What to do and see in Tuscany, Italy: The Best Wine Tours & Tastings

January 5, 2022 Cedrick Jardin

Tuscany (/ˈtʌskəni/ TUSK-ə-nee; Italian: Toscana, pronounced [toˈskaːna]) is a region in central Italy with an area of about 23,000 square kilometres (8,900 square miles) and a population of about 3.8 million inhabitants (2013). The regional capital is Florence (Firenze).
Restaurants in Tuscany

1. Flavours of Lucca Small Group Art, History, Food and Wine tastings Tour

Piazzale Ricasoli, 55100 Lucca LU, Italy Tuscany like a Local
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5.0 based on 1 reviews

Join us for an interesting morning food tour that will dive you into the gastronomy, history, art and culture of our fascinating city. This experience is a perfect introduction to the city that you will discover from different points of view. We look forward to letting you experience a chill-out tour seen from a local perspective.

Inclusions: selection of local sweet treats plus espresso or capuccino, local snack with secret recipe (vegetarian), selection of cured meats, cheese and crostini plus a glass of wine or beer

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Reviewed By 885nancyb

Did this tour in the summer of 2019 (not 2020) with our extended family, led by Luca and Chiara. It was such a fun and memorable experience. The bikes were in great condition. The guides were so helpful and informative and the treats we stopped to enjoy were fabulous. We also did their Pisa tour with them too, to make it a very full day. We loved every minute. Thanks Luca and Chiara and we wish you great success with your new company. Can't wait to return to Tuscany!

2. PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

UniqueTuscany private Tours
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5.0 based on 27 reviews

• EXPERIENCE FOR YOUR PRIVATE GROUP • With this fascinating tour you will discover a unique part of Tuscany in a private day-trip from Florence. With an expert local driver/guide, immerse yourself in the renowned Chianti wine region and explore the cities of Siena and San Gimignano. You will tour historic landmarks such as Piazza del Campo in Siena, home to the annual Palio, and the medieval towers of San Gimignano. Add an optional, unforgettable lunch to savor traditional Tuscan wines and specialties in a local organic farm or winery! • 8/9-hr Full-Day private tour of Tuscany • Visit the medieval cities of Monteriggioni, San Gimignano and Siena • Hear live commentary of the wine cellars by your guide • Taste Craft Chianti Classico wine at a local vineyard • Pick-up and drop-off at your Hotel or at the address provided • Travel in a Mercedes-Benz minivan

Inclusions: Pick-up and drop-off at your selected hotel/location (in Downtown Florence), Private transportation by Mercedes-Benz MiniVan, Air-Conditioned, English-speaking licensed driver, Free time in Siena and San Gimignano, Unlimited cold mineral water , On-Board WiFi

Exclusions: Local guides in Siena and San Gimignano, Lunch in farm or winery available at an extra cost 25€pp to 50€pp, depending on option chosen, Entrance fees (Cathedral of Siena ia approx. 7€ pp.)

Reviewed By Gabriel S

This was our 2nd private tour that we did through Uniquetuscany (2017/2020). Our guide, Alessandro was very specific to the covid restrictions and offered us new masks during the day! He did a wonderful job explaining the history of the towns. Our highlight was the visit to Tuscany organic farm where we had our lunch with amazing view. We stopped at Siena, San Gimignano and Pisa. There was a lot of walking and moving from in and out of the minivan so make sure you wear comfortable shoes. I definitely recommend this tour while visiting Florence since you get a lot of history while on the minivan to each town. Just not enough time in all the towns but 10 hours is a long day! still worth the trip! Highly recommended..

3. Tuscan Wine Tour in Lucca by shuttle

Autoservizi DB Tuscany - Private Drivers
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5.0 based on 6 reviews

The only authentic wine tour in Lucca. Two wineries. Two different ways of making wines, different opinions, and different methods, but united by the same aim: producing the best wine of Lucca. I will pick you up at your accommodation with my van, and I will drive you through the hills of Tuscany. For every winery we will visit the cellar where you will discover all the secrets about Tuscan wine, thanks to the explanations and the life stories of the farmers. Than, you will taste 3 wines of the production. Every wine will be matched with products from the garden and some specialties, like finocchiona or pecorino cheese, plus a final dessert... a dip in the Tuscan table culture! You won't be hungry :) "It's not just drinking wine: we want to make you know the real Tuscany and to tell you the story of our roots" N.B.: ! The price includes the transportation and the guided tour, but not the cost of the tastings: you will pay 15€ per person at every winery, directly on the spot !

Inclusions: Private transportation, Guided Tour on the hills of Tuscany, Bottled water

Exclusions: Snacks, Alcoholic Beverages

Reviewed By 591paulinek

We used Tommaso for a ladies trip to Tuscany in September. He provided airport transfers to and from Pisa to our hotel in Florence as well as a half day tour in Chianti with some stops for wine tasting. Tommaso and his colleague were punctual, extremely friendly and helpful, spoke very good English and offered very competitive rates. I would recommend him to anyone needing transport in the area. Thank you for a brilliant few days!

