Villas, vibes, and unforgettable connections
Our Vision
At Diamond Hippie Tours, we’re redefining what it means to travel. Our experiences are curated for those who crave something extraordinary—a chance to explore destinations in a way the mainstream will never know. Imagine discovering offbeat villas, castles, and boutique retreats that exude character and charm. Picture yourself in a community of like-minded adventurers who value creativity, connection, and authentic moments. We strip away the predictable and replace it with journeys that inspire, delight, and surprise you at every turn.
Our tours are designed for the tasteful hedonist, the adventurous professional, and the seeker who refuses to settle for generic. We take care of every detail— unique accommodations, curated itineraries, and unforgettable dining—so you can relax, explore, and connect.
You won’t just visit a destination; you’ll become part of its story. You’ll go beyond the surface, diving into the soul of a destination and experiencing it in a way that feels deeply personal, meaningful, and vibrant.
Why You Should Go
Exclusive Experiences:
Forget crowded museums, basic hotel bars, and cookie-cutter itineraries. Whether it’s truffle hunting, dining with emerging chefs, or creating your own sandals, every activity is a chance to explore the unknown, unlock your creativity and form authentic connections with people who share your vibe.
Unique Accommodations:
Stay in off-the-beaten-path villas, chalets and castles that are as unique as they are welcoming, with all the amenities you need to feel completely at home.
Curated Connections:
Travel with an invite-only group of creative, open-minded individuals who value connection, community, and festivities as much as you do.
Stress-Free Adventure:
Leave the planning to us; accommodations, transportation, meals, and activities - all you need to do is show up and let the magic unfold.
Tuscany September 2025: Our inaugural Five-Day Journey of Experience and Creativity
Nestled near Monte San Savino, an hours drive from Florence, Grandi di Toscana will be your agriturismo retreat. This historically restored operating winery offers panoramic views, quirky interiors, and amenities like a sparkling pool and lush gardens. Each room combines traditional Tuscan charm with modern conveniences, creating a warm and inviting space to relax after a day of adventure. Whether sipping wine on the terrace or wandering through the vineyards, the villa feels like your own private sanctuary in the heart of Tuscany.
This is not just a place to stay—it’s the foundation for an unforgettable week of creativity, exploration, and connection. The villa provides the perfect backdrop for intimate gatherings, workshops, and dinners that celebrate the best of Tuscany.
Grandi di
Toscana
Itinerary
Saturday Sept 20th - Thursday Sept 25th, 2025
Saturday: Arrival & Connections
As you arrive at the villa, you’ll be greeted by breathtaking views and a warm welcome. Explore the grounds, unwind by the pool, and settle into your accommodations. In the evening, join us for a wine tasting hosted by San Ferdinando Vini, founded by the Grifoni family in 1850. Sip on organic vintages while enjoying a spread of antipasti and apericena, featuring Tuscan cheeses, cured meats, and seasonal vegetables prepared with flair. It’s the perfect way to break the ice and start forming connections with your fellow travellers.
Sunday: Creation & Natural Connection
Kick off your first full day with a creative workshop where you’ll embellish your own sunglasses. This isn’t just a craft session—it’s a chance to let your personality shine. From bold and playful to sleek and minimalist, your one-of-a-kind shades will be a conversation starter long after the trip. Afterwards, head to the Chianti hills for a wine tasting and truffle hunting adventure. Led by expert guides and their trained dogs, you’ll roam the forests in search of these culinary treasures. The experience is as much about the journey as it is about the reward, with breathtaking views and plenty of local lore along the way. In the evening, we’ll gather at a charming local restaurant to indulge in a truffle feast. With our freshly unearthed finds, you’ll savor a lineup of regional dishes infused with the prized ingredient, from simple, rustic plates to refined culinary creations.
Monday: Art & Exploration in Florence
Start your day with another hands-on workshop, this time crafting a chic water bottle holder. Perfect for turning any San Pellegrino bottle into a reusable accessory, it’s both practical and stylish. Later, we’ll head to Florence for a magical walking tour led by a mentalist. This isn’t your average city stroll—it’s an immersive journey through Florence’s secrets, blending historical insights with mind-bending performances. Afterwards, let Camille the Creatrix, our local expert, show you her favourite underground artistic haunts. Or feel free to explore the city’s boutiques, art galleries, or cafes on your own before dinner (location TBD). Here, chefs prepare your meal in an open kitchen, transforming cooking into a theatrical experience. The food is communal, the atmosphere lively, and the flavors unforgettable.
