Italy Activities

Get acquainted with a new destination or explore one of your favorite Greek cities in a new and exciting way!

Whether you are looking to cover the must-see's, have more hands on experience with a cooking class, we have a wide selection for you to choose from. 

Below are lists by city or category for you to browse while dreaming up your perfect vacation.

Use our Travel Planner to book your vacation easily!

Private Tour - Pienza & Montepulciano - Excursion from Gaiole in Chianti

Venture to the beautiful countryside of the Orcia Valley to discover ancient, hilltop villages, rows of vineyards, and culinary specialties while surrounded by unique scents and amazing tastes. Crossed by the Orcia River, from which the Valley was named, this amazing region of Tuscany has been recognized as a UNESCO World Heritage Site in 2004, and it is considered to be a rustic treasure with breathtaking views and picturesque landscapes.

Your journey will take you to the Renaissance town of Pienza, celebrated as the 'ideal city' for its harmonious blend of stunning architectural treasures. You will also explore Montepulciano, famous for its medieval architecture and renowned Vino Nobile wine. The tour includes a visit to a charming local winery, where you will enjoy a delicious lunch and an exquisite wine tasting session, immersing you in the rich flavors of the region.

Exact time will be provided in final documents. Pick up at your hotel. 

Private Tour - Siena & San Gimignano - Excursion from Gaiole in Chianti

The tour begins with a guided visit to Siena, where you'll be captivated by the stunning architecture of the Cathedral and the majestic Municipal Building in Piazza del Campo, the heart of the city and the thrilling venue for the legendary Palio horse race.

Next, the journey continues to the medieval gem of San Gimignano, renowned for its iconic skyline of soaring towers. Famous for its Vernaccia wine, saffron, and the exquisite Santa Fina pottery, the town offers a rich blend of history and craftsmanship. A knowledgeable guide will lead you through its charming streets, uncovering the hidden corners and stories of this UNESCO World Heritage site.

Exact time will be provided in final documents. Pick up at your hotel.

Private Tour - Taste of Chianti - Excursion from Gaiole in Chianti

In the rolling hills of Chianti, you’ll immerse yourself in the rich history of medieval villages, savor local delicacies, and taste the world-famous Chianti Classico wine. This enchanting region is celebrated for its picturesque towns, ancient castles and abbeys, and long-standing wine making traditions.

Your journey will take you through two of Chianti’s most captivating villages: Castellina in Chianti, known for its historic charm and panoramic views, and Radda in Chianti, a medieval treasure that captures the essence of Tuscany. Along the way, you’ll visit two renowned wineries, tour their wine cellars, indulge in exquisite wine tastings and enjoy a traditional Tuscan lunch.

Exact time will be provided in final documents. Pick up at your hotel. 

Private Tour - Best of Tuscany - Excursion from Gaiole in Chianti

Enjoy a full-day private tour through the heart of Tuscany, visiting the stunning cities of Siena, San Gimignano, and the renowned Chianti Classico wine region.

Your adventure begins in Siena, where you can explore at your own pace the magnificent Siena Cathedral and the famous Piazza del Campo, home to the thrilling Palio horse race. Afterward, head to San Gimignano, the “Town of Towers,” known for its medieval charm and sweeping views of the Tuscan countryside. Enjoy the freedom to stroll through its picturesque streets and visit local artisan shops on your own. In the afternoon, journey into the Chianti Classico region, where you’ll visit a local winery for a wine tasting, sampling some of the finest Chianti Classico wines.

Exact time will be provided in final documents. Pick up at your hotel.

Private Tour - Arezzo & Cortona - Excursion from Gaiole in Chianti

Traveling through the hills of Crete Senesi, just around an hour from Siena, you will discover the ancient cities of Arezzo and Cortona. On this full day tour, you will first stop in Arezzo, an ancient city with Etruscan roots, famous for its stunning works of art by Piero della Francesca and Cimabue. Visit the Basilica of San Francesco, Piazza Grande, and the medieval Church of San Domenico, home to Cimabue’s remarkable crucifix. Stroll through charming antique shops and boutiques, soaking in the city's rich artistic heritage.

Next, travel through the picturesque Val di Chiana to Cortona, a hilltop town offering sweeping views of the valley below. You may explore the Sanctuary of Santa Margherita, perched at the highest point of the village, and take in the panoramic scenery. Descend into the city center, where you can visit the tranquil Eremo delle Celle, a 13th-century convent founded by St. Francis. As you arrive in the main square, admire the historic Town Hall and Clock Tower. You’ll have time to shop, capture stunning photos, and soak in the timeless beauty of Cortona.

Exact time will be provided in final documents. Pick up at your hotel. 

Private Tour - Chianti Medieval Towns and Wine Tour - Excursion from Gaiole in Chianti

Take an excursion to a land of ancient wine making traditions, unique landscapes, medieval castles and abbeys, and gorgeous vineyards surrounded by woods, olive groves and cypress trees.  A region filled with exceptional beauty – Chianti.  First stop along the winding hills of the Chianti Castles Route is the beautiful medieval town enclosed by massive walls, Radda in Chianti.  This magnificent town is the perfect place to enjoy good wine and embrace the natural picturesque landscapes that surround you.  Next is the ancient village of Castellina in Chianti, a town rich with history as if time itself has stopped. 

In this beautiful region you will visit one historical wine estate in the heart of Chianti.  Here you will be guided through the estate cellars and enjoy a wine tasting.

Exact time will be provided in final documents. Pick up at your hotel.