Date:
May 31, 2026 @ 3:00 pm –
June 8, 2026 @ 10:00 am
Start Location:
Florence, Metropolitan City of Florence, Italy
Nearest Airport: Florence Airport, Peretola (FLR) in Italian called Aeroporto di Firenze-Peretola
End Location:
Florence, Metropolitan City of Florence, Italy
Florence Airport, Peretola (FLR) in Italian called Aeroporto di Firenze-Peretola
Duration:
9 days / 8 nights
Price:
$6,390 per person, double occupancy$7,660 per person, single occupancy, limited availability
A Connoisseur’s Exploration of Italian Wine, Food & Culture in the Heart of Tuscany
May 31- June 8, 2026
9 days/8 nights
Please Note: This tour is limited to a maximum of 16 guests.This Tour Is Sold Out- You Can Wait List by Clicking on the Link Below
A Connoisseur’s Exploration of Italian Wine, Food & Culture in the Green Heart of Italy
May 24 to May 31, 2026
8 days/7 nights
Feel free to Email or Call Us at 1-888-846-2337 with any questions,
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As always, we have arranged for private VIP tours and tastings, great local guides, daily breakfasts, some amazing dinners including a cooking class and dinner at our inn overlooking the vineyards of San Gimignano. There will be 6 dinners and 4 lunches, leaving you a few opportunities for you to explore the local culinary offerings on your own, as well.
This tour will be run on land, moving properties only once, so that we have time to experience both the energetic romantic riverside city of Florence, as well as living the dream in the gorgeous scenic countryside form our wine estate near San Gimignano.
Please Note: This tour will be limited to a maximum of 16 guests.
$6390 per person for Double Occupancy Rooms
Upgrades available to 1 or 2 bedroom apartments with living room, kitchen, etc.
Please call us to discuss options and availability.
$7660 per person for Single Occupancy Rooms.
Please call if interested in sharing an apartment with other guests.
Space is very limited and room assignments will be based on a first come first serve basis.
Wait list me for the 2026 Bella Tuscany Tour Today !
A Connoisseur’s Exploration of Italian Wine, Food & Culture in the Green Heart of Italy
May 24 to May 31, 2026
8 days/7 nights
Booking our Umbria and Tuscany trips as back-to-back tours is possible for a limited number of guests. We will provide seamless transportation between the venues, so you can enjoy a smooth and stress-free journey from one beautiful region of Italy to the next!
Please make sure to Read our Terms & Conditions for this trip and complete your Signature & Release Form upon registration. Please note- due to the high demand for our tours and the boutique properties we partner with, a non-refundable deposit per person, per tour, will be required upon booking. This ensures we can secure the best accommodations and experiences for you, as well as confirm your spot on the tours. Details can be found on the Terms and Conditions for the Italy tours.
Our tour itineraries are subject to change due to unforeseen circumstances such as inclement weather, transportation problems, or an unexpected business closure. We’re continually looking for ways to improve our tours and we sometimes come across a special new event, winery or sight since the itinerary was published that we’d like to share with you. Since our tours are planned far in advance, we may occasionally adjust the itinerary as necessary to provide you with the best trip possible! Since a minimum number of passengers are required in order to run each trip, we suggest you refrain from non-refundable air purchases until 2 months prior to your departure date or confirmation that the tour is a go.
Check into your home for the next few days—an eclectic, design-forward 4-star hotel that blends whimsical character with modern comfort, tucked right in the heart of the city. Every corner offers a little surprise, setting the tone for the adventures ahead.
We’ll gather in the hotel’s serene courtyard for a welcome toast—your first sip of la dolce vita under the Tuscan sky.
Later, a privately guided walking tour will lead us through Florence’s captivating streets, where centuries of art, history, and culture unfold around every corner. Along the way, we may just follow our appetites and explore the city through its flavors—more details to come, but trust us, your taste buds are in for a treat.
Dinner
Start your day with a leisurely breakfast at the hotel, then enjoy the morning and early afternoon at your own pace. Whether you’re in the mood to wander artisan-lined streets, explore a gallery, or sip espresso in a sun-dappled piazza, Florence invites you to follow your curiosity. Lunch is yours to discover—this city is full of culinary gems waiting to be stumbled upon.
In the afternoon, we’ll journey west to the charming walled city of Lucca, where a privately guided walking tour will introduce us to its graceful piazzas, quiet lanes, and Renaissance-era ramparts. You’ll have a bit of free time to explore on your own before we gather again for a truly special experience: an intimate Puccini concert in a centuries-old church. As the birthplace of the composer himself, Lucca offers the perfect setting to hear his music come to life.
