Val d’Orcia Day Trip with Two Wine Tastings from Florence

Sip on Brunello in Montalcino, wander through Pienza, and savor pecorino cheese in Montelpuciano

Travel Flexibly · 11.50h · Florence, Italy

Searching for the ultimate Tuscan wine tour while you’re in Florence? Join this magnificent day trip to Val d’Orcia, a stunning UNESCO World Heritage Site renowned for its enchanting vineyards. Savor delicious Brunello wine in Montalcino, explore the ancient city of Pienza, and visit a winery in Montepulciano for a delicious tasting of Vino Nobile and pecorino cheese. All the while, admire Tuscany’s captivating rolling hills, idyllic olive groves, and picturesque vineyards!

  • Meet your guide in the Piazzale Montelungo bus Terminal
  • Montalcino
  • Wine tasting
  • Pienza
  • Views
  • Montepulciano
  • Wine and Pecorino tasting
  • End your tour in Piazzale Montelungo

Before you can begin sipping your way through the decadent wines of Val d’Orcia, head to the Piazzale Montelungo Bus Terminal in Florence. After finding your local guide, hop on your comfortable coach bus and meet your group of fellow-wine lovers.

An idyllic winery in Montalcino will be your first stop, where you and your group will explore their charming wine cellar and sample delicious Brunello wine, which the town is famous for.

Take in a scenic viewpoint of Val d’Orcia from the town’s peak before exploring Pienza, a historic city with magnificent architecture. Follow your friendly guide to a panoramic viewpoint of the region, where you’ll marvel at the picturesque hills, vineyards and olive groves that surround you.

Finally, end your tour in Montepulciano, renowned for being the land of Vino Nobile. Enjoy a captivating winery visit, where you will even have the opportunity to visit a real dungeon! Indulge in the region’s delicacies during a delicious wine and pecorino cheese tasting as you take in the stunning setting.

Cheers with your group one more time before hopping back on your coach bus for a peaceful ride back to Florence.

Val D’Orcia Day Trip with Two Wine Tastings Tour Description

Your 11.5-hour day trip includes:

  • Local, multilingual guide

  • Roundtrip transportation in Coach

  • Explore Montalcino, Pienza, and Montepulciano

  • Two wine tastings and pecorino cheese tasting

  • Option to purchase wine and cheese

  • Breathtaking views of Val d’Orcia

Drive to the Tuscan Countryside

To begin tasting your way through the magnificent Val d’Orcia, make your way to the Piazzale Montelungo Bus Terminal in Florence. Once you’ve spotted your friendly guide, board your fully fitted, GT coach bus and meet the rest of the fellow wine-lovers you’ll be traveling with!

Sit back and and relax as you enjoy a comfortable ride outside of the city into the gorgeous hills of the Tuscan countryside. Before long, you will arrive in Val d’Orcia, a stunning UNESCO World Heritage Site.

Sample Brunello in Montalcino

After a beautifully scenic drive from Florence, your first stop will be the enchanting town of Montalcino, celebrated for being the land of Brunello wine. After arriving at a charming winery in the region, you and your excited group members will be given a special tour of the charming wine cellar as you learn trade secrets of how their delicious Brunello is produced.

Of course, you can’t leave Montalcino without sampling the wine it’s renowned for. Indulge in a decadent Brunello tasting before departing for your next marvelous stop of the day.

View Wine Country from Above

Hop back in your coach and grab a window seat as you continue to drive through the picturesque village of Montalcino. Your driver will bring you to the town’s peak, where you will be met with jaw-dropping views of wine country. Admire the classic rolling hills, winding roads through picturesque vineyards, stunning olive groves, ancient oaks, and cypress trees. Capture the moment with your camera as you take in the incredible landscape.

Wander Through Beautiful Pienza

Next, your driver will transport you to Pienza, coined as the “ideal city.” Pienza was built in the 15the century by the legendary architect Bernardo Rossellino at the request of Pope Pius II.

