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Florence, Umbria

Oct 12 - 18, 2026

Sold out!

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.

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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
Day 1

Benvenuti a Firenze!

Today, you’ll meet up with your group in Florence. After time to check into your accommodations and settle, join the group for an immersive tour of the heart of the Italian Renaissance, where centuries of history overlap and unfold before you with the help of an expert local guide. Visit highlights like the Florence Duomo – with its iconic red dome – and of course, Michelangelo’s masterpiece, The David. In the evening, celebrate the start of this Italian adventure with a welcome dinner at one of our favorite Florentine restaurants.

Day 2

Wine & Dine in Tuscan Tradition

Enjoy breakfast at your hotel before heading into the Tuscan countryside for a day exploring the beautiful scenery and delectable cuisine of Tuscany. Today, you’ll visit the world-renowned Chianti wine region and enjoy a vineyard tour, wine tasting and lunch at a winery, and return to Florence for a little afternoon down time (perfect for shopping or writing practice). In the evening, reconnect with the group for a tour of the charming Oltrarno neighborhood of Florence, ending with an evening aperitivo in a local wine bar.

Day 3

Into the Umbrian Countryside

Check out of your hotel after breakfast and bid arrivederci to Florence, as today the group journeys into the hills of Umbria. On your way, stop in the beautiful hill town of Orvieto for a guided tour of its historic city center, with layers of history stretching from the medieval era all the way back to ancient Etruscan roots. After arrival in Umbria, check into your hotel and settle in at your new home base.

Day 4

Hunting for Black Diamonds

Today, the group will embark on a truly unforgettable experience – a truffle hunt! Led by an expert truffle hunter and his dogs, you’ll explore the forests of Umbria in search of theculinary “black diamond.” Following your hunt, you’ll enjoy lunch together with dishes highlighting this sought-after delicacy. Enjoy the evening and dinner on your own.

Day 5

Umbrian Villages & Winery Tour

After breakfast at your hotel, the group will embark into the Umbrian countryside, visiting the villages that dot the rolling hills and valleys of the landscape, such as Spello and Bevagna. You’ll have time to explore as a group and on your own, and between towns you’ll stop at a winery in the renowned Montefalco wine region for lunch paired with local wine.

Day 6

Through the Olive Groves

Today the group will explore the production of Extra Virgin Olive Oil, with a tour of a modern olive oil producer and tastings of the “liquid gold,” produced in the heart of Umbria for hundreds of years. Next, the group will head to a cooking class featuring typical regional dishes and products, followed by a lunch of your own creation. In the evening, the group will gather for a farewell dinner, toasting to the memories shared together on your tour.

Day 7

Arrivederci!

Today, bid farewell to the group as everyone goes their separate ways. Enjoy private car transfer back to Florence to catch your return flight, or continue your exploration of Italy further by adding on additional touring. We wish you buon viaggio!

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

Hand-Selected Hotels

Expert Local Guides

Private Tours

Insider Access

One-On-One Expert Planning

Personal Concierge in Italy

Receive Your Full Itinerary


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