We’ll end the evening with dinner at one of our personal favorites—a cozy local gem we’ve loved for years. The owners recently moved to a new location, but the heart and soul of the place remain the same. It’s the kind of spot where we’re greeted like old friends, and where every dish feels like it was made just for us. We can’t wait to share it with you.
Breakfast, Dinner
Start your day with a delicious breakfast at our hotel, setting you up for an exciting day ahead. Afterward, enjoy some free time to explore the enchanting streets of Florence, soaking in its art, culture, and history.
Later, we’ll check out of our Florence hotel and head to a truly special destination: Campo Sasso. Featured in several episodes of Fixer to Fabulous Italiano, this beautiful estate is home to a renowned cheese cellar where the owners expertly age their exceptional cheeses. During our visit, the owners will guide us through the property, sharing their passion for the craft and explaining the fascinating aging process. We’ll also explore the estate’s vineyards and olive groves, immersing ourselves in the natural beauty of the land. Afterward, enjoy a delicious lunch, highlighting their exquisite cheeses alongside local wines.
Following this unforgettable experience, we’ll continue our journey to our amazing winery villa, where we’ll be staying for the rest of the trip. Nestled in the heart of Tuscany, surrounded by vineyards and rolling hills, this villa offers the perfect blend of comfort and tranquility.
To end the day, join us for a warm welcome dinner at the villa, savoring traditional Tuscan dishes made from the freshest local ingredients. It’s the ideal way to cap off a day filled with exploration, indulgence, and new memories.
Breakfast, Lunch, Dinner
Start your day with a delicious breakfast at the villa, then take some time to relax and enjoy the peaceful beauty of your surroundings.
Afterward, we’ll head out for a premium wine tour experience at our winery villa. First, enjoy a guided tour of the vineyards, learning about the region’s winemaking history and the unique qualities of the land. Then, explore the wine cellar to see the winemaking process up close. Following the tour, indulge in a wine tasting of five exceptional wines, accompanied by a delicious lunch that highlights the best of Tuscan flavors.
In the afternoon, we’ll make our way to Siena, one of Tuscany’s most captivating cities, steeped in history and tradition. Famous for its medieval charm, winding streets, and the iconic Piazza del Campo, Siena is a must-see destination. During our privately guided walking tour, you’ll explore the city’s rich history, including a visit to the awe-inspiring Siena Cathedral. Learn about the legendary Palio, the thrilling horse race that takes place in the Piazza del Campo every summer, a tradition that’s deeply ingrained in the city’s culture.
After the tour, you’ll have free time to explore Siena on your own. Stroll through its cobblestone streets, enjoy the charming cafés, or shop for local crafts.
For dinner, enjoy the freedom to choose from Siena’s renowned eateries. Whether you opt for a rustic trattoria or a fine dining experience, you’ll find a perfect spot to savor the authentic flavors of Tuscany.
Breakfast, Lunch
Begin your day with a hearty breakfast at the villa, preparing you for a day rich in Tuscan culinary traditions.
Our first destination is Pastificio Artigiano Fabbri, a fifth-generation, family-owned pasta factory established in 1893 in Strada in Chianti. Here, you’ll enjoy a private guided tour of their pasta museum and production facility. Discover the history of this multi-generational enterprise, which has been crafting artisanal pasta using traditional methods for over a century. Learn about their unique “Fabbri Drying Method,” a low-temperature process that ensures the wheat is never cooked before it hits boiling water, preserving both flavor and texture.
Next, we visit Castello di Verrazzano, a historic winery nestled in the heart of Tuscany. Here, we will embark on a privately guided tour of the estate, exploring its rich history and winemaking traditions. The tour includes tastings of their renowned wines, followed by a delightful lunch that showcases the best of Tuscan cuisine.
In the evening, we return to Tenuta Guardastelle for a relaxed dinner, savoring traditional Tuscan dishes made with the freshest local ingredients. It’s the perfect end to a day immersed in the region’s rich culinary heritage.
Breakfast, Lunch, Dinner
Start your day with a delicious breakfast at the villa, preparing you for another wonderful day in Tuscany.
Our first stop today is Podere La Marronaia, a picturesque winery known for its exceptional wines. Here, enjoy a guided tour of the estate, walking through the lush vineyards and learning about the winemaking process that produces some of the finest bottles in the region. After the tour, indulge in a delicious lunch paired with their wines, offering a true taste of Tuscany’s rich culinary heritage.
