Top Tuscany Wine Tasting Tours - page 41

"Chianti Segreto: Winter Tour Wines and Tuscan Lunch."

6 to 7 hoursFree Cancellation

from $192

Private Wine & Evo oil Tasting with Vegetarian Meal

✅ Exclusive Wine, Olive Oil & Balsamic Vinegar Tasting – Savor our organic wines and premium olive oils, straight from our estate. ✅ Farm-to-Table Vegetarian Cuisine – Enjoy a homemade meal featuring fresh, seasonal, and locally sourced ingredients. ✅ Authentic Tuscan Atmosphere – Dine in a rustic farmhouse with stunning views of vineyards, olive groves, and medieval towers. ✅ Biodynamic Farming Experience – Learn about our sustainable agricultural practices and how they shape our products. ✅ Private & Personalized – A family-led experience with a warm, welcoming touch. ✅ Convenient Location – Just minutes from San Gimignano’s historic center, offering a peaceful countryside escape.

Private Wine & Evo oil Tasting with Vegetarian Meal

1 hour 30 minutesFree Cancellation

During this practical and engaging experience, you will have the unique opportunity to learn the secrets of homemade fresh pasta. At the end of the lesson, your culinary efforts will be rewarded. You will sit at the table for a convivial lunch where you will taste the dishes that you yourselves have prepared. It will be a moment of joyful sharing, a true concentration of Italian spirit and Tuscan tradition. The Flavors of Brunello: To make the experience even more complete and unforgettable, you have the option to enrich your lunch with a guided tasting of one of Italy’s most prestigious wines: Brunello di Montalcino. Cooking Class with Wine Tasting: This formula combines the passion of the Cooking Class and the joy of lunch with a special wine tasting. You will be accompanied on a journey of discovery, sampling 2 glasses of the majestic Brunello and 1 glass of Brunello Riserva. A sip of history, passion, and territory that will complete your culinary experience.

from $87

Cooking Class in Historical Villa in Montalcino

Cooking Class in Historical Villa in Montalcino

3 hoursFree Cancellation

4.5

from $245

Exclusive Private Assisi & Sagrantino Wines Experience

True travelers are always driven by a desire to discover new places. This same curiosity inspires those who visit the birthplace of the famous Saint Francis of Assisi. It’s also the region where one of Italy’s finest wines, Sagrantino di Montefalco, is produced. Ever-changing, untouched landscapes in the green of winding valleys make Umbria a region that will never fail to amaze. Umbria is also a region rich in art, history, culture and spirituality—characterized by an important cultural heritage. Assisi is a town with religion very close to its heart. Visitors shouldn’t be surprised to see monks in long brown robes roaming the streets or bands of pilgrims walking the country roads surrounding the town. Pilgrims have been coming to Assisi since the 13th century to venerate St. Francesco, who was born and buried here. But you don’t have to be religious to enjoy one of the best-preserved medieval towns in the world, which is also one of Italy’s most spell-binding gems.

Exclusive Private Assisi & Sagrantino Wines Experience

13 hoursFree Cancellation

(2)

from $815

On the border between Tuscany and Umbria lies one of the prettiest, charming and historical towns in Italy; Cortona. Cortona is enclosed by ancient stone walls dating back to Etruscan and Roman times. Known for its picturesque landscapes and the film "Under The Tuscan Sun", this medieval town is also supposedly the birthplace of the founder of Troy (Dardano), whose descendants eventually left Troy and founded Rome! But what many do not know is that this town is also home of the most delicious wines in Italy. Discover Cortona and its wines in a private Tour, through a meticulously curated guided wine tasting experience showcasing the winery’s finest creations. The DOC wines of Cortona are renowned for their high quality and unique flavors, with a wide range of styles and flavors, there is something for every wine lover to enjoy. The wines of Cortona are sure to Impress. Enjoy a lunch prepared inside the winery and paired with the winery’s best wines.

Exclusive Private Cortona Experience from Florence: Tuscan Syrah.

Exclusive Private Cortona Experience from Florence: Tuscan Syrah.

