There are places you don’t just visit—you breathe them in and take them home with you. Chianti is one of them: hills that change color with the seasons, dirt roads that smell of earth and wine, and villages where time seems to have stood still. If you’re looking for a weekend to remember, you’ve come to the right place.
A weekend in Chianti is one of those gifts you can give yourself (or someone else) that will leave a lasting impression. With WeHike, we’ll take you on a journey to discover this extraordinary region through hikes along trails surrounded by nature, stops at historic wineries, and authentic experiences that let you get to know local traditions better. Every weekend is designed for those who want to slow down, recharge, and return home with something extra.
Easter Weekend in the Terre del Gallo Nero
Easter in the heart of Chianti Classico: three days in the land of the Black Rooster, the historic symbol of this region. A leisurely food and wine trek with an easy hiking level, perfect for discovering trails still fresh with spring, walking among ancient parish churches and the Conca d’Oro of Panzano, tasting the great wines of local wineries, and getting lost in the narrow streets of Greve in Chianti and Montefioralle. If you love strolling at a leisurely pace, good food paired with the right red wine, and excellent company, this is the weekend for you: an authentic and unforgettable Easter experience in the heart of Tuscany.
Discover Easter Weekend in Tuscany
Long Weekend of June 2: The Scents of Lamole in Chianti
Four days immersed in the nature of the Chianti—its most secluded and fragrant region—in the Lamole area, one of the most charming wine-growing regions in the area yet still waiting to be discovered. Four days with a base-and-explore itinerary, featuring hikes through terraced vineyards, ancient abbeys, and parish churches: each day offers the chance to explore extraordinary places, from the Badia a Passignano Nature Reserve to the picturesque views of Greve in Chianti and Montefioralle, with tastings of fine wines that tell the story of this landscape and its producers. The long June holiday weekend is the perfect opportunity for a natural reset away from the city, dedicated to deep relaxation.
Discover the June 2 Long Weekend in Chianti
Mid-August in Chianti
Want to escape the chaos of August? Yes, but without sacrificing beauty. Ferragosto in Chianti with WeHike means three days of hiking through woods and hills in the Terre del Gallo Nero, swimming and rafting in the crystal-clear waters of the Elsa River, immersing yourself in local history, and savoring authentic flavors that come together as if by magic, in a region that in summer is cloaked in intense, fragrant greenery. A group weekend with a base-camp format, all about sunshine, good wine, relaxation, and genuine camaraderie: a true alternative to the usual August destinations, for those who want to experience the height of summer in a different, slower, more authentic way. There’s plenty of time for music and nightclubs all winter long.
Discover Ferragosto in Chianti
Divino Weekend – Montefioralle Wine Festival
Two days in the medieval village of Montefioralle, one of Italy’s most beautiful villages, during the Divino Wine Festival. WeHike’s first autumn weekend is designed for those who love to walk at a leisurely pace: a 7-kilometer scenic hike with 270 meters of elevation gain through the rolling hills of Chianti, vineyards golden at harvest time, and picturesque views that will take your breath away. Chianti Classico tastings accompanied by stories from local producers, convivial dinners, and cobblestone alleys: this weekend is a total immersion in the tradition and soul of Chianti, allowing you to take home not just images, but deep emotions and unique memories.
Discover the Divine Weekend in Montefioralle
Plan your weekend in Chianti
Each itinerary has its own character, its own season, and its own pace, but they all share the same promise: to take you to the heart of authentic Chianti, far from the beaten path, with an expert guide who knows every trail and every story of this region. And if you’re not sure which one to choose, explore all the options and let yourself be inspired: your weekend in Chianti awaits.