Small Groups Tours. Big Experiences.
Experience the Italian way of life through local eyes, in the most immersive and seamless way possible.
Join a small group with other like-minded travelers on one of our Insider Journeys. Led by a dedicated Italian tour leader (often one of Ciao Andiamo’s co-owners), these multi-day adventures delve deep into the regions of Italy, beyond the major cities and tourist attractions – the ultimate insider’s experience.
From private tours and tastings to curated dinners and artisanal experiences, our Italian experts create journeys that are best enjoyed with like-minded new friends in a close-knit setting. When we say small, we mean small – most trips feature no more than 7 travelers.
We take care of everything, from accommodations and logistics to daily excursions and meals. All you have to do is show up!
Come and join our famiglia on a Ciao Andiamo’s Insider Journey. They’re not just about seeing the sights; they’re about creating one-of-a-kind, immersive memories and emotions to last a lifetime.
Dedicated Tour Leader
Travel seamlessly in the trusted hands of a knowledgeable local for the entirety of your trip.
Small Group Excursions
Join up to 6 other like-minded travelers, or make the experience private with your own group.
Insider Access
Authentic experiences that go deeper than the typical tourist path.
Expert Guides
Passionate local partners ready to welcome you and share Italy through their eyes.
Wine & Dine with Locals
Fully immerse yourself in the regions of Italy and live la dolce vita.
Curated Hotels
Hand-selected accommodations with local charm and your style in mind.
Discover our Insider Journeys
Ciao’s Grand Tour of Italy
Oct 11 - 22, 2026
Apr 5 - 16, 2027
Oct 18 - 29, 2027
Rome, Assisi, Florence, Verona & Venice
12 days, 11 nights
Experience the best that Italy has to offer, from the major cities of Rome, Florence, Verona, and Venice to the medieval villages of Umbria and Tuscany. Uncover the history and culture of each city, enjoy wine tasting in the famous Chianti area, learn how Balsamic vinegar has been made for centuries, and discover the iconic local cuisine every region has to offer.
Book Club With a View
Oct 12 - 18, 2026
Florence, Umbria
7 days, 6 nights
Join us for a journey with author Michelle Damiani through the heart of Italy, where great stories, unforgettable meals, and beautiful landscapes intertwine. Explore cultural treasures and off-the-beaten path neighborhoods in Florence. Immerse yourself in the green hills of Umbria, with vineyard lunches, village strolls, and hands-on culinary experiences. This exclusive small group tour comes with a unique twist: a lively travel book club! Over relaxed breakfasts and evening aperitivi, gather for fun, informal discussions about books inspired by the places you’ll visit—sharing ideas, laughs, and travel reflections along the way. Guests will also have the option to join a casual travel journaling workshop to help make this and future travel adventures unforgettable.
Wondering why you’d travel all the way to Italy to read? Don’t worry – this is vacation, not school! The set up is just like a regular book club. First you’ll read the books on your own at home, and then you’ll get to visit the places you’ve read about with a group of fellow book lovers.
Meet your tour leader
Max: The Ultimate Insider
As one of Ciao Andiamo’s co-owners and Chief Italy Officer, Max is a true insider who knows the hidden gems, local secrets, and authentic flavors that make this country so extraordinary. With decades of experience in the Italian travel industry, he’s befriended countless food and wine producers, restaurateurs, artisans, and guides across the country.
Max doesn’t just show you the sights—he introduces you to Italy in a way that’s personal and unforgettable. That’s what you get on a small group Insider Journey.
Join Max and discover Italy from the inside out, the way the locals live it.