Weave through the city’s charming streets, admiring the breathtaking architecture within the Duomo and Palazzo Piccolomini, which you may recognize from Zeffirelli’s film of Romeo and Juliet. Follow your guide to the city’s most captivating viewpoint, where you’ll find mesmerizing views of Val d’Orcia. After taking in the extraordinary sights, it will be time for your final stop of the day.

Wine and Pecorino Tasting in Montepulciano

Cap off your journey through Val d’Orcia with a delightful winery in Montepulciano, famous for producing Vino Nobile. Visit their gorgeous vineyard and explore a real dungeon, where the wine is stored underneath the ancient walls of the winery. Finally, enjoy a tasting of their exquisite Vino Nobile as well as pecorino cheese, another regional specialty.

Cheers one last time with your newfound friends before boarding the bus back to Florence.

What you get with this tour
Passionate English-speaking guide
Roundtrip transportation
Wine cellar
Montepulciano winery
Montalcino, Pienza, Montepulciano and more
Group size of 50 people max
Additional food and beverages
Hotel pick up and drop off
Guide gratuities
Tripadvisor Logo

See what people are saying

0 total reviews

Leave a review
0.0/5 (based on 0 reviews)
5 stars
4 stars
3 stars
2 stars
1 stars

Frequently Asked Questions

What to bring?

Please make sure to wear comfortable clothing and wear sun protection.

What to bring?

Please make sure to wear comfortable clothing and wear sun protection.

Is this tour run by The Tour Guy?

No, this tour is operated by one of our trusted and vetted partners in Florence.

What if I have concerns about my mobility on this tour?

Unfortunately, due to the locations visited on this tour, it is not suitable for guests with wheelchairs or impaired mobility. 

What happens if it rains?

We run our tours rain or shine.

Is lunch included in the price of the tour?

No, but you'll have a break to find delicious food. We're happy to recommend one of our favorite spots, but your guide is sure to point you in the right direction too.

How many glasses of wine will I get?

You'll enjoy two separate wine tastings, one in Montalcino where you will savor Brunello, and the second in Montepulciano, for Vino Nobile.

Can I bring my kids and do I have to pay for them?

Kids are welcome on this tour, and children aged 0-3 may join for free. Children aged 4-12 pay a reduced fee.

Start From: $103.04

available days discounted days

Free 24-hr cancellation on group tours! Learn more

Reserve Now $103.04 / per person
$103.04 / per person
You may also like
Skip the Line
Up to 12% off

Skip the Line

Florence in a Day Combo Tour with David and Uffizi

Explore Accademia Gallery, Ponte Vecchio, Florence Duomo, Uffizi Gallery, and so much more

Skip the Line

Skip the Line

Complete Florence Duomo Tour with Dome Climb

View this charming city from the terraces of Brunelleschi’s famous dome after touring the cathedral

Day Trip

Day Trip

Tuscany Wine Tour from Florence to Siena & Chianti

Enjoy a luxury Tuscany day trip to visit Siena and San Gimignano then taste food and wine in Chianti

Skip the Line
Up to 24% off

Skip the Line

Skip the Line Uffizi Gallery Tour

See Botticelli, Caravaggio, and Michelangelo's masterpieces in Florence's famous Uffizi Gallery

New Tour

New Tour

Tuscany Wine Tour by Vespa from Florence

Taste the food and wine of Chianti as you ride through the Tuscan countryside on a vintage scooter

Guided Tour

Guided Tour

Florence Local Food Tour in Santo Spirito

Get an authentic taste of Florence’s exquisite food and wine in a lively local neighborhood

New Tour

New Tour

Tuscany Day Trip from Rome with Vineyard Lunch and Wine Tasting

Wander through the medieval towns of Montepulciano and Pienza and enjoy a 3-course meal!

Skip the Line

Skip the Line

Florence Walking Tour with Statue of David

Uncover the best of Florence at the Duomo and Ponte Vecchio, and skip the line at Accademia

Skip the Line
Up to 16% off

Skip the Line

Statue of David Evening Tour

Skip the line to see Michelangelo's David on a later tour of the Accademia Gallery with fewer crowds

New Tour

New Tour

Tuscany in a Day Tour from Florence

Visit Siena, dine at a Chianti vineyard, explore San Gimignano, and see the Leaning Tower of Pisa!