4. Osteria senz'Oste: not a ordinary Osteria at Ripalte

Tenuta delle Ripalte, Loc. Ripalte, 57031 Capoliveri LI, Italy CANTINA Tenuta delle Ripalte
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5.0 based on 1 reviews

Serve yourselves and enjoy your tasting! This is the spirit of our wine experience at Tenuta delle Ripalte. After welcoming you on the terrace of Cantina delle Ripalte, you will receive instructions to explore the estate on your own, looking for the Osteria senz'Oste: an isolated little house among the vineyards of Poggio Turco, overlooking the Tuscan Archipelago. In this magical context, you will find a set ready for an aperitif with friends: a private sitting room, wine Spumante Brut Tenuta Ripalte (rosé sparking wine) (one bottle for every 6 participants) and various appetizers from Tuscan cuisine (cold cuts, cheeses and other local food). Once finished, you can extend your stay by tasting other products of the Cantina delle Ripalte (wines and local food) by ordering à la carte. Enjoy your meal and the wine with friends in this rustic and exclusive venue, as the sun sets into the sea!

Inclusions: Equipped cottage in the vineyards, secluded in the Mediterranean Trees, Aperitif kit: a bottle of Spumante Brut Rosé Tenuta Ripalte (sparkling rosé wine) every 6 participants, Aperitif kit: appetizers from Tuscan traditional cuisine (variety of cold cuts, cheeses and other local food), Aperitif with friends at sunset overlooking the Tyrrhenian Sea in complete autonomy, Extension of time: additional wines and appetizers can be ordered à la carte on the spot (extra charge)

Exclusions: The host is not provided: you will receive instructions to reach the cottage by yourself and find the aperitif kit

Reviewed By globetrotter880

We were sailing from Punta Ala and booked this tour with friends. The guide picked us up at the beach and it was punctual and very knowledgeable. We had a lot of fun, sipping very good wines in a location with a very clear view of the sea. You can anchor in the bay and check your boat all the time.Very easy going for all sailers

5. Aperitif at Ripalte for Sailors

Unnamed Road, 57031 Capoliveri LI, Italy CANTINA Tenuta delle Ripalte
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5.0 based on 1 reviews

We meet you at the Remaiolo Beach where a private Jeep will pick you up and bring to the excursion, directing you to the Tenuta delle Ripalte Winery. On the magnificent panoramic terrace, we will introduce you to the history of the Estate and the vineyards, presenting the wines that will frame your exclusive aperitif. You will taste three of our wines produced from Aleatico grapes: the Spumante Brut Rosato (sparking rosé), the Rosato delle Ripalte from Aleatico grapes (dry rosé wine), the Aleatico Passito dell'Elba (sweet red wine). The wines will be paired with a variety of flavors from Tuscan cuisine (artisan cured meats, spiced cheeses and a typical dish). Aperitif time-extension ordering more wines and food à la carte! At the end, the Jeep will take you back to Remaiolo Beach, to return to your boat.

Inclusions: Anchorage at Remaiolo Beach with private Pickup, Jeep excursion with private driver to Tenuta delle Ripalte, Visit to one of the 14 Design Wineries of the Toscana Wine Architecture Circuit, Aperitif with typical wines and local food, with guided tasting, Food accompaniment of Tuscan flavors. Additional wine and appetizers can be ordered à la carte

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Reviewed By P F

I had an unforgettable moment during this aperitif with friends. The place is truly unique and you can go with friends to celebrate a birthday in an exclusive way. The place was reserved for us only and the sunset was magical. The observation point on the coast is truly privileged. The wines were delicious and the snacks tasted great, you can order more if you want with your mobile!

6. Chianti Classico and Super Tuscan 3 Winery Tour

Piazza dei Cavalleggeri, 50122 Firenze FI, Italy Tuscan Wine Tour by Italy and Wine
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5.0 based on 70 reviews

This tour goes in the famous Chianti wine growing region, to taste Chianti e Super Tuscan wines, lunch in a small boutique of wine.

Inclusions: Local taxes, 3 Winery to visit, 3-course lunch, Wine tasting, Extra Virgin Olive Oil tasting, Local wine expert, Small-group tour up to 8 attendees, Transport by air-conditioned minivan

Exclusions: Hotel pickup and drop-off, Tips

Reviewed By ElisabethG947

We had a wonderful day hunting truffles and tasting wine. The hunt was so interesting and informative. Lunch at the family estate was amazing. The best truffle dishes I have ever had, paired with wine from their family estate. Do not miss out on this wonderful experience.

7. Private Chianti Wine Tour with Lunch, a Visit of San Gimignano, Organic Wineries

Via Curtatone, 9, 50123 Firenze FI, Italy Chianti Wine Tour by Fun In Tuscany
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4.9 based on 276 reviews

Private Tour. First we tour vineyards and cellar of an organic farm in the heart of the Chianti region, receiving an up close look at the production and ageing process of the Chianti wines and learning about the secrets of the extra virgin olive oil making. This experience includes a  wine tasting and the opportunity to buy for cheap the best tuscan wines. Our trip continues on to the  medieval town of San Gimignano, where you will also have the chance to try the famous world champion Dondoli gelato. We then move on to a second winery where we enjoy an authentic  tuscan lunch, combined to a wine tasting class. A fine selection of Tuscan wines are presented by a wine expert to be paired with antipasti toscani, ribollita soup, lasagna with truffle olive oil and more.. On our way back we stop at  Piazzale Michelangelo, in the top ten of the most romantic spots in Europe.

