Report this Experience

Dare Retreat | Italy 2024

Hosted By: Dare to Detour

$2,029 / month for 6 months

Seven days in Tuscany – La dolce vita!

A Wine & Food Exploration (It’s truffle season!)

Traveling with a group of all-women is incredible for the soul — at any age. And Italy is an amazing place to do it. (Especially in the fall!) We’ll be staying in a beautiful Italian villa and exploring the culture Italians do best – food and wine! Indulge in the flavors of truffle season, immerse yourself in the beauty of Tuscany, and create lifelong connections on this unforgettable retreat.

Date: October 14 – 20, 2024

Session Type : Retreat
Modality : In Person
Language : English
Date : From 10-14-2024
Duration : 7 days
Location : Castiglione d'Orcia, Province of Siena, Italy

Report Abuse

Dare | Italy 2024

October 14 – 20, 2024

Seven Days in Tuscany – La Dolce Vita

Trip Itinerary

Tuscany’s Chianti region showcases a breathtaking landscape with gentle green hills dotted with vineyards, olive groves, stone farmhouses and villas. Villa Amerigo, our home for the week, is a 16th century newly restored farmhouse located on over 20 acres including Il Cellese vineyards and winery, an outdoor pool, fire pit, kitchen gardens, estate chickens, bocce ball court, and outdoor gym.

Southern facing, the villa has sunrise and sunset exposures and 25-mile views. It is a true Italian oasis, less than 30 minutes from Siena. Once a critical medieval European community, Siena’s historic city center is now a UNESCO World Heritage Site, famous for art, museums, a local horse race, and cuisine. With a focus on Italian cuisine, our days will be full but relaxed as we immerse ourselves in “la dolce vita.”

Note: This trip overview is subject to change due to weather and availability


A warm welcome and aperitivo at Villa Amerigo
Artisanal pizza making with our personal Tuscan guide, Francesco Barone

Day Two

Tuscan breakfast
Tuscan wine safari
Dinner at Tenuta di Perano Osteria

Day Three

Tuscan breakfast
Vintage Fiat 500 adventure
Italian cooking class with Chef Alessio

Day Four

Tuscan breakfast
Chianti tour and Tuscan wine & food pairing at an organic winery and farm
Dinner at Osteria di Brolio – Brolio Castle

Day Five

Tuscan breakfast
Mini L’Eroica E-bike tour
Dinner at Villa Amerigo

Day Six

Tuscan breakfast
Tuscan truffle hunt
In-villa bartender experience to celebrate our week together
Dinner at Villa Amerigo

Day Seven

Tuscan breakfast
Depart for Florence

Travel Logistics


Aeroporto di Firenze-Peretola / FLR

Please plan to arrive in Florence by 2 pm, Monday, October 14, 2024. If your schedule allows, I recommend that you arrive a day or so earlier to explore. This will ease your travel logistics and give you time to acclimate to the time zone. The time zone in Italy for our Detour will be Central European Summer Time (CEST). Another option is to fly into Rome / Leonardo da Vinci – Fiumicino / FCO, and take the train to Florence. There are 17 trains per day that travel from Leonardo da Vinci – Fiumicino to Florence. If you do arrive early in Florence, we will arrange a time and place to pick you up.

Airport Shuttle

The Dare Crew and I will meet you at Aeroporto di Firenze-Peretola in Florence at 2:30 pm CEST on Monday, October 14, 2024. From the airport, we will head to Villa Amergio, our home for the week, located in the heart of the Chianti region near Siena. The drive will take about an hour, and we will be traveling through the rolling hills of Tuscany, passing by vineyards and olive groves, and arriving at our villa to a warm welcome and aperitivo, a true Italian ritual. Cin Cin Darlings!


We will travel back to Florence from our villa on the morning of October 20th, with our arrival at the airport planned for 12:30 pm. If you book return flights on the 2oth, we recommend a flight time of no earlier than 3 pm. Depending on your flight/train options, an overnight in either Florence or Rome may be necessary.


Due to the unpredictability of current global events, I require that you purchase flight insurance through the airline when you book your flights AND travel/trip cancellation insurance to cover your retreat investment. Insurance is not offered through Dare to Detour. I recommend AIG Travel Guard Insurance. AIG Travel Guard provides a variety of insurance packages for you to choose from. I ask that purchase travel insurance that includes medical coverage and emergency airlift evacuation. Proof of insurance coverage will be required one month prior to our Detour together.

Visit the AIG website to learn more: HTTPS://WWW.TRAVELGUARD.COM/


Your Detour investment is fully refundable, except for a $750 non-refundable deposit, up to 31 days prior to the start of your trip.  Should you cancel within 31 days of travel, you will forfeit your investment.


There are no reviews yet.

Only logged in customers who have purchased this product may leave a review.

To leave a review please login


Castiglione d'Orcia, Province of Siena, Italy

Castiglione d'Orcia, Province of Siena, Italy

Sheryl Wright, founder of Dare to Detour, empowers feminine leadership through workshops, retreats, and expeditions worldwide. Based in Bozeman, Montana, she embraces nature, coffee, and laughter. Dare to Detour supports women in transitions, offering all-inclusive retreats for self-discovery and empowerment. Through curated workshops and activities, participants shift mindsets, fostering clarity and positive change. The goal is to push women out of their comfort zones, inspiring confidence in their true capabilities.

Store name : Dare to Detour

More Experiences from Practitioner