Tour Dates and Location
This exclusive tour is limited to 25 couples
Monastero D'Ombrone, 19, 53019 Castelnuovo Berardenga SI, Italy
Castel Monastero
August 3 - 9, 2026
Accommodations and
On-site Dining
Castel Monastero began life as an eleventh-century village. It became a monastery, complete with an incredible Chianti cellar. Now, roughly a thousand years later, it still sits majestically on a hill. A high-end luxury hotel, placed close to Siena and situated peacefully in the countryside. Absolutely worth a visit.
As you’d expect, given such a pedigree, there are vaulted ceilings, rough-hewn stone walls, broad beams, and vineyard views. Rooms are scattered among various buildings a short walk from the main one, heightening the sense of seclusion (the super-thick walls and private courtyard help too). Tours by bike, hike, horse, or car into neighboring countryside can be arranged, or you might prefer to hang out by one of the indoor or outdoor pools. The hotel also offers mushroom foraging, truffle hunting and cooking classes.
And while life here was tranquil enough during the property’s years as a monastery, a more accessible form of relaxation is offered by the dazzling and modern Spa Monasterii.
Room amenities included in room stay
- Flat screen TV
- WIFI
- Tea
- Please note, the hotel does not provide an iron or a steamer.
Hotel amenities
- Spa Monasterii
- 3 Pools
- Yoga pad
- Tennis court
- Fitness Center
Check-in: 3:00pm
Checkout: 11:00am
Two restaurants serve Castel Monastero’s guests: the fine-dining Michelin star, Contrada, is open for breakfast and dinner. The more casual Cantina, set in the old medieval wine cellar and offers seasonal Tuscan flavors for lunch and dinner. The lobby bar offers light fare for a quick snack.
Monastero D'Ombrone, 19, 53019 Castelnuovo Berardenga SI, Italy
+39 0577 570570
Castel Monastero
Wineries
We will visit a variety of beautiful Tuscan wineries. Below is additional information.
Surrounding Area
- The Tuscan countryside is a captivating landscape of rolling hills, golden fields, and cypress-lined roads that stretch into the horizon. Dotted with medieval hilltop villages, rustic farmhouses, and ancient olive groves, the region exudes a timeless charm. Vineyards stripe the hillsides, producing world-renowned wines like Chianti and Brunello, while sunflower fields bloom under the warm Mediterranean sun. The air carries the scent of wild herbs and the soft hum of nature, creating a peaceful and romantic atmosphere that feels both idyllic and authentic.
- Each season in Tuscany brings its own palette and rhythm, from the vibrant greens of spring to the rich, earthy tones of autumn during harvest. Local markets overflow with fresh produce, truffles, and handmade cheeses, reflecting the deep connection between the land and its people. As the sun sets, casting a golden glow over the terracotta rooftops, the countryside seems to slow down in reverence, inviting visitors to savor the beauty, history, and simple pleasures that define life in Tuscany.
Optional Hosted Activities
Man does not live by wine alone. Or so I’ve been told. During your tour you’ll have your choice of a hosted activity. You’ll be able to select from the following activities:
Full Day Trip to Florence, Italy:
A Journey Through Art, Architecture, and Culture
- Begin your unforgettable day in Florence with a morning visit to the Basilica of Santa Croce, one of the most iconic churches in the city. Admire its stunning neo-Gothic façade and step inside to explore the tombs of legendary Italians such as Michelangelo, Galileo, and Machiavelli. The peaceful cloisters and frescoes by Giotto offer a quiet glimpse into Florence’s religious and artistic heritage.
- Next, make your way to the Basilica of Santa Maria Novella, located near the main train station. This Dominican church is renowned for its exquisite Renaissance architecture and masterpieces like Masaccio’s Holy Trinity and frescoes by Ghirlandaio. The green-and-white marble façade and the peaceful cloister garden are perfect for photos and quiet reflection.
Continue your artistic journey with a guided visit to the Galleria dell’Accademia, home of Michelangelo’s David. Stand in awe of this iconic sculpture, then explore other highlights including Michelangelo’s unfinished Prisoners and a fine collection of Renaissance paintings. - After soaking in Florence’s cultural treasures, enjoy a well-earned lunch at a local restaurant.
