THE ULTIMATE WINE LOVER'S GUIDE TO TUSCANY

 

12 Best Wine Regions From Florence, Tuscany

Florence is the perfect base for discovering the best of Tuscany’s world-renowned wine regions. With its central location, the city gives easy access to everything from the rolling vineyards of Chianti Classico to the coastal estates of Bolgheri. Wine lovers will find an incredible range of tasting experiences just a short drive away, with each region offering its own distinctive grape varietals, traditions, and scenery. These 12 wine regions are ideal for every type of traveler—from casual sippers to dedicated connoisseurs. Each region combines unforgettable landscapes, charming Tuscan towns, and expert-guided tastings at celebrated wineries. Many include extras like traditional farm lunches, cooking classes, or visits to olive oil producers and medieval villages. Whether you’re short on time and want a half-day excursion or you’re looking to spend a full day soaking up vineyard views and sampling fine vintages, there’s a wine experience tailored for you. Let this guide help you discover the best of Tuscan wine-and one unforgettable view.’

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 – SKYSCANNER – we always start here and usually always finish here. They price check over 1,200 travel sites to help you find the best prices. You can also try GOING to search prices across a variety of sites.

TRAVEL OPTIONS

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

 

Picking The Perfect Wine Tour

  1. Know Your Wine Preferences

Do you prefer reds like Chianti or Brunello, or are you curious about whites like Vernaccia? Choose a tour that highlights the wines you enjoy or want to learn more about.

  1. Decide on Duration

Tours range from half-day trips to full-day countryside escapes. If you’re short on time, a local tasting in Florence works well. For deeper experiences, go for a full-day adventure into Chianti or Val d’Orcia.

  1. Look for Extras

Some tours include gourmet lunches, cheese or olive oil tastings, cooking classes, or stops in medieval villages. Consider what kind of full experience you’re after.

  1. Group vs. Private Tours

Small-group or private tours often offer more personal attention and flexibility. Larger tours are more budget-friendly but can be less intimate.

  1. Check Transportation

Most tours include round-trip transport from Florence. Always confirm pickup points and travel time, especially for further regions like Montalcino or Bolgheri. Some tour operators include pick up/drop off from their hotel/hostel in Florence. (Booking.com link)

  1. Read Recent Reviews

Not all tours are created equal. Look for tours with high ratings and recent positive feedback to ensure a quality experience.

 

1. Chianti Classico Wine Tour

A timeless favorite, the Chianti Classico Wine Tour is a must for anyone visiting Florence. You’ll venture into the iconic Tuscan countryside, where cypress-lined roads lead to stone villages and terraced vineyards. This tour typically includes visits to two or three wineries, each offering tastings of bold Sangiovese-based reds and fresh olive oils. You’ll learn about the Chianti Classico DOCG classification, fermentation techniques, and food pairings.

Many tours also include stops in charming towns like Greve, Radda, or Castellina in Chianti, as well as a full Tuscan lunch overlooking vineyard views. The atmosphere is relaxed and inviting, ideal for wine novices. You’ll likely meet local producers who take pride in their traditions, sharing stories that make every sip more meaningful. If it’s your first wine tour in Tuscany, this is the perfect introduction to the heart and soul of the region. [Find a recommended Chianti Classico Wine tour here.]

 

2. Brunello di Montalcino Tour

Discover one of Italy’s most prestigious wines with a tour to Montalcino, nestled in the rolling hills of Val d’Orcia. Known for producing the powerful Brunello di Montalcino, this region is all about elegance, and age-worthy reds. The tour begins with a scenic drive through breathtaking landscapes dotted with cypress trees and stone villas.

You’ll visit top-rated wineries—often family-owned estates—where you’ll tour ancient cellars, walk through vineyards, and enjoy tastings of Brunello and its younger sibling, Rosso di Montalcino. Expert guides explain the aging requirements and unique terroir that define these wines. A gourmet lunch is often included, served in a countryside villa or trattoria with regional dishes like wild boar ragu or pecorino cheese.

This experience is perfect for seasoned wine lovers looking to deepen their appreciation for Tuscan reds. With panoramic views and profound flavors, it’s one of the most luxurious wine tours from Florence. [Find a recommended Brunello tour here.]

