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Top Arezzo Tours & Sightseeing

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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
Cortona - eBike tour and wine tasting in the Val di Chiana [+40€]

- Guaranteed departure with 4+ guests. - This is a bike tour, so it’s important that you feel confident riding for your safety and the …More

Likely to Sell Out
Likely to Sell Out
4.9 (43)

Cortona - eBike tour and wine tasting in the Val di Chiana [+40€]

- Guaranteed departure with 4+ guests. - This is a bike tour, so it’s important that you feel confident riding for your safety and the...

5 to 6 hours • Free Cancellation
4.9 (43)
from
$217
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 - Easy guided eBike tour around the Etruscan City.

- Departure is guaranteed with 4+ guests. - We have discount codes for each booking—contact us before you book. - Contact us before if you …More

5.0 (62)

Cortona - Easy guided eBike tour around the Etruscan City.

- Departure is guaranteed with 4+ guests. - We have discount codes for each booking—contact us before you book. - Contact us before if you...

2 to 3 hours • Free Cancellation
5.0 (62)
from
$172
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
$302
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

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
Brunello and Montepulciano Wine Tour from Cortona

In you are in Cortona, come enjoy the “Brunello and Montepulciano Tour”.. with its picturesque villages, rolling hills and unforgettable red wines… this is a tour for …More

Likely to Sell Out
Likely to Sell Out
4.9 (23)

Brunello and Montepulciano Wine Tour from Cortona

In you are in Cortona, come enjoy the “Brunello and Montepulciano Tour”.. with its picturesque villages, rolling hills and unforgettable red wines… this is a tour for...

6 to 8 hours • Hotel pickup offered • Free Cancellation
4.9 (23)
from
$336
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
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
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
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
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
$91
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
Bike Ride immersion val d'Orcia

Let’s enjoy downhill and easy rolling hills and admire the breathtaking scenery ending thermal bath of Bagno Vignoni, only 20 miles – easy ride with …More

5.0 (5)

Bike Ride immersion val d'Orcia

Let’s enjoy downhill and easy rolling hills and admire the breathtaking scenery ending thermal bath of Bagno Vignoni, only 20 miles – easy ride with...

3 to 6 hours • Free Cancellation
5.0 (5)
from
$139
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
$423
Private visit to the House of Grand Duke Leopold of Tuscany with invitation

If we talk about Tuscany, we cannot ignore the culture linked to tradition and history: the proposed activity is one of a kind, and interesting, …More

5.0 (1)

Private visit to the House of Grand Duke Leopold of Tuscany with invitation

If we talk about Tuscany, we cannot ignore the culture linked to tradition and history: the proposed activity is one of a kind, and interesting,...

2 hours 30 minutes • Free Cancellation
5.0 (1)
from
$32

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
One of the absolute highlights of our 2 weeks in Italy
New York City
Cortona – Easy guided eBike tour around the Etruscan City.
Connie_B, Sep 2026
One of the absolute highlights of our 2 weeks in Italy
Our bike tour in Cortona was definitely a highlight of our two weeks in Italy. First off, our guide (sadly we cannot remember her name) was amazing. She was personable, knowledgeable, very skilled, and extremely good at her job.She was focused on safety first. She was great at teaching new electric bike riders and calming fears. She was personable, listened to our questions and concerns, and was very good at sharing the most interesting details of the places we visited.We loved seeing and learning about St. Francis monastery. The views on the ride were awesome.Thank you for the lifetime memory. And please thank our guide, our guide's assistant guide, and Asia for us.
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 day with two...
New York City
Brunello and Montepulciano Wine Tour from Cortona
Kathleen_L, Sep 2026
Great day with two...
Great day with two wineries and plenty of wine and food. Luca, our driver was fantastic and very knowledgeable and accommodating. Was a full day. Would definitely recommend.
Read more
Excellent Tour!
New York City
Cortona – Easy guided eBike tour around the Etruscan City.
Sheila_C, Sep 2026
Excellent Tour!
Great way to see Tuscany on the E-bike! Tour guide was excellent!! The 3-4 stops were very interesting!
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
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
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
Cycling in Tuscany. Wow!
New York City
Cortona – eBike tour and wine tasting in the Val di Chiana [+40€]
jimdQ3039FN, Aug 2026
Cycling in Tuscany. Wow!
Epic designed a self guided tour to two wineries for the four of us. Beautiful route that only had a short part with car traffic. Two wineries were wonderful! Great trip and service from Asia at Epic!
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
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