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Discover Italy’s Heart: Family trip in Tuscany & Umbria

Italy
Discover Italy’s Heart: Family trip in Tuscany & UmbriaDiscover Italy’s Heart: Family trip in Tuscany & UmbriaDiscover Italy’s Heart: Family trip in Tuscany & UmbriaDiscover Italy’s Heart: Family trip in Tuscany & Umbria
Duration
8 days
Accommodation
Standard
Ages
18-99 yrs
Locations
Umbria, Siena

This eight-day family adventure takes you through the rolling hills of Tuscany and the tranquil beauty of Umbria. This is a trip designed for families to step into Italy not rushing, just moving with it. Instead of fast tours, there's time to breathe, watch, learn. A local nonna shows how pasta feels when made by hand. Roads wind through green vineyards where bikes roll without noise. Ancient villages sit quiet under stone walls. Food arrives simple, grown nearby, served warm. Moments stretch because nothing hurries. With activities that engage both parents and children, it’s the perfect blend of culture and leisure.

What's included

Private airport pick-up and hotel transfers
Private transfers between cities 
Guided tours
Entrance fees to historical sites
Meals & dining (on specific destinations)
Umbrian olive oil estate tasting
Guided truffle hunt with a dog 
Truffle-focused pasta/cooking workshop
International flights
Travel Insurance
Personal expenses

Itinerary

Day 1 – Arrival in Florence and Transfer to the Tuscan Countryside

Arrive at Florence Airport where your personal driver is waiting for you. A quiet ride begins and you will already start observing the beautiful landscape, winding past soft green hills dotted with ancient olive trees. You arrive at a farm-style retreat built just for families like yours. 

Spend your first afternoon while swimming laps in the pool or strolling through the grounds under golden light. Maybe take a short trip into a charming nearby town just to taste a cold gelato under soft streetlamps. As the evening settles in, a simple yet rich meal unfolds. You will experience dishes made fresh with what the region naturally offers: fragrant truffles, rich local oil and hand-crafted noodles shaped by tradition.

Inclusions:

- Private transfer from Florence Airport to agriturismo
- Accommodation in a countryside farmhouse with pool
- Welcome dinner with local ingredients

Florence
Day 2 – Siena and San Gimignano – A Day of Medieval Discovery

After breakfast, the day starts on a private excursion to two of Tuscany’s most iconic medieval towns. In Siena, walk through the Piazza del Campo and visit the stunning Duomo, with its beautiful mosaics. Children will enjoy learning about the Palio horse race and imagining the medieval celebrations that still define and happen in the city. 

Continue to San Gimignano, famous for its medieval towers and delicious gelato. Wander through the cobbled streets, climb a tower for panoramic views and enjoy a family lunch before returning to your farmhouse.

Inclusions:

- Private driver for full-day excursion
- Guided tour of Siena and San Gimignano
- Lunch in a local trattoria

Siena Duomo
Day 3 – Tuscan Cooking Class and Family Relaxation

Today is all about tasting and enjoying the flavors of Tuscany. Begin with a visit to a local market to pick up fresh, seasonal products. Then, join a private cooking class with a local chef or nonna. Children can help roll pasta or shape biscotti, while parents learn the secrets of authentic sauces. 

After lunch, enjoy a leisurely afternoon at your agriturismo, swimming in the pool, taking a walk among the olive trees or simply observing the peaceful surroundings.

Inclusions:

- Market visit with local chef
- Private cooking class and lunch
- Afternoon at leisure

Cooking class
Day 4 – Transfer to Umbria with Stop in Cortona

Say goodbye to Tuscany and head toward Umbria. On the way, stop in Cortona, a charming town on top of a hill known for its Etruscan heritage. Walk through its narrow streets, visit small boutiques and enjoy a coffee in a local café before continuing to your countryside accommodation near Assisi. 

In the evening, enjoy a delicious dinner on the terrace with views of the Umbrian hills.

Inclusions:

- Private transfer from Tuscany to Umbria
- Stop in Cortona for free exploration
- Accommodation near Assisi with dinner

Assisi
Day 5 – Assisi and Umbrian Olive Oil Experience

Start your day in Assisi, a town rich in spirituality and history. Visit the Basilica of St. Francis and explore its quiet streets full with flowers. 

In the afternoon, head to a local olive oil estate, where you’ll learn about the traditional methods used to make the region’s famous oil. Walk through olive groves, taste freshly pressed oil with crusty bread and enjoy a light lunch before returning to your agriturismo.

Inclusions:

- Guided tour of Assisi
- Olive oil tasting experience and light lunch
- Private transfers

Assisi landscape
Day 6 – Truffle Hunting and Pasta Workshop

Step into the rolling hills of Umbria for a truffle hunt like few have seen. With your guide leading the way, meet your truffle hunter and his dog trained to track those elusive underground treasures. Together, you explore the woodlands where these fragrant mushrooms lie waiting. 

Once back, head to a small village tucked between ancient stone walls. There, everyone pitches in, regardless of their age, as the group shapes fresh pasta by hand during an intimate cooking session. What gets served isn’t fancy restaurant fare but hearty local recipes infused with truffle essence, shared around a single table under open sky. The afternoon stretches into quiet ease, spent simply sitting under open skies or wandering Assisi's streets at sunset.

Inclusions:

- Guided truffle hunt with local expert and dog
- Truffle-based cooking workshop and lunch
- Transfers included

Day 7 – Orvieto and Lake Trasimeno – History and Nature

Head south to Orvieto, a town built atop volcanic rock, known for its magnificent cathedral. Explore the medieval alleys and visit the fascinating underground tunnels made by ancient civilizations. 

In the afternoon, take a ferry ride to Isola Maggiore on Lake Trasimeno for a peaceful stroll and a lakeside picnic. Return to your agriturismo for your farewell dinner, enjoying the flavors of Umbrian specialties like lentil soup and roasted meats.

Inclusions:

- Guided tour of Orvieto
- Ferry ride on Lake Trasimeno
- Farewell dinner at the agriturismo

Orvieto
Day 8 – Departure from Florence or Rome

The final day has arrived. Once you are done with your breakfast, your driver will take you to either Florence or Rome for your onward journey. As you leave Central Italy, you’ll carry the memories of peaceful hilltop towns, hands-on experiences and the warm hospitality of the locals who welcomed you like family.

Inclusions:

- Breakfast at accommodation
- Private transfer to Florence or Rome Airport

Departure Florence
From
$2,900
Start Date
Travelers
Adult (12+ years)
1
Children (2-12 years)
0
Infants (0-2 years)
0
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