Itinerary
Day 1: Benvenuti in Toscana!!! Welcome Day and Dinner Welcome to Florence, the capital of Tuscany and the Renaissance! We will be meeting at the meeting point at 3:00 pm. Our driver will pick us up and take us North-East for a beautiful drive into Mugello, where we will be spending our first three nights in the small town of Vicchio. On our way to Mugello, we will make a quick pit stop in Fiesole, the ancient Etruscan town, for a panoramic view of Florence and the surrounding valley. Once we arrive to Vicchio, we will check into our BnB, Montelleri, where you will have some free time to relax before our welcome dinner. This accommodation is located with easy access to shopping and cafes in Vicchio, trails for the nearby lake and forest, has its own authentic Mugello style restaurant, and most importantly, is walking distance from the local winery we will be spending time with on Day 3, Bacco del Monte. At 8:00 pm, we will meet up together as a group for a beautiful welcome dinner on the patio of Montelleri’s restaurant. This is the perfect time to not only stuff our faces, but to get to know one another. Get ready for a fun night full of wine, accompanied by rustic and authentic food!
Day 2: Florence Like a Local Buongiorno!! It’s Florence Day! We already met up in Florence yesterday, but that was just to get you organized. We are heading back for the day, but this time as a group. After a quick breakfast at our BnB, we will take the short ride back down the hill together so that we can experience Florence as a local. Don’t eat too much at breakfast, as you will be snacking throughout the day in Florence. Ryan, Grape Stained founder, spent two and a half years living, studying, working and exploring the lesser known, more authentic side of the city, especially gastronomically. Florence is his backyard and passion. While we will of course be making some stops along our route to those photo perfect places like the Duomo, Ponte Vecchio, Santa Croce, Santa Maria Novella, and Piazzale Michelangelo, we will also be exploring some back streets of Santo Spirito, Sant’Ambrogio, Santa Croce, and San Frediano in search of the best local delicacies and wines. Whereas most people that visit Florence for a day wait in long lines for a famous Instagrammable panino, we will be skipping that and instead visiting a hidden gem, known for their award winning breads, spreads, meats and cheeses. We will visit hidden wine bars with incredible lists, local farmers markets, wine windows, true hand-made leather shops, small cafe’s, delicious bakeries, street food vendors, and more! Our goal is to show you the authentic side of Florence and get you out of your comfort zone a little bit. Other than taking endless photos and indulging on an overwhelming amount of snacks and wines, one of the biggest highlights of the day will be meeting Pietro, a local chef. He will meet up with us in Mercato Centrale, before leading us to the local favorite, Mercato Sant’Ambrogio. Pietro will lead us along on a gastronomic tour of Florence’s markets, to better explain the purest style of Italian food, local and seasonal. We will have the unique opportunity to choose the ingredients that we will have for dinner later that night as Pietro has invited us to a dinner at his house in Mugello, close to our BnB. Get you’re walking shoes and your stomach ready to be Florentine for the day.
Day 3: Mugello's Authenticity, Discovered We will have a light breakfast at the BnB, followed by a lovely morning stroll through nearby Vicchio. This is town is very smaller and relatively unknown to most tourists, therefore it gives visitors a nice window into the more authentic side of Tuscany, away from the bustling tourist scene of Florence. Silvia (wine producer - Bacco del Monte) and Benedetta (local chef - Bosco di Mezzo), will be meeting up with us to lead us through the streets to share their home. Benedetta will help us find the perfect ingredients from the local produce stand and butcher before going home to prepare an incredible dinner for us later in the evening at her house. After exploring and shopping, local Truffle Hunter, Mattia Crescioli, will lead us to a gorgeous and tranquil forest nearby for our own truffle hunt. Mattia’s dogs are very well trained and experts in sniffing out the prized kitchen ingredient. Depending on the season, we can find different kinds of truffles. If we are lucky, we might even find the highly sought after and expensive White Truffle… Silvia will be waiting for us at Bacco del Monte, with a raised glass and a collection of snacks. Yes, this means cheese. You better get used to the word “Formaggio” in Italy. The winery is still quite young, as their Pinot Noir vineyard was planted in 2016. Unlike the majority of Tuscany, at Bacco del Monte we will be enjoying the international grape varieties, Pinot Noir and Chardonnay. The lesser-known Mugello region is becoming more recognized with the ever-changing climate and high-quality production. Don’t expect this Pinot Noir to be similar to that of Oregon or Burgundy though, we are still in Tuscany and Pinot Noir is notorious for adapting to its terroir. After a perfect tasting, you have a few hours of free time before dinner. You can nap, shop in town, drink more wine with Silvia, go for a hike, relax with a book, or go for a lovely pre dinner “Passeggiata” (stroll). The time is up to you!!! At 8:00pm, we will head out for dinner at Benedetta’s house, just a few minutes away. Give a pep talk to your stomachs for this one, you won’t want to miss out on anything. Benedetta specializes in whatever ingredients are in season and local, preparing them with the perfect mix of artistry and home cooked comfort. We can’t know now what Benedetta will prepare for us on this evening, but we can promise you that you will never forget it.