10 hours 30 minutesFree Cancellation

from $698

Explore the scenic Italian Riviera on our Winter Cinque Terre Day Trip from Florence! Visit the 4 fishing villages of this coastal national park overlooking the Ligurian Sea. Cinque Terre consists of the villages of Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. Each village has its own unique charm, featuring narrow alleys, terraced vineyards, and breathtaking vistas. Historically, these villages were isolated from the rest of Italy, which helped preserve their traditional way of life and architecture. Nestled along the rugged Italian Riviera coastline, Cinque Terre is a collection of five enchanting villages that captivate visitors with their colorful houses, stunning sea views, and rich cultural heritage. A Cinque Terre day trip in Winter season offers a perfect blend of scenic beauty, historical intrigue, and cultural immersion, making it an ideal excursion for all travelers.

Exclusive Private Winter Cinque Terre Day Trip from Florence

Exclusive Private Winter Cinque Terre Day Trip from Florence

11 hoursFree Cancellation

from $582

This sparkling red wine, lively and refreshing, has been cherished for centuries as the perfect companion to the region’s rich gastronomy. During this immersive tour, you will explore not just the wine itself but also the stories of the people and families who have been cultivating it for generations. Amid rolling hills, sunlit vineyards, and charming cellars, you will uncover the authentic character of a wine that is as effervescent as the culture it represents. This experience is designed for wine lovers, food enthusiasts, and curious travelers alike — anyone who wishes to deepen their connection to the Italian way of life while savoring unforgettable flavors. A Celebration of Senses From the fragrance of freshly pressed grapes to the sparkle of each glass and the warmth of Emilia-Romagna’s hospitality, this tour is more than a wine experience — it is a journey into the heart of Italian culture.

Exclusive Private Lambrusco Experience from Florence

Exclusive Private Lambrusco Experience from Florence

11 hoursFree Cancellation

from $698

Valpolicella is a region rich in cultural and artistic heritage, with landscapes and landmarks recognized as UNESCO World Heritage Sites. In Valpolicella, the joy of life is found in the pleasures of good food and fine wine, as well as in relaxation and rejuvenation. As in all Italian regions, Valpolicella's gastronomy is diverse, offering unique dishes across, reflecting the area’s history and traditions. From Valpolicella, Soave, Piave, and Prosecco wine regions, Veneto is truly a land of infinite variety. With private local guide, you can explore the city of Verona. Indulge in this private wine experience in Valpolicella as you embark on an exclusive journey through the region's renowned vineyards. Enjoy VIP wine tastings at premium estates and boutique wineries.

Exclusive Private 3 Days Amarone Wine Experience from Florence

Exclusive Private 3 Days Amarone Wine Experience from Florence

3 daysFree Cancellation

from $3,964

Discover the beauty of Tuscany on a private DA Florence to Cortona and Montepulciano tour. Start your adventure in Cortona, where you will explore the historic center, listening to fascinating stories told by your Guide. Next, head to Montepulciano for a guided tour of a historic winery, where you will have the opportunity to taste fine wines and enjoy a light lunch. This tour is perfect for wine and history lovers, offering an authentic experience of Tuscany. - Private DA Florence to Cortona and Montepulciano tour with driver - Guided tour in the center of Cortona with local stories - Wine tasting in a historic winery in Montepulciano - Light lunch included during the tour

DA Florence Cortona and Montepulciano Day with Wine Tasting

DA Florence Cortona and Montepulciano Day with Wine Tasting

8 hoursFree Cancellation

4.0

from $933

"Gourmet" Wine Tasting at Cesani's

1 hour 45 minutesFree Cancellation

This idyllic combination of our self-tour aboard our Fiat 500s with the picnic lunch of our partner winery will take you on a most authentic journey around unexplored back roads of the Lucchese countryside. Starting from our shop, you will follow our GoogleMaps itinerary to pass underneath the Neoclassical acqueduct and through the lush scenery of Compitese, an area famous for it's olive oil and natural landscapes. Arriving then at the winery, the hosts will prepare for you a picturesque picnic set by the shade of the olive groves. Local cheeses and cold cuts, "giardiniera" style pickled veggies and other Tuscan classics (like bruschetta) will be paired with the wines of the property, in a series of simple pleasures that go a long way. Please note that the picnic has to be paid on the spot and is not included in the price. After lunch you'll continue down the road and over the mountain to arrive at a spectacular viewpoint overlooking the Massaciuccoli Lake, before heading back.

