Tuscany Wine Lovers’ Guide: Best 5 Wineries in Chianti

Exploring Chianti Through its Wineries

Chianti is more than just a name on a wine label—it’s a way of life, a landscape of rolling hills, ancient stone villages, and rows of vineyards that stretch toward the horizon under the Tuscan sun. Located between Florence and Siena, the Chianti region is one of the most historic and picturesque wine-producing areas in the world.

Its vineyards have been cultivated since Etruscan times, and today, the region is world-renowned for Chianti Classico wines, (our favorite)  made primarily from Sangiovese grapes.

Exploring Chianti through its wineries is one of the most rewarding ways to experience Tuscany. In this guide, we share five of our best wineries to visit in Chianti—each offering a unique blend of tradition, wine making, and breathtaking scenery.

You’ll find practical travel tips, detailed introductions, and honest pros and cons for each winery, along with advice on where to stay and the best times to visit.

Table of Contents

1. Castello di Ama — Art, Elegance, and Elevated Wine in Gaiole in Chianti

Perched among the rolling hills of Gaiole in Chianti, Castello di Ama is more than just a winery — it’s a full immersion into Tuscan wine, art, and landscape. This centuries-old estate has earned a global reputation not only for producing Chianti Classico wines but also for housing one of the most fascinating  art collections in rural Italy.

The winery’s passion for excellence is evident in every sip. From their signature L’Apparita Merlot to their elegant Chianti Classico Gran Selezione, the wines here are expressive, and deeply rooted in place.

A tour of the cellars reveals the process behind the wines — and a walk through the vineyards gives you a sense of how nature and tradition collaborate here. The estate also features elegant tasting rooms and an exceptional onsite restaurant for a full sensory experience.

If you’re seeking a wine-tasting experience that blends culture, luxury, and authenticity, Castello di Ama offers something unforgettable.

✅ Pros of Visiting Castello di Ama

  • World-Class Wines

  • Contemporary Art Experience

  • Historic Setting

  • Luxury Wine Tasting

  • Scenic Location

⚠️ Cons of Visiting Castello di Ama

  • Advanced Booking Required

  • Higher Price Point

  • Less Family-Friendly

    How to Get There:

    Drive from Siena in about 35 minutes or from Florence in just over an hour. GPS or Google Maps is essential due to remote rural roads.

    Car Rental: Check availability and prices here.
    Where to Stay Nearby:
    Best Time to Visit:

    Late spring (May–June) and early fall (September–October) for fewer crowds and harvest activity.

2. Castello di Brolio (Barone Ricasoli) – Gaiole in Chianti

 No winery captures the deep roots of Chianti’s history like Castello di Brolio. This estate is considered the birthplace of Chianti wine, thanks to Baron Bettino Ricasoli, who defined the original Chianti recipe in the 19th century.

With over 850 years of family ownership, Brolio offers a visit steeped in history, complete with a fairy-tale castle overlooking a panoramic landscape of vineyards and olive groves.

The estate offers several tour types, from basic tastings to full historical and vineyard experiences, including access to the family chapel and private gardens.

Wines include Chianti Classico DOCG, Gran Selezione, and high-end Supertuscans. This winery is perfect for visitors who want a strong connection to Chianti’s legacy.

✅ Pros of Visiting Castello di Brolio

  • Historic Castle Setting

  • Iconic Chianti Classico Wines

  • Panoramic Views and Vineyards

  • On-site Museum and Castle Access

  • Wine Shop and Tasting Room Experience

⚠️ Cons of Visiting Castello di Brolio

3. Castello Vicchiomaggio – Greve in Chianti

 Just outside beautiful Greve in Chianti, Castello Vicchiomaggio is an elegant Renaissance-era estate that boasts both award-winning wines and incredible views over the Greve Valley. Dating back to the 1400s, the castle has hosted historical figures like Leonardo da Vinci and Francesco Redi.

Today, it combines history with hospitality, offering guided tastings, cooking classes, and even overnight stays in the beautifully restored suites.

Vicchiomaggio produces Chianti Classico, Riserva, and IGT wines, all using traditional methods with modern precision.

The guided tastings are informative and generous, with options to enjoy your wine on a terrace overlooking the Tuscan hills. For travelers looking to combine wine tasting with romance and overnight charm, this is our a top pick.

