Welcome to Castellina in Chianti

Top experiences in Castellina in Chianti

Amazing hotels and hostels

We've pre-picked the best hotels, hostels and bed and breakfasts to make your stay as enjoyable as possible.

Travel guides

Starting at $36.39

Image for

Castellina in Chianti activities

$101.64 Food, Wine & Nightlife

Chianti Culinary Tour from Florence with Dinner, Wine Pairings

Hop aboard your air-conditioned coach in central Florence and settle in for the 40-minute drive through the Tuscan countryside to begin your tour. On route, listen as your guide shares details of the Chianti region’s rich history and heritage, and gain insight into the many wines for which the area is famous. Take in stunning views of the Italian countryside as you drive past olive groves, cypress trees, and vineyards bursting with juicy grapes before arriving near the Tuscan town of Greve. Head first to the wine estate and enjoy a guided tour of the ancient cellars where barrels of Chianti Classico lie slowly maturing. Afterward, follow a wonderful hilly route in your bus along the "Via Chiantigiana." Reach a family-run winery where you'll visit the cellars and the barrique room and taste four excellent limited-production Chianti wines, as well as local products.  Head into Greve, and soak up the atmosphere in the town’s Medieval square. Admire the traditional architecture and charming shops selling regional produce, and enjoy a little free time to explore at your leisure. Continue on to Castellina in Chianti, an ancient hamlet set high on a hillside between rolling vineyards and olive groves. Take in beautiful views out over the rolling vineyards below and enjoy free time to wander at your leisure. Travel on to San Donato in Poggio — an ancient village nestled in the rolling Tuscan hills — and sit down to your evening meal in a local tavern. Enjoy regional specialities perfectly complemented by excellent Chianti wine, and experience first-hand a traditional dining experience for which the Italians are famous. (Dinner will be held in the open, weather permitting, so do bring suitable clothing.) Upgrade to enjoy a delicious bistecca alla Fiorentina — a rich, flavorsome Florentine T-bone steak simply dressed with olive oil, rosemary and salt, and widely considered to be the most famous Tuscan meat dish of all! When it’s time to leave San Donato in Poggio behind, hop back aboard your coach for the 40-minute drive back to Florence where your tour will come to an end. Please note: The order of these visits might change.

$119.57 Tours & Sightseeing

Siena Vespa Tour and Chianti Winery Lunch and Wine Tasting

Meet your guide and tour escorts at your hotel, they'll drive you to Badesse where you'll put on your helmet and get acquainted with your quintessentially Italian mode of transport – a beautiful Vespa scooter! After a safety briefing and a few practice sessions to get used to the Vespa’s automatic gears, follow the lead of your guide and set off on your way. Alternatively, hop on behind one of your tour escorts if you prefer not to drive yourself. Following your guide, take a leisurely drive through the Chianti Area, passing by Lornano, Fonterutoli you'll reach Castellina in Chianti where you'll get the change to visit this Etruscan village.  Half-way through the day, stop at a Chianti winery in the heart of the region to learn all about winemaking in Tuscany. Explore the vineyards and cellars with your guide, and then taste several local wines, including prestigious varieties such as Chianti Classico, Gallo Nero and Super Tuscan. After your wine-tasting session, sit down inside the winery and enjoy a traditional Tuscan lunch of cured meats, mild cheeses, freshly baked bread and olives, while chatting with your guide about life in the idyllic Chianti region. Then, head into the luscious Chianti hills of Tuscany, passing along quiet countryside lanes that meander through medieval villages and flower-filled fields. If you’ve chosen to share your scooter with a traveling companion, there will be plenty of breaks factored in to stop and switch drivers, or to simply stretch your legs while soaking up the views. Spend some free time here relaxing in the sunshine before driving back into Badesse where you'll leave your Vespa and your driver will drop you off back to your Hotel in Siena.

$237.95 Day Trips & Excursions

Siena, San Gimignano, Chianti Wine Region Tour from Florence

You'll leave from Florence at 9am and will start with a visit of Siena, a beautiful Tuscan hill town famous for its Piazza del Campo where the famous Palio di Siena (horse race) is held twice a year. You'll spend time in Siena touring the city and experiencing its medieval narrow streets. From Siena, your driver guide will take you to a well-known winery in the Chianti area, Monterinaldi or similar, where you'll spend approx. 2-hours. Here you’ll find out about how the regional popular wines are produced, and then enjoy a light lunch with a selection of bruschettas, cold cuts and cheeses, paired with 3 superb chianti wines plus vinsanto.After lunch you'll visit San Gimignano, stroll around this enchanting medieval town and admire the breathtaking scenery with incredible vistas of the Chianti from 'Torre Grossa', the Cathedral tower, and appreciate the slower pace of life that hasn't changed for centuries. Stroll around the streets of this enchanting hill town and enjoy a gelato (ice-cream) in Cistern Square.After leaving San Gimignano, the tour returns to Florence via the Chianti area stopping by the charming villages of Castellina in Chianti and Monteriggioni. And while sitting back savoring the subtle textures and tones of the wine, contemplate the beautiful countryside that has been your constant companion during the day.

