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Top Tuscany Multi-day Tours

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Tuscany Tours

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2-Day E-Bike Tuscany Tour with Meals, Wineries, and Farmstay

Two days of cycling, wine tasting, and authentic Tuscan countryside from Florence. Discover the beauty of Tuscany on a 2-day Chianti Classico E-bike tour from …More

Likely to Sell Out
Likely to Sell Out
Florence, Italy
5.0 (15)

2-Day E-Bike Tuscany Tour with Meals, Wineries, and Farmstay

Two days of cycling, wine tasting, and authentic Tuscan countryside from Florence. Discover the beauty of Tuscany on a 2-day Chianti Classico E-bike tour from...

2 days
5.0 (15)
from
$756
Florence : Brunelleschi's Dome Climb Entry Ticket & Duomo

Ascend Brunelleschi’s Dome, the crown jewel of Florence Cathedral. Designed by Filippo Brunelleschi, this engineering marvel took 15 years to complete, becoming the largest dome …More

Likely to Sell Out
Likely to Sell Out
Florence, Italy
4.4 (7)

Florence : Brunelleschi's Dome Climb Entry Ticket & Duomo

Ascend Brunelleschi’s Dome, the crown jewel of Florence Cathedral. Designed by Filippo Brunelleschi, this engineering marvel took 15 years to complete, becoming the largest dome...

3 days • Free Cancellation
4.4 (7)
from
$133
The Best of Tuscany in 3 Days

Discover the best of Tuscany on this 4-day tour for young adventure seekers 18-39! Lead by a team of passionate, local experts, this tour has …More

Florence, Italy
4.9 (12)

The Best of Tuscany in 3 Days

Discover the best of Tuscany on this 4-day tour for young adventure seekers 18-39! Lead by a team of passionate, local experts, this tour has...

3 days
4.9 (12)
from
$405
Authentic 7 Day Tuscany Tour

Discover All the Hidden Gems of Tuscany with our Ultimate Seven-day Tour... If you would like to experience the real Tuscany avoiding tourist areas, this …More

Florence, Italy
5.0 (10)

Authentic 7 Day Tuscany Tour

Discover All the Hidden Gems of Tuscany with our Ultimate Seven-day Tour... If you would like to experience the real Tuscany avoiding tourist areas, this...

8 days • Hotel pickup offered
5.0 (10)
from
$3,813
Uffizi Combined Ticket:UFFIZI, PITTI, BOBOLI & digital audioguide

Discover Florence’s must-see museums with one convenient 5-day pass including the Uffizi Gallery, Pitti Palace, and Boboli Gardens. No voucher exchange is required: simply check …More

Florence, Italy
4.2 (21)

Uffizi Combined Ticket:UFFIZI, PITTI, BOBOLI & digital audioguide

Discover Florence’s must-see museums with one convenient 5-day pass including the Uffizi Gallery, Pitti Palace, and Boboli Gardens. No voucher exchange is required: simply check...

5 days
4.2 (21)
from
$69
3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns

Escape the city and immerse yourself in the timeless beauty of Tuscany on a fully private, 3-day journey through rolling hills, historic villages, and unforgettable …More

Florence, Italy
5.0 (1)

3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns

Escape the city and immerse yourself in the timeless beauty of Tuscany on a fully private, 3-day journey through rolling hills, historic villages, and unforgettable...

3 days • Hotel pickup offered
5.0 (1)
from
$1,314
Best of Tuscany in 3 days with a local

When you think of Tuscany, you imagine its beautiful landscapes, stunning medieval villages, and amazing culture of food and wine. On our fully-escorted three-day tours, …More

Florence, Italy
5.0 (5)

Best of Tuscany in 3 days with a local

When you think of Tuscany, you imagine its beautiful landscapes, stunning medieval villages, and amazing culture of food and wine. On our fully-escorted three-day tours,...

