Siena, which would be a shame to miss. You can easily spend several hours in this historical gem and still have something to admire. Have lunch in one of the many trattorias and then head to Montepulciano, where you will stay. You will have the whole next day for the city, but if you have the time and inclination, head out in the evening to the narrow streets surrounded by stone palaces and taste some of the excellent wines offered here at every turn.

3

Day 3
The friendliest city in the world and wine cellars

2 places
18 km(31 min)

You'll dedicate this day to exploring the town where you're staying. It's sure to win you over with its authentic atmosphere. And not just that! The rolling hills, vineyards, and the paths between them are not only a feast for the eyes but also invite you to take a short walk. If you have the time and inclination, put on your shoes and head along the dirt roads towards Montefollonico. You don't have to go all the way there, after all, it's almost eight kilometers, just a short distance is enough to enjoy this beautiful landscape up close. 

Accommodation where you'll rest easy
included

5 Nights
2 accommodations
Accommodation for night 1
Recommended
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
Hotel Dali
Booking.com8.7 / 10
Google4.2 / 5
No food
1 Night
Central location: Hotel Dali accommodation in Florence offers a central base with the Santa Maria del Fiore Cathedral a 4-minute walk away, Piazza della Signoria 700 meters away and the Uffizi Gallery less than 1 km from the accommodation. Comfortable accommodation: Rooms are equipped with air conditioning, free WiFi, a desk and a private bathroom with free toiletries. Additional amenities include a kitchenette, washing machine and sofa bed. Practical facilities: Guests can take advantage of free WiFi, a lift, daily cleaning service, family rooms and luggage storage. Paid parking is available off-site. Nearby attractions: The hotel is located 12 km from Florence Airport and close to the ice rink. Other attractions include Piazza del Duomo di Firenze and the Accademia Gallery.
1-bedroom apartment
Accommodation for night 2 - 5
Recommended
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
La casina di Iole
Booking.com9.1 / 10
No food
4 Nights
La casina di Iole is located in Montepulciano. Mount Amiata is 48 km away, Bagno Vignoni is 21 km away and Bagni San Filippo is 29 km away. This air-conditioned apartment has 1 bedroom, a fully equipped kitchenette and 1 bathroom. The apartment also has a bathroom. Perugia San Francesco d'Assisi – Umbria International Airport is 76 km from the property.
1-bedroom apartment

Flights that get you there
included

1 h 35 min
No transfer
Sun 1. 11. 20:5522:30
PRG
FLR
PragueFlorence
1 h 35 min
No transfer
Fri 6. 11. 06:1507:50
FLR
PRG
FlorencePrague

The car you'll be driving
included

Car for day 1 - 6
car
Small car
Toyota Aygo X or similar
1 driver
4 seats
Automatic
Credit card required
Basic coverage
No extras

In-app guide
included

common/cursor
NavigationTo all places in the itinerary
common/headphones
Audio guideWith stories of each location
common/document
Documents in one placeAll your tickets and vouchers

Select your travel group

Choose the dates that work best for you

Includes:
Itinerary
Flights
Accommodation
Car
In-app guide

Just pay a deposit of 6 708 Kč today and pay the balance by 2. 10. 2026

Worldee Guarantee
Best price guarantee
Option to cancel or modify
100% Satisfaction Guarantee
24/7 Support
We have a 4.9/5 ratingRead over a thousand reviews from our clients on Worldee, Google, Mapy.cz and Slevomatu.
You are protected by statutory insuranceWe have statutory insurance against insolvency valid within the EU. The insurer is Euroins, insurance policy number 03700100006396.
countryFlags/CZ
We are a Czech companyWorldee s.r.o. was founded in Olomouc in 2020. Our founder is Tomáš Zapletal.
Leading Czech media write about usRead articles on Seznam Zprávy, Forbes, iDNES.cz, Deník, Czechcrunch.
Tens of thousands of people follow usOver 32,000 people follow us on Instagramu and over 8,000 on Facebook. See what is new with us. Our app has been downloaded by 120,000 people.
We have our clients' backs 24/7If something goes wrong on your trip, our customer support in Olomouc is available 24/7. A real person, no AI, no automation.