Inclusions: Transport by air-conditioned confortable minivan, Lunch, Wine tastings, A visit of two wineries, Private wine tour, Live commentary on board, A visit of San Gimignano, A visit of Michelangelo Square

Exclusions: Hotel pickup and drop-off

Reviewed By KFDOCTOR

Your trip to Tuscany is incomplete if you do not go on this tour !! Amazing selection of Wines and Cheese. You are served some great food and the scenery is out of the world. Do not miss San gimignano you will get to taste the world's best gelato !!

8. Tuscany Vespa Tour

Tuscany Vespa Cycle and Bike Tour, Via Ghibellina, 133/red, 50122 Firenze FI, Italy Tuscany Cycle
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4.9 based on 278 reviews

Escape from the crowded streets of the city to see life as a local as you zip around the stunning Tuscan countryside on a REAL Vespa (with automatic gears)! The tour is perfect for all levels as we always begin with a lesson so that beginners may get the hang of driving. After the lesson, the real fun begins. We will zip through the winding country roads and stop for pictures along the way. You won't want to forget your camera on this trip - the sights are incredible and you will be in the heart of the Chianti region! After our picture break we will continue driving until we return to a private Tuscan winery to learn a little bit about how local wine and olive oil is created. With this tour you won't feel like just another tourist, you will get to explore Chianti like a real local!

Inclusions: Tour escort/host, Transport by air-conditioned minivan, Beverages, Lunch (Sunset Vespa Tour no lunch wine tasting and snack)

Exclusions: Hotel drop-off

Reviewed By DublinNoodle

I hired a road bike for 4 days. Dejan was extremely helpful and made it very straightforward. The bike was good spec and well maintained and it was very enjoyable to explore the Tuscan countryside.

9. Taste of Chianti: Tuscan Cheese, Wine and Lunch from Florence

Walkabout Florence Tours, Via Vinegia, 23R, 50122 Firenze FI, Italy Walkabout Florence Tours
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4.9 based on 1,360 reviews

Treat your taste buds on a full-day Chianti wine and food tour from Florence and sample some of Tuscany’s finest wine, cheese, meat, chocolate and more! With a local guide who is passionate about the region’s food heritage, travel through the countryside by 4x4 off-road vehicle and tour an historic villa, and a Chianti Classico winery. Up to seven glasses of wine are included throughout the day, plus several food samples and a 3-course meal at a traditional restaurant in the Chianti hills.

Inclusions: Transport by air-conditioned 4x4 vehicle, Professional guide, 9 samples of wine, 2 samples of olive oil, Food tastings, Lunch

Exclusions: Gratuities, Hotel pickup and drop-off

Reviewed By katiegN3709NB

Christian helped make our Florence experience memorable! My husband and I traveled throughout Italy with our two young children ( 8 and 5 years old) and they were so excited for their Fiat tour. They were the only kids on the tour but Christian made sure it fun and educational for them. The whole group was inviting and it was great to get to meet people from all around the world! My kids can not wait to travel more and still talk about how awesome the tour was. I highly recommend this tour with or without kids. We were taken to scenic views throughout Tuscany and even had to maneuver through the streets of Florence in a super fun classic Fiat. Everywhere we drove people would stop and wave because of the group of Fiats brought joy to everyone! This was the best tour we took in Italy and when we come back for a visit we are definitely doing it again! (Our tour was pre-covid)

10. Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

Tours of Tuscany
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4.9 based on 27 reviews

This full-day tour will bring you a taste of the complex, full-bodied Brunello reds that make this region every wine lover’s dream. We will pick you up at your hotel & take you to some of the lesser-known vineyards with high-quality wines. After your first tasting, take some time to explore the hilltop town of Montalcino, where we will visit a second Brunello winery. Then we will continue to Pienza, a UNESCO World Heritage Site & a unique example of the ideal city according to Renaissance architecture. Then one last stop in the small town of Montepulciano, where you can taste the exquisite Nobile di Montepulciano wine & meet the winemakers that make the magic happen. Enjoy a special lunch featuring local specialities. Pick-up & Drop-off at your accommodation 3 wine tastings at boutique wine cellars Lunch with wine pairings & local specialities Visit Pienza & Montepulciano Small group: limited to 8 guests Don’t drive while you wine & dine! Let us take care of everything.

Inclusions: 3 Winery tour and tasting, Pairing lunch at a historic winery, Bottled water, Air-conditioned vehicle, WiFi on board

Exclusions: Gratuities

Reviewed By Sogufa

Amazing experience. Kindness and professionalism at the same time. Well organised and safe in all aspects.

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