Skip the Line

Skip the Line

Uffizi Private Tour in Florence

Skip the line to see Birth of Venus, Medusa, Doni Tondo, and more with your own private art guide

Florence Duomo Skip-the-Line Tour with Dome Climb

Florence Duomo Skip-the-Line Tour with Dome Climb

Explore the breathtaking cathedral and take in captivating views from Brunelleschi’s Cupola!

New tour

New tour

Authentic 4-Course Meal at a Local’s Home in Florence

Watch your host’s cooking demo from her own kitchen, then enjoy a family lunch or dinner together!

New tour

New tour

Pisa and The Leaning Tower Half Day Tour from Florence

Explore the City famous for its Piazza dei Miracoli and enjoy skip-the-line access with this tour

New Tour

New Tour

Florence Duomo Skip-the-Line Tour

Explore the iconic cathedral with an expert guide and visit the fascinating Misericordia Museum

New Tour

New Tour

Florence Accademia Gallery Express Guided Tour

Skip the line, marvel at renowned masterpieces and see Michelangelo’s iconic David statue!

New Tour

New Tour

Cinque Terre Tour with Locally Produced Limoncino Tasting from La Spezia

Explore the Beaches and Picturesque Peaks in a Small Group

New Tour

New Tour

Pizza and Gelato Making Cooking Class in Florence

Create the authentic food of Italy with an expert pizzaiolo chef, homemade lunch, and wine

New Tour

New Tour

Cinque Terre Hiking Tour from La Spezia

Walk clifftop trails to discover vineyards, epic views, and famous villages on Italy's magical coast

New Tour

New Tour

Tuscany Wine Making Experience and Gourmet Dinner from Florence

Dine like Tuscan royalty and create your own Chianti wine blend on this small group VIP evening tour

New Tour

New Tour

Semi-Private Cinque Terre Day Trip & Vineyard Tour from Florence

Discover the best of Cinque Terre with seafood lunch, wine tasting, and transportation included

New Tour

New Tour

Authentic Tuscan Cooking Class in Florence with San Lorenzo Market

Create delicious pasta, tiramisu, and more with market-fresh ingredients and an expert local chef

New Tour

New Tour

Pisa and Lucca Day Trip from Florence

Book a stress-free trip to see the Leaning Tower of Pisa and Lucca's medieval walls in a day

New Tour

New Tour

Florentine Gondola Boat Tour

Sip wine on the Arno River and cruise by Ponte Vecchio, Uffizi, and more on a classic Barchetto boat

New Tour

New Tour

Tuscany Wineland Safari from Florence

Get off the beaten track to explore vineyards, castles, food, and Chianti wine on this 4x4 day tour

New Tour

New Tour

Florence in a Half Day by Bike Tour

Take a ride through the city's hidden gems from Ponte Vecchio to the Oltrarno neighborhood

New Tour

New Tour

Cinque Terre Day Trip from Florence with Boat Ride

Visit these iconic fishing villages the easy way on this tour to the beautiful Italian Riviera

Skip the Line

Skip the Line

Kid-Friendly Private Florence Walking Tour: David & Gelato

Bring the fun to Florence on this family walking tour that includes a merry-go-round and papermaking

Skip the Line

Skip the Line

Florence Private Walking Tour with Michelangelo's David

Explore the famous sites of Florence, with Ponte Vecchio, Duomo, and skip-the-line Accademia entry

Private Tour

Private Tour

Private Wine Day in the Chianti Hills from Florence

Enjoy an intimate day trip tasting wine and organic food from local farms and vineyards in Tuscany

Private Tour

Private Tour

Private Pisa Day Trip from Florence with Lunch in Vinci

Discover Tuscany on this VIP private tour, with Leaning Tower of Pisa, Da Vinci Museum, and more!