(4)

from $70

Fiat 500 Picnic Experience

3 to 6 hours

from $292

Per group

Private Tuscany Day Trip from Florence with Vineyard Lunch

Discover the best of Tuscany on a private journey through its beautiful towns and landscapes. Travel from Florence with a professional English-speaking driver who takes the stress out of navigating. In Siena, meet a licensed local guide for a walking tour through medieval streets. Along the way you'll learn about the majestic cathedral and famous Palio horse race. Then, savor a leisurely Tuscan lunch with wine pairings at a family-run Chianti farmhouse, surrounded by vineyards and olive groves. End your day in the hilltop gem of San Gimignano, a UNESCO-listed village, where you’ll enjoy free time to explore artisan shops, climb the towers, or simply soak in the views. With private transport and a relaxed pace, this day offers an intimate and authentic way to experience Tuscany.

Private Tuscany Day Trip from Florence with Vineyard Lunch

9 hours

from $787

This private evening food tour explores five small local businesses in the Oltrarno district with an expert foodie focused solely on you. This intimate tour makes it easy to ask questions, enjoy unhurried moments, and connect more closely with Florence’s food culture. Begin with a classic aperitivo of Tuscan wine and regional snacks, then stop at a historic wine window for Prosecco. Continue to a neighborhood wine bar for a hands on Negroni lesson where you can take your time learning each step and savor cold cuts and freshly baked schiacciata. Dinner at an upscale trattoria features pasta and signature Florentine steak, as your guide explains how these dishes fit into local culinary traditions. End at an artisan gelateria with rotating seasonal flavors for a sweet finale. This private food tour keeps the evening comfortable, flexible, and ideal for a special occasion or simply enjoying Florence at your own pace.

Private Florence Food & Wine Tour with Authentic Tuscan Tastings

Private Florence Food & Wine Tour with Authentic Tuscan Tastings

3 hours 30 minutes

from $245

⭐ Experience Highlights — What’s Included Historic Tour Explore our 1810 cellar, family chapel, and ancient olive press. Immerse yourself in Montechiaro’s heritage. Wine Tasting 3 organic wines: Chianti & Super Tuscans. Sommelier-led pairing with local specialties. Fresh & Organic Ingredients Garden-grown vegetables Extra virgin olive oil & organic jams Local cheeses (fresh & aged) Traditional Tuscan Flavors Bruschetta with tomato & basil, Artisanal cured meats Truffle sauces Notes Reservation required Dietary preferences/intolerances accommodated ✨ Taste Tuscany, sip tradition, and enjoy an unforgettable experience! ✨

Tuscan Brunch & Organic Wines

2 hoursFree Cancellation

The Experience includes: - Guided by your chefs and Sommeliers, you will prepare a seasonal menu using fresh, organic ingredients sourced directly from your estate. - The experience will be led by a Sommelier who will pair three organic wines with your traditional dishes. - Tasting of your organic extra-virgin olive oil. - The menu can be adapted for special dietary needs or intolerances. Minors can be offered alternative beverages.