$119.57 Tours & Sightseeing

Full Day Tuscany Vespa Tour with Lunch from Florence

Discover the countryside from a different prospective. Have fun riding a Vespa along scenic and peaceful roads in the heart of Tuscany. Meet your tour leader in Florence and head to the Chianti area (Badesse) by minivan. Upon arrival start your tour listening to some guidelines and suggestions, your tour leader will show you how to ride a Vespa and will make sure you are ready and good to go. If you don’t feel confident enough about riding on your own you can always choose to ride with one of our expert Vespa drivers. Then start to ride in Chianti roads surrounded by olive trees, vineyards, historical villas and cypresses. You'll stop in Castellina in Chianti, a small village and its origins go back to Etruscan times, that represent together with Greve and Radda the heart of Chianti Classico area. The ancient "borgo" still keeps all the characteristic and shape of the medieval fortification, so leave your Vespa and take a walk in this charming village.  Take your Vespa and continue your ride to the Winery where you'll learn the main steps of the Chianti wine production, you'll visit the cellars and then you'll enjoy a Tuscan meal.  After lunch take your Vespa and continue the itinerary direction Radda in Chianti passing  along small medieval villages and have the chances to stop in the best spots to take amazing pictures. Upon arrival in Radda in Chianti, wander in the village discovering its hidden spots and have some time before taking your Vespa for the ride back to Badesse.  Here, a minivan will be waiting for you and you will be driven back to Florence where the tour will end.

$179.36 Day Trips & Excursions

Small-Group Chianti and San Gimignano Sunset Trip from Siena

Your small-group tour begins in the afternoon with a comfortable drive in a luxury minivan from Siena to Chianti -- a region of Italy famous for its beautiful vineyards and landscapes shaped into works of art by the combined actions of nature and man. Arrive first in the village of Castellina in Chianti, and enjoy a gelato (own expense) as you walk through its medieval alleyways and town center with your guide. From here, enjoy the drive to a Chianti wine estate, where you'll tour the grounds and wine cellars while learning about the winemaking process. Sit down and savor a tasting of Black Rooster Chianti Classico wine and olive oil (included).Then head to Monteriggioni, a perfectly preserved medieval town with a complete ring of walls and turrets built in the 13th century. It was Siena’s main bastion of defense against the armies of Florence during the Middle Ages, and today it is a quiet hamlet. Enjoy leisure time here to explore the charming city on your own. In the late afternoon, arrive in San Gimignano and explore this romantic town of towers. You'll have free time to enter its impressive church, the Collegiata di San Gimignano, or explore the Civic Museum (entrance fees at own expense). Alternatively, shop in the artisan boutiques for leather goods and hand-painted pottery; sample the fruits of the soil in the food shops and wine bars; or discover the town’s many hidden beauties. After your time in San Gimignano, head out of town to a nearby rustic farmhouse, where you'll be treated to a classic Tuscan dinner, accompanied by tastings of Vernaccia (the famous white wine of San Gimignano) and red Chianti wine. Your Tuscan dinner, consisting of cured meats, home-grown vegetables and cheeses, will be served on a terrace overlooking the cultivated fields and the ‘skyline’ of San Gimignano’s towers during sunset. As your tour comes to an end, meet your guide back at the minivan for the relaxing return journey to Siena.

$71.74 Food, Wine & Nightlife

Siena to Chianti and Monteriggioni Tour with Wine Tasting

Depart from your Hotel in Siena, where our driver-guide will pick you up in a comfortable, air-conditioned minivan and immerse yourself in the beauty of the Tuscan countryside on this  small-group tour. Get the chance to admire the Tuscan hills that frame the scenic road through the lush countryside. Leave Siena and reach the first winery located in Castellina in Chianti in the heart of the stunning Chianti Classico area. After a visit to the wine cellars, gain insight into the various stages of wine-production.  Learn about the process of the blending Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes that culminates in Chianti wine.  Then, try this world-known wines enjoying a wine-tasting paired with delicacies such as sliced cured meats, bruschetta and salami. Afterwords head to Monteriggioni castle, a charming walled village known and famous also thanks to Dante Alighieri who cited it in his masterpiece the Divine Comedy. Here you can make the best from your free time and you might visit the small church,  take a walk on the medieval walls (at your own expense), go shopping or enjoy a delicious cup of coffee at a local cafe. Then, always driving on Tuscan hills roads reach the second winery and fall in love with its unique style. Learn its history, visit the cellars and take unique photos. Sample more Tuscan products including wine-tastings and oil-tastings. When the tasting is over, our driver will take you back to your Hotel in Siena where the end of the tour.

Castellina in Chianti in detail