Truffle Hunting:
Immerse yourself in an enchanting truffle-hunting adventure at Castel Monastero, a stunning 11th‑century estate nestled in Tuscany’s Chianti countryside. Here’s what to expect on this extraordinary outing:
- 🌲 Meet the Experts & Canine Team
Your morning begins in the cool, fragrant woodlands surrounding Castel Monastero. You’ll be greeted by a seasoned truffle hunter and his highly trained Lagotto Romagnolo (truffle dogs), masters at sniffing out the elusive treasures hidden beneath the forest floor. - 🍄 The Hunt (≈ 1½ hours)
Set off on a relaxed, guided walk through wooded trails, inhaling the earthy aromas of chestnut and oak. Watching the dogs work—keenly alert and weaving between the trees—adds to the thrill. Although there’s no guarantee of finding truffles, the experience offers a deep connection to Tuscany’s wild side. The excursion lasts approximately an hour and a half and the hunt will be led by an expert truffle hunter and his pack of dogs. - 🍽️ Truffle‑Infused Lunch in La Cantina
Right after the hunt, enjoy a sumptuous lunch at Castel Monastero’s La Cantina utilizing your room credit.
Spa Monasterii
- Breathe the deep sense of well-being; the attention to detail the spa team will create with a unique and unforgettable experience of harmony and relaxation.
- Enjoy a 50 minute massage to rejuvenate your senses and prepare you for what comes next on your journey.
Tour Itinerary
Day 1: – Monday, August 3, 2026:
- Airport transfers from Amerigo Vespucci Airport (FLR) to Castel Monastero
- Approximately 90 min. transfer
- 6:00pm Welcome Reception in Cantina Garden
- Airport transfers from Amerigo Vespucci Airport (FLR) to Castel Monastero
Day 2: – Tuesday, August 4, 2026
- Breakfast at leisure beginning at 7:00am at Contrada
- Winery tours and tasting at two wineries with lunch
- 6:00pm dine around at restaurants in Siena
Day 3: – Wednesday, August 5, 2026
- Breakfast at leisure beginning at 7:00am at Contrada
- Choice of hosted activities:
- Full day guided tour to Florence
- Truffle Hunting followed by truffle lunch
- Spa followed by lunch at Cantina utilizing hotel credit
- Dinner on own utilizing hotel credit
Day 4: – Thursday, August 6, 2026
- Breakfast at leisure beginning at 7:00am at Contrada
- Winery tours and tasting at two wineries with lunch
- 6:00pm dine around at restaurants in Siena
Day 5: – Friday, August 7, 2026
- Day at leisure
- Dinner on own utilizing hotel credit
Day 6: – Saturday, August 8, 2026
- Breakfast at leisure beginning at 7:00am at Contrada
- Group winery tour, tasting and lunch at the world famous Antinoi vineyard.
- Grand Gala at 6:00pm in Castel Monastero Courtyard
Day 7: – Sunday, August 9, 2026
- Breakfast at leisure beginning at 7:00am at Contrada
- Transfer to Amerigo Vespucci Airport (FLR) for trip home
Trip Inclusions
What is included in the tour?
- Roundtrip transfers to and from Amerigo Vespucci Airport (FLR) during program dates
- Six night accommodations at Castel Monastero
- Daily breakfast
- One hosted activity of your choice
- Lunch on winery tours
- Hotel credit to use for dinner on own
- Dine arounds with open bar in Siena, Italy
- Opening night reception with open bar
- Final night Grand Gala with open bar
What is NOT included in the tour?
- Roundtrip airfare
- Please book your travel to and from the Amerigo Vespucci Airport (FLR)
- Any activities and/or meals not specifically outlined
- Incidentals at Castel Monastero
- Room mini bar at Castel Monastero
- Room upgrades at Castel Monastero
- Transfer to Castel Monastero if not during program dates or if not from the Amerigo Vespucci Airport (FLR).
- Roundtrip airfare
Pricing
$13,497.00 per couple plus airfare to Florence, Italy.
$10,305.00 per single person plus airfare to Florence, Italy.
Price includes currency conversion from dollars to euros.
A $3,000.00 non – refundable deposit is required to hold a spot on this trip.
Space is limited
