Trip Type : Small Group Tour
Chianti Walking & Wine tour
Culinary & Wine Culture Chianti Walking & Wine package
Cultural Hiking Chianti Walking & Wine package

Chianti Walking & Wine

Exodus Travels Premier
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
4.6 . Excellent
99%
Travel Style: For those looking to maximize their sight seeing time. You thrive on a packed day’s schedule from 8 am to 6pm, with some (but limited) free time. Most activities and meals included. Full on
Physical Level: Regular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps. Moderate
Lodging Level: Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels. Value - 3 star
8 days
From: $ 1,399 $ 175 / day
Checking price

Overview

Highlights

  • Walk the classic rolling hills of Tuscany
  • Stay in a converted farmhouse
  • Enjoy the fabulous Chianti wines

Short Description

With its Renaissance cities, mediaeval villages and cypress-lined avenues snaking through vineyards, southern Tuscany is the perfect place for a relaxing guided walking holiday. Based at the tranquil Villa Casalta, on our tour we visit beautiful San Gimignano, the market town of Greve in Chianti, the UNESCO World Heritage Site of Siena and the magnificent city of Florence. During the week we sample several varieties of the world-renowned local Chianti and have the opportunity to learn more about Italian wine at the Wine School of Siena.Experience the magic of Italy in Tuscany

Small groups are usually defined as between 10 and 24 travelers, often less. If you're the kind of person who enjoys more intimate experiences and personal service this is a good choice. All else being equal you will pay a premium for this style vs a larger group tour.
Trip Type Small Group Tour
Off the beaten track trips will stretch your comfort zone. They don't always feature tourist highlights, but dive deeper into local life and culture.
Itinerary Focus Off the Beaten Path
Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Lodging Level Value - 3 star
Flights & Transport Only ground transport
Start City Castellina
End City Castellina

Destinations

Italy

Cities & Attractions

Florence

Activities

Culture Hiking

Age Requirement

18

No Single Supplement
See more

Trip Includes

  • All breakfasts, 5 dinners, 3 wine tastings
  • All accommodation 
  • All transport and listed activities
  • Tour leader throughout
  • Flights from London (if booking incl. flights)

Find your perfect trip
A vast selection of trips on every continent, for every style. Thousands of itineraries from hundreds of trusted travel companies.
Save time
Use simple search and comparison tools to easily find the best trip. Don't sweat the logistics -- travel providers plan for you.
Save money
Book directly with the operator. Find inclusive packages for the best value and get access to amazing deals.
Travel confidently
Read unbiased user reviews, pick the company that fits your style, and connect with them directly. No worries, just memories.

Itinerary

Flight Inclusive

Day 1 Fly to Pisa; transfer to Castellina in Chianti.

Fly to Pisa; transfer to Villa Casalta, 2kms from Castellina in Chinati (transfer approx. 1hr30mins).

Day 2 Visit mediaeval market town of Greve in Chianti and the hilltop village of Montefioralle; afternoon wine tasting in Castellina.

Today we head to the mediaeval market town of Greve in Chianti walking through a magnificent setting of olive groves and vineyards. On the way, we will stop in the fortified hilltop village of Montefioralle, considered the most ancient 'borgo' in Chianti. After lunch we enjoy a wine tasting in a local winery before heading back to our farmhouse for dinner.

Day 3 Walk to Radda in Chianti, the heart of the Chianti area

This morning we will set out for a local history walk to the heart of the Chianti area, covering the route from Villa Casalta to Radda in Chianti. We will take a walk through local woodlands where we can admire the so famous emerald vineyards valleys. In the afternoon we will have the chance to taste the much acclaimed Chianti Classico wine at a local winery.

Day 4 Travel to Siena and explore the stunning historic centre; learn about Tuscan and Italian wines at the Wine School.

After breakfast we make our way to the centre of Siena for a day exploring this fascinating city. We have time to visit the numerous museums and stunning Duomo and to relax in one of the many outdoor cafés in Piazza del Campo, home of the world famous Palio horse race. Please note that shoulders should be covered for entering the Duomo. You may also like to visit the many boutiques specializing in local products and cutting edge Italian fashion. In the afternoon we also have the opportunity to learn about Tuscan wines on a 1-hour fun interactive course at the Tuscan Wine School.