✅ Pros of Visiting Castello Vicchiomaggio

  • Historic Renaissance Castle

  • Award-Winning Chianti Wines

  • On-site Accommodation Available

  • Cooking Classes and Experiences

  • Stunning Views Over Greve Valley

⚠️ Cons of Visiting Castello Vicchiomaggio

  • Limited Public Transport Access

  • Advanced Booking Needed for Experiences

  • Less Suitable for Large Groups

    How to Get There:

  • From Florence, drive south on SR222 for about 45 minutes. The route through Chiantigiana road is scenic and dotted with wine estates.

  • Check availibility and rates for Car Rental.

     
    Where to stay nearby:
    Best Time to Visit:

  • Mid-May to mid-October, especially during harvest festivals.

4. Fattoria La Loggia – San Casciano in Val di Pesa

Fattoria La Loggia is a haven for art lovers, wine enthusiasts, and slow travelers. Set in the hills near San Casciano in Val di Pesa, this winery and agriturismo offers a relaxed and authentic Chianti experience.

What sets it apart is the creativity and culture—outdoor sculptures dot the vineyards and gardens, and the estate hosts artist residencies throughout the year.

The wines are organic and made with minimal intervention, focusing on Chianti Classico and a handful of experimental blends. The owners are passionate and hands-on, and tastings often feel like you’re visiting old friends.

This is an ideal stop for travelers seeking something off the beaten path. In this guide we share pros and cons, how to get here, best places to stay, ant the ideal times to visit.

✅ Pros of Visiting Fattoria La Loggia

  • Organic and Minimal Intervention Wines

  • Artistic Outdoor Sculpture Gardens

  • Intimate and Personal Tastings

  • Agriturismo Accommodation On-site

  • Authentic, Off-the-Beaten-Path Experience

⚠️ Cons of Visiting Fattoria La Loggia

  • No On-site Restaurant

  • Requires Car for Access

  • Smaller Scale Production

    How to Get There:

    About 35 minutes from Florence via the Raccordo Autostradale Firenze-Siena. Public transport is limited.

    Compare these Car Rental prices.

    Where to Stay Nearby:
    Best Time to Visit:

  • May–June and September–October for the best art events and vineyard walks.

5. Casa del Sole – Boutique Winery in Chianti

 For a truly boutique, family-run experience, Casa del Sole offers warmth, authenticity, and stunning surroundings near Castellina in Chianti. This small-scale estate is known for its dedication to sustainable farming and natural winemaking.

The vineyard produces limited batches of Chianti Classico and Rosé, using biodynamic techniques and native yeast fermentation.

Tastings here are intimate and led by the winemakers themselves—often accompanied by homemade bruschetta, local cheeses, and heartwarming stories about the land and the family’s journey.

You’ll feel like part of the family by the time you leave. It’s a beautiful contrast to the larger, more commercial wineries. In this guide we share the best places to stay nearby, how to get here, pros and cons, and best time of year to visit.

✅ Pros of Visiting Casa del Sole

  • Boutique, Family-Run Winery

  • Sustainable and Biodynamic Practices

  • Small-Batch, High-Quality Wines

  • Personalized Tastings with Winemakers

  • Warm, Authentic Atmosphere

⚠️ Cons of Visiting Casa del Sole

  • Limited Wine Variety Due to Small Production

  • Advance Booking Required

  • Remote Location Necessitates a Car

    How to Get There:

    Drive from Florence (1 hour) or Siena (40 minutes) via SR222. A car is essential.

    Check here for availability and prices for Car Rental 

     
    Where to Stay Nearby:
    Best Time to Visit:

    June and September are ideal for perfect weather and peaceful tasting.

Chianti Wine Pairing Guide: What to Sip With What

Chianti Classico (Sangiovese-based wines)

  • Pairs well with: Classic Tuscan dishes like bistecca alla fiorentina (grilled T-bone steak), hearty pasta with tomato-based sauces (like pappardelle al cinghiale — wild boar), roasted lamb, and aged pecorino cheese. The wine’s bright acidity and firm tannins cut through rich, savory flavors perfectly.

  • Try it with: Tomato bruschetta or grilled vegetables for lighter fare.

