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Re-Written, The Retreat with Aisha Beau
Dates
Apr 21–27, 2026
Group Size
10–23 Travelers
Duration
7 days, 6 nights
Activity Level
Adventure
About This Trip
Travelers
Meet Your Host
View Full ProfileAisha Beau
Aisha Beau is an influential host, wellness advocate, public speaker whose digital platform and mission is to empower individuals to embrace their unique beauty and live a life rooted in authenticity, style, and wellness.
Trip Activities
Free Time in San Gimignano
Creamery Visit and Pecorino Cheese Tasting
Montepulciano Visit
Olive Oil Mill Visit and Tasting
Radda Visit
Chianti Winery Visit
Free time in Siena
Tuscan Cooking Class and Dinner
Included in Your Trip
Double occupancy in 4-star hotels (limited single rooms available)
Local guide throughout trip
All city transfers
Not Included
Flights (except as noted)
Food and Alcohol (except as noted)
Visas and Travel Insurance
Airport Transfers
Tips & Gratuity
What's included by Your Host
Signature Workshop with Aisha Beau 10:00 AM (1.5 hours)
Live Podcast Taping: Meanwhile, She - 10:00 AM (2 hours)
Itinerary
*All durations are approximate
Welcome to Italy!
dinner
Welcome dinner at the hotel is included. Your meal will typically be a 3-course set menu which includes a first course, second course, dessert, and one non-alcoholic drink, subject to change. *Vegetarian and gluten free options are available; Vegan options unavailable.
Grand Hotel Adriatico (or similar)
Overnight in Florence
Florence City Sights & Hilltop Towns
breakfast
Breakfast at the hotel is included. Hotel breakfasts typically offer continental or buffet-style options. The specific breakfast menu will be determined by your confirmed hotel.
Transfer to San Gimignano
Take a private transfer to San Gimignano. Stops for bathrooms/snacks will be made along the way as needed.
Free Time in San Gimignano
Your first stop in Tuscany is San Gimignano, a charming medieval hilltop town in the province of Siena, often referred to as the "Town of Fine Towers." Renowned for its stunning preservation, the town is home to around a dozen towers that rise gracefully against the backdrop of the Tuscan countryside, creating a remarkable medieval skyline that is truly unique. Encircled by well-preserved walls, San Gimignano offers a rare glimpse into the past, where both Romanesque and Gothic architectural styles are beautifully represented in its buildings. Here you’re free to explore this Tuscan hill town on your own with your guide making recommendations of landmarks to visit along the way. Wander through the town's historic streets and you'll encounter not only impressive secular structures but also magnificent churches. The Palazzo Comunale, the Collegiate Church, and the Church of Sant'Agostino house breathtaking frescoes, including remarkable cycles from the 14th and 15th centuries. These works of art, combined with the town's rich history and its timeless architecture, make San Gimignano a living testament to medieval Italy at its finest.
Transfer to the Hotel
Take a private transfer to your hotel. Stops for bathrooms/snacks will be made along the way as needed.
dinner
Dinner at the hotel is included. Your meal will typically be a 3-course set menu with a glass of wine or water, subject to change. *Vegetarian and gluten free options are available; Vegan options unavailable.
Borgo San Luigi (or similar)
Overnight in Tuscany
Experience the Tuscan Countryside
breakfast
Breakfast at the hotel is included. Hotel breakfasts typically offer continental or buffet-style options. The specific breakfast menu will be determined by your confirmed hotel.
Transfer to typical Creamery
Take a private transfer to Tuscan Creamery. Stops for bathrooms/snacks will be made along the way as needed.
Creamery Visit and Pecorino Cheese Tasting
On a trip to Tuscany, culinary delights are not to be missed as the region abounds in amazing products, including pecorino cheese. From your hotel, you’ll take a transfer to the Val d'Orcia, to a local creamery to learn more about pecorino cheese. The origins of Tuscan pecorino go back to Etruscan times. Pecorino toscano DOP (Protected Designation of Origin) is made from two different types of whole sheep's milk, to which calf rennet is added. The mass is boiled until curdled into flakes the size of corn kernels of semi-solid to soft textures. It is then pressed and salted before the maturing phase begins which varies according to the type of cheese required. During your visit at a local creamery, you’ll learn more about all that goes into making authentic Pecorino cheese. Then, you’ll have the opportunity to taste at least three types of cheeses.
