Top Italy Holidays in 2026

Leave the busy streets of Florence behind and soak up Tuscany's views on this small-group Vespa tour. Hop onto your scooter once you reach the beautiful country roads of Chianti, so you don't have to navigate inner-city traffic. Stop for a traditional Tuscan meal at a farmhouse and taste olive oils and Chianti wines for an authentic taste of Florence's culinary scene. You can also enjoy the journey in a Fiat Topolino e-car.

Take a break from the bustle of Rome and experience two pillars of Italian cuisine in the peaceful Franscati countryside with this unique day trip. Visit a traditional family-run winery to sample local red and white wines, then learn the secrets to making perfect pasta from scratch during a hands-on lesson. Cap off your visit with dinner featuring your own fresh pasta topped with a traditional Roman sauce.

While most Pompeii tours only visit the UNESCO-listed ruins, this small-group tour takes it one step further with a tasty lunch on the slopes of Mount Vesuvius. First, delve into the history and fate of the ancient city of Pompeii with an archaeologist guide. Then relax over lunch at a nearby winery to taste several wines produced on the volcanic slopes.

Don't just learn about Italian farm-to-table cooking—have the rare opportunity to immerse yourself in a real working farm on this half-day tour. Convenient transportation takes you from downtown Sorrento straight into nature. Upon arrival, explore olive and lemon groves, learn how wine is made, and discover the pace of farming life. Then, enjoy a generous sampling of the farm’s products, as well as a freshly prepared lunch.

Get to know Rome's popular Trastevere neighborhood through its food and wine—and discover bites and restaurants you'd otherwise miss—on this half-day walking tour. With just a small group for company, visit local-favorite venues for multiple tastings, including cheese, ham, pizza, pasta, and aged balsamic vinegar. Explore Trastevere’s cobblestone streets between sampling local wines and beers. Save room for the tour’s final bite: traditional gelato.

Tying together Florence's historical, cultural, and architectural highlights takes planning—more than most travelers can manage alone. Leave the itinerary to a guide; check off sights such as the Piazza della Signoria and Ponte Vecchio Bridge, and stop to see Michelangelo's "David" in the Accademia Gallery. Cap the experience with a visit to the Florence Duomo, the city's Gothic-style cathedral.

Learn how to make pasta from scratch in this interactive cooking workshop in Rome. See how authentic gelato is made up close, then improve your cooking skills with guidance from a chef. Feel like a professional as you use high-quality tools and ingredients to make your meal. The reward for your hard work is delicious food and unlimited wine.

Immerse yourself in Florence’s food and wine scene on this tasting tour. Uncover the city's culinary scene without having to plan a thing yourself. Enjoy carefully selected Tuscan specialities and expertly paired wines, including the city’s notable Negroni cocktail. Dine in comfort at sit-down stops, experience the atmosphere of a centuries-old wine cellar, and learn about the history of Florence’s wine windows.

Tuscany is world-renowned for its wine, so ensure you get an insider’s glimpse into the industry during a tasting tour of the vineyards surrounding Siena. Receive personalized attention in a small group as you visit a historical cellar and educate your palate to recognize subtle flavors with the help of a sommelier.

Learn the secret to preparing pasta from scratch like a true Italian “nonna” in the heart of Florence with this hands-on pasta cooking class. Make three types of fresh pasta plus traditional sauces with guidance from your instructor as you sip unlimited Tuscan wine and connect with fellow foodies. Then cap off your lesson by sampling your creations with a celebratory meal served with even more wine.

Venice is more than an open-air museum; it’s also a world-renowned gastronomy hub. Discover the full-flavored wines of Veneto during this insider’s wine crawl, and see where famed writer Ernest Hemingway loved to sit and write. Enjoy tasty food pairings along the way from fresh regional ingredients, as you learn how to eat—and more importantly, drink—like a true Venetian local.

Discover Tuscany on a full-day trip from Rome that combines history, gastronomy, and spectacular scenery. Alternating guided experiences with free time in both Civita di Bagnoregio and Pienza means you’ll have the best of expert curation and independent exploration—with a driver to handle the winding roads. During a three-course lunch of Tuscan cuisine, you'll sample local wines alongside regional dishes few tourist menus feature.