from $70

Tuscan Cooking Class and Tasting Lunch

3 hours

I am Simone Vergamini, "Best Sommelier of Tuscany 2023", 3rd place at the Best Sommelier of Italy 2018, 2021 and 2022, and it will be a pleasure to accompany you to discover the best wineries. During the journeys I will tell you the history of the area and its traditions, the vines and the peculiarities of the area. We will visit 1 splendid winery representative of the beautiful Garfagnana and, after touching the vineyards and visiting the cellars, we will taste the wines produced in combination with a light lunch with seasonal products. I love my work and I constantly travel to discover the best wineries in Tuscany and the rest of Italy

from $197

Light lunch and wine tasting in Garfagnana with sommelier

3 hoursFree Cancellation

from $152

Discover the iconic "Via Francigena" in just one unforgettable day! Immerse yourself in the heart of Chianti on this exclusive tour, following the ancient route once traveled by Crusaders and pilgrims on their way to Rome. Experience the magic of Chianti’s hills and historic gems, including: • Siena (a UNESCO World Heritage Site) • San Gimignano (famous for its Medieval Towers) • Monteriggioni Castle (a fortress once guarding the Via Francigena) Enjoy a delicious lunch at a family-run Tuscan farm and savor Chianti wines at two renowned wineries. Our expert drivers will guide you through picturesque villages, offering insights into Tuscany’s rich history and craftsmanship. Taste the finest wines, olive oil, balsamic vinegar, cheeses, and truffles! Check out "What to Expect" for more details!

Private Tour: "FRANCIGENA WAY" in Chianti with Lunch & 2 Wine-tastings

Private Tour: "FRANCIGENA WAY" in Chianti with Lunch & 2 Wine-tastings

11 hoursFree Cancellation

(2)

from $350

This private tour blends Tuscany’s history, culture, gourmet flavors, and stunning scenery for an unforgettable experience that captures the essence of the region. • Explore Tuscany on a private, full-day tour through historic towns, rolling hills, and breathtaking landscapes. • Start in Volterra, the “City of Vampires” from Twilight, wandering ancient Etruscan streets and medieval architecture full of mystery. • Enjoy a three-course lunch at a charming family-run organic farm, featuring fresh local ingredients and a guided tasting of Chianti wines, extra virgin olive oil, and balsamic vinegar—a true Tuscan culinary experience. • Continue to San Gimignano, the "Medieval Manhattan" famous for its iconic towers. Stroll cobblestone streets, admire artisan shops, and don’t miss the world-renowned gelato.

Volterra & San Gimignano:Tour, Lunch & Chianti Wine Tasting

8 hoursFree Cancellation

from $303

Getting around the Tuscan countryside is slow going without your own wheels. Savor the atmosphere of two of Tuscany’s less hectic medieval settlements—Lucca and Montecatini Alto—on this private tour that includes all of your transportation. Enjoy a local lunch with wine on a typical Tuscan farm, ride the historic Funicolare di Montecatini Terme funicular (in season), and see the Nievole Valley.

PRIVATE TOUR: Lucca and Funicular ride in Montecatini Alto with Lunch Experience

PRIVATE TOUR: Lucca and Funicular ride in Montecatini Alto with Lunch Experience

8 hoursFree Cancellation

from $292

Spend a unique day in the Tuscan countryside and discover the essence of our region: delicious wine and food, breathtaking views, medieval castles, and unrivaled architectural wonders. Travel in a luxury vehicle or minivan, upon request, you can be accompanied by a tour guide. Choose where to have lunch or enjoy an exclusive tasting or if you don't have a particular place in mind - we can suggest a few places.

Private Tour Of Chianti with Wine Tastings

Private Tour Of Chianti with Wine Tastings

8 hours

THE TASTING AT OUR CELLAR IS A WAY TO IMMERSE YOURSELF IN A FAMILY ATMOSPHERE TO DISCOVER TYPICAL WINES OF THE PRODUCTION AREA OF CHIANTI CLASSICO, AN EXPERIENCE THAT ALLOWS YOU TO REDISCOVER ANCIENT FLAVORS AND THE LOVE FOR CREATING A PRODUCT THAT CONTAINS THE STORY OF A WHOLE FAMILY. YOU WILL HAVE THE OPPORTUNITY TO MAKE A GUIDED TOUR OF THE WINERY AND AGING CELLAR WITH EXPLANATION OF PRODUCTION PROCESSES, HISTORY AND PHILOSOPHY. BUT…NOT ONLY WINES!! THE GUIDED TOUR LEADS TO THE DISCOVERY OF AN ANCIENT BRICKS FOURNACE DATING BACK TO THE XV CENTURY- PAST, PRESENT AND FUTURE!! IT END WITH A TASTING OF 6 WINES AND A GREAT “ TAGLIERE” : LOCALS AND TRADITIONAL CHEESES AND COLD CUTS, CROSTINI AND BRUSCHETTE. COME DISCOVER THE BEST COMBINATION OF FOOD AND WINE! THE CUTTING BOARDS MAY VARY ACCORDING TO THE SEASON OF PRODUCTS. PLEASE WE RACOMMEND TO REPORT FOOD ALLERGIES OR INTOLERANCES