Day 5 Free day to visit other Chianti villages or relax by the pool.

Today is free to rest any tired legs at the poolside. Alternatively, your leader can advise on local Chianti wine tasting tours and cooking classes or offer assistance for unguided walks or daytrips.

Day 6 Discover the magnificent city of Florence, considered the birthplace of the Renaissance.

Our destination today is the magnificent city of Florence, the birthplace of the Italian Renaissance with an enormous wealth of historical sites, museums, galleries, churches and architectural delights. Most of the great artists, thinkers and builders from Renaissance history passed through or lived in Florence when it was under the rule of the Medici family, the most famous patrons of the 16th century. But Florence is not just a Renaissance showpiece: once you have had your fill of the historical trail there are many other things to see and do. The city has not ceased to be a centre of learning, and there is a university, many art and language schools and a large student population to liven up the café-bars, restaurants and nightclubs. There are also some great markets and chic boutiques. From April to July, Florence also holds one of Europe's major cultural events, a festival of opera and classical music called the Maggio Musicale Fiorentino. There are no guided tours organised for the day but there's an option to join one of the free walking tours in the morning. This will then leave you enough time to visit the Uffizi galleries. If you wish to do so we recommend that you prebook your ticket online to avoid lengthy queues. An ideal slot time would be around 2 pm. it can be earlier if you're not interested in joining the morning free walking tour. Tickets can be purchased through  https://webshop.b-ticket.com/webshop/webticket/eventlist?production=1 .  ">https://webshop.b-ticket.com/webshop/webticket/eventlist?production=1">h...

Day 7 Walk to picturesque San Gimignano with free time to explore Palazzo Comunale, Pinacoteca and Torre Grossa.

After a  transfer to the quaint hamlet of San Donato, we walk through the farm grounds following the pathway to Montauto and on up to the picturesque mediaeval town of San Gimignano. The walk is not long and should take approximately 3 hours. The afternoon is spent exploring this beautiful town including visits to the Palazzo Comunale, Pinacoteca and Torre Grossa and there is some free time to wander and soak up the atmosphere. 

Day 8 Transfer to Pisa; fly to London.

Transfer to Pisa; fly to London. Please note that at times, especially during summer months, the inbound flight can be late in the evening. In this instance you will have additional time to spend in Pisa. Leader will take care of all arrangements in terms of transport from/to the airport and the city centre and luggage storage. It may also happen that, for logistical reasons, on return we will have to be at the airport earlier than normally scheduled. This will mean a longer waiting time before checking in. 



Land Only

Day 1 Start Castellina in Chianti.

Start at Villa Casalta, our beautiful villa 2km from Castellina in Chianti. In the evening our guide will hold a welcome meeting to discuss the week ahead, give advice on the local area and answer any questions.

Day 2 Visit mediaeval market town of Greve in Chianti and the hilltop village of Montefioralle; afternoon wine tasting in Castellina.

Today we head to the mediaeval market town of Greve in Chianti walking through a magnificent setting of olive groves and vineyards. On the way, we will stop in the fortified hilltop village of Montefioralle, considered the most ancient 'borgo' in Chianti. After lunch we enjoy a wine tasting in a local winery before heading back to our farmhouse for dinner.

Day 3 Walk to Radda in Chianti, the heart of the Chianti area

This morning we will set out for a local history walk to the heart of the Chianti area, covering the route from Villa Casalta to Radda in Chianti. We will take a walk through local woodlands where we can admire the so famous emerald vineyards valleys. In the afternoon we will have the chance to taste the much acclaimed Chianti Classico wine at a local winery.

Day 4 Travel to Siena and explore the stunning historic centre; learn about Tuscan and Italian wines at the Wine School.

