OCT 11 - 21:








On this 11-day trip with just 5 - 7 travelers, we bypass tourists to move through Tuscany's most authentic and lesser-known places. Through friendly encounters with locals, immersive culinary adventures, and walks through truly hidden and ancient villages, we'll experience the stories and traditions of Tuscany's fall harvest.


Linger over a dinner party with our local friends. 

Learn traditional chestnut flour recipes at an abandoned mill in the mountains.

Sip the finest wine made from the pure passion of one dedicated farmer.

Relax in natural hot springs.

Experience a cooking class in the Chianti countryside.

Wander hilltop villages with views you'll dream of for years to come!

We add that CREATIVE EDGE to help you connect with locals on a deeper level and have a more meaningful travel experience. 

2019 DATES


October 11 - 21:  

Starting from $3,150 USD per person

Dates don't work? Need a shorter trip? Ask us about flexible options!

"It was obvious throughout the entire trip what great amounts of experience, knowledge and effort have been put into Creative Edge Travel. We were able to experience true Italy in a way that would not have been possible without Sierra and her amazing team of contacts." 

-Hannah Woodruff, Australia


Slower-paced & stress-free travel

Unique activities sourced from locals from the region and our extensive research in the area

Exclusive group of 7 like-minded travelers

Free time to do your own thing

Explore places your friends have never been to

Thoughtfully crafted for genuine connection with locals

Starting from $3,150 USD per person


10 nights' accommodation


All activities from pasta-making, to nature excursions, to hanging out on a local family farm

All breakfasts, 2 lunches, and 3 dinners including wine

Transportation + private driver

Arrival/Departure Transfers from Florence

24/7 Trip Leader fluent in English and Italian

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. 

They are the laid-back couple you just met, but already want to get dinner with. The young woman whose story sounds so intriguing over a cappuccino. The creative guys in the hotel lobby you laugh with over the woes of pronouncing ‘bruschetta’. 


Our travelers are warm. They’re curious. And they want to know your story as much as you want to know theirs. They want to see Italy with open hearts, open minds, and without the growl of a giant tour bus announcing their arrival to another tourist-packed site.


Sound like you?


Book your place today: all ages above 18 are welcome and we tend to have a beautiful mix of middle-aged groups of friends, a solo traveler or two, and retired couples. We encourage cross-generational exchange, and love the sharing of experience and perspective that a small group affords. 

Who is this trip for?

Travelers who want to access authentic

Italy without the logistics.



Arrival & Departure Airport

2 nights

San Miniato

2 nights


3 nights

Chianti Countryside

3 nights

Experiences based on authentic connection with locals and their home.  

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 farmhouse, expect a deeper travel experience.




"It was obvious throughout the entire tour what great amounts of experience, knowledge and effort has been put into the Creative Edge tours. We were able to experience true Italy in a way that would not have been possible without Sierra and her amazing team of contacts. We are extremely grateful for Creative Edge Travel in making our time in Italy one of the highlights of our entire Europe trip! Could not recommend these tours any more highly!"

-Hannah Woodruff, Australia

"An "Immersive Dinner with Locals", in the Tuscan Hillsides left me feeling at home and in love. We enjoyed a home cooked meal prepared by our hosts, Lucia and her husband Maurizio. Over a five course meal, we enjoyed fresh olive oil, fine wine, and typical Italian dishes. We laughed together, told stories, and shared a common culture. This will be a night I will remember for years to come. 

Creative Edge Travel and the organizer, Sierra, deliver a high-quality experience. The adventures you will take will be off the beaten path. The people you meet with be authentic and genuine. The experience of your travels will be so fulfilling you will look forward till you can come back for more!"

-Tyler Hanzel, USA

"Sierra designed everything to be authentic, bespoke, intimate and personalized. I joined the Intarsia workshop in Anghiari, which was led by one of the leading artisans of inlaid wood parquet in Tuscany. Truly an immersive workshop to rediscover an interesting art that has been passed down from one generation to another. An Italian experience like no other!"

-Jason Alinsunurin, Philippines

"The trip Sierra and her team designed for me and my friend was just way above my expectations. She brought us to a small typical village (San Miniato) and we had a magical day there, talking with locals and discovering traditional products. We went to little tiny restaurants, and took walks that we never would have found without her and her knowledge of Tuscany. We felt like the only ones in the world of Italy, able to take a deep breath from our busy lives. Thanks again Sierra, and see you soon for another trip!"

-Elodie Levert, France

"If you want to experience something no other agency will offer you, or something that takes so much time and research to find... if you want to tell your friends back home about places no other tourists have seen, to discover the real heart of Tuscany...then..you only have one choice- Sierra and Creative Edge Travel partners will let you live something unique. Something you will feel to be one of the few to have experienced. Till the point you'll almost be too selfish to share with others."

-Marco Fabbri, Italy

"I am naturally skeptical of tours and prefer to plan my own unique trips. However, after traveling into the villages of Tuscany with Sierra, I can honestly say that no amount of research could have provided me with that type of experience. Her expertise in the area and connection with the locals allows you to get a taste and feel of the true culture of Italy. Every part of the trip was generally laid out, but each experience felt very unique. Sierra works passionately to ensure that the Italy she knows and loves is exactly what you see. If you want to get off the beaten path and see parts of Italy that otherwise would be inaccessible without local connections and the necessary language skills, these are the trips for you. Thanks, Sierra!"

-Seth Mason, USA

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