Montepulciano Visit
After a 15 minute transfer to Montepulciano, you’re free to explore this Tuscan hill town on your own with your guide making recommendations of landmarks to visit along the way. Reach the highest point of the town, in the middle of Piazza Grande, to soak up a 360-degree architectural panorama. On the west side of the square, the Palazzo Comunale was built in the late 1300s then revamped in 1424 by one of the Medici’s favourite architects, Michelozzo, in homage to Florence’s Palazzo Vecchio. Just outside the town gates, a stiff downhill walk from Piazza Grande, is Sangallo the Elder’s masterpiece, and one of the most photographed churches in Tuscany. Fronted entirely in travertine, San Biagio is designed on a perfect Greek cross pattern, and dedicated to St. Blaise, an Armenian doctor martyred in the 4th century. After exploring, you’ll have time at leisure for dinner before being transferred to your accommodation.
Transfer to the Hotel
In the evening, meet your driver and bus and return to your accommodation.
Signature Workshop with Aisha Beau 10:00 AM (1.5 hours)
Step into a guided experience designed to spark reflection, clarity, and connection. In this intimate workshop, Aisha will lead you through powerful exercises that blend journaling, conversation, and personal storytelling—all curated to help you realign with your truest self. Expect a space that is both expansive and grounding, where breakthroughs happen alongside laughter and community.
Borgo San Luigi (or similar)
Overnight in Tuscany
Chianti Wines, Olive Oil & Castles
breakfast
Breakfast at the hotel is included. Hotel breakfasts typically offer continental or buffet-style options. The specific breakfast menu will be determined by your confirmed hotel.
Olive Oil Mill Visit and Tasting
Transfer 30 minutes and step into the heart of Tuscany’s olive-growing tradition with a visit to an authentic olive oil mill. Nestled amidst rolling hills blanketed with ancient olive groves, this experience offers a glimpse into the time-honored craftsmanship that has made Tuscany a beacon of quality in the olive oil world. Your visit begins with a tour of the mill, where expert producers guide you through the fascinating process of turning freshly harvested olives into liquid gold. Learn about traditional and modern pressing techniques, the importance of selecting the finest olives, and the care that goes into every step to ensure a superior product. The highlight of your visit is a guided tasting of three types of olive oil, where you’ll discover the nuances of extra virgin olive oil. Savor its rich, fruity flavors and peppery finish, and learn how to distinguish its quality and pair it perfectly with food.
Radda Visit
After your visit to the Olive Oil Mill, enjoy a scenic 20 minute transfer to Radda, a hilltop village nestled in the Chianti hills. With its ivy-draped walls and winding cobblestone lanes, Radda exudes timeless Tuscan charm. Join your guide for a stroll through the town’s stone archways and historic streets, then enjoy free time to wander at your own pace and choose a local spot for lunch. Don’t miss the opportunity to sample Chianti Classico—bold and full of character—paired with regional cheeses and cured meats. Intimate in scale and rich in atmosphere, Radda offers a tranquil window into the heart of Tuscany’s wine country.
Chianti Winery Visit
After lunch and your visit to Radda, you’ll transfer 30 minutes to a local winery to learn more about the iconic Chianti Classico wine. One of the most known wines of the world with its unmistakable logo of the Black Rooster, it shines as an authentic taste of Tuscan wine. At a local winery, you’ll explore the vineyards that produce some of the best wines in the world using a blend of a variety of grapes including the Sangiovese, Canaiolo varietals. During your visit you will learn the different characteristics of the wines from this region, and learn to distinguish the acidity, the taste, and flavor. Your visit will include a tasting of at least 3 different wines.
dinner
Dinner at the hotel is included. Your meal will typically be a 3-course set menu with a glass of wine or water, subject to change. *Vegetarian and gluten free options are available; Vegan options unavailable.
Borgo San Luigi (or similar)
Overnight in Tuscany
Siena Tour & Free Time
breakfast
Breakfast at the hotel is included. Hotel breakfasts typically offer continental or buffet-style options. The specific breakfast menu will be determined by your confirmed hotel.
Free time in Siena
From your hotel, you’ll take a 30 minute transfer to Siena where you will have free time to explore this amazing twon at your leisure. Explore the city's historic neighborhoods and the iconic Piazza del Campo, home to the legendary Palio horse race, a tradition dating back to 1656. Not to be missed a visit to the stunning Duomo. Have dinner on your own in Siena before returning to your accommodation. After dinner, you’ll take a 30 minute transfer back to your hotel.
Live Podcast Taping: Meanwhile, She - 10:00 AM (2 hours)
For the first time, join Aisha Beau for a live recording of her soon-to-relaunch podcast, Meanwhile, She (formerly Re-Written: The Aisha Beau Podcast)—an intimate, stylish, and thought-provoking space where ambition, identity, and everyday life intersect. Set against the breathtaking backdrop of our Tuscan retreat grounds, this special episode will be interactive, blending candid conversation, cultural reflection, and moments of laughter with the voices and energy of our retreat community. Here, you’ll witness the podcast come to life—raw, real, and rooted in connection. Just as Meanwhile, She invites women everywhere to explore who they are and who they’re becoming, this live taping will allow you to be part of the story itself.
