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Top Arezzo Walking Tours

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Arezzo Tours

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Brunello Wine Tour and Val D'Orcia Landscape

I was born and raised here in Tuscany and I know the best wine maker but the key is small wineries with high quality where …More

Likely to Sell Out
Likely to Sell Out
5.0 (97)

Brunello Wine Tour and Val D'Orcia Landscape

I was born and raised here in Tuscany and I know the best wine maker but the key is small wineries with high quality where...

4 hours • Free Cancellation
5.0 (97)
from
$257
Wine & Oil Tasting Experience

You will be welcome by the owners of the old tradition family-run business. The Wine&EVO Oil tour will start from the visit of one of …More

4.9 (17)

Wine & Oil Tasting Experience

You will be welcome by the owners of the old tradition family-run business. The Wine&EVO Oil tour will start from the visit of one of...

1 to 3 hours • Free Cancellation
4.9 (17)
from
$47
Val D'Orcia Dreaming!!

I was Born and raised in this magical region od Tuscany, I have key villagers that I have known for many years and you know …More

Likely to Sell Out
Likely to Sell Out
5.0 (19)

Val D'Orcia Dreaming!!

I was Born and raised in this magical region od Tuscany, I have key villagers that I have known for many years and you know...

4 hours • Hotel pickup offered • Free Cancellation
5.0 (19)
from
$230
Cortona Private Guided Tour

Cortona has become very popular several years ago thanks to the book by Frances Mayes, Under the Tuscan Sun (and the movie with Diane Lane) which is …More

4.9 (24)

Cortona Private Guided Tour

Cortona has become very popular several years ago thanks to the book by Frances Mayes, Under the Tuscan Sun (and the movie with Diane Lane) which is...

2 hours • Free Cancellation
4.9 (24)
from
$304
Arezzo Walking Tour with Audio and Written Guide by a Local

If you're looking for a fun and curious way to visit Arezzo, you've come to the right place! With this digital guide created with the …More

4.3 (15)

Arezzo Walking Tour with Audio and Written Guide by a Local

If you're looking for a fun and curious way to visit Arezzo, you've come to the right place! With this digital guide created with the...

3 to 4 hours • Free Cancellation
4.3 (15)
from
$6
Castiglion del lago, Spello & Assisi tour

It’s an incredibile experience that will take you to learn not just local history but culture keys to entry deeply inside the Italian style of …More

Likely to Sell Out
Likely to Sell Out
4.8 (9)

Castiglion del lago, Spello & Assisi tour

It’s an incredibile experience that will take you to learn not just local history but culture keys to entry deeply inside the Italian style of...

8 hours • Free Cancellation
4.8 (9)
from
$257
Private Walking Tour of Pienza with Licensed Tour Guide

During our visit we will discover everything about the past of this wonderful town, known as the "ideal city". We will talk about its origins …More

Likely to Sell Out
Likely to Sell Out
5.0 (3)

Private Walking Tour of Pienza with Licensed Tour Guide

During our visit we will discover everything about the past of this wonderful town, known as the "ideal city". We will talk about its origins...

2 hours • Free Cancellation
5.0 (3)
from
$30
Olive experience Walk among the olive trees with tasting

You will understand how vast and interesting the world of oil is. The walk extends over two gentle hills covered with olive trees. The view …More

5.0 (7)

Olive experience Walk among the olive trees with tasting

You will understand how vast and interesting the world of oil is. The walk extends over two gentle hills covered with olive trees. The view...

1 hour • Free Cancellation
5.0 (7)
from
$35
Walking Tour in Cortona

We are going to do a walking tour of the city visiting the most attractive places and views from the city to the valley around. …More

5.0 (21)

Walking Tour in Cortona

We are going to do a walking tour of the city visiting the most attractive places and views from the city to the valley around....

90 to 120 minutes • Free Cancellation
5.0 (21)
from
$59
Arezzo: Wine Tasting Experience in Valdichiana area

Enjoy 2 hours wine tasting experience in an elegant and exclusive location, an ancient Tuscan villa located in Valdichiana, in the heart of Tuscany. Together …More

4.9 (8)

Arezzo: Wine Tasting Experience in Valdichiana area

Enjoy 2 hours wine tasting experience in an elegant and exclusive location, an ancient Tuscan villa located in Valdichiana, in the heart of Tuscany. Together...

2 hours • Free Cancellation
4.9 (8)
from
$47
Private Tasting of Organic Wines in the Cellar in Mugliano

In the cellar, in Mugliano, we offer the opportunity to taste our organic products combined with cutting boards made with local products in the different …More

5.0 (5)

Private Tasting of Organic Wines in the Cellar in Mugliano

In the cellar, in Mugliano, we offer the opportunity to taste our organic products combined with cutting boards made with local products in the different...