Overall trip rating

4.6/5
common/star-emptycommon/star-emptycommon/star-emptycommon/star-emptycommon/star-empty
common/star-filledcommon/star-filledcommon/star-filledcommon/star-filledcommon/star-filled
A summary of experiences from travelers who completed this trip and the quality of the offerings included in the journey.
Worldee
4.9/5
Accommodation
4.4/5
Places
4.6/5

Trip creator

Alice
Verified traveler
Alice
3 trips on Worldee
Guaranteed itinerary quality

You travel with confidence

custom/location_filled
Itineraries verified by expertsEvery trip is reviewed so your experience is flawless.
common/document
You are covered by statutory insuranceWe carry statutory insolvency insurance valid across the EU.
common/headphones
We have your back 24/7Our customer support is available to you 24/7.
4.9/5 rating on Google
Statutory insurance protects you
countryFlags/CZWe are a Czech company
We have your back 24/7
Top Czech media write about us
32,000 followers on Instagram
Show more
4.9/5 rating on Google
Statutory insurance protects you
countryFlags/CZWe are a Czech company
We have your back 24/7
Top Czech media write about us
32,000 followers on Instagram
More

The Heart of Tuscany (Florence, Siena and Montalcino) - Medieval Towns, Wines and Landscapes

Worldee logo
From
Where
Where
common/star-emptycommon/star-emptycommon/star-emptycommon/star-emptycommon/star-empty
common/star-filledcommon/star-filledcommon/star-filledcommon/star-filledcommon/star-filled
4.6/ 5
(WorldeeAccommodationPlaces)

The adventure awaits

custom/phone_filled
On my own
without a group, at your own pace
custom/calendar_filled
6 Days
(5 Nights)
custom/location_filled
23 places
visited

Experience Tuscany as you know it from postcards and photographs. Discover the rolling landscape with olive groves and groups of cypresses, stroll through the narrow stone streets of hilltop towns, immerse yourself in hot thermal springs that travel agencies won't take you to. Visit Montepulciano, named the friendliest city in the world by the Time Out travel website. And taste some of the best wines this land has produced: the sparkling Brunello di Montalcino and Nobile di Montepulciano (you'll gladly forget about the Chianti in straw-covered bottles for tourists :-)). And as an added bonus, Siena: a Renaissance pearl of Tuscany, somewhat unfairly in the shadow of the more famous Florence. 

Experience Tuscany as you know it from postcards and photographs. Discover the rolling landscape with olive groves and groups of cypresses, stroll through the narrow stone streets of hilltop towns, immerse yourself in hot thermal springs that travel agencies won't take you to. Visit Montepulciano, named the friendliest city in the world by the Time Out travel website. And taste some of the best wines this land has produced: the sparkling Brunello di Montalcino and Nobile di Montepulciano (you'll gladly forget about the Chianti in straw-covered bottles for tourists :-)). And as an added bonus, Siena: a Renaissance pearl of Tuscany, somewhat unfairly in the shadow of the more famous Florence. 

Included in the price
included
ItineraryPrepared by someone who has actually been to the destination.
Accommodation
Flights
Car
Accommodation
Flights
Car
In-app guideGuides you day by day. Important documents, audio guide, and navigation all in one place.
from11 370 Kč
/ person
Selected date
1. - 6. 11. 20265 Nights
Change date


Total trip price
22 740 Kč
for 2 people
Deposit
6 708 Kč
Your money is protected by our statutory insurance.

Deposit

6 708 Kč
2 people
1. - 6. 11. 2026
Total trip price:22 740 Kč
Worldee Guarantee
Best price guarantee
Option to cancel or modify
100% Satisfaction Guarantee
24/7 Support
Secure payment via Stripe:
custom/visa_chipcustom/mastercard_chipcustom/apple_pay_chipcustom/google_pay_chip

Your itinerary - Easy to personalize
included

Alice
Alice created the itinerary based on personal experience to help you enjoy the trip to the fullest.
No unnecessary transfers
Well-organized days
Top spots and hidden gems
6 days
9 places
Road trip
Worldee logo
The Heart of Tuscany (Florence, Siena and Montalcino) - Medieval Towns, Wines and Landscapes
Day 1–3 / 6
1

Day 1
Florence, the cradle of the Renaissance

1 place
14 km(41 min)

After landing at Florence Airport, pick up your reserved car (according to the instructions you will receive before departure). This will give you freedom of movement and allow you to reach places less accessible by public transport. The program depends on your arrival time. If you arrive in the evening, check in and have a seat in one of the countless bars, either near your hotel or perhaps in Piazza della Signoria with a breathtaking view of Palazzo Vecchio. If you have more time, I have prepared a walking tour of the most important monuments of Florence, where you can admire the palaces, churches and squares of this Renaissance jewel of Tuscany.

2

Day 2
Siena and the most beautiful Italian square

1 place
144 km(2 h 05 min)

Head south to your destination, Montepulciano, the "friendliest city in the world". Before you get there, stop in Siena, which would be a shame to miss. You can easily spend several hours in this historical gem and still have something to admire. Have lunch in one of the many trattorias and then head to Montepulciano, where you will stay. You will have the whole next day for the city, but if you have the time and inclination, head out in the evening to the narrow streets surrounded by stone palaces and taste some of the excellent wines offered here at every turn.