3 days • Hotel pickup offered
5.0 (5)
from
$2,170
3-Day Tuscany Wine Tour Experience from Florence

Get picked up at your accommodation to experience a three-day full immersion Wine Tour and stay in a private Villa situated in a conventional cosy Tuscan …More

Florence, Italy
5.0 (2)

3-Day Tuscany Wine Tour Experience from Florence

Get picked up at your accommodation to experience a three-day full immersion Wine Tour and stay in a private Villa situated in a conventional cosy Tuscan...

3 days
5.0 (2)
from
$2,374
Unique Tuscany Experience in 1 week with the locals

• SMALL INTIMATE GROUP with a maximum of 8 people. • Experience life as a local in a beautiful private room in a genuine local …More

Florence, Italy
5.0 (3)

Unique Tuscany Experience in 1 week with the locals

• SMALL INTIMATE GROUP with a maximum of 8 people. • Experience life as a local in a beautiful private room in a genuine local...

8 days • Hotel pickup offered
5.0 (3)
from
$3,626
2-Day Tuscany Combo Tour: Florence, Pisa, Cinque Terre & Tuscany

Why choose between the coast and the countryside when you can have both? Our Combo 2-Day Tour lets you experience two of Italy’s most breathtaking …More

Florence, Italy
5.0 (2)

2-Day Tuscany Combo Tour: Florence, Pisa, Cinque Terre & Tuscany

Why choose between the coast and the countryside when you can have both? Our Combo 2-Day Tour lets you experience two of Italy’s most breathtaking...

2 days • Free Cancellation
5.0 (2)
from
$405
Two days of Tuscany discovering the Nobile, Brunello, Chianti area

Get a personalized tour of Montalcino, Montepulciano, and the Chianti region during this two Days and one Night private excursion from Florence. Enjoy three different …More

Florence, Italy
5.0 (1)

Two days of Tuscany discovering the Nobile, Brunello, Chianti area

Get a personalized tour of Montalcino, Montepulciano, and the Chianti region during this two Days and one Night private excursion from Florence. Enjoy three different...

2 days • Free Cancellation
5.0 (1)
from
$474
Private educational and guided custom tours by walk and by confortable M/B van

Tuscany itself should be enough but we enrich your experience with a professional local (a real local) driving guides with the confort of air conditioned …More

Florence, Italy
5.0 (1)

Private educational and guided custom tours by walk and by confortable M/B van

Tuscany itself should be enough but we enrich your experience with a professional local (a real local) driving guides with the confort of air conditioned...

2 days • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$162
7 Day intense weekly cooking course from Florence

The best intense cooking experience for foodies & professionals! This 8 day full immersion course will help you discover the delights of Tuscan cooking. The …More

Florence, Italy
5.0 (1)

7 Day intense weekly cooking course from Florence

The best intense cooking experience for foodies & professionals! This 8 day full immersion course will help you discover the delights of Tuscan cooking. The...

8 days
5.0 (1)
from
$2,455
From Florence to Tuscany Winerys

Always wondered about the Tuscany landscape and Italian Winerys would be like? This is the right moment to discover it with us. 3, 2, 1 …More

Florence, Italy
5.0 (1)

From Florence to Tuscany Winerys

Always wondered about the Tuscany landscape and Italian Winerys would be like? This is the right moment to discover it with us. 3, 2, 1...

2 days
5.0 (1)
from
$2,803
6-Day Learn to Cook on a Budget Getaway in Tuscany

A great culinary Experience, UNDER THE TUSCAN SUN… in one of the most beautiful and historical corner of Tuscany ….. Arezzo is its 4 valleys.. …More

Arezzo, Italy
5.0 (1)

6-Day Learn to Cook on a Budget Getaway in Tuscany

A great culinary Experience, UNDER THE TUSCAN SUN… in one of the most beautiful and historical corner of Tuscany ….. Arezzo is its 4 valleys.....

6 days • Hotel pickup offered
5.0 (1)
from
$3,028
4 days,all inclusive Cooking holiday and tours, in Tuscany

Escape to Tuscany for an Unforgettable Culinary Break! Immerse yourself in the ultimate cooking holiday, with an executive chef at your service, where you’ll cook, …More

Arezzo, Italy
3.0 (1)

4 days,all inclusive Cooking holiday and tours, in Tuscany

Escape to Tuscany for an Unforgettable Culinary Break! Immerse yourself in the ultimate cooking holiday, with an executive chef at your service, where you’ll cook,...

