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Top Arezzo Private Sightseeing 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
$256
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
$228
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 (25)

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 (25)
from
$301
Private Tour: Montalcino Wine Tasting Experience

Private guided wine tour and tasting in Montalcino, Tuscany to discover Brunello and the most amazing wine estates and cellars that give birth to this …More

Likely to Sell Out
Likely to Sell Out
5.0 (71)

Private Tour: Montalcino Wine Tasting Experience

Private guided wine tour and tasting in Montalcino, Tuscany to discover Brunello and the most amazing wine estates and cellars that give birth to this...

8 hours • Hotel pickup offered • Free Cancellation
5.0 (71)
from
$313
PRIVATE TOUR: Savor Exquisite Wines, Brunello & Nobile Wine Tour

A superb Experience in the wonderful Val d'Orcia between Noble vines & Medieval cities • Our driver escort will pick you up at your location …More

Likely to Sell Out
Likely to Sell Out
4.8 (6)

PRIVATE TOUR: Savor Exquisite Wines, Brunello & Nobile Wine Tour

A superb Experience in the wonderful Val d'Orcia between Noble vines & Medieval cities • Our driver escort will pick you up at your location...

8 hours • Hotel pickup offered • Free Cancellation
4.8 (6)
from
$221
Montepulciano Vineyards Wine Tour with 3 Estates Visit

Embark on a guided journey through the picturesque vineyards and historic cellars of Montepulciano, the home of the celebrated Vino Nobile di Montepulciano. This exclusive …More

5.0 (24)

Montepulciano Vineyards Wine Tour with 3 Estates Visit

Embark on a guided journey through the picturesque vineyards and historic cellars of Montepulciano, the home of the celebrated Vino Nobile di Montepulciano. This exclusive...

7 to 8 hours • Hotel pickup offered
5.0 (24)
from
$348
Private Tour Siena San Gimignano and Chianti from Cortona

Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore …More

Likely to Sell Out
Likely to Sell Out
5.0 (7)

Private Tour Siena San Gimignano and Chianti from Cortona

Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore...

8 to 9 hours • Hotel pickup offered • Free Cancellation
5.0 (7)
from
$290
Private tour Wine and cheese a perfect combinations val 'Orcia

Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a …More

Likely to Sell Out
Likely to Sell Out
4.6 (7)

Private tour Wine and cheese a perfect combinations val 'Orcia

Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a...

8 to 9 hours • Hotel pickup offered • Free Cancellation
4.6 (7)
from
$325
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
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
$133
Cortona E-Bike Scenic Ride - Private Medieval Countryside tour

This is not simply an e-bike tour — it is a curated private experience for travelers who value authenticity, comfort, and true local elegance. Set …More

5.0 (11)

Cortona E-Bike Scenic Ride - Private Medieval Countryside tour

This is not simply an e-bike tour — it is a curated private experience for travelers who value authenticity, comfort, and true local elegance. Set...

3 to 4 hours • Free Cancellation
5.0 (11)
from
$323
Val d'Orcia: eBike Tour Virtual-guided

After booking, the tour begins at the rental point with e-bike collection and activation of the virtual navigation system. The 24 km loop has 400 …More

5.0 (4)

Val d'Orcia: eBike Tour Virtual-guided

After booking, the tour begins at the rental point with e-bike collection and activation of the virtual navigation system. The 24 km loop has 400...

2 to 3 hours • Free Cancellation
5.0 (4)
from
$90
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
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
$243
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
$336
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
Around Lucignano Private ebike tour and Cooking Class

Explore the charming Tuscan village of Lucignano on an exhilarating eBike tour that takes you through picturesque landscapes and hidden gems only locals know. Visit …More

5.0 (2)

Around Lucignano Private ebike tour and Cooking Class

Explore the charming Tuscan village of Lucignano on an exhilarating eBike tour that takes you through picturesque landscapes and hidden gems only locals know. Visit...

4 to 6 hours • Free Cancellation
5.0 (2)
from
$626
PRIVATE Hero E-Bike Experience - Cortona and Montepulciano Valley

This experience follows the same high-level luxury format offered in Cortona, reimagined in Montepulciano and the Chiana Valley. Set among Tuscany’s rolling hills, the journey …More

5.0 (3)

PRIVATE Hero E-Bike Experience - Cortona and Montepulciano Valley

This experience follows the same high-level luxury format offered in Cortona, reimagined in Montepulciano and the Chiana Valley. Set among Tuscany’s rolling hills, the journey...