 

3. Montepulcian Wine Day Trip

Montepulciano is a jewel of southern Tuscany and an ideal day trip for wine and culture enthusiasts. Renowned for its Vino Nobile di Montepulciano, this town combines stunning medieval architecture with a rich winemaking heritage. Your tour begins with a stroll through Montepulciano’s hilltop center, where Renaissance palaces overlook sun-drenched valleys.

You’ll descend into historic underground cellars, many carved directly into the rock beneath the city. Here, barrels of wine age in cool darkness, just as they have for centuries. Wine tastings include robust reds made primarily from the Prugnolo Gentile grape, often paired with local delicacies like pecorino cheese, cured meats, and olive oil.

Some tours offer hands-on cooking classes or olive oil tastings to complement the wine experience. [Click here to book a Montepulciano wine experience.]

 4. San Gimignano & Vernaccia Tour                                                                                                           

    The wineries here specialize in Vernaccia, a dry white with floral and mineral notes, often aged in steel or oak barrels. You’ll visit boutique estates where vintners share their techniques, followed by seated tastings that may include food pairings such as saffron risotto or pecorino. Many tours feature lunch at a local farmhouse with stunning countryside views. It’s the perfect experience for white wine lovers or travelers looking for a more relaxed, scenic wine day. San Gimignano’s beauty and Vernaccia’s refreshing character make this a tour to remember  [Reserve a Vernaccia tour from Florence here.]

5. Bolgheri & Super Tuscan Experience

Break away from tradition and explore Bolgheri, home of Italy’s bold and innovative Super Tuscan wines. Located along Tuscany’s stunning coast, this tour introduces you to powerful reds crafted from international grapes like Cabernet Sauvignon and Merlot. The journey starts with a scenic drive west, passing olive groves and medieval towns.

In Bolgheri, you’ll visit modern wineries known for their sleek looks, high-tech cellars, and exceptional wines. Tastings often include iconic labels such as Sassicaia or Ornellaia, you’ll learn how Super Tuscans challenged Italy’s wine regulations and redefined what Tuscan wine could be.

Many tours include time in the village of Bolgheri or a stop at a nearby beach, blending wine, history, and natural beauty. Ideal for wine connoisseurs or those seeking a fresh take on Tuscan culture, this tour is luxurious, educational, and full of flavor. [Explore Super Tuscan tours here.]

6. Chianti Rufina Wine Tour

Tucked into the hill’s northeast of Florence, Chianti Rufina is a lesser-known gem that offers a more intimate wine-tasting experience. With higher elevations and cooler temperatures, the wines from this area are refined, structured, and deeply expressive. A Chianti Rufina tour offers a peaceful alternative to the more touristic Chianti Classico.

You’ll visit small, often family-run estates with traditional methods. Walk through hillside vineyards, and enjoy tastings of elegant reds made primarily from Sangiovese. Many experiences include food pairings with seasonal ingredients, like truffle pasta or roasted vegetables.

Tours here often include visits to historical estates, monasteries, or villas that have produced wine for generations. Because it’s less crowded, you’ll enjoy a more personal connection with your hosts and the land. Perfect for travelers seeking authenticity and quiet beauty. [Book a Chianti Rufina tour today.]

                                                               

  1. Carmignano Wine Day Trip 

Carmignano, just west of Florence, is a historic and often overlooked wine region that packs a flavorful punch. With a winemaking tradition dating back to the Etruscans and Medici influence encouraging Cabernet Sauvignon plantings, Carmignano produces unique blends that stand out in Tuscany.

This day trip takes you to the heart of the region, visiting small wineries nestled among rolling hills and olive groves. The wines here combine Sangiovese with Cabernet and other varietals for bold, balanced reds. You’ll enjoy tastings with the winemakers themselves, who share their stories.

Tours often include a visit to the Medici Villa in Artimino or a walk through ancient vineyards. A traditional lunch, often with dishes like rabbit stew or hand-rolled pasta, adds to the experience. With fewer crowds and rich history, Carmignano offers a deep, personal look at Tuscany’s winemaking diversity. [Find a Carmignano tour here.]