After breakfast we make our way to the centre of Siena for a day exploring this fascinating city. We have time to visit the numerous museums and stunning Duomo and to relax in one of the many outdoor cafés in Piazza del Campo, home of the world famous Palio horse race. Please note that shoulders should be covered for entering the Duomo. You may also like to visit the many boutiques specializing in local products and cutting edge Italian fashion. In the afternoon we also have the opportunity to learn about Tuscan wines on a 1-hour fun interactive course at the Tuscan Wine School.

Day 5 Free day to visit other Chianti villages or relax by the pool.

Today is free to rest any tired legs at the poolside. Alternatively, your leader can advise on local Chianti wine tasting tours and cooking classes or offer assistance for unguided walks or daytrips.

Day 6 Discover the magnificent city of Florence, considered the birthplace of the Renaissance.

Our destination today is the magnificent city of Florence, the birthplace of the Italian Renaissance with an enormous wealth of historical sites, museums, galleries, churches and architectural delights. Most of the great artists, thinkers and builders from Renaissance history passed through or lived in Florence when it was under the rule of the Medici family, the most famous patrons of the 16th century. But Florence is not just a Renaissance showpiece: once you have had your fill of the historical trail there are many other things to see and do. The city has not ceased to be a centre of learning, and there is a university, many art and language schools and a large student population to liven up the café-bars, restaurants and nightclubs. There are also some great markets and chic boutiques. From April to July, Florence also holds one of Europe's major cultural events, a festival of opera and classical music called the Maggio Musicale Fiorentino. There are no guided tours organised for the day but there's an option to join one of the free walking tours in the morning. This will then leave you enough time to visit the Uffizi galleries. If you wish to do so we recommend that you prebook your ticket online to avoid lengthy queues. An ideal slot time would be around 2 pm. it can be earlier if you're not interested in joining the morning free walking tour. Tickets can be purchased through  https://webshop.b-ticket.com/webshop/webticket/eventlist?production=1 .  ">https://webshop.b-ticket.com/webshop/webticket/eventlist?production=1">h...

Day 7 Walk to picturesque San Gimignano with free time to explore Palazzo Comunale, Pinacoteca and Torre Grossa.

After a  transfer to the quaint hamlet of San Donato, we walk through the farm grounds following the pathway to Montauto and on up to the picturesque mediaeval town of San Gimignano. The walk is not long and should take approximately 3 hours. The afternoon is spent exploring this beautiful town including visits to the Palazzo Comunale, Pinacoteca and Torre Grossa and there is some free time to wander and soak up the atmosphere. 

Day 8 End Castellina in Chianti.

Trip ends at Villa Casalta.

Availability

Checking price
Price From $ 1,399
Price Per Day: $ 175 per day
Check Availability
Checking price
Start DateFinish DateDouble StandardDeparture GuaranteedAvailability 
Jul-06-2019Jul-13-2019$ 1,649Yes7 spots left Reserve
Aug-17-2019Aug-24-2019$ 1,479Yes8 spots left Reserve
Aug-24-2019Aug-31-2019$ 1,479Yes8 spots left Reserve
Aug-31-2019Sep-07-2019$ 1,649Yes2 spots left Reserve
Sep-07-2019Sep-14-2019$ 1,749YesLimited Reserve
Sep-14-2019Sep-21-2019$ 1,749YesLimited Reserve
Sep-21-2019Sep-28-2019$ 1,749YesLimited Reserve
Sep-28-2019Oct-05-2019$ 1,479Yes8 spots left Reserve
Oct-05-2019Oct-12-2019$ 1,549YesLimited Reserve
Oct-12-2019Oct-19-2019$ 1,549YesLimited Reserve
Oct-19-2019Oct-26-2019$ 1,399No8 spots left Reserve
Oct-26-2019Nov-02-2019$ 1,549No8 spots left Reserve
Apr-18-2020Apr-25-2020$ 1,749No8 spots left Reserve
Apr-25-2020May-02-2020$ 1,749No8 spots left Reserve
May-02-2020May-09-2020$ 1,749No8 spots left Reserve
May-16-2020May-23-2020$ 1,749No8 spots left Reserve
May-30-2020Jun-06-2020$ 1,749No8 spots left Reserve
Jun-06-2020Jun-13-2020$ 1,749No8 spots left Reserve
Jun-20-2020Jun-27-2020$ 1,749No8 spots left Reserve
Aug-15-2020Aug-22-2020$ 1,749No8 spots left Reserve
Aug-22-2020Aug-29-2020$ 1,749No8 spots left Reserve
Aug-29-2020Sep-05-2020$ 1,749No8 spots left Reserve
Sep-05-2020Sep-12-2020$ 1,749No8 spots left Reserve
Sep-12-2020Sep-19-2020$ 1,749No8 spots left Reserve
Sep-19-2020Sep-26-2020$ 1,749No8 spots left Reserve
Sep-26-2020Oct-03-2020$ 1,749No8 spots left Reserve
Oct-03-2020Oct-10-2020$ 1,679No8 spots left Reserve
Oct-10-2020Oct-17-2020$ 1,679No8 spots left Reserve
Oct-17-2020Oct-24-2020$ 1,679No8 spots left Reserve
See more