3

Day 3
The friendliest city in the world and wine cellars

2 places
18 km(31 min)

You'll dedicate this day to exploring the town where you're staying. It's sure to win you over with its authentic atmosphere. And not just that! The rolling hills, vineyards, and the paths between them are not only a feast for the eyes but also invite you to take a short walk. If you have the time and inclination, put on your shoes and head along the dirt roads towards Montefollonico. You don't have to go all the way there, after all, it's almost eight kilometers, just a short distance is enough to enjoy this beautiful landscape up close. 

Accommodation where you'll rest easy
included

5 Nights
2 accommodations
Accommodation for night 1
Recommended
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
Hotel Dali
Booking.com8.7 / 10
Google4.2 / 5
No food
1 Night
Central location: Hotel Dali accommodation in Florence offers a central base with the Santa Maria del Fiore Cathedral a 4-minute walk away, Piazza della Signoria 700 meters away and the Uffizi Gallery less than 1 km from the accommodation. Comfortable accommodation: Rooms are equipped with air conditioning, free WiFi, a desk and a private bathroom with free toiletries. Additional amenities include a kitchenette, washing machine and sofa bed. Practical facilities: Guests can take advantage of free WiFi, a lift, daily cleaning service, family rooms and luggage storage. Paid parking is available off-site. Nearby attractions: The hotel is located 12 km from Florence Airport and close to the ice rink. Other attractions include Piazza del Duomo di Firenze and the Accademia Gallery.
1-bedroom apartment
Accommodation for night 2 - 5
Recommended
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
La casina di Iole
Booking.com9.1 / 10
No food
4 Nights
La casina di Iole is located in Montepulciano. Mount Amiata is 48 km away, Bagno Vignoni is 21 km away and Bagni San Filippo is 29 km away. This air-conditioned apartment has 1 bedroom, a fully equipped kitchenette and 1 bathroom. The apartment also has a bathroom. Perugia San Francesco d'Assisi – Umbria International Airport is 76 km from the property.
1-bedroom apartment

Flights that get you there
included

1 h 35 min
No transfer
Sun 1. 11. 20:5522:30
PRG
FLR
PragueFlorence
1 h 35 min
No transfer
Fri 6. 11. 06:1507:50
FLR
PRG
FlorencePrague

The car you'll be driving
included

Car for day 1 - 6
car
Small car
Toyota Aygo X or similar
1 driver
4 seats
Automatic
Credit card required
Basic coverage
No extras

In-app guide
included

common/cursor
NavigationTo all places in the itinerary
common/headphones
Audio guideWith stories of each location
common/document
Documents in one placeAll your tickets and vouchers

Select your travel group

Choose the dates that work best for you

Includes:
Itinerary
Flights
Accommodation
Car
In-app guide

Just pay a deposit of 6 708 Kč today and pay the balance by 2. 10. 2026

Worldee Guarantee
Best price guarantee
Option to cancel or modify
100% Satisfaction Guarantee
24/7 Support
We have a 4.9/5 ratingRead over a thousand reviews from our clients on Worldee, Google, Mapy.cz and Slevomatu.
You are protected by statutory insuranceWe have statutory insurance against insolvency valid within the EU. The insurer is Euroins, insurance policy number 03700100006396.
countryFlags/CZ
We are a Czech companyWorldee s.r.o. was founded in Olomouc in 2020. Our founder is Tomáš Zapletal.
Leading Czech media write about usRead articles on Seznam Zprávy, Forbes, iDNES.cz, Deník, Czechcrunch.
Tens of thousands of people follow usOver 32,000 people follow us on Instagramu and over 8,000 on Facebook. See what is new with us. Our app has been downloaded by 120,000 people.
We have our clients' backs 24/7If something goes wrong on your trip, our customer support in Olomouc is available 24/7. A real person, no AI, no automation.

Overall trip rating

4.6/5
common/star-emptycommon/star-emptycommon/star-emptycommon/star-emptycommon/star-empty
common/star-filledcommon/star-filledcommon/star-filledcommon/star-filledcommon/star-filled
A summary of experiences from travelers who completed this trip and the quality of the offerings included in the journey.
Worldee
4.9/5
Accommodation
4.4/5
Places
4.6/5

Trip creator

Alice
Verified traveler
Alice
3 trips on Worldee
Guaranteed itinerary quality

You travel with confidence

custom/location_filled
Itineraries verified by expertsEvery trip is reviewed so your experience is flawless.
common/document
You are covered by statutory insuranceWe carry statutory insolvency insurance valid across the EU.
common/headphones
We have your back 24/7Our customer support is available to you 24/7.
Price
from11 370 Kč
/ person