Small Group  |  Off the Beaten Path  | Authentic & Immersive



5 - 7 total




2021:OCT 16 - 23

2022: OCT 15 - 22

2023: OCT 14 - 21



Pre-book for 2022 & 2023!

For those who seek to live the culture instead of snapping pictures, this journey will satisfy daydreams of wandering untouched medieval villages, connecting with the land, and learning from locals along the way. This Fall adventure will have you hunting for truffles, helping with the olive harvest, & experiencing a local chestnut festival, all while surrendering to the magic of the unexpected!




yourself in rural farm life, away from the crowds.



a fall chestnut festival with locally-produced food & crafts.



in the olive harvest and truffle hunting.


with locals and learn about history through their family stories.


mouth-watering recipes in a villa inhabited by the same family for 500 years.

Step into Italy as if you're a Local.

Let's Get this Party Started!

In the morning, we'll pick you up from Florence and head straight to the countryside where we'll have the absolute treat of meeting a flock of sheep and learning how their milk is turned into delicious local cheese. After tasting the best cheese you've ever had, we'll check out a low-key spot known to locals in the tiny village of Sant'Agata. It's unassuming but serves the best "Tortelli di Patate", or potato-filled pasta with meat sauce (the area's typical dish). Driving through a green valley dotted with autumn colors and gentle hills in the distance, we'll arrive at Palazzo Torriani, our first accommodations in the town of Marradi. Our hosts, Anna Maria and Mariaemilia, will walk us through this gorgeous villa where their family has lived for over 500 years. Finally, we'll relax into the evening with an aperitivo cocktail before a homemade dinner. Welcome to Tuscany! Meals Included: Cheese Tasting, Aperitivo, Dinner

Festival + Free Time

Marradi is known for its marrons glacés (candied chestnuts) and October is the season they are revered and celebrated! Today you'll be free to enjoy the local chestnut festival which is full of food stands offering all the best local products and traditional recipes based on their prized chestnuts! Enjoy the full day to wander the village on your own. Later, we'll put our aprons on for a cooking class to tease our senses!

Truffle Hunting

After a delicious breakfast featuring homemade cakes and local meats & cheeses, we'll head to our home for the remainder of the trip; a beautiful agriturismo farm with authentic stone cottages surrounded by olive trees and forests. After checking in, we'll walk into the woods to hunt for truffles then linger over a homemade, truffle-themed lunch! After lunch you'll be free to find a sunny spot for a cat nap, sketching, or journaling. You may even opt for a game of bocce. In the evening, our hosts Raffaele and Ioana will teach us how to make homemade pizza! Meals Included: Breakfast, Lunch, Dinner

Medieval Village Visit

The medieval village of Scarperia is famous for its production of artisanal, handcrafted knives since the 1400s. After some free time to explore the village, we'll visit a knife workshop that has been preserved as it was left in the 1900s. Next, we'll step inside the stunning Palazzo dei Vicari where medieval history is brought to life! To wrap up an exciting day, we'll pause for "la dolce vita" with a typical Tuscan aperitivo (don't be surprised if you end up calling this dinner)! Meals Included: Breakfast, Aperitivo

Winery Visit

The highlight of today is spending time at a gorgeous winery where we'll wander the vine-covered grounds and have a homemade lunch with wine while getting to know the family that runs it. Next, we'll stop by the nearby village of Dicomano for a gelato tasting! The rest of the day depends on how the group feels. We can go back to relax or visit another charming village and stay for dinner, we'll go with the flow and surrender ourselves to the magic of the unexpected! Meals Included: Breakfast, Lunch

Olive Harvest

After a lazy morning, we'll connect with the culture by helping out with the olive harvest followed by another family-style lunch at the farm! You'll have the afternoon to relax and sink the details of this experience into your memory in anticipation of your departure tomorrow. Over an evening aperitivo, we'll have a special inside look at Italian culture thanks to a local association working to keep women's traditional handicrafts alive. You'll hear about the history and cultural significance as you get to touch and feel the intricate work up close. Our local guests will join us for a dinner that you'll wish would never end! Meals Included: Breakfast, Lunch, Aperitivo, Dinner


A presto! (See you again soon!) Haven't had enough yet? We can help you plan an extended stay in Florence, Tuscany, or beyond. Just get in touch!


