Tuscany Tours and Trips 2024/2025

Whether you’re going for the superbly crafted fine wines of Tuscan vineyards or the incomparable renaissance art of Florence, a  Tuscany tour is cultural awakening. The region is found on Italy’s west coast and is greeted by the Tyrrhenian sea. One of Italy’s most popular tourist regions, the many faces of Tuscany create an authentic taste of what makes Italy such a fascinating travel destination. 

36 Trips in Tuscany with 132 Reviews

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Small Group Brunello Wine Tour from Siena

of 1 review
  • Free cancellation
  • Trip customizable
We had the most fantastic trip on our brunello wine tour. It was the best tour on our whole Italian
  • Tour Type Small Group Tour
  • Activities Wine tasting tours & Farm and plantation visits
  • Accommodation No Accommodation
  • Age Range 17-79 yrs
  • Operated in English
hours09 From US$ 192 View Tour
Next Departures
  • Apr 27
  • Apr 28
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Half-Day Guided Hike to Monteriggioni from Siena

of 1 review
  • Free cancellation
  • Trip customizable
4 hour countryside and village visits trip through Siena and Monteriggioni. Read More
  • Tour Type Small Group Tour
  • Activities Countryside and village visits & Trekking and Hiking +2 more
  • Accommodation No Accommodation
  • Age Range 5-79 yrs
  • Operated in English
hours04 From US$ 59 View Tour
Next Departures
  • Apr 29
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Small Group San Gimignano & Volterra Tour from Siena

  • Free cancellation
  • Trip customizable
8 hour cultural, religious and historic sites tour through Tuscany and Siena. Read More
  • Tour Type Small Group Tour
  • Activities Cultural, religious and historic sites & Art and architecture +3 more
  • Accommodation No Accommodation
  • Age Range 5-79 yrs
  • Operated in English
hours08 From US$ 192 View Tour
Next Departures
  • Apr 28
  • Apr 30
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Small Group Pienza & Montepulciano Tour from Siena

  • Free cancellation
  • Trip customizable
8 hour cultural, religious and historic sites trip in Siena. Read More
  • Tour Type Small Group Tour
  • Activities Cultural, religious and historic sites & Farm and plantation visits +1 more
  • Accommodation No Accommodation
  • Age Range 5-79 yrs
  • Operated in English
hours08 From US$ 192 View Tour
Next Departures
  • Apr 27
  • Apr 29
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Small Group Chianti & San Gimignano Sunset Wine Tour

  • Free cancellation
  • Trip customizable
On this day trip you will visit Chianti, Tuscany and Siena. Read More
  • Tour Type Small Group Tour
  • Activities Beer and drinks tasting
  • Accommodation No Accommodation
  • Age Range 5-79 yrs
  • Operated in English
hours08 From US$ 192 View Tour
Next Departures
  • Apr 27
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Private Gourmet Wine Tour in Tuscany

of 2 reviews
  • Free cancellation
  • Trip customizable
What a beautiful time spent in Tuscany on this trip. This was a wonderful tour. Great accommodations ...
  • Tour Type Private Tour
  • Activities Food tours & Wine tasting tours +1 more
  • Accommodation Hotel
  • Transport Train
  • Age Range 22-89 yrs
  • Operated in English, German
days04 From US$ 2,370 View Tour
Next Departures
  • Apr 30
  • Apr 29
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Via Francigena: Lucca to Siena

of 1 review
  • Best price guaranteed
  • No booking fees
This was an absolutely wonderful trip. The organisation was excellent, accommodation much better tha ...
  • Tour Type Private Tour
  • Activities Trekking and Hiking
  • Accommodation Hotel
  • Transport Train
  • Age Range 18-99 yrs
  • Operated in English
days08 From US$ 1,190 View Tour
Next Departures
  • Apr 28 10+ seats left
  • Apr 29 10+ seats left
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Guided Walking Tour of Siena with Cathedral

  • Free cancellation
  • Best price guaranteed
1 hour walking trip in Siena. Read More
  • Tour Type Group Tour
  • Activities Walking tours
  • Accommodation No Accommodation
  • Age Range 1-99 yrs
  • Operated in English, Italian
hours01 From US$ 43 View Tour
Next Departures
  • Apr 27
  • Apr 28
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San Gimignano, Siena & Chianti from Florence

