Small Group  |  Off the Beaten Path  | Authentic & Immersive



5 - 7 total




2021:OCT 18 - 25

2022: OCT 17 - 24

2023: OCT 16 - 23



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 Poggio alle Ville, our first accommodations at a beautiful agriturismo farm with authentic Tuscan cottages surrounded by olive trees and forests. After settling in and relaxing, we'll kick things off with a Welcome Aperitivo followed by a homemade dinner on the farm! Welcome to Tuscany! Meals Included: Cheese Tasting, Aperitivo, Dinner

Truffle Hunting + Pizza Class

After a leisurely morning, 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! Included Meals: Breakfast, Lunch, Dinner

Winery Visit

In the morning we'll visit the historic home of the Chini family, now a museum dedicated to Art Nouveau. Afterwards, you'll have some free time to wander the village of Borgo San Lorenzo, keeping an eye out for Art Nouveau details! But the highlight today is spending time at a gorgeous winery where we'll wander the vinecovered grounds and have a homemade lunch while getting to know the family that runs the vineyard. The rest of the day depends on how the group feels. We can go back to relax, visit another charming village, or perhaps an ancient stone mill forgotten in the forest! We'll go with the flow and surrender ourselves to the magic of the unexpected! Meals Included: Breakfast, Lunch, Dinner

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 free to relax and sink the details of this experience into your memory. 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 dinner, giving you the unique opportunity to get to know Italians as fellow friends! Meals Included: Breakfast, Lunch, Aperitivo, Dinner

Medieval Village Visit

The medieval village of Scarperia is famous for its production of artisanal, handcrafted knives since the 1400s. 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


After a delicious breakfast featuring homemade cakes and local meats & cheeses, we'll drop you at the Florence Airport. 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! Meals Included: Breakfast

Cooking Class

This morning, we'll bid farewell to our home on the farm and head to Palazzo Torriani 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. After a break to settle in, we'll step into the kitchen for a cooking class. Prepare to delight your taste buds and soul! Meals Included: Breakfast, Dinner

Festival + Free Time

Marradi is known for its marrons glacés (candied chestnuts) and October is the season they are 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 food based on their prized chestnuts! Enjoy the full day to wander the village on your own and shop for souvenirs. Later, we'll enjoy a farewell dinner at the Palazzo! Meals Included: Breakfast, Dinner



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! 


  • Flights: We'll help you find the best flights for your dates, free of charge!

  • Some Meals: Meals not described in the itinerary. (We believe scoping out your own hole-in-the-wall is part of the experience and we leave room for that!) Our included meals are so abundant that guests usually stick to gelato or something light when a meal is not included.

  • Incidental Expenses: A/C or Heat may cost extra at some locations, but it is unlikely that it will be needed.

  • Mandatory Travel Insurance: Click here for more info and resources.

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! We welcome everyone 18+!

The Important Details

  • 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.


October 18 - 25, 2021

Starting from $3,650 USD per person

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.

This also means that sometimes reasonable flexibility is required on your part. There's no science to getting a 90 year old Italian grandpa to show up on time, you just take what you get and roll with it! If you're the type of traveler who can stay flexible and relaxed knowing no matter WHAT you do, it's going to be awesome, then you're a great fit for this trip!


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!