Check Current Availability, prices, specials with Exodus Travels.

Prices may vary due to local taxes and trip seasonality. Click "Request Info" to inquire directly with the tour operator for the final trip price.

Ask Our Destination Experts

Clark Norton
Email Us

Stride Featured in

Stride Feature In

13,051 Exodus Travels Travel Reviews & Ratings

99%
4.6 out of 5 (100+ reviews)
Excellent 9,189
Great 3,171
Average 528
Disappointing 113
Terrible 50
Value
4.6
Guide
4.6
Activities
4.6
Lodging
4.6
Transportation
4.6
Meals
4.6

Chianti Walking & Wine

Write a Review

Italy October 2018

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
The Chianti Walking and Wine Tour was truly incredible. It was a vacation
for my personal sensory system....to touch the ground that leads to...….the
smell of the crisp Italian forest air, the taste of the locally sourced wine
and fresh cheese, to see the vineyards, the cypress trees and the villas and
to hear the sound of silence and peace, that can only be found walking the
Tuscany Country. The tour was about being aware and in the moment, then
taking those memories and sharing them with friends.
The whole trip was inspirational. For me to comprehend we walked where only
the local people walked. The only other tourists were the nine people within
the group and our group leader. That's it....no crowds, no noise....how much
more inspirational can that be...


Mark Middleton....super, great and loved his job. This made us enjoy the
tour even more.


From personal experience....proper hikers or really supportive runners. The
walks can be more adventurous than expected.


Villa Casalta is amazing - built in 1749!! Pictures and words cannot
explain. Roberta and Margarita always made it feel like coming home.
Absolutely loved it...


Read more

A leisurely week in beautiful Tuscany

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
This holiday is ideal if you are not sure if you want a walking or a
sight-seeing holiday. There are three walks, all of which are well within the
capabilities of a reasonably fit person. These walks take in the vineyards,
olive groves and woods of this part of Italy and also go via small towns with
plenty of opportunity for good lunches or shopping. There are also visits to
Sienna, Florence and San Gimignano. In the first there is a guided walk
included, the second also has the choice to do a guided walk and the third is
a lovely small town for wandering or looking at the frescos in the Duomo. The
three wine-tastings are all very good, and there is plenty of opportunity to
do more either local to the farmhouse where the trip is based or on the
visits to the small towns along the way. For food lovers the meals were all
very good and vegetarians are well catered for.
Looking at the frescos in the Duomo at San Gimignano. I was blown away by the
clarity of the story-telling and the beauty of the painting.

The guided tour of Sienna was excellent. There was so much packed into the
three hours, included an excellent stop for coffee and cake.

Castelina where the trip was based had some interesting Etruscan tombs that,
despite having no artefacts remaining, are well worth a visit.


Liz was the best driver I have come cross, ferrying us about with great
efficiency. She knows the local area well so was able to fit in a quick visit
to see the Leaning Tower of Pisa on the way to the airport, an unforeseen
bonus. This local knowledge came in useful when suggesting things to do on
our day off and during the walks, where she ensured that we were able to see
lots of interesting things along the way. All together one of the best tour
guides I have met.