  • Free cancellation
  • Best price guaranteed
11 hour wine tasting trip through Tuscany and Florence. Read More
  • Tour Type Group Tour
  • Activities Wine tasting tours & Countryside and village visits +2 more
  • Accommodation No Accommodation
  • Age Range 1-99 yrs
  • Operated in English, Italian, Portuguese, Spanish
hours11 From US$ 64 View Tour
Next Departures
  • Apr 27
  • Apr 30
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Tuscany Walking and Wine

of 1 review
  • Best price guaranteed
  • No booking fees
A well paced trip with an excellent guide, I really enjoyed it, despite the covid rules.
  • Tour Type Small Group Tour
  • Activities Walking tours & Cultural, religious and historic sites +3 more
  • Accommodation Hotel
  • Transport Train, Bus, Minibus & Taxi
  • Age Range 16-95 yrs
  • Operated in English
days08 From US$ 2,280 View Tour
Next Departures
  • Apr 28 10+ seats left
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Small Group Chianti and Castles Wine Tour from Siena

  • Free cancellation
  • Trip customizable
8 hour farm and plantation visits tour through Chianti and Siena. Read More
  • Tour Type Small Group Tour
  • Activities Farm and plantation visits & Wine tasting tours
  • Accommodation No Accommodation
  • Age Range 5-79 yrs
  • Operated in English
hours08 From US$ 192 View Tour
Next Departures
  • Apr 29
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E-Bike Chianti Tour from Siena with Winery Lunch

  • Free cancellation
  • Trip customizable
6 hour bicycle tour in Siena. Read More
  • Tour Type Small Group Tour
  • Activities Bicycle tours
  • Accommodation No Accommodation
  • Age Range 13-79 yrs
  • Operated in English
hours06 From US$ 192 View Tour
Next Departures
  • Apr 27
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A Taste of Italy: 11 Days

  • Trip customizable
  • Best price guaranteed
11 day cultural, religious and historic sites trip through Rome, Florence, Venice and 6 other destinations in Italy. Read More
  • Tour Type Group Tour
  • Activities Cultural, religious and historic sites & City sightseeing +1 more
  • Accommodation Hotel
  • Transport Boat, Bus, Coach, Taxi & Train
  • Age Range 7-99 yrs
  • Operated in English
days11 From US$ 2,700 View Tour
Next Departures
  • Apr 28 10+ seats left
Skip the queue Add to your Tour Wish List

Siena City & Duomo Walking Tour

  • Free cancellation
  • Trip customizable
2 hour walking trip in Siena. Read More
  • Tour Type Group Tour
  • Activities Walking tours
  • Accommodation No Accommodation
  • Age Range 2-79 yrs
  • Operated in English
hours02 From US$ 43 View Tour
Next Departures
  • Apr 27
  • Apr 28
Showing 1 - 14 of 36 results
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Tuscany Tour Reviews

5 - Excellent
Based on 132 customer reviews
Tuscany Cycle Siena and Florence
5 - Excellent
  • Anonymous
“One week cycling the hills of Tuscany. One day off in Siena. We finished in Florence. It was like cycling through a postcard of Tuscany: Cypress trees, vineyards, wine tasting places, hilltop mediaeval villages. In 10 years of cylcing in Europe, this scenery and these roads were the most captivating. The food was delicious, loads of salads and veg for people like me who do not like meat but loads of meat if you like it. And the wine, you could get the finest wine that Italy had to offer in the smallest Pizzarias. The bikes: lightweight ridgebacks were really good.”
A great week
5 - Excellent
  • Anonymous
“I went on a challenging grade week and it lived up to the bill. Long walks across constantly changing terrain with temperatures changing just as quick. Really enjoyed the challenge - forests, grasslands, rocky terrain, scrambling - it had it all and there was never a dull moment, all the while I felt completely safe in the hands of fantastic guides.”
CYCLE THROUGH SIENA & CHIANTI
5 - Excellent
  • Anonymous
“What a fantastic holiday. The views and towns were amazing, a fantastic guide and challenging cycling. I would seriously recommend this holiday to someone that loves excercise, sightseeing, eating and drinking.”

Tuscany - Tour Highlights and Travel Tips

Travel Highlights

  • Wine lovers should head to Chianti, the birthplace of internationally renowned red wines.
  • Florence’s Galleria degli Uffizi is home to the biggest collection of renaissance art in the world. Even the Palazzo that houses the galleria is a masterpiece.
  • An iconic building of Tuscany is Florence’s Duomo, which took nearly 150 years to build.
  • The infamous Leaning Tower of Pisa needs no explanation, but does need to be witnessed.
  • The beaches of Viareggio are within an hour of Florence, Pisa, Livorno and Lucca.
  • Drive through the Crete Senesi and visit the renaissance city of Pienza.

Travel Tips

  • Driving is a great way to explore Tuscany, but beware of the lax approach to road rules in Italy.
  • The Firenze Card is a 72 hour tourist card for Florence covering attractions, public transport and even lets you skip queues.
  • Get ready to walk in Florence as most of the historic center is off-limits to cars, but the city is smaller than expected and very pedestrian friendly.
  • The markets of Tuscany offer some of the best places to shop. Leather goods and souvenirs are a fraction of the price than what you’ll find in a boutique.
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