Explore Milan's most significant historical landmarks, including skip-the-line access to da Vinci's 'The Last Supper', during this walking tour. With your local art historian guide, visit sites like Sforza Castle, the Scala Theater, Piazza dei Mercanti, and the Duomo. View 'The Last Supper', Leonardo da Vinci's masterpiece, without waiting in the general admission line. All entrance fees are included on this small-group walking tour.

Discover the many delights of Tuscany’s wine country on this small-group tasting tour from Florence. Travel along beautiful hillside roads through vineyards, olive groves and cypress trees. Visit 2 top-rated wineries in the famed Chianti Classico region, tour the cellars and learn how wine is produced using traditional methods. Taste different wines, along with olive oil and Tuscan specialties like fresh cheeses and bruschetta. Group size is limited to twenty-five participants for a more personalized experience.

Learn to make pizza, and either tiramisu or gelato, by hand with a professional chef in Rome. Use top-quality, local ingredients to create delicious, traditional pizza, then pop your culinary creations into a woodfired oven to crisp to a golden brown. After cooking, enjoy your pizza alongside tiramisu or gelato, paired with a selection of wines to complement your meal.

While in Verona, don’t miss out on visiting the well-known Valpolicella wine region. Avoid the hassle of self-driving on this small-group guided tour where you stop at vineyards to taste some of the best Italian wines, including an Amarone, a rich red wine made from partially dried grapes. Along the way, learn about the winemaking process and snap pictures of the beautiful vineyards.

Savor Florence's celebrated cuisine on an evening food tour featuring Florentine steak and Tuscan wine. Explore the vibrant districts of Oltrarno and Santo Spirito, making stops at five carefully selected foodie hotspots. With 14 delicious tastings—including tomato bruschetta, two paccheri pasta dishes, and a sit-down Tuscan dinner—this experience offers a flavorful escape from typical tourist traps.

Venetian cooking traditions don't translate easily from cookbook to home kitchen without seeing the techniques first-hand. Unravel the mystery with this small-group hands-on cooking class held in a working Venice restaurant kitchen. Learn how to make a traditional Venetian pasta dish and tiramisu from scratch and enjoy the fruits of your labor with a glass of wine.

Learn how to prepare food like a local with this hands-on cooking class in Florence, revealing the art of pasta-making and tiramisu creation. Roll up your sleeves in a beloved local restaurant, then feast on your creations with included wine and coffee while chatting with your host and fellow classmates about Italian cuisine.

Knowing where to visit in the Tuscan countryside can be daunting for first-timers, especially if you're starting off in Florence. Simplify your day out with this group tour. Once you've boarded your coach, sit back knowing the transportation and activities are covered, meaning you can fully immerse yourself in the experience. Enjoy visiting Pienza, Montalcino, and Montepulciano, the Orcia Valley, and taking part in a wine and cheese tasting.

Rome is most beautiful at night, with its illuminated buildings, lively cafes, and bustling atmosphere. With this small-group tour, you'll explore the city when the temps drop and daytime crowds depart, from the seat of a zippy electronic bicycle. This tour also includes a welcome aperitif and local food and wine samples.

Delve into Venetian history on this tour that showcases two of the city's most iconic structures and sheds light on the stories behind them both. Your first stop is legendary St. Mark's Basilica. Wander around the mosaic-covered interior and Byzantine treasures while a local guide fills you in on how this collection came to be. Then continue to the Doge’s Palace to explore the former political heart of Venice.

Tick off several of Tuscany's most renowned locations during this full-day Vespa tour. Enjoy some photo stops in the vineyards and take a guided stroll through the picture-perfect village of San Gimignano, with free time to explore. The tour includes a typical Tuscan light lunch paired with a tasting of some local wines and olive oils.

Explore Florence's Duomo in greater depth on this guided tour. Choose from a range of tour options to suit your budget and interests. If chosen, learn about Brunelleschi’s dome as you climb to the top, stopping along the way to visit the North Terrace, closed to the general public. Depending on your tour, use your passes to explore the rest of the cathedral complex at your own pace.