2 hours • Free Cancellation
5.0 (5)
from
$35
Cortona private walking Tour

Discover the iconic Tuscan town of Cortona (made famous in the book by Frances Mayes "Under The Tuscan Sun"). Located between Florence and Rome, Cortona …More

5.0 (10)

Cortona private walking Tour

Discover the iconic Tuscan town of Cortona (made famous in the book by Frances Mayes "Under The Tuscan Sun"). Located between Florence and Rome, Cortona...

2 hours 30 minutes • Free Cancellation
5.0 (10)
from
$134
Discover Montepulciano!

That's a walking tour in the center of Montepulciano. We are going to visit the main attractive, the narrow streets, the panoramic views of the …More

5.0 (12)

Discover Montepulciano!

That's a walking tour in the center of Montepulciano. We are going to visit the main attractive, the narrow streets, the panoramic views of the...

120 to 150 minutes • Free Cancellation
5.0 (12)
from
$58
Private Guided Tour of Pienza on Foot

Born from a "dream of love and an idea of beauty", Pienza, the ideal city of the Italian Renaissance, is still today an intact testimony …More

5.0 (5)

Private Guided Tour of Pienza on Foot

Born from a "dream of love and an idea of beauty", Pienza, the ideal city of the Italian Renaissance, is still today an intact testimony...

3 hours • Free Cancellation
5.0 (5)
from
$245
Arezzo Private Tour with Official Guide

Sitting on top of a hill at the junction of the 4 valleys that compose its province, Arezzo was a great Etruscan and Roman city. …More

5.0 (8)

Arezzo Private Tour with Official Guide

Sitting on top of a hill at the junction of the 4 valleys that compose its province, Arezzo was a great Etruscan and Roman city....

2 hours • Free Cancellation
5.0 (8)
from
$340
Arezzo Private walking tour

During this 2-hour private tour, your expert guide will lead you through the most important and interesting sites of the beautiful city of Arezzo. You …More

5.0 (4)

Arezzo Private walking tour

During this 2-hour private tour, your expert guide will lead you through the most important and interesting sites of the beautiful city of Arezzo. You...

2 hours • Free Cancellation
5.0 (4)
from
$128
Cortona Private walking Tour under the Tuscan sun

Everyone loves Cortona, because it is an authentic and fascinating place. Village of Etruscan origin with stone houses, which stands in the center of an …More

5.0 (3)

Cortona Private walking Tour under the Tuscan sun

Everyone loves Cortona, because it is an authentic and fascinating place. Village of Etruscan origin with stone houses, which stands in the center of an...

2 hours • Free Cancellation
5.0 (3)
from
$57
Lunch Time Tasting & Winery Tour

You will visit with us our winery and vineyard to discover our philosophy and passion. A unique experience in which you can then taste 4 …More

4.7 (9)

Lunch Time Tasting & Winery Tour

You will visit with us our winery and vineyard to discover our philosophy and passion. A unique experience in which you can then taste 4...

2 hours • Free Cancellation
4.7 (9)
from
$70
Private and Guided Walking Tour of Arezzo City of Gold

Walking through the medieval streets of Arezzo is a unique experience. Tradition, history and beautiful landscapes to photograph. Arezzo offers all this and much more. …More

5.0 (1)

Private and Guided Walking Tour of Arezzo City of Gold

Walking through the medieval streets of Arezzo is a unique experience. Tradition, history and beautiful landscapes to photograph. Arezzo offers all this and much more....

2 to 3 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$257
Umbria The Way Of Saint Francis Private Tour

More than a walking holiday, this is a journey through the places that shaped the life of Saint Francis of Assisi. Follow one of Italy's …More

Umbria The Way Of Saint Francis Private Tour

More than a walking holiday, this is a journey through the places that shaped the life of Saint Francis of Assisi. Follow one of Italy's...