Borgo San Luigi (or similar)
Overnight in Tuscany
Florence Artisans & Farewell Feast
breakfast
Breakfast at the hotel is included. Hotel breakfasts typically offer continental or buffet-style options. The specific breakfast menu will be determined by your confirmed hotel.
Transfer to Florence
Take a private transfer to your hotel in Florence. Stops for bathrooms/snacks will be made along the way as needed.
Tuscan Cooking Class and Dinner
In the evening you will attend an amazing Tuscan Cooking Class. Departing on foot from your hotel, you’ll enjoy a 20 minute leisurely walk to the Cooking School. Your private chef will be glad to share the secrets of Florentine cuisine with you. During the class you will learn how to select the highest quality ingredients and taste local foods. Create your own three course meal (starters, home made fresh pasta and a main course) under the expert supervision of the Chef. The cooking class will end with a delicious dinner.
dinner
Dinner is included as part of the cooking class. Your meal will be a 3-course meal with a starter, home made fresh pasta and a main course with water and a glass of Tuscan wine included. *Vegetarian and gluten free options are available; Vegan options unavailable.
Grand Hotel Adriatico (or similar)
Overnight in Florence
Arrivederci, Italy!
breakfast
Breakfast at the hotel is included. Hotel breakfasts typically offer continental or buffet-style options. The specific breakfast menu will be determined by your confirmed hotel.
Physical Activity Level:Adventure
These trips are great if you want to get moving. These itineraries may include scenic hikes and/or exercise. A moderate level of fitness is required to enjoy these trips.
Cancellation Policy
We get it—life happens. Here's how cancellations work depending on where you're at in the process:
Spot Pending
Spot Confirmed With 91 or More Days Before Your Trip
Spot Confirmed With 90 or Fewer Days Before Your Trip
HIGHLY RECOMMENDED: Protect Your Adventure-Invest in Peace of Mind
After booking, you'll receive a personalized recommendation for coverage tailored to your trip. For full details on our cancellation policy, please refer to our Terms & Conditions.
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FAQ
Traveling with TrovaTrip
What's it like to travel on a Trova Trip?
Trova Trips are curated group travel experiences designed to help you see the world, meet new people, and connect over shared interests. Each trip is hosted by a community leader you know and trust, and run by professional local Operators who handle the logistics. Expect meaningful experiences, authentic activities, and a like-minded group to share it all with.
What's the difference between the Host, the Operator, and Trova?
Great question! Each plays a key role in bringing your trip to life:
- The Host is your community leader—the person who brings the group together, sets the vibe, and curates the overall experience. They may lead a workshop or activity during the trip, but their main focus is connection and community, not logistics.
- The Operator is the certified, independent company that runs the trip on the ground. They handle the logistics like accommodations, transportation, Guides, activities, and safety. Every Operator we partner with is licensed, insured, and vetted to ensure a high-quality travel experience.
- TrovaTrip is the platform that powers it all. We connect Hosts with trusted Operators, provide the tools to design and manage trips, and support Travelers before and during their journey to ensure everything runs smoothly.
In short: The Host shapes the experience and brings the vibe, the Operator runs the trip, and we make it all happen. Read more about who does what here.
I'm nervous to book. How can I feel more confident?
First, let us say—it's totally understandable, and you're not alone! Travel can feel intimidating, but we built Trova to take the guesswork out of group travel and earn your trust every step of the way:
- Every trip is run by licensed Tour Operators with vetted local Guides.
- Hosts are there to foster connection, meaning you'll arrive solo but never feel alone.
- Itineraries are clearly outlined so you know what to expect, including activity level, example accommodations, and what's included.
- Our team is available to support you pre-departure, and Operators—plus your local Guide—are on the ground to assist during the trip. And rest assured, all our Operating partners are trained in crisis management.
- We always recommend travel insurance for extra peace of mind, whether you're traveling with Trova or solo. It can cover medical issues, lost luggage, or even cancellations.
We know it takes trust to book a trip with new people, and we're here to make sure you feel ready, supported, and excited!”
Can I book solo?
Absolutely! As of 2025, almost 84% of TrovaTrip Travelers go solo. (And yes, we may be a little biased, but we think group travel is one of the best ways to meet new people!) You'll have your own bed and the option to book a private room on most trips. Plus you'll be traveling with others who are just as excited to explore and connect.
What if I need to cancel?
We understand that life happens. Our cancellation policy is designed to provide flexibility while balancing the logistics of group travel:
- Spot pending – 100% refundable. Not confirmed yet? No worries. You can cancel at any time for a full refund.