Updated Itinerary Coming Soon!


Slower-paced & stress-free travel

Unique experiences crafted directly with locals to highlight the authentic culture.

Exclusive group of just 7 like-minded travelers.

Plenty of free time to do your own thing.

Explore places that tourists have never heard of.

Thoughtfully crafted with extensive research in the area for genuine & meaningful connection with locals.


7 nights' accommodation in a private room (2 nights in Marradi, 5 nights in the countryside)

All breakfasts, 3 lunches and 6 dinners including wine, and 5 tastings/aperitivi

Carbon Footprint Offset: A donation will be made to fund projects that reduce carbon emissions and improve daily life in impoverished areas.

Transportation + Private Driver

Flight Expert to research and book flights

Arrival Transfer from center of Florence, Departure Transfer to Florence Airport

Trip Leader fluent in English and Italian

Tips for the driver & guides

Pre-Trip Prep: Cultural and Italian language guidance, packing tips, and additional resources to fully connect you with what you'll experience! Local recommendations in each location.

All Activities

Welcome Cocktail & Dinner

Olive Harvest

Truffle Hunting

Pizza-Making Class

Cheese Farm Visit & Tasting

Visit Historic Palazzo dei Vicari

Winery Visit, Tasting, & Lunch

Visits to Lesser-Known Villages

Gelato Tasting

Truffle Hunting

Homemade Truffle Lunch

Nature Walk

Evening with Women's Handicrafts

Private Palazzo Tour

Sunset Aperitivo

Cooking Class

Local Chestnut Festival

Free Time for Your Own Discoveries! 

From $3,650 USD per person


Active travelers who want to access authentic

Italy without the logistics.

Who is this trip for?

Our travelers want to leave the crowded tourist paths behind, without spending weeks researching. They want to connect with locals, but don't have years to perfect a new language. And while they love back roads and hidden villages, they're not up for the hassle and risk of driving a rental.


Our travelers are warm. They’re curious. And they want to see Italy with open hearts, open minds, and without the growl of a giant tour bus announcing their arrival. They are immersion seekers who want to step into the everyday life of authentic Italy!


Sound like you?

Our travelers are generally 35 - 55 years old but we also get adventurers into their 70's or 80's!

  • This trip involves walking on uneven ground for multiple hours, and a 1.5 hour hike (each way) without bathrooms (lots of bushes though!).

  • Please note that you'll need to carry your own luggage up and down stairs at hotels and across cobblestone.

  • The longest drive will be a little over 3 hours, with breaks.

  • Wifi is available in all locations but connection may be weak.

  • Most dietary restrictions can be accommodated if you let us know well in advance.

The Important Details


October 16 - 23, 2021

Starting from $3,650 USD per person

Updated Itinerary Coming Soon!

Click Here to Pre-Book for 2022 & 2023!


I was lucky enough to take part in Sierra's Secrets of Southern Italy tour. It was a magical experience from start to finish. She is an expert planner and things flowed perfectly from beginning to end. This was true even when we experienced inclement weather. She always had backup plans. The professional driver was a great touch and made things so easy. There is no better way to have an authentic experience and to enjoy the wonderful food and people of Puglia than by joining Sierra on one of her amazing tours. A+++


-David Yaugo, Secrets of Southern Italy

At Creative Edge Travel, we believe every journey should be meaningful. It should teach you about the authentic local culture and a bit about yourself, too. That's why we push the boundaries of the typical Italian tour and add our own creative edge. We design our experiences with individual locals in off-the-beaten-path places to give you a culturally-immersive adventure. Each activity is an opportunity to learn about both the beauty and the challenges of everyday life in Italy. Whether it's exploring a village with a local grandpa as he shares his stories growing up there, or learning traditional music and dance at a historic masseria, expect a deeper travel experience.

Experiences based on authentic connection with locals and their home.  


 Want more details? We love to talk about our trips!

Click below to schedule a call!