Dare | Italy 2025

Seven Days in Tuscany - La Dolce Vita

DETOUR WITH US

Retreat Snapshot

When: October 12th-18th 2025

Where: The Chianti Region | Tuscany

Theme: A Food & Wine Exploration

Investment: $11,821 all-inclusive (excluding airfare) $925 Non-Refundable Deposit

What All- Inclusive Really Means

Overview

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.

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A WINE AND FOOD EXPLORATION

IT'S TRUFFLE SEASON

A WINE AND FOOD EXPLORATION IT'S TRUFFLE SEASON

Tuscan table setting at the villa, where the retreat will be held.

Accommodations

Villa Amerigo

Each darling will have their own private space to retreat to. Each suite is complete with a cozy lounge area, ensuite bathroom and expansive views of the Tuscan countryside.

"The connection, the quality, the destination… all exquisite, all what my soul needed. Grateful for the attention to detail and planning to make the experience worth my time, energy, and investment. Will go again 100 times to feel this aligned."

- M.O. | PAST RETREAT PARTICIPANT

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 the 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 horserace 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.)

• Pick up from Aeroporto di Firenze-Peretola
• Warm Cuvée Welcome
• Villa Tour: Our villa manager will give us a tour and help us settle into our rooms
•Dinner at home with our personal Tuscan chef, a farm-to-table feast paired with regional wines
• Buonasera Darlings!
• Buongiorno! In Villa Breakfast
• L 'Eroica E-Bike Tour following the route of the famous L 'Eroica bike touring experience which will have just happened the prior weekend. We will ride along cypress-lined gravel roads, through vineyards, ending at a local Tuscan farm for lunch, and of course, a wine tasting
• Dinner at Taverna Squarcialupi in Castellina in Chianti
• Buonasera Darlings!
• Buongiorno! In Villa Breakfast
• Truffle Hunting Excursion: A guided tour of the Tuscan countryside with a truffle hunter and his dog. We will learn the secrets of truffles, the environment they prefer, how they grow, and how truffle dogs are trained. Our hunt will end with a truffle inspired lunch at a local organic farm, and of course, a wine tasting. We will also get the chance to taste extra virgin olive oils as well.
•Pizza Making at the Villa with Francesco Barone
• Buonasera Darlings!
• Buongiorno! In Villa Breakfast
•Tuscan Wine Safari: We will explore the Tuscan hills via vintage Land Rovers with expert drivers and guides, taste vintage reserves from private producers, tour historic castles and discover some of the most celebrated red wines in the world.
• Dinner at Antico Ristorante Pestello
• Buonasera Darlings!
• Buongiorno! In Villa Breakfast
•Yoga poolside, weather permitting
• Massage: Darlings may choose to add on a 60 or 90 minute massage, or they may opt out from massage and choose to explore the grounds, rest and relax
• Cooking Class + Dinner at Home: Hands on cooking class at the Villa with our Cuvée Chef. We will explore Tuscan specialties and prepare our dinner together.
• Buonasera Darlings!
• Buongiorno! In Villa Breakfast
• Cheese Farm Tour: We will learn about the production of sheep’s milk cheese from the field to the table. We will also try the farm’s own Chianti Classico and enjoy lunch together.
• Party at the Villa! We will celebrate our week together with cocktails, live music, and a special dinner prepared by our Cuvée Chef.
• Buonasera Darlings!
• Buongiorno! In Villa Breakfast
• Depart for Aeroporto di Firenze-Peretola
• Caio Darlings!

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Travel Logistics + Trip Insurance

ARRIVAL

Aeroporto di Firenze-Peretola / FLR

Please plan to arrive in Florence by 2pm, Sunday, October 12, 2025. 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

You will be met at the Aeroporto di Firenze-Peretola in Florence at 2:30pm CEST on Sunday, October 12, 2025 by a private transportation service with two vans to ensure your comfort and ample room for your luggage. 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, arriving at our villa to a warm welcome and aperitivo, a true Italian ritual. Cin Cin Darlings!