Breakfast
Ideas
Breakfast
Ideas
Tuesday: Magic & Celebration
Dive into the mystical with a morning of manifestation workshops, exploring tarot, alchemy, and the power of intention. In the afternoon, step into a world of wonder at our Magic and Miracles Day Party, inspired by the glamour and vibrancy of "Baz Luhrmann" and the ethereal vibes of “All Day I Dream.” Picture soulful beats, colourful decor, and captivating performances that transport you to another realm. For dinner, join our Chef for a Pizza and Pasta Party, where you’ll craft your own gourmet creations and savor freshly made dishes bursting with flavor.
Wednesday: Relaxation and Culinary Discovery
The morning begins with a workshop on crafting Huarache sandals, the original barefoot shoe. Perfect for grounding yourself in nature, these minimalist sandals are both comfortable and stylish. Afterward, we’ll head to Piscine Termali Theia in Chianciano Terme, where you’ll immerse yourself in over 900 square meters of indoor and outdoor thermal pools, fed by the ancient Sillene spring. With water jets, whirlpools, and a wellness center offering saunas and Turkish baths, it’s the ultimate relaxation experience. In the evening, we’ll dine at Zenzero Restaurant in Lucignano, where Chef Fabrizio Peruzzi blends traditional Italian flavors with contemporary techniques, crafting dishes that are both innovative and rooted in local tradition. It’s a delightful way to conclude a day of creativity and rejuvenation.
Thursday: Departure
Enjoy a leisurely breakfast with new friends and take a moment to reflect on the memories you’ve made. As you say goodbye, you’ll leave with a full heart, unique creations, and the inspiration to seek out more magic in your everyday life.
INCLUSIVE PRICING: €1750 per person
Price based on Double Occupancy. Price includes accommodations, daily breakfast and dinner, wine & beer (at villa), all experiences, and all internal transportation. Departure and Arrival from Florence. (Flight not included)
Your Hosts
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Interested in Attending?
We've only have 30 spots available. To save your spot, we'll need a refundable deposit of €250 (CAD$375). Just click below to grab yours! More questions?, feel free to reach out at jason@diamondhippietours.com—we’re here to help!
1 / Are there vegan and vegetarian options to choose from?
Yes, we offer vegan and vegetarian options. However, we cannot ensure that there be any cross-contamination, as the vegetables will be cooked using the same utensils as other items.
2 / What are the accommodations like? How are they structured?
Grand di Toscana is an operating winery, and consists of 10 individual AirBnB style rowhouse apartments that create a charming village atmosphere. Most of these apartments feature 2 bedrooms, offering options for a queen bed or 2 twin beds in each room. Most apartments include a kitchenette and a seating area, and all are equipped with heating and air conditioning.
3 / How are rooms assigned? Can I choose who to room with?
Absolutely! Once you pay a deposit, we'll add everyone to a WhatsApp group. Attendees can select their housemates and we will match you to the appropriate room. If you don't know anyone, no worries—everyone attending is friendly, and we'll help connect you with someone we think you'll click with
4 / How many people will be travelling with me?
We anticipate having 30 participants for this trip.
5 / How do I know who else is attending?
Once the deposit is paid, we will add everyone to a WhatsApp group to help you get to know each other better. This will also serve a platform to coordinate the trip moving forward.
6 / Can I invite my friends?
This trip is exclusive to invitees, but we do accept referrals, which will undergo a vetting process. Kindly email the name, contact information, and your reasons for believing they would contribute positively to the vibe to jason@diamondhippietours.com.
7 / How many parties are there?
We are organizing two party events: a daytime gathering at the villa and an opening celebration. Our goal is to ensure you get your party fix, while still getting enough rest to feel refreshed the next day.
8 / Are there DJs going to be playing? What is the music experience?
A local DJ will be performing at the day party. We are also planning to offer additional entertainment, which will not be DJ-focused. A sound-system will be available throughout the trip, so we encourage those who are DJs to showcase their talents!
9 / What if I don't want to do an experience?
Enjoy your vacation your way! There's no pressure to do anything. Sleep in, relax by the pool, or embark on your own adventure. This is all about you—no need for group consensus!
10 / Is there any way to contribute to the event?
Absolutely! As burners understand, it's the individuals and their contributions to the community that create a memorable experience. If you have something to share, whether leading a yoga class or teaching about a specific topic, we'd love to hear from you!
11 / What is the deposit and cancellation policy?
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€250 fully refundable deposit to secure your space
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€750 non-refundable payment due 90 days before the trip.
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The remaining €750 non-refundable payment is due 30 days before the trip.
12 / Are pet allowed?
Small pets are welcome at the villa for an fee of €10 per day. Please be aware that pets may not be permitted at the experiences and will need to remain at the villa.