4 days
3.0 (1)
from
$2,795
Private Italy Route: Rome, Florence, Venice and Milan

Let us help you to make your best from your visit to Italy. We are specialised in private tours and private routes in Italy. All …More

Milan, Italy

Private Italy Route: Rome, Florence, Venice and Milan

Let us help you to make your best from your visit to Italy. We are specialised in private tours and private routes in Italy. All...

13 days • Hotel pickup offered
from
$2,135
Private 3 days Route in Tuscany Region from Florence with Hotel pick-up

Enjoy this private 3 day experience to get to know the best sites of Tuscany Region. This tour has been divided in three separate days …More

San Gimignano, Italy

Private 3 days Route in Tuscany Region from Florence with Hotel pick-up

Enjoy this private 3 day experience to get to know the best sites of Tuscany Region. This tour has been divided in three separate days...

3 days • Hotel pickup offered
from
$455
DA Florence: 2 days in Assisi and Gubbio

A 2-day tour in the heart of Umbria between Assisi and Gubbio, two Italian pearls. 1 day departure from Tuscany and arrival in Assisi where …More

Florence, Italy

DA Florence: 2 days in Assisi and Gubbio

A 2-day tour in the heart of Umbria between Assisi and Gubbio, two Italian pearls. 1 day departure from Tuscany and arrival in Assisi where...

2 days • Hotel pickup offered
from
$928
5 days Intense cooking and tours holiday all inclusive

Our all-inclusive cooking holiday is delighted to offer a unique and rare opportunity to live and experience real Tuscany life. This tour provides the best …More

Arezzo, Italy

5 days Intense cooking and tours holiday all inclusive

Our all-inclusive cooking holiday is delighted to offer a unique and rare opportunity to live and experience real Tuscany life. This tour provides the best...