7 days
from
$2,459

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
We really enjoyed our...
New York City
Walking Tour in Cortona
Alaina_K, Sep 2026
We really enjoyed our...
We really enjoyed our tour of Cortona. Very informative and was the perfect way to start our week-long stay here.
Read more
It was an outstanding...
New York City
Lunch Time Tasting & Winery Tour
AnnaMaris_G, Sep 2026
It was an outstanding...
It was an outstanding afternoon tasting wines and having lunch. Claudia and Virginia were so wonderful to meet. Would definitely go back
Read more
Great walking tour of the...
New York City
Arezzo Walking Tour with Audio and Written Guide by a Local
Julie_K, Sep 2026
Great walking tour of the...
Great walking tour of the city covering all key sites. Easy to use app and appreciated the ability to self manage the tour vs being in a large group.
Read more
Great walking tour for Arezzo
New York City
Arezzo Walking Tour with Audio and Written Guide by a Local
Q787TQjuliek, Sep 2026
Great walking tour for Arezzo
We really enjoyed the walking tour; hit all of the highlights and allowed us to see them at our own pace and without a large group. Highly recommend.
Read more
Captivating History from our Tour Guide!
New York City
Private Guided Tour of Pienza on Foot
860baileyh, Aug 2026
Captivating History from our Tour Guide!
Sara was an absolutely amazing tour guide on this trip to her beloved city of Pienza! We loved hearing about the rich history of Pienza while interacting with local business owners. Sara helped us understand the history of her city in relation to the Renaissance and how Pienza keeps ancient traditions alive. We toured for about two hours and the time frame was perfect. Grazie mille, Sara!!!😊
Read more
Just wonderful
New York City
Brunello Wine Tour and Val D’Orcia Landscape
P1KGK, Jul 2026
Just wonderful
I booked a tour with Fabrizio to celebrate my husbands 50th, which involved a visit to Innocenti vineyard which much to my husband’s delight involved a wine tasting of Brunello wine. We had a lovely lunch at the vineyard with home made pasta which was very flavoursome and definitely made me want more. We then visited the small villages of Bagno Vignoni and Pienza. Some of the views were absolutely breathtaking taking. I had to pinch myself at times and found it very moving. Fabrizio was a very thoughtful and intuitive guide, full of local knowledge and interest that made it a very special occasion. Many thanks for making it a day to remember. Look forward to catching up on English soil my Friend!
Read more
Cortona a gem
New York City
Cortona private walking Tour
Borneo55, Jul 2026
Cortona a gem
Guide was please, informative and considerate of my slightly limited mobility. In depth history and cultural both ancient and recent great.
Read more
Excellent Tour
New York City
Cortona private walking Tour
Erica_I, Jun 2026
Excellent Tour
This tour was very laid back and fun. We really enjoyed learning about the many layers of Cortona history. Debora was wonderful, welcoming and a wealth of knowledge.
Read more
A great way to start our week in Cortona
New York City
Walking Tour in Cortona
Kevin B, Jun 2026
A great way to start our week in Cortona
Elisiana was well educated about local and regional history, as well as friendly, patient, and accommodating. We enjoyed every minute.
Read more
Exceeded Our Expectations
New York City
Brunello Wine Tour and Val D’Orcia Landscape
P8654UIcheryls, Jun 2026
Exceeded Our Expectations
My husband and I thoroughly enjoyed our time in Moltacino all thanks to Fabrizio. My husband loves Brunello wine and we have been looking forward to some wine tasting in Moltacino. We tasted wine at a small family vineyard. We learned about their history and the process. We enjoyed a delicious lunch with several flights of wine, leading up to the spectacular “Reserva”. The drive was beautiful and Fabrizio was full of information, sharing first hand knowledge of this lovely region.There are many outstanding reviews for Fabrizio. They are true. He is wonderful. We have spent two weeks touring all over Italy, with many lovely places and tour guides. But without a doubt, our time in Moltacino with Fabrizio was the highlight of our trip. Molte Grazie Fabrizio!
Read more
Great day with Debora
New York City
Castiglion del lago, Spello & Assisi tour
Kelsie J, Jun 2026
Great day with Debora
We loved our time with Debora! She was knowledgeable, patient and easy to converse with. We loved spending our day with her, highly recommend!
Read more
Beautiful Arezzo
New York City
Arezzo Private walking tour
Karen_R, Jun 2026
Beautiful Arezzo
Wonderful experience with Rachele. Her knowledge and passion for Arezzo made the tour a joy. What a beautiful city!
Read more
Incredible Personalized Tour
New York City
Val D’Orcia Dreaming!!
denisep909, Jun 2026
Incredible Personalized Tour
We had a SPECTACULAR day with Fabrizio. It was such a privilege to get a beautiful insiders view of Val d'Orcia and beyond...Tuscany... So special to visit the sheep farmer and we wish him continued success..The Cenzoni vineyard and personalized tasting was extraordinaire. And the dinner at Fabrizio's beautiful Montipulciano home was so appreciated and of course delicious. And all the other visits....A perfect introduction to a beautiful part of the world. Run..don't walk and sign up today. It certainly is worth it! So, on behalf of Emilie, Don, and myself, a GRAZIE MILLE !!
Read more
Great
New York City
Private Guided Tour of Pienza on Foot
Mark_C, May 2026
Great
Guide extremely knowledgeable. Really enjoyed conversation and meeting locals. Duration of tour was good. Provided great perspective of Pienza.
Read more
Personal experience
New York City
Olive experience Walk among the olive trees with tasting
William_B, May 2026
Personal experience
Personal, informal, informative, intimate setting. A lovely way to learn about the olive oil making process and supporting a small farm making delicious oil!
Read more
Deguation Top by Gabriele Mazzeschi
New York City
Wine & Oil Tasting Experience
luisafB3626WH, Apr 2026
Deguation Top by Gabriele Mazzeschi
Beautiful experience last Saturday in Castiglion Fiorentino, we tasted all the delicious wines of the cellar in a family environment and surrounded by nature. The owner Gabriele is competent and made us taste the wines from the barrels. I suggest you go.
Read more
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