The walking is a little hilly, but someone with a reasonable level of fitness
will not find it a problem. There are a lot of mosquitos about (and we were
there late in the season) so come prepared with repellent etc. Castelina,
where the trip is based, is a town well worth exploring, the Etruscan tombs
are more interesting than you might think. The archaeological museum is
small, but worth a visit, as the entrance fee includes being able to go to
the top of the tower, where there are some excellent views.
If you like ice-cream be sure to visit the gelateria in town, it is very
good.


I thought the tour was a good balance of sight-seeing, walking and
wine-tasting. We didn't go on the Florence trip as we know the city quite
well, and really appreciated a day getting to know the local area better.


Read more

1st time Exodus experience

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
This was our first holiday with Exodus. Usually we are independent travellers
so we were both a bit nervous about a group 'organised ' trip but we needn't
have worried. We had a great group of people; different backgrounds and
nationalities which made for an interesting week of getting to know each
other. Our fabulous guide Mark was absolutely brilliant, patient, helpful and
very accommodating, keeping us out of too much sun, well watered and well
informed about the various places we visited. Roberta, our host at the villa
was absolutely lovely and looked after us wonderfully with the help of
Margarita. We really had a great week and as well as being very impressed
with our trip we've also been inspired by the experiences of Exodus from our
fellow travelers; definitely food for thought for future trips.
We loved Siena, such a beautiful city, full of history, culture and of course
wine. We really enjoyed the walking tour with Alicia, she was so passionate
about her home and the history of the districts. We had a great wine school
experience and just thoroughly enjoyed our day there.


Mark was just brilliant, we really can't praise him highly enough. He really
looked after us all, making various arrangements for individuals, giving us
lots of local history and information and taking the time to check
information and relay info after we'd returned from the trip.


Take insect repellent as there were definitely more biting bugs than we'd
anticipated. Have room in your case for wine and olive oil, managed to get 10
bottles home in total between 2 of us but there were so many lovely wines to
try, you don't want to miss out.


Just that we were very impressed with the whole holiday and felt it was very
good value for money. We also did the cookery school on our free day which
was great fun and another opportunity to meet some new people and learn about
Tuscan food.


Read more

Beautiful Tuscany

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
Wonderful week - three lovely walks through the Italian countryside and some
delicious wine tasting! The wonderful Hill top towns we walked to and through
were beautiful and, Siena and Florence were amazing. However, the latter was
very busy, but that I suspect is due to the place.
Arriving at the airport in Pisa to a welcome and then meeting others in the
group. I knew it would be a good week.

Looking down on Florence from the car park

enjoying good food, wine and company


Our tour leader Mark was well organised, knowledgeable and made everything
interesting and great fun. his attention to detail was second to none and he
knew where to find the best coffee, cakes, wine, ice cream everywhere we
went!


The walking is not flat so be prepared to walk up and down hills!
Mosquitos and insects abound, so some insect repellant and bit cream is a
must!
A liking for red wine and good food certainly helps, as does enjoying
breakfast outside looking over the beautiful Tuscan hills.


Great trip and would certainly recommend.


Read more

Totally Tuscany ...

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
One week of great walks , great hospitality and great food .. superb leader
in Mark and combined with the warmth of the late summer sun we couldn’t ask
for a better way to spend a holiday than to walk the vineyards and taste the
grape
Read more

Too much Chianti in Chianti . . hic!

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
This trip is a superb blend of walking, culture and fun. The villa is
wonderful and in a great location a short walk from Castellina in Chianti;
I especially liked the outdoors breakfast area but everything about it is so
quintessentially Tuscan. The scenery is stunning and visits to Siena and
Florence gave the balance of walking and culture with the bonus of the wine
tastings which added the fun. The walks were well graded and much as I
expected in terms of length, but there was also plenty of free time to enjoy
the area. The Chianti flowed at dinner time and made for great evenings for
the lovely group I was in even if some nights there was just a tad too much
Chianti in Chianti!
Without doubt the Uffizi gallery in Florence; the gallery itself, the
location with views over the city, and the art was quite breath-taking. I
had to pinch myself to believe that I was standing next to a Leonardo da
Vinci, Botticelli, Caravaggio or Michelangelo original. Florence itself is
quite breath-taking too.


