Wine Tasting Tours in Tuscany
Luxury Tuscany Wine Tours
SmoothRed’s Tuscany wine tours are a brilliant way to soak up Italy’s stunning scenery, explore historic towns like Florence and Siena, and enjoy some of the best wines in the world. From rolling vineyards to charming hilltop villages, every stop is packed with flavour and character.
You might find yourself on a classic Chianti wine tour, sipping bold reds straight from the source, or enjoy wandering Florence’s cobbled streets with an art historian, where culture and wine go hand in hand. Whether you’re after relaxed Tuscan wine tasting weekend or a full-on luxury Tuscany wine holiday, we’ll tailor everything to suit you.
Below are just a few ideas to get you started — get in touch to plan your own uniquely crafted trip to Tuscany.
Popular Tuscany Wine Experiences
Featured Tuscany Itinerary
Why choose SmoothRed for your Tuscan wine holidays
Tuscany has captivated wine lovers for centuries, ever since the ancient Etruscans first cultivated vines on its rolling hills. Over the ages, this land of vineyards has been shaped by Romans, Byzantines, and the powerful Medici family, each leaving a legacy that still influences the region’s winemaking traditions today.
At SmoothRed, we don’t just take you to Tuscany, we open doors that few others can. With over 20 years of crafting bespoke wine holidays, our team combines deep-rooted expertise with authentic local connections, giving you insider access to both prestigious estates and hidden, family-run wineries. Many of us have Italian roots and and are fluent in the language, ensuring peace of mind throughout your journey.
From Chianti Classico to Brunello di Montalcino and the coastal gems of Bolgheri, our intimate knowledge of Tuscany’s wine regions ensures your journey is as rich and nuanced as the wines you’ll taste.
Highlights of Tuscany
With a rich medieval heritage, Tuscany is not just known for its verdant rolling hills and open countryside, but also its stunning cities. We feel the best trips combine both, visiting or staying a few nights in Florence or Siena, contrasted with a tranquil vineyard stay.
Plan your trip to Tuscany with our complete wine guide, discover the top 10 things to do across the region and its vineyards, and find out where to stay — from historic palazzi to traditional farmhouses.
Tuscany's Wine Regions
Among the most famous of Tuscany’s wine regions is Chianti, stretching between Florence and Siena, known for its medium-bodied, cherry-toned wines. Further south lies Montalcino, home to Brunello di Montalcino, a powerful and age-worthy wine made exclusively from Sangiovese. Nearby, Montepulciano produces Vino Nobile di Montepulciano, another refined expression of the grape.
Along the Tuscan coast, regions like Bolgheri have gained international acclaim for “Super Tuscan” wines, bold blends often featuring Cabernet Sauvignon and Merlot alongside traditional varieties.
Our Tuscany Wine Guide
Things to do in Tuscany
From its Renaissance cities to its peaceful countryside, Tuscany has something for everyone. Art and history lovers will be drawn to Florence, Siena and Pisa, with their striking architecture, world-class museums and iconic attractions.
Beyond the cities, Tuscany’s countryside is perfect for slower exploration. Cycle or stroll through breathtaking surroundings, tour dinky hilltop villages like San Gimignano and visit the region’s famed vineyards for exceptional wine tastings. Here are ten things worth adding to your Tuscany itinerary.
10 Things to do in Tuscany
Where to Stay in Tuscany
From centuries-old palazzi in Florence and Siena to sprawling vineyard estates, Tuscany boasts some stunning places to stay.
Discover a few of our favourites at the link below.
Where to Stay in Tuscany
When to Visit Tuscany
Tuscany is a beautiful destination year-round, but the best time to visit depends on the kind of experience you’re looking for.
Spring and autumn offer mild weather and fewer crowds, while summer brings lively festivals and rising temperatures. No matter the season, Tuscany has something for every wine lover. Find our full seasonal guide below.
When to Visit Tuscany
Where to Eat in Tuscany
Every great glass of wine deserves a meal to match and Tuscany knows its stuff when it comes to pairing fine wines with flavourful dishes.
Explore our favourite food and wine experiences below.
Where to Eat in Tuscany
We craft each itinerary just for you. Contact our Travel Designers to plan an unforgettable wine tour of Tuscany.
Start PlanningExpert answers to common questions about Tuscany
What’s the best month to go to Tuscany, Italy?
The ideal months to go to Tuscany are late September to early October during the grape harvest, when vineyards are alive with activity, the weather is pleasant, and festivals celebrate the season. May and June are also beautiful, with wildflowers and long sunny days.
What is the best wine region in Tuscany?
Tuscany is made up of several celebrated wine regions, each with its own style and character, so it is hard to say which is the best. Here is a short overview:
Chianti Classico: The historic heart of Tuscan wine between Florence and Siena. Known for elegant, bright, and food-friendly Sangiovese wines. Easily accessible and full of charming villages like Greve, Radda, and Castellina.
Montalcino: Produces the prestigious Brunello di Montalcino, one of Italy’s most age-worthy reds, made from 100% Sangiovese Grosso. The rolling hills here offer spectacular views and luxury wine estates.
Montepulciano: Famous for Vino Nobile di Montepulciano, a softer, fruit-driven expression of Sangiovese. The hilltop town is stunning and less crowded than Montalcino.
Bolgheri (Tuscan Coast): Known for Super Tuscans like Sassicaia, Ornellaia, and Guado al Tasso, bold blends of Cabernet Sauvignon, Merlot, and other international grapes. A different feel from inland Tuscany with cypress-lined roads and sea breezes.
Where to stay in Tuscany for wine tasting?
For the perfect Tuscan wine tasting trip, stay a few nights in a city like Florence or Siena, then stay in the countryside. The Chianti Hills, Montalcino, or Montepulciano are surrounded by vineyards and close to famous wineries. We arrange beautiful vineyard hotels, farm stays, or villas so you can enjoy both the culture of the cities and the charm of wine country.
Here you can find our guide to where to stay in Tuscany.
Which Antinori tour is the best?
The best Antinori tour in our opinion is at Badia a Passignano, with historic abbey cellars, premium Chianti Classico Gran Selezione tastings, and the option to dine at their Osteria. Booking in advance is essential.
Here’s a guide to some of our favourite wineries in Tuscany.
Do you need to book wineries in Tuscany?
You absolutely must book wineries in Tuscany in advance of visiting. Tuscany’s best wineries welcome guests by appointment only. As a wine travel specialist, we will take care of arranging exclusive access, private tastings, all within a curated itinerary to ensure you don’t miss out on highly sought‑after estates.
Have more questions?
(+44) 020 8877 4940 (UK)
(+1) 646 968 0388 (US and Canada)
Call us today