Next, we’ll head to Volterra, an ancient hilltop town with a history that dates back to the Etruscans. During our privately guided walking tour, we’ll dive deep into Volterra’s fascinating past, exploring its Etruscan gates, ancient walls, and the well-preserved Roman Theater. Volterra was one of the most important Etruscan cities, and its archaeological sites offer a glimpse into the life of this early civilization. While the Etruscan history is the star of the show, Volterra is also renowned for its alabaster craftsmanship. The town’s artisans have been carving this beautiful stone for centuries, and you’ll have the chance to see the exquisite alabaster sculptures and pieces that are still crafted here today.
After the tour, enjoy some free time to explore Volterra on your own. Wander through the narrow streets, shop for local alabaster art, or relax at a café and soak in the ancient charm of this historic town.
For dinner, you’ll have the freedom to choose from one of Volterra’s excellent restaurants. Whether you prefer a cozy trattoria or a fine dining experience, you’ll find plenty of delicious options to savor the authentic flavors of Tuscany.
Breakfast, Lunch
Today is a free day to unwind and enjoy the serene beauty of Tenuta Guardastelle, the perfect opportunity to recharge during your Tuscany journey. Begin the day with a relaxing breakfast, savoring that second cup of coffee while taking in the breathtaking views that stretch endlessly over the Tuscan landscape surrounding San Gimignano. After breakfast, the rest of the day is yours to enjoy at your own pace. You can take a leisurely stroll through the vineyards, relax in the peaceful atmosphere, enjoy a refreshing dip in the pool, or simply immerse yourself in the natural beauty of the estate.
For those who signed up or feel motivated beyond a day of complete relaxation, there are a couple of options to enhance your experience. You can walk to San Gimignano (about 20 min) and explore the picturesque countryside at your leisure. Alternatively, you can participate in an onsite cooking class where you’ll learn to prepare traditional Italian dishes. The evening culminates with a delightful dinner featuring the dishes you’ve prepared. However, if today is all about true nothingness for you, feel free to simply enjoy the estate and recharge — no participation required!
Breakfast, Cooking Class Dinner
Enjoy a delicious breakfast at the villa before setting off for a memorable day exploring San Gimignano, the “Medieval Manhattan” of Tuscany, renowned for its stunning skyline of towers. During a privately guided walking tour, you’ll wander through the town’s historic streets, uncovering its rich medieval heritage, ancient churches, and panoramic views of the surrounding countryside. San Gimignano’s charm is enhanced by its famous vernaccia wine, which you’ll learn about as you immerse yourself in the beauty of this UNESCO World Heritage site.
Following the tour, take some time to explore San Gimignano at your own pace. Meander through its cobbled streets, browse the local shops, or relax in one of its delightful cafés. For lunch, you’ll have the opportunity to choose from a variety of local eateries, each serving up traditional Tuscan flavors.
In the afternoon, shuttle vans will be available to return you to Tenuta Guardastelle, or if you prefer, you can take a leisurely walk back to the villa (about 9/10 of a mile) through the scenic Tuscan landscape.
Once back at the villa, enjoy some free time to relax by the pool, take in the serene surroundings, or simply unwind in the peaceful ambiance of the estate.
The day culminates with a farewell experience at nearby Tenuta Torciano Winery, where you’ll embark on a guided tour of their estate followed by a farewell dinner in the vineyard. Celebrate the end of your unforgettable Tuscan adventure with delicious wines and a meal that perfectly captures the essence of the region, all set against the breathtaking backdrop of the vineyard.
Breakfast, Dinner
Savor a final breakfast at the villa, taking in the peaceful surroundings before the journey home.
After breakfast, we’ll check out of Tenuta Guardastelle. For those who have not made private arrangements, a private group shuttle will be available to transfer you back to Florence, with stops at:
Florence Airport (FLR) – for those departing by air.
Firenze Santa Maria Novella Train Station – for those traveling by train or who will be staying in Florence.
A final arrivederci until our next tour, as we bid farewell to beautiful Tuscany. Safe travels!
Breakfast
Please Note: This tour will be limited to a maximum of 16 guests.
$6390 per person for Double Occupancy Rooms
Upgrades available to 1 or 2 bedroom apartments with living room, kitchen, etc.
Please call us to discuss options and availability.
$7660 per person for Single Occupancy Rooms.
Please call if interested in sharing an apartment with other guests.
Space is very limited and room assignments will be based on a first come first serve basis.
As we strive to constantly improve our tours and come across a special new event or winery, we may occasionally adjust the itinerary as necessary to provide you with the best wine-cation experience possible.
Given that there is a minimum number of passengers required for each trip, we suggest you refrain from non-refundable transportation purchases until two months prior to your departure date or confirmation of tour.
