
Florence, Umbria
Oct 12 - 18, 2026
7 days, 6 nights
Exclusive Small Group (7 passengers max)
Social travelers, book lovers, and culture seekers
From $6,453 for one person (including single supplement)
From $5,381 per person based on 2 people
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.
Why You'll Love It
- Explore Florence’s iconic landmarks, sip Chianti in the Tuscan hills, wander Umbrian villages like Spello and Bevagna, and savor regional specialties
- Hunt for prized Umbrian truffles with expert guides and their dogs, enjoy vineyard lunches in renowned wine regions, and take part in a hands-on cooking class featuring beloved local dishes
- Share relaxed, social discussions over breakfast and evening drinks as the group dives into stories set in the very places you’re exploring—an engaging way to connect with fellow travelers and Italy
- Relax knowing that your tour will be led by Max, one of Ciao Andiamo’s co-owners, who will ensure that every travel detail is taken care of, and that you’ll get to enjoy a mix of tours & excursions balanced with free time for independent exploration
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 Puglia from the inside out, the way the locals live it.
Getting around
Dedicated Private Driver
Throughout your tour, travel seamlessly in the comfort of dedicated car service, as you journey on daily excursions spanning small towns and off-the-beaten path adventures.
Where You'll Stay
Home Away From Home
Where you call home when you are away from home can make all the difference. That’s why we’ve handpicked accommodations across all our small group tours that blend a mix of Italian hospitality, comfort and local character (you want to feel like you’re in Italy, not Idaho).
Our Guides
We partner with local guides, drivers, chefs and artisans of the highest caliber across all 20 regions of Italy. Every Ciao Andiamo expert is hand-selected by our team and passionate about sharing the best of Italy with our travelers.
Getting Around
In Italy, getting around isn’t always easy, which is why we design each trip to flow as seamlessly as possible. From private transfers to expert guidance and assistance with public transportation, we’ll make sure you get from point A to point B without the stress.
Dedicated Private Driver
Throughout your tour, travel seamlessly in the comfort of dedicated car service, as you journey on daily excursions spanning small towns and off-the-beaten path adventures.
Where You'll Stay
Where you call home when you are away from home can make all the difference. That’s why we’ve handpicked accommodations across all our small group tours that blend a mix of Italian hospitality, comfort and local character (you want to feel like you’re in Italy, not Idaho).
What's Included
6 nights accommodations with daily breakfast included
7 additional group meals (lunch or dinner)
Transportation via luxury van
Dedicated tour leader & Ciao Andiamo co-founder, Max
Full-day private walking tour of Florence with admissions included
Two winery visits with wine tasting (in Chianti and Montefalco regions)
Private twilight walking tour of the Oltrarno in Florence with aperitivo
Private walking tour of Orvieto
Private truffle hunt experience
Visits to typical Umbrian towns like Spello, Bevagna & Montefalco
Private cooking class in Umbria
Visit to an olive oil producer with tour and tasting
Transfer from accommodations in Umbria to Florence via luxury van with private driver
Ciao Andiamo’s dedicated planning services and on-the- ground support while traveling
Author-led book club discussions with the tour group before and during travel in a fun, social atmosphere
Optional travel journaling workshop to develop your writing abilities, chronicle your travels, and experience those travels in a whole new way
Not Included
Airfare, ground transportation, meals not specified, optional gratuities, and personal expenses
The Ciao Difference
Every Ciao Andiamo Trip Includes
Hand-Selected Hotels
Expert Local Guides
Private Tours
Insider Access
One-On-One Expert Planning
Personal Concierge in Italy
Receive Your Full Itinerary
Other Small Group Tours
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
Perfect for: First-time travelers to Italy
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.