5 days
from
$3,494

Frequently Asked Questions

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

Recent tour reviews
Tuscany delight
New York City
Best of Tuscany in 3 days with a local
FarAway50056003960, Sep 2026
Tuscany delight
It was an excellent few days with great drivers. Well paced and enjoyable. We particularly enjoyed the winery lunches and the lunch at Mimmo and Barbara’s ristorante was amazing! We also enjoyed our stay with Francesca at Loro Ciuffencia. And of course the Tuscany scenery was just spectacular. Excellent choice of wineries we visited from the largish Castello del Verrazzaro to a local family winery.
Read more
Worth it!!!
New York City
2-Day Tuscany Combo Tour: Florence, Pisa, Cinque Terre & Tuscany
Q5559BZheatherl, Sep 2026
Worth it!!!
Driver was very nice and gave us some history about Tuscany Swell
Read more
A must do while in Florence
New York City
Florence : Brunelleschi’s Dome Climb Entry Ticket & Duomo
thomasmA6953UW, Jul 2026
A must do while in Florence
The view from the top of the Duomo was breathtaking and the experience of climbing to the top will never be forgotten. It’s a must do while in Florence
Read more
Glorious 2 day Chianti bike tour
New York City
2-Day E-Bike Tuscany Tour with Meals, Wineries, and Farmstay
Seshelg, Jul 2026
Glorious 2 day Chianti bike tour
We did the 2 day Chianti bike tour from Florence to Sienna. Despite the near 100 F temp., we were able to ride out of the city walls and immediately enjoy the views of rolling hills full of vineyards and olive trees. On our occasional stops, our knowledgeable guide Giovanni shared interesting facts throughout the ride. On the first day we lunched at a rustic, family owned farm and in the evening relaxed at a beautiful villa. On our second day, we lunched at a scenic winery. Giovanni was really good at adapting to our level and interests! Then we rolled into Sienna. What a great way to travel to Sienna, the next stop on our trip. It was an amazing experience despite the heat. Just be sure to make sure your e-bike fits you before you head out on this 2 day adventure—both the seat height and the distance to your handlebars since you’ll be on your bike for a while! The 4 of us are just casual bike riders but with the e-bikes we scaled amazing hills and experienced beautiful views! Highly, highly recommend!
Read more
Very grand tour. We only...
New York City
Uffizi Combined Ticket:UFFIZI, PITTI, BOBOLI & digital audioguide
Maureen_K, Apr 2026
Very grand tour. We only...
Very grand tour. We only had two days in Florence. This was a five day ticket. If I was in Florence longer, I would’ve returned to the Uffizi to see more than what I had been able to cram into one day. We crossed the Ponte Vecchio and then we had lunch on the other side before we entered the Pitti Palace. We got into the Boboli Gardens but no one was there to guide us so we wandered for a long time and got lost and finally ended up on the way other side, and then we had to take a taxi back to our hotel by the Santa Maria Novella.
Read more
Tuscany Untouched is not to be missed!
New York City
3-Day Tuscany Wine Tour Experience from Florence
Adventurer769820, Oct 2025
Tuscany Untouched is not to be missed!
My husband and I just finished our 3 day tour with Paolo, who is not only an amazing guide with first hand knowledge of the area but a lovely, professional and accommodating gentleman. Every minute of our tour was pleasant and filled with interesting historical and current information and stories. Paola made sure we were settled in wherever we visited, introduced us to our hosts and made sure we were well taken care of. The wineries we visited were top notch and the farm house we stayed at in Loro was full of charm with hosts who were eager to please us and couldn’t have been more accommodating. When we found out we needed to leave earlier than planned on the 3rd day Paolo and Mateo restructured the day to our preferences - without a moment’s hesitation and did an excellent job with little time for planning. We give Tuscany Untouched, Paolo and Mateo five stars and our thanks for a memorable 3 days and for making our trip so very special. We highly recommend Tuscany Untouched and would love to revisit this beautiful region with them again!
Read more
Skip the line!
New York City
Uffizi Combined Ticket:UFFIZI, PITTI, BOBOLI & digital audioguide
Laurel_L, Oct 2025
Skip the line!
The ticket office is a few blocks from the Uffizi. We didn't realize this at first. Therefore, plan your time carefully, so you that you can pick up your tickets at least 1/2 hour to 45 minutes before your entry time (unfortunately, you don't get to "skip the line" to get into the Uffizi).But, this company did truly allow you to "skip the line," and, they were very easy to deal with.
Read more
10 Star Rave Review for 2-day E-bike tour!
New York City
2-Day E-Bike Tuscany Tour with Meals, Wineries, and Farmstay
Emmy_P, Oct 2025
10 Star Rave Review for 2-day E-bike tour!