Super Tuscan Wines (like Castello di Ama’s L’Apparita)

  • Pairs well with: More structured and full-bodied meats such as ribeye steak, game meats like venison, truffle dishes, and aged hard cheeses like Parmigiano-Reggiano. The complex layers and bold tannins match intense flavors.

  • Try it with: Dark chocolate desserts or blue cheese for an adventurous finish.

Organic and Minimal Intervention Wines (Fattoria La Loggia & Casa del Sole)

  • Pairs well with: Fresh seasonal dishes—think spring vegetable risottos, grilled fish, or herb-roasted chicken. Their subtle complexity and natural balance enhance simple, clean flavors.

  • Try it with: Light salads and mild cheeses for casual gatherings.

4–5 Day Chianti Wine Itinerary: Sip, Savor, and Explore

 Day 1: Arrival & Castello di Brolio

  • Morning: Arrive in Tuscany (Florence or Siena). Pick up rental car.

  • Late Morning: Drive to Castello di Brolio (about 25 minutes from Siena).
    Take a guided tour of the historic castle, explore the museum, and enjoy a tasting of Chianti Classico and Supertuscans.

  • Lunch: On-site at Castello di Brolio or nearby trattoria.

  • Afternoon: Leisurely drive through Chianti countryside toward Gaiole in Chianti.

  • Evening: Check in at Borgo San Felice or another nearby luxury agriturismo. Dinner onsite or in local village.

 

 Day 2: Art & Wine at Castello di Ama

  • Morning: Head to Castello di Ama in Gaiole in Chianti.
    Enjoy an immersive wine tasting combined with a walk through the contemporary art installations.

  • Lunch: At Il Ristoro di Villa Pianigiani restaurant onsite or a local trattoria.

  • Afternoon: Explore nearby medieval villages like Radda in Chianti or Lecchi in Chianti.

  • Evening: Return to your accommodation for rest and local Tuscan dinner.

 

Day 3: Renaissance Charm at Castello Vicchiomaggio

  • Morning: Drive to Castello Vicchiomaggio near Greve in Chianti.
    Participate in a guided wine tasting and, if interested, book a cooking class or tour of the castle grounds.

  • Lunch: Enjoy lunch at a Greve in Chianti café or vineyard restaurant.

  • Afternoon: Stroll the main piazza of Greve, visit the Wine Museum, or browse local artisan shops.

  • Evening: Overnight near Greve at a local inn or villa, such as Villa Bordoni or Albergo del Chianti.

 

 Day 4: Authenticity at Fattoria La Loggia & Casa del Sole

  • Morning: Drive to Fattoria La Loggia for an intimate, organic wine tasting amid outdoor sculptures and tranquil vineyards.

  • Lunch: Picnic from a local deli in San Casciano in Val di Pesa or dine in nearby restaurant.

  • Afternoon: Head to Casa del Sole near Castellina in Chianti. Enjoy a warm, personal tasting with the family-run winemakers and learn about biodynamic practices.

  • Evening: Stay overnight near Castellina or San Casciano at an agriturismo like Agriturismo Querceto di Castellina or Villa Mangiacane.

 

Optional Day 5: Explore Chianti Villages & Leisure

  • Morning: Take a scenic drive to explore charming towns such as Panzano, Volpaia, or Montefioralle.

  • Lunch: Try local specialties at a countryside osteria.

  • Afternoon: Relax at your accommodation, visit a local spa, or revisit a favorite winery for a last tasting.

  • Evening: Enjoy a farewell Tuscan dinner soaking in the sunset over the vineyards.

Travel Tips:

  • Renting a car is essential to fully explore the wineries and towns at your own pace.

  • Book winery tastings and accommodations well in advance, especially for weekends and harvest season.

  • Consider visiting during May–June or September–October for pleasant weather and smaller crowds.

  • Pair tastings with local food experiences to savor the full richness of Tuscan culture.

Final Thoughts

Chianti offers wine lovers a rich history, breathtaking landscapes, and exceptional wines. Whether you love grand castles, intimate family estates, or wineries that double as art galleries, each of these five destinations provides a unique and memorable experience. Plan your visit to enjoy the flavors, take in the scenery, and create lasting memories in the heart of Tuscany’s most iconic wine region. Cheers to your great adventure in Chianti!

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.

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