from $1,882

Large cutting board, 6 wine tasting and Guided tour

Large cutting board, 6 wine tasting and Guided tour

2 hours

This exclusive private wine tour takes you from Cortona to the heart of the Chianti Classico Black Rooster, an iconic wine area rarely reached from this part of Tuscany. Travel in comfort with a local professional driver and enjoy a personalized journey through one of Tuscany’s most celebrated wine landscapes. The experience includes visits to three carefully selected Chianti Classico DOCG wineries, where you will enjoy guided cellar tours and premium wine tastings. Each winery offers a different perspective on the Black Rooster tradition, allowing you to discover the diversity, history, and craftsmanship behind authentic Chianti Classico wines. A traditional Tuscan lunch is included, perfectly paired with local wines and seasonal products, for a complete and immersive Chianti experience. Designed for travelers seeking authenticity, privacy, and high-quality wine experiences, this tour combines culture, scenery, and exceptional flavors in a relaxed and exclusive setting.

from $70

Chianti Classico Black Rooster Private Wine Tour from Cortona

Chianti Classico Black Rooster Private Wine Tour from Cortona

8 to 9 hoursFree Cancellation

from $548

Discover the rich flavors of Tuscany on this immersive food and wine tour. Begin your day at a family farm in Pienza, renowned for its pecorino cheese, where you'll explore the grounds and enjoy a cheese tasting featuring six varieties, along with homemade accompaniments. Next, savor a delightful three-course lunch paired with Brunello wine in Montalcino, and take a guided tour of the vineyard and aging room. Conclude your adventure in Pienza, heritage UNESCO with a breathtaking view from the town - Explore a family farm in Pienza, the heart of pecorino cheese - Enjoy a tasting of six cheeses with local products and wines - Indulge in a three-course lunch paired with Brunello in Montalcino - Visit the medieval underground city of Montepulciano with a wine tasting

Pecorino Cheese and Brunello Tasting Tour in Tuscany

Pecorino Cheese and Brunello Tasting Tour in Tuscany

9 hoursFree Cancellation

Private and Tuscan Wine Tasting in Montepulciano

(2)

from $385

2 hoursFree Cancellation

Florence Chianti Vespa Tour with Wine Tasting & Meal

from $227

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What are people saying about Tuscany

Kylie_M, Jul 2026

A beautiful way to experience Tuscany!

We loved this experience for the Vespa tour! We got to ride it a lot longer than we had expected! Be warned - you will have to pass a driving test in order to drive! It’s not hard, but plan on someone being able to pass it! The Tuscan meal we had at a winery was delicious! I wish we could have tried more wines, but that’s a personal preference! It was a great day!

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

Deanna_D, Jul 2026

Great Tour

A special tour - small group and only one other couple in our case. First winery was small family-run and intimate where we did tour of wine making process - sat outside with beautiful backdrop of vineyard and also sampled olive oil. Second was larger facility and we sampled more wines at a table for the group in a row with lovely views - bonus was a delicious lunch of a charcuterie platter and lasagna. Last stop in San Gimignano was wonderful - a beautiful town and nice shopping. Tour guides were great and gave us plenty of time.

Half-Day Chianti Wine Tasting from Florence with Two Wineries

Matt_R, Jul 2026

Maria Louisa is perfect tour guide

Maria Louisa was fantastic. Warm kind intelligent and beautiful eyes! Tour was comfortable and half day and two wineries was perfect! Highly recommended especially if you have been to Florence before and want to get away from city center. Really well done.