8. Val d’Orcia Scenic Wine Tour

The Val d’Orcia is not just a feast for the palate—it’s a visual masterpiece. This tour combines the best of Tuscan wine with some of the region’s most iconic scenery. You’ll travel through rolling hills, golden fields, and postcard-perfect towns like Pienza, San Quirico d’Orcia, and Montalcino.

Wineries here produce top-tier Brunello di Montalcino and Rosso di Montalcino, as well as smaller DOC wines that capture the essence of the region. Expect vineyard walks, tastings in family-run estates, and perhaps a stop at a thermal spa or pecorino cheese farm.

Guides highlight local history, architectural gems, and food traditions, offering a full cultural experience alongside the wine. If you’re looking for a wine tour that’s equally about beauty and flavor, the Val d’Orcia delivers. [Plan your Val d’Orcia wine trip here.]

9. Lucca & Montecarlo Wine Region

This delightful day trip blends culture and viticulture in one of Tuscany’s most relaxed regions. Start in Lucca, a charming city known for its Renaissance walls and elegant piazzas. After a morning of sightseeing, head into the Montecarlo DOC zone for tastings of aromatic whites and light reds.

The Montecarlo region is cooler and perfect for varietals like Vermentino, Sauvignon Blanc, and Sangiovese. You’ll visit intimate, family-owned wineries where the focus is on quality and innovation. Many tours include extra experiences like olive oil tasting or vineyard picnics.

The relaxed pace and cultural highlights make this tour great for couples or groups who want a mix of city and countryside. With less travel time and more local charm, it’s a lovely escape from Florence. [Check availability for a Lucca wine tour.]

10. Arezzo & Tuscan Countryside Wineries

Head east to discover the understated elegance of Arezzo and its surrounding wine regions. This tour is ideal for travelers seeking tranquility, authenticity, and unspoiled landscapes. Arezzo is a city of art and antiquity, but the countryside is dotted with organic vineyards and family-run estates.

Your tour might begin with a short walking tour of Arezzo’s historic center before heading into the hills. There, you’ll taste wines that reflect passion and sustainability— Expect hearty reds and crisp whites served alongside homemade pasta, salumi, and farm-fresh cheeses.

Because it’s off the typical tourist radar, you’ll receive personal attention from winemakers who are thrilled to share their craft. It’s a warm, intimate experience that reflects the soul of rural Tuscany. [Click to discover Arezzo wine day tours.]

11. Morellino di Scansano Wine Tour

Venture into southern Tuscany for a wine experience that’s as wild as it is wonderful. Morellino di Scansano, a lesser-known DOCG, is made mostly from Sangiovese but carries the freshness of its coastal terroir. The Maremma region’s untamed landscapes and ancient roots set the tone for this adventurous tour.

You’ll visit wineries surrounded by oak forests and vineyards that stretch toward the sea. The tastings are dynamic, showcasing young, fruit-forward wines. Many tours include stops at Etruscan ruins, medieval towns, or regional food producers.

Expect a more rustic and off-the-beaten-path feel. The experience is perfect for wine lovers eager to explore Tuscany beyond the well-trodden trails. [Browse Morellino wine tours here.]

12. Florence Urban Wine Experience

Short on time? No problem—Florence offers fantastic wine tastings without ever leaving the city. The Urban Wine Experience is a great way to sample Tuscany’s top varietals in a stylish setting. Guided by expert sommeliers, you’ll taste Chianti, Brunello, and Super Tuscans paired with artisanal cheeses and meats.

These tastings usually take place in enotecas (wine bars) or private cellars, where you’ll learn about regional wines, flavor profiles, and ideal pairings. It’s educational and entertaining—a fun evening activity or rainy-day backup plan.

Some tours include walking between tastings, combining city sights with sips of Italy’s best. Great for beginners or those on tight schedules, it’s a simple, satisfying way to get your wine fix. [Book a Florence wine tasting session here.]

Final Thoughts

Tuscany is a wine lover’s dream, and from Florence, it’s never been easier to explore. These tours let you relax and sip your way through vineyards, stories, and unforgettable views. Whether you’re new to wine or a seasoned taster, there’s a perfect tour waiting for you. Cin cin!

 

   Some of our Favorite Wine Tours