5 Best Wineries in Tuscany to Visit in 2025
Exploring Tuscany Through Its Wines
Tuscany is known the world over for its rolling hills, cypress-lined roads, and historic towns—but it’s the wine that often leaves the most lasting impression.
From bold reds aged in ancient cellars to crisp whites enjoyed on sun-drenched terraces, Tuscany offers a wine experience like no other.
In this guide we take you to our five best wineries in Tuscany for 2025, each with its own story, setting, and unforgettable wines.
Whether you’re drawn to the classic Chianti countryside, the elegance of Brunello di Montalcino, or the coastal sophistication of Bolgheri, you’ll find everything you need to plan the perfect visit.
We’ve included tips on how to get there, where to stay nearby, and the best time to go—so you can sip, swirl, and explore at your own pace.
Table of Contents
1. Antinori nel Chianti Classico – Innovation in the Heart of Tradition
Why Visit:
A visit to Antinori nel Chianti Classico is not just about wine—it’s a journey through 600 years of winemaking history. Located just south of Florence in the heart of the Chianti Classico region, this architecturally stunning winery seamlessly blends innovation with tradition. Its underground design allows for a gravity-fed winemaking process and showcases a modern approach to sustainability. But it’s the wine that truly stands out: their Chianti Classico Riserva is refined, structured, and elegant.
Visitors can enjoy guided tours that take you through the fermentation halls, barrel cellars, and panoramic tasting rooms that overlook the vineyards. There’s also a gourmet restaurant, Rinuccio 1180, offering Tuscan cuisine with spectacular views. Whether you’re a wine connoisseur or a curious traveler, Antinori is a must-see.
Location:
Bargino, Chianti (30 km south of Florence)
Wine Highlights: Tignanello, Solaia, Chianti Classico Riserva
Where to Stay:
Villa le Calvane (luxury villa-style hotel with vineyard views)
Castello Vicchiomaggio (historic estate with on-site tastings)
How to Get There:
The winery is an easy 40-minute drive from Florence. “Rent a car” to enjoy the scenic drive through olive groves and vineyards. Private transfers and small-group wine tours are also available from Florence via “Viator or GetYourGuide”.
Best Time to Visit:
April to June or September to October. Autumn is especially beautiful during harvest.
2. Castello di Ama – Where Wine Meets Contemporary Art
Location: Gaiole in Chianti
Wine Highlights: L’Apparita (100% Merlot), Chianti Classico Gran Selezione
Why Visit:
Set in the hills of Gaiole in Chianti, Castello di Ama is an immersive experience that combines world-class wine with contemporary art and medieval architecture. The estate, dating back to the 1700s, is surrounded by rolling vineyards and olive groves.
It’s most famous for its Chianti Classico Gran Selezione and its unique ability to marry traditional winemaking with a creative spirit. What makes a visit to Castello di Ama unforgettable is the modern art installations by internationally renowned artists such as Anish Kapoor and Louise Bourgeois.
The estate offers guided art and wine tours, taking guests through historic cellars and modern tasting rooms.
Where to Stay:
Borgo Argenina (rustic, romantic farmhouse B&B)
Hotel Le Pozze di Lecchi (tranquil, countryside escape with spa)
How to Get There:
A car is essential. From Siena, the drive is around 40 minutes through rolling Chianti hills. Alternatively, some small-group Chianti wine tours include Castello di Ama as a stop. Compare these ‘Car rental” prices.
Best Time to Visit:
Late spring and early autumn. Visit mid-week for a quieter experience.
Wine tours with “Viator or Get Your Guide“
3. Avignonesi – Organic Excellence in Montepulciano
Location:
Valiano, Montepulciano
Wine Highlights:
Vino Nobile di Montepulciano, Desiderio Merlot, Vin Santo di Montepulciano
Why Visit:
Located near Montepulciano, Avignonesi is a leader in sustainable and organic winemaking. The estate spans over 400 hectares and is best known for its elegant Vino Nobile di Montepulciano. Avignonesi is deeply committed to biodiversity, holistic vineyard practices, and producing wines that express the character of the land.
Visitors are welcomed with warmth and invited to tour the vineyards, visit the historical cellars, and enjoy tastings paired with local Tuscan food. The winery also offers immersive experiences such as blending sessions, picnics among the vines, and cooking classes with wine pairings.
If you’re passionate about organic farming and exceptional red wines, Avignonesi offers a perfect blend of education and indulgence. A must-visit for any wine lover.
Where to Stay:
Lupaia (romantic farmhouse-style luxury, incredible dining)
Agriturismo La Corte del Cavalierino (comfortable and eco-friendly)
How to Get There:
From Florence, it’s a 1.5–2-hour drive. If you’re not renting a car, take a train to Montepulciano and arrange a taxi or shuttle. Many Tuscan wine tours now include this estate in full-day Val d’Orcia itineraries. You can book a “Car Rental” here or compare these half day or full day wine tours from Florence or Siena.
Best Time to Visit:
May–June and September–October are ideal. September brings the grape harvest and vibrant vineyard life.
4. Ornellaia – Bolgheri’s Bordeaux-Inspired Beauty
Location:
Bolgheri, on Tuscany’s Etruscan Coast
Wine Highlights: Ornellaia, Le Serre Nuove, Masseto
Why Visit:
Tucked away on the Etruscan Coast near Bolgheri, Ornellaia is synonymous with elegance, power, and prestige. Known for producing some of Italy’s finest Super Tuscans, including the iconic Ornellaia and Le Serre Nuove, this estate is a benchmark for excellence.