DEPARTURE

We will travel back to Florence from our villa the morning of October 18th, with our arrival at the airport planned for 12:30pm. We will make a second stop at the Firenze Santa Maria Novella train station, the main railway station in Florence by 1:30pm, for those of you staying in Florence or traveling by train elsewhere. If you book return flights on the 18th, we recommend a flight time of no earlier than 3pm out of the Florence airport, later if you are flying out of Rome. Depending on your flight / train options, an overnight in either Florence or Rome may be necessary.

TRIP INSURANCE

Due to the unpredictability of current global events, I require that you purchase flight insurance through the airline when you book your flights AND trip insurance to cover you and your retreat investment while you're Detouring with me. Insurance is not offered through Dare to Detour. I recommend Faye travel insurance. Faye offers a variety of insurance packages for you to choose from, and supports you while you're traveling through their mobile app which is super easy to navigate. I ask that you 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 Faye website to learn more: https://www.withfaye.com

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Is a Detour for Me?

Dare is for you if…

You want to travel with like-minded women.
You are curious about solo travel, and want to try it out within the safety of a curated experience.
You want to travel with your besties, or your mom and sister, and meaningfully connect through a shared experience together.
You want to try something new, like summiting a mountain peak or riding a horse for the first time, or traveling abroad on your own.
You're looking to escape the noise of your day-to-day and find ways to be quiet in nature and reconnect with your core values and inner self.
You've been planning all the logistics for every aspect of your family's travel and extra curricular, and want to treat yourself to a trip where everything is planned and managed for YOU!

Dare is NOT for you if…

You are currently in deep crisis - our Detours are not for those in need of professional help as we do NOT have a licensed clinician on staff.
You don't feel comfortable offering your heart-forward, non-judgmental support to others from a wide range of life experiences and identities.
You can't hold safe emotional space for those around you, or refrain from offering unsolicited advice.

Two Ways to Pay

Pay in Full

You have the option to pay in full at one time. This includes a $925 NON REFUNDABLE Deposit.

6 Month Payment Plan

Choose to pay over time with a 3% simple interest on the total amount. This includes a $925 NON REFUNDABLE Deposit.

I'm Ready

Frequently Asked Questions

All-inclusive for ALL Detours means that everything except airfare is covered, from the moment I pick you up at the airport, to when I drop you back off at the airport. My intention is to enable you to plan for your Detour and know that once you arrive everything is handled. Any shopping you may do or service add-on's like a massage or a 1:1 session with myself or one of my experts are your responsibility however, and are things I work to outline before you arrive so you are well aware.
Detours are NOT yoga retreats. Nothing against yoga, but Detours are different. They are curated experiences designed to push you just outside your comfort zone to the place where you feel most vibrant and alive. Hopefully, they offer opportunities for you to try things for the first time, supported by a group of like-minded women. And they are intended to provide time for you to reorient yourself back to what matters most to you.
My intention behind every Detour is to enable you to arrive knowing that all the logistics and small details have been planned for in advance, and that your safety and comfort given great consideration. This Detour is curated to offer comfortable accommodations and the space for you to truly relax and let your guard down. And most importantly, Detours are fun, with opportunities to play and connect and simply be.
For each Detour, you have the option to pay in full at one time, or to pay over a period of 6 months through a payment plan. If you choose to pay over time, you will incur 3% simple interest on the total amount. Payment plans must be completed one month prior to the start of each Detour. Both payment in full and payment plans include a $925 non-refundable deposit. If you need to cancel your Detour, you must do so 30 days in advance to receive your investment minus the non-refundable deposit. Any cancelation within 30 days of departure, means that you will forfeit the entire amount of your trip investment.
We do our best to manage all food intolerances and allergies. Each Darling completes a Detour Intake Form, and has the opportunity to outline her dietary needs, which we then share with each Detour location. Should we dine out in a restaurant, it is the Darling's responsibility to inform the service staff of her dietary restrictions.
Yes, this experience is single occupancy. You will have your own private suite with a cozy lounge area, ensuite bathroom and views of the Tuscan countryside.