Siena, San Gimignano and Chianti Wines Day Tour from Florence

Diana_M, Jul 2026

Roberto and Leon were...

Roberto and Leon were amazing tour guides.we loved the trip. It was so organized and clear from the beginning to the end. It was just enough for all that we saw. Unbelievable landscapes and the preparation of Roberto was excellent. Mario is the best bus driver I've ever had. He's an expert at driving and carefulness.

Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner

Allie_H, Jul 2026

What an incredible wine...

What an incredible wine tasting tour! We had the absolute best time from start to finish. Our guide, Leo, was exceptional—friendly, knowledgeable, and made the entire experience so much fun. He kept the day organized while making everyone feel relaxed and welcome. The wineries were fantastic, and the whole experience exceeded our expectations. If you’re considering this tour, don’t hesitate! Highly recommend, and we’d absolutely do it again.

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

nora_m, Jun 2026

So much more than a wine-tasting!

More than a corporate wine tour, this felt like a home visit with friends. Alice was a warm and wonderful guide who explained the history of the castle, the origins of winemaking in the region, and daily life in her part of Tuscany. A wonderful, unexpected afternoon. And of course, the wine was top-notch.

Tasting Tour in One of The Most Beautiful Cellars in the World

Cosmin_C, Jun 2026

spectacular underground "Cathedral of Wine" experience

Our tasting tour at De'Ricci Cantine Storiche was nothing short of magical! It is easy to see why this is considered one of the most beautiful cellars in the world. The architecture and atmosphere alone are breathtaking, but the experience was made truly extraordinary by our guide, Emilio. Emilio was amazing—incredibly engaging, knowledgeable, and passionate. He took the time to explain the history of the cellars and the nuances of each wine, making the entire tasting both educational and fun. He didn't just lead a tour; he provided us with a world-class experience. If you are a wine lover or just appreciate incredible history and beauty, this tour is an absolute must. Highly recommended!

Wine Experience In Chianti Hills from Florence

Leah_W, Jun 2026

Great experience meeting point not clear

The Wine tasting was lovely however the meeting point was not clear at all - it’s tucked away. Other tours I’ve been on the meeting point was at the bus parking lot (where our guide actually led us to) and that was actually easier to find than meeting in the station. I would suggest someone waiting out of the ticked away place with a clear flag as it was a stressful start to the trip and also meant as a couple we couldn’t sit together on the bus.

Half day Chianti Vineyard Escape from Florence with Wine Tastings

Samantha_P, Jun 2026

BEAUTIFUL scenery and...

BEAUTIFUL scenery and delicious wine! As someone who has never done a wine tasting, there was wonderful variety and the vineyards felt like a fairytale. Bus ride was about an hour but there were snacks provided with the tasting and the opportunity to purchase wine. They also gave 20 minutes at each vineyard for taking pictures and exploring

Lucca: Wine Tasting Experience - Tenuta Adamo Winery

Rosina_G, May 2026

Beautiful Winery!

Had a great experience at this winery. They offered pick-up transportation which made everything really easy, and the driver was super friendly! The winery grounds and views overlooking the Tuscan hills were so beautiful. Our guide was very knowledgeable, and the wines were excellent, smooth and perfectly paired with fresh bread and olive oil. Definitely recommend if you’re visiting Tuscany for a day trip!

Montepulciano: Winery Tour & Tasting Experience

Margaret_D, Nov 2025

Private Tour: Highly Recommend

We happened to be the only family on the morning tour, so we enjoyed a private tour with our sommelier, Luigi. He provided a wealth of insight into the wine making process, effects of soil and climate, as well as regional differences that impact taste and quality. We tasted four wines with local bread, cheese, salami, and pancetta during which Luigi answered our many questions with good humor. The newly renovated tasting room in the deep Etruscan cellars was captivating and added to the experience. We enjoyed the Talosa Reserve and Rossi IGT Pietrose so much we shipped several home. A terrific experience; we highly recommend.