Clearly Mark comes with much experience and he hugely enhanced the trip with
his variety of much appreciated snacks on the walks, finding cheap and good
coffee with clean toilets in Florence, and giving us free time in the
afternoons whilst he collected the minibus to take us back to the villa. His
advice on where to eat or drink was always spot on. The icing on the cake for
me was Mark finding a way for me to spend the last afternoon in Pisa and
visit the Leaning Tower, whilst he took my luggage to the airport. Full
marks Mark!


My calf muscles did ache on a few days so get some exercise in before you go
- Tuscany is hilly! Pre-book the Uffizi to avoid the queues - I did and it
worked perfectly.


The villa has a great attitude to its guests consuming their own food and
drink by the pool, and free tea and coffee is always available. The shower
was a bit small for me but this is nit-picking in an otherwise perfect trip.


Read more

Details

Flights & Transport

Only ground transport

Group Size:

Small Group - 24 max

Maximum Number of People in Group: 16

Accomodations

7 nights renovated farmhouse with panoramic swimming pool
5 days gentle walking and sightseeing
Low altitude throughout
Centre-based holiday

Age Notes

Min. Age: 18

Additional Information:

  • 7 nights renovated farmhouse with panoramic swimming pool
  • 5 days gentle walking and sightseeing
  • Low altitude throughout
  • Centre-based holiday

Trip ID#:

exodus-TDC

Trip Excludes

  • Travel insurance
  • Single accommodation (available on request)
  • Visas or vaccinations

Meals Included:

Dinner: All breakfasts 5 dinners and 3 wine tastings are included. Breakfast is usually a continental style buffet. Of the 5 included dinners, three are taken at Villa Casalta and a reasonable amount of wine is included. Two are taken in local restaurants (drinks not included). Vegetarian choices are available - please advise us of dietary requirements on booking.

Similar Trips

See all similar trips
×
Great Choice!

Now, Unlock Member Savings

Our Stride Select trips allow you and your travel companions to save up to $700. You wouldn’t want to miss that, right?

or
or
Provide email and password

With your FREE membership you get to:

  • Save up to $700 per person!*
  • Access private deals and offers
  • See personalized trip recommendations
  • Save favorite trips
*See Member Savings Program details
Already a member?

We respect your privacy and take great care to protect your information. By joining you agree to our Privacy Policy and Terms of Use.

×
×
Sign in to Save Trips
Welcome back! We're so happy to see you. ? Forgot Password?
Don't have an account? Join
  • Bookmark trips you like
  • Share with your travel companions
  • Track price changes
  • Access private discounts on trips you save
×
Sign in to see your results

TripFinder is a member-only feature. Don’t worry, it’s free!

With a membership you:

  • Save up to $700 per person!*
  • Access private deals and offers
  • See personalized trip recommendations
  • Save favorite trips
*See Member Savings Program details
×
Activate your free Stride membership

Just use the email address and password provided in the email we sent.

? Forgot Password?

With your free membership you:

  • Save up to $700 per person!*
  • Access private deals and offers
  • See personalized trip recommendations
  • Save favorite trips
*See Member Savings Program details
×
To Follow, sign in or sign up (it's free) ? Forgot Password?
Don't have an account? Join
member benefits
First name is required!
Last name is required!
First name is not valid!
Last name is not valid!
This is not an email address!
Email address is required!
This email is already registered!
Please enter valid email address
Password is required!
Enter a valid password!
Please enter 6 or more characters!
Please enter 16 or less characters!
Passwords are not the same!
Terms and Conditions are required!
Email or Password is wrong!
Please select the captcha checkbox!
Please select the valid captcha!
Something went wrong! Try again later!

x
x
Download your brochure

Enter your email to get the "" brochure.

x
Brochure successfully sent!

We've sent the "" brochure to "". Check your inbox!