- Spot confirmed with 91 or more days before your trip – Partially refundable + credit towards a future trip. You'll receive a future trip credit for the amount of your down payment (minus a $100 cancellation fee per Traveler). This trip credit is valid for one year from the date it is issued. Additionally, any payments made beyond the original 25% down payment will be refunded to your original form of payment.
- Spot confirmed with 90 days or fewer before your trip – Non-refundable. At this point, all payments are non-refundable because your experience is already in motion behind the scenes. By this time, our operating partners will be working with local businesses to secure your accommodations and finalize your activities.
HIGHLY RECOMMENDED: Protect Your Adventure–Invest in Peace of Mind
We strongly encourage purchasing travel insurance with trip cancellation coverage to safeguard your investment. With travel insurance, you're covered in case of unexpected events–from illness to emergencies–that could affect your plans. Life is unpredictable, but your dream trip doesn't have to be.
After booking, you'll receive a personalized recommendation for coverage tailored to your trip. For full details on our cancellation policy, please refer to our Terms & Conditions.
What's included in the trip cost?
Most trips include accommodations, daily activities, ground transportation, some meals, and a dedicated local Guide. Because Travelers are coming from all around the world, flights to and from your destination are not included. Each trip page breaks it all down for you.
Will I have free time?
Yes! While we pack in incredible experiences, most itineraries include built-in free time so you can relax, wander, or check out personal must-sees.
What do the activity levels mean?
Every trip has a physical Activity Level from 1 to 5 so you can find the right fit for your travel style:
- Level 1 – Relax + Unwind: Minimal movement (spa days, beach lounging, local markets)
- Level 2 – Low-Key Movement: Light, easy-paced activity (snorkeling, boat tours, gentle hikes)
- Level 3 – Moderate Activity: Ready to move (multi-day hikes, skiing, camping)
- Level 4 – Get Your Heart Rate Up: More intense movement (long hikes, biking, active days)
- Level 5 – Extreme Adventure: High-adrenaline travel (challenging hikes, dives, technical climbs – experience may be required)
You'll find the Activity Level clearly listed on each trip page, and a more in-depth explanation of each level here.
Who can I contact with more questions?
Our support team is here to help! Visit trovatrip.com/company/contact-us to reach out. You can expect to hear back within 2 business days, but probably sooner—our Trova elves are pretty speedy!
Accommodations
What does "or similar" mean next to the accommodations?
When we say “or similar,” it means the hotel listed is an example of what you can expect—not always the exact spot you'll be staying. Sometimes Operators adjust accommodations due to seasonal availability or group size. But rest assured: the quality and comfort will match what's shown.
Why would the accommodations change from time of booking?
Flexibility allows Operators to choose the best-fit accommodations closer to your trip—based on availability, logistics, and what works best for the group (like the number of Travelers and room configurations). This ensures a smooth experience without sacrificing comfort or quality.
Finalized hotel info is typically shared about 30 days before departure in your Traveler Portal, along with your final itinerary.
Trip Operations & Compliance
Who actually runs my trip, and how does Trova keep things safe?
Your trip is operated by licensed, certified Tour Operators who manage all trip logistics and safety—from accommodations and local Guides and day-to-day logistics. All trips comply with local legal and regulatory standards. We vet each Operating partner carefully so you can travel with confidence.
Who do I talk to if I have questions about safety or compliance?
If you have any questions about safety protocols or trip compliance, reach out to us at safety@trovatrip.com. We're here to help.
General Travel Questions
Do I need any documentation to travel?
It depends on where you're headed. Though it is not a universal requirement, many countries require that your passport be valid for at least six months beyond your arrival date. This ensures Travelers have sufficient time to return home even if their visas are extended or if unexpected circumstances arise.
Some destinations may also require a visa. Check our visa page to consult your country's travel resources.
Do I need any vaccines?
It's always best to check with your healthcare provider or a travel doctor before your trip. You can also visit the CDC website (or your local government's travel health resource) for destination-specific vaccine guidance. Health and safety first!
Are flights included in the trip cost?
Because our Hosts and Travelers are coming from all around the world, flights to and from your destination are not included. Some trips include internal flights (like a short domestic hop), and those details will always be listed on the trip page if applicable.
Can you accommodate my dietary needs?
We’ll do our very best! Our Operators aim to accommodate dietary restrictions, though availability varies by destination. For example, some places offer plenty of vegan and vegetarian choices, while others might be quite limited. The earlier you let us know—through your trip form or by contacting our support team—the better we can prepare. Once you arrive, be sure to remind your local Guide about any allergies or restrictions so they can help you enjoy your meals safely and comfortably.