4 to 5 hours • Free Cancellation
5.0 (3)
from
$424
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
$255

Frequently Asked Questions

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

Recent tour reviews
Introduction to Cortona
New York City
Cortona Private Guided Tour
Joni_B, Sep 2026
Introduction to Cortona
Wonderful tour of Cortona with our guide Elisona. She explained the history of the area and we visited three of the lovely churches and discussed their history. We walked at comfortable pace on the steep pathes, all our questions were answered and ended at the fun outdoor market Wonderful and educational morning
Read more
Memories are made…….
New York City
Private Tour: Montalcino Wine Tasting Experience
cherylvX8031GE, Sep 2026
Memories are made…….
This is our second time in Cortona using this vendor and have the same guide, Francesco. Such good memories made the first time we did it again because of his knowledge and professionalism. I highly recommend if you are planning a visit to the area!
Read more
Extremely knowledgeable guide!
New York City
Montepulciano Vineyards Wine Tour with 3 Estates Visit
terryvF8050PM, Sep 2026
Extremely knowledgeable guide!
This was the most informative wine tour that I’ve been on. The guide spoke about wine making in general as well as the various wines we tasted. The accompanying lunch was excellent! I recommend this tour highly.
Read more
Spectacular.
New York City
Private Tour Siena San Gimignano and Chianti from Cortona
Erin_M, Sep 2026
Spectacular.
This trip was incredible. Luca was a stellar driver, knows everything about the area. The winery is fantastic and worth every penny and more. This was a day we will never forget. If you do nothing else, do this!
Read more
Great wine day with Francesco!
New York City
Private Tour: Montalcino Wine Tasting Experience
T952TMalisonb, Sep 2026
Great wine day with Francesco!
Francesco was absolutely wonderful! He was fun, knowledgeable and easy going. We had a great afternoon learning about wine and all things Italy! Would highly recommend!
Read more
A Truly Personalized Tuscany Experience
New York City
Private Tour Siena San Gimignano and Chianti from Cortona
netray722, Aug 2026
A Truly Personalized Tuscany Experience
Massimo made our two days in Tuscany feel completely effortless. From the planning stage onward, he was deeply involved in shaping a fully customized itinerary, patiently answering questions, refining details, and making sure the final plan suited us perfectly.Our itinerary included visits to two medieval towns, a winery tour and tasting, a truffle hunt, and a pasta-making class. It was varied, well paced, and thoughtfully arranged for the whole family—the kids especially loved the hands-on experiences.Both days were seamless, with punctual hotel pick-up and drop-off, yet the experience never felt rigid. Massimo was always flexible when we wanted to adjust the pace or spend a little more time somewhere. He is warm, knowledgeable, and genuinely informative without ever making the day feel scripted.He also very kindly helped me practice my Italian throughout the trip, which made the experience even more personal.Professional, thoughtful, reliable, and truly customer-first. I would recommend Massimo without hesitation to anyone looking for a private and genuinely personalized way to experience Tuscany.
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
Francesco and the best day in Montepulciano!
New York City
Montepulciano Vineyards Wine Tour with 3 Estates Visit
Christina_D, Jul 2026
Francesco and the best day in Montepulciano!
Francesco is an absolute pro! Our tour was phenomenal and we learned so much from Francesco and the vintners we visited. What a thoughtful curation of our Montepulciano wine experience complete with tastings, lunch personal touches and a really beautiful day well spent. Choose this tour.
Read more
It was an amazing bike...
New York City
Val d’Orcia: eBike Tour Virtual-guided
Rita_M, Jul 2026
It was an amazing bike...
It was an amazing bike trip through the Tuscan area. Steffi was amazing and so welcoming. I would recommend this tour
Read more
Fantastic Tour
New York City
Cortona E-Bike Scenic Ride – Private Medieval Countryside tour
C1493WVjimb, Jul 2026
Fantastic Tour
We have been in this Tuscany region for six days and our bike tour has been the most memorable thing we have done. Roberto, “Robbie”, is a wonderful guide. Everything from the ease of the bikes, to the historical stops and information, to the wonderful wine and lunch stop for at the end of the trip. I was curious about the price compared to some of the other trips, but we feel it was well worth it and the reviews that helpedus pull the trigger were spot on. Highly Recomend
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
Used both men on two different days. They are so professional and respectful. I will use again and highly recommend.
New York City
Private tour Wine and cheese a perfect combinations val ‘Orcia
glennnancy819, Jun 2026
Used both men on two different days. They are so professional and respectful. I will use again and highly recommend.
Great customer service and knowledge of the area!
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
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
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