My husband and I took the two day bike trip from Florence to Siena. Our Guide was Alejandro and we were assisted on the route by a lovely young woman whose name I have forgotten and by Gabriele — a total gem. Every detail on this tour was carefully thought through. Alejandro is a an attentive and expert guide. He was easily able to help my husband and I even though we have different levels of experience on bikes. (I felt completely safe even though I’m not the best bike rider. And on day 2 Alejandro brought me a padded seat for my bike — so thoughtful!) The areas we rode through were incredibly beautiful. We were delighted to see the changes in topography as we rode from Florence, through the Chianti region, and into Siena. In addition to being funny, kind, and at the same time utterly professional, Alejandro was knowledgeable about all of the plants and trees that we saw and gave us lots of interesting facts about the flora and fauna. He also had lots to say about the historical significance of the sites we were seeing. Now I must rave about the two wine tastings that we did. We Like Tuscany partners with several small wine producers, and on each day we were blown away by the wines and the food and the decor! Alejandro has a personal relationship with the people who run these small wineries. Being on a tour with this kind of an insider was very special. I think the best way to sum this up is that I am now trying to figure out a way to organize a whole family reunion around a bicycle trip in the area with Alejandro and the team at We Like Tuscany! It was the highlight of our 5 week trip to Europe. I simply cannot recommend it highly enough!
Read more
Loved it
New York City
Unique Tuscany Experience in 1 week with the locals
F5868ZWchristiney, Sep 2025
Loved it
Completed a 7 day experience of Tuscany Tour. Our accomodation was superb and so welcoming and authentic. It was in Loro Ciufenna which really is the most picture perfect location and base. So naturally beautiful. We spent our days exploring Tuscany and our evenings savouring 3 course local cuisine in a beautiful restaurant overlooking the stream and ravine chatting to fellow travellers. Such a unique and special experience- thoroughly enjoyed every minute. Sad to leave. Christine and Karen from Sydney and Central Coast.
Read more
Tuscany from a Unique Perspective
New York City
Authentic 7 Day Tuscany Tour
TravelWarrior48, Sep 2025
Tuscany from a Unique Perspective
A truly wonderful and unique way to be fully entrenched into the many aspects of the Toscana region. This tour allows one to see and capture the history and culture of this beautiful area. From the accommodations, food, wine and vitality, one feels the warmth and friendliness of Tuscany provided by the host(s). A true 5 star experience.
Read more
Great 2-Day Italian Trip
New York City
2-Day Tuscany Combo Tour: Florence, Pisa, Cinque Terre & Tuscany
H2629XTjennad, May 2025
Great 2-Day Italian Trip
My husband and I went on this tour for our anniversary. It was absolutely incredible! We got to have our free time in each place and got great recommendations from our tour guide, Elisa. Elisa was so sweet and answered all of our questions! We had a great time with the others on the tour too, and wish we could have been on a longer tour with them.
Read more
Florence on foot
New York City
Unique Tuscany Experience in 1 week with the locals
carlossK9461ZM, Apr 2025
Florence on foot
Walking through Florence on foot is a fantastic experience. To enter all the alleys, in every corner, there is always a shop or a cafe that draws our attention. Relatively flat city, helps to the walk. Buy the monuments tickets in advance so you can visit them with minimal time loss in queues. The only care to have is with the irregularity of the floor.
Read more
Great Tuscany Wine Tour....magnifico
New York City
From Florence to Tuscany Winerys
juliegO8664GJ, Apr 2025
Great Tuscany Wine Tour....magnifico
Two fantastic wineries. Great experience. Breathtaking views. Our driver, Michele Amenta, was fantastic. Personable, knowledgeable and easy going. Win win. Grazie.
Read more
Great Italy experience
New York City
The Best of Tuscany in 3 Days
B5669ISmariel, Mar 2025
Great Italy experience
Great experience with great knowledgeable tour guide! Would highly recommend to anyone interested in exploring Florence and the towns around florence.
Read more
The best Italy Adventures
New York City
The Best of Tuscany in 3 Days
hannalR5818XR, Mar 2025
The best Italy Adventures
We did a 4 day trip with Italy on a budget and we had an amazing time. We learned a lot about the best local shops and eateries, but also about the culture in Florence and the other parts of Italy we explored. I would recommend this 4 day Florence, Tuscany, Pisa and cinque terra visit to anyone interested in exploring more of what Italy has to offer.
Read more
Great experience in the other Tuscany
New York City
Authentic 7 Day Tuscany Tour
BobNCarol, May 2024
Great experience in the other Tuscany
My wife and I recently had a wonderful time visiting places in Tuscany, some of which were well off the beaten path. The base for our tour was provided through the hospitality of Francesca and Carlo at the Dimora Casa Eugenia in Loro Ciuffenna. They and their staff supplied excellent accommodations and wonderful food at the beginning and end of each tour day. In between we were driven and guided by Paolo who filled each trip with interesting history and personal stories filled with his passion for the region. You should definitely ask for Paolo to be your driver if at all possible. We benefitted by the fact that we were the only people on our tour. This gave us freedom and opportunity to know the people better than being part of a larger group. I am sure our 2-person tour barely paid for expenses, but it was very nice to know that our tour wasn't cancelled because of the low attendance. I thank Matteo for this courtesy.
Read more
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