Private Tour

Private Tour

Orvieto, Civita di Bagnoregio & Winery Private Day Trip from Rome

Escape the city on a memorable journey through Umbria’s historic towns to taste fine local wines

Private Tour

Private Tour

Livorno Shore Excursion: Florence & Pisa

Maximize your day ashore on this jam-packed private tour with Leaning Tower, David, and more!

Private Tour

Private Tour

Tuscany Shore Excursion: Chianti Wine Country and San Gimignano

A Chianti Wine Tasting Excursion

Skip the Line

Skip the Line

Private Siena Walking Tour

Explore this charming Tuscan city with an engaging local guide to see the Duomo, San Domenico & more

Brunello di Montalcino Helicopter Tour from Rome or Florence

Brunello di Montalcino Helicopter Tour from Rome or Florence

Soar above Tuscany on an exclusive VIP tour, complete with private wine tastings and a gourmet lunch

Pisa & Cinque Terre Day Trip From Florence

Pisa & Cinque Terre Day Trip From Florence

Explore the charming towns of Monterosso and Manarola, embark on a coastal hike, and tour Pisa

New Tour

New Tour

Tuscan Countryside Vespa Tour from Florence

Cruise to the rolling hills of Tuscany and taste local food and wine!

E-Bike Tour Through Florence and Tuscan Countryside
Up to 20% off

E-Bike Tour Through Florence and Tuscan Countryside

Ride along Tuscany’s majestic rolling hills, visit a medieval village, and sample local delicacies!

New Tour

New Tour

Tuscany Winery Tour and Gourmet Bites in Montalcino

Pair irresistible wine with delicious gourmet bites after strolling through picturesque vineyards

New Tour

New Tour

Brunello di Montalcino Winery Tour & Tasting

Sip wine and stroll through vineyards alongside an expert guide in the hills of Montalcino

New Tour

New Tour

Exclusive Florence Duomo and Secret Terraces Tour

Discover Florence's Duomo with our small group, skip the line tour with hidden terrace access

500 tour from Florence​
Up to 20% off

500 tour from Florence​

Private Vintage FIAT 500 Chianti Tour with Driver from Florence

Cruise through the hills of Tuscany in style and dine at a Tuscan villa on this exclusive experience

Palazzo Vecchio Small Group Skip the Line Guided Tour

Palazzo Vecchio Small Group Skip the Line Guided Tour

Roam through the lavish apartments and halls that were home to the iconic Medici family in Florence

New Tour

New Tour

Skip the Line Duomo Terraces Tour with Dome Climb

Admire the Florence Cathedral, climb to the top of Brunelleschi’s Dome, and enjoy breathtaking views

Three-Day Chianti Vineyard Wine & Spa Getaway

Three-Day Chianti Vineyard Wine & Spa Getaway

Rejuvenate at the rustic Borgo Casa al Vento while learning the secrets of Tuscan wine and cuisine

New Tour

New Tour

Early Morning Duomo Tour with Exclusive Entry and Brunelleschi's Dome

Be among the first of the day to enter Florence cathedral on this VIP experience

New Tour

New Tour

San Lorenzo Market Tour and Wine Tasting in Florence

Eat your way through Florence’s historic market, enjoy a wine tasting, and try real Italian gelato!

New Tour

New Tour

Pizza and Gelato Cooking Class in a Tuscany Farmhouse in Florence

Pick fresh ingredients and learn to make authentic, Italian cuisine on an unforgettable day trip!

New Tour

New Tour

Oltrarno Local Food Tour in Florence

Take a break from the crowds and eat like a local in the lively neighborhood of Oltrarno

New Tour

New Tour

Chianti Vineyards Tour and Wine Tastings from Florence

See two luxurious wine estates, taste local wine, and sample delicious produce on this half day tour

Vintage FIAT 500 Tour from Florence​

Vintage FIAT 500 Tour from Florence​

Vintage FIAT 500 Self-Drive Tuscany Tour from Florence

Get behind the wheel of an iconic Italian car, cruising to the Tuscan countryside