The experience at Ornellaia is intimate and refined. Guests are led on private tours through the vineyards, state-of-the-art cellars, and art-adorned tasting rooms. The estate also partners with artists annually to create unique labels for their Vendemmia d’Artista series—where wine meets artistic expression.
The proximity to the sea influences the terroir, resulting in wines of incredible complexity and freshness. It’s a coastal paradise for wine lovers.
Where to Stay:
Relais Sant’Elena (peaceful country retreat)
La Bandita Townhouse in nearby Pienza for those exploring the coast and countryside
How to Get There:
A car is a must. From Pisa, it’s a 1.5-hour coastal drive. Public transport is limited in Bolgheri, but private drivers or small-group wine tours from Pisa or Lucca are a great option. Compare “Car Rental” prices here, or book a wine tour with Get your Guide and Viator.
Best Time to Visit:
Late April to October. Combine your visit with a beach day on the nearby coast in summer.
5. Castiglion del Bosco – Brunello Grandeur in Montalcino
Location: Montalcino, Val d’Orcia
Wine Highlights: Brunello di Montalcino, Rosso di Montalcino, Millecento
Why Visit:
Owned by Massimo Ferragamo, Castiglion del Bosco is a luxurious wine estate and resort nestled in the UNESCO-listed Val d’Orcia. The winery specializes in Brunello di Montalcino—one of Italy’s most revered wines—crafted with precision and aged to perfection.
The estate’s setting is breathtaking, surrounded by cypress trees, rolling hills, and medieval ruins. Guests can book private tastings, explore the historic borgo, and even join vertical tastings of different Brunello vintages. The estate also features a golf course, spa, and high-end lodging at Rosewood Castiglion del Bosco.
This is a must-visit for anyone seeking a top-tier Tuscan wine experience in an extraordinary setting.
Where to Stay:
Rosewood Castiglion del Bosco (ultra-luxury estate with golf, spa & winery access)
Hotel dei Capitani (great value with panoramic views)
How to Get There:
Easiest via car from Siena (1 hour). For public transport, take a train to Buonconvento and arrange a local taxi or shuttle. Some Val d’Orcia tours include this stop. Check out these “Car Rental” Prices or small wine tours are also available with Viator or Get Your Guide.
Best Time to Visit:
Spring or early autumn for ideal temperatures and fewer crowds. October is especially magical as the vines
Bonus Tip: Plan a Tuscan Wine Trail
If you’re planning more than one visit, base yourself in Florence, Siena, or Montepulciano, and “rent a car” to explore the wine regions at your own pace.
A 5–7 day itinerary lets you savor Chianti, Montalcino, and coastal Bolgheri with time for hilltop towns, thermal springs, and unforgettable meals.
Best Time of Year for Wine Travel in Tuscany
April to June: Spring bloom, warm days, perfect for vineyard walks.
September to October: Our favorite time to visit, it’s harvest season, grape stomping festivals, golden vineyard views.
July–August: Hot, crowded, but good if you’re combining with beach trips.
November–March: Quiet season, ideal for truffle hunting and wine cellars, but less vineyard activity.
How to Book Winery Visits
Most top wineries require reservations, often booked via their websites. Many now offer curated tasting experiences, cellar tours, cooking classes, and even picnic packages in the vines.
Or, if you prefer a guided experience, platforms like Viator and Get Your Guide offer full-day wine tours from Florence, Siena, or Lucca with transport included.
Final Thoughts: Taste Tuscany, One Glass at a Time
Tuscany’s wine country is more than just tastings—it’s a story told in centuries-old cellars, long vineyard lunches, and unforgettable views. Whether you’re raising a glass of bold Brunello or sipping a crisp Chianti under the sun, every drop brings you closer to this region.
So plan your route, reserve those tastings, and get ready to fall in love with Tuscany—one glass at a time.
PLAN YOUR TUSCANY ADVENTURE
These are our favorite companies we use when planning a trip, they consistently have the best prices, great customer service, and overall, are better than their competitors.
BOOK YOUR FLIGHT – Going is a great search engine if you are flexible about your travel destination and dates. Sign up for their newsletter and get the latest deals on destinations around the world. GOING is our new go to.
CAR RENTAL – We recommend using Discover Cars or Rental Cars when booking a car rental, they work with hundreds of companies worldwide to help you find the best car for your needs.
TRAINS – TRAINLINE – is our favorite, this site is very reliable and easy to use.
BUS – OMIO – this website allows you to book train or bus tickets to travel from city to city the best and cheapest way. FLIXBUS is another terrific website with routes between 20 European countries.
ACCOMMODATIONS
BOOKING.com – is our go to for hotel searches around the world, we find they always have the cheapest rates and offer different payment options. In addition, VRBO is another terrific website for all types of accommodations.
HOSTELWORLD – is great if you’re traveling on a budget, and if you need a cheap place to stay.
SIGHTSEEING TOURS
GET YOUR GUIDE – is our favorite; they have stacks of tours and excursions available in cities all over the world. VIATOR is another great website for all types of tours.
TAKE WALKS – This walking tour company provides inside access to attractions and places you can’t get elsewhere.
TRAVEL INSURANCE
SAFETY WING – is our go to travel medical insurance company, especially for longer trips. You can either purchase a monthly plan or a plan for specific trip dates (i.e. 1-2 week trips). They cover people from all over the world, while outside their home country.
ARC’TERYX – is a go to reliable brand for outdoor adventure and travel, their wide range includes light weight durable, easy to clean travel gear.
Check out our RESOURCE PAGE for more additional planning.