Day 4: San Gimignano’s Towers, Hills, and Vines We are off to San Gimignano, our home base for the next 3 nights. The ride from Vicchio to San Gimignano is roughly an hour and a half, but is smooth and full of beautiful scenery. Upon arriving to San Gimignano, its Medieval skyline demands your attention. Today, 14 of the original 72 towers are still standing in this UNESCO World Heritage site. To show you the real side of town, we found one of the most charismatic and lovable locals possible, Filippo. This man is every bit of the word, authentic. Filippo is a walking dictionary of knowledge, especially when it comes to his hometown. You are in for an incredible day in San Gimignano, discovering its history, as well as the culture of Tuscany, the Renaissance and Italy as a whole. Walking through a town full of medieval history will have your stomach growling. We are off to a big lunch, wine tasting, and our home base for the next 3 nights. Fattoria di Fugnano is not only an incredible winery, but also an agriturismo with one of the most stunning views in the area. Before moving into our rooms, we will embark on a guided tour of the winery and farm accompanied by a a big lunch and tasting of 7 different wines. Known as the White Queen of Tuscany amongst a sea of Red Kings, Vernaccia is famous for its “sting and bite” of refreshing acidity. Vernaccia di San Gimignano is one of Italy’s most beloved white wines as it was the very first DOC wine of Italy, yet it is lesser-known in the international market. Wine from different vintages will probably be pulled out as well knowing the producer, Laura, and her son, Andrea. Get ready for an extremely fun tasting, you will absolutely need a siesta afterwards! Luckily for you, after the tasting, you will find more bottles in your room ;) After our lunch and overwhelming amount of wine, the next few hours are yours. You can go back into town for some shopping, follow one of the surrounding hiking trails linked up to the ancient Roman road and medieval pilgrimage route, Via Francigena, or you can walk through the vines and drink more wine with Laura. You will definitely need to knock off the food somehow, as Laura and her team are preparing an authentic Tuscan barbecue for our dinner. We will all meet back up with Laura and her team for an incredible evening of food, wine, family and friends. There aren’t many better things in life than taking in a colorful Tuscan sunset with good company and a full stomach.
Day 5: Quiet Chianti Classico A quick and light Italian styled breakfast will be served at Factorial di Fugnano before we head out for one of Tuscany’s most famous areas, Chianti Classico. The zone of Chianti Classico makes up the area between Florence and Siena. The steep and rocky hill sides are dominated by forests, olive groves, historic castles, stunning and villas, and of course, vines. The ride along these hilly roads is stunning at every turn. There will be plenty of opportunities for photo stops Chianti Classico is an area full of history and legends. You will be lead through multiple stories of how Chianti Classico became a region, the symbolic black rooster labeling, its original recipe, its rise and fall to fame, and its current DOCG requirements. The area plays host to over 480 producers, many of which produce and export thousands upon thousands of bottles every year. Our excursion will not take us to one of the bigger producers, rather one of the smallest. Podere Bucine, is located just above the beautifully rustic and quaint hilltop town of Montefioralle. Loreto, the producer and winemaker, is originally from Sicily. Loreto continues to learn, grow, and adapt with his production, increasing change of climate factors, and the general market. His wines are fresh and simple, perfect for any occasion, especially with a charcuterie board or classic pasta dishes with fresh tomatoes. Loreto and Podere Bucine’s future is very bright and we cannot wait for you to meet him! After a small farm tasting, you are in for a treat, both metaphorically and literally. Get your aprons ready, Gian Luca of Alcanto del Forno is taking us through a Tuscan gastronomic experience. At the bottom of Loreto’s hill, Gian Luca will be waiting, welcoming us into his beautiful home. A cooking class at Alcanto del Forno is always full of laughs, smiles, messy hands, and very full stomachs. Listening to Gian Luca talk you through a dish is both charming and spellbinding, while his smile and laugh are extremely contagious. Everything being prepared will be local and seasonal, the Tuscan way! After yet another afternoon of wine and food, we will take our time back to Fattoria di Fugnano in San Gimignano, making a few more pit stops along the way for some photo stops. The rest of the evening is up to you!! After a little bit of free time to recharge your batteries, many of us will be heading into San Gimignano for a classic Tuscan aperitivo. Laura will be joining us in town as she will show us some nice spots for small bites and wines. If you prefer a date night, a solo dinner, or to stay and cook something in your bnb, please feel free! This night is up to you.
Day 6: The Lesser Known Side of Chianti What many people don’t know, is that Chianti and Chianti Classico are entirely different regions, with Chianti being broken down into 7 sub regions. Today, we will journey through two other zones, Chianti Colli Fiorentini and Chianti Montalbano, in search of tasting the differences. After today, you will surely be a Chianti Pro, able to pick up on the differences of Chianti Classico, Chianti Colli Senesi, Chianti Colli Fiorentini, and Chianti Montalbano in a blind tasting. First, we will visit Podere la Botta, a family run winery in the town of Limite, part of the Chianti Montalbano zone. This little winery, also a farm, is truly one to experience first hand. The vines are managed by Andrea Bartolini and his 95 year old father, Beppe. You will definitely feel a generational influence here. Andrea’s husband, Mauro, works hard in management of the winery as well as labeling designs and marketing. The two own a couple of gorgeous greyhounds that run around the property, watching over their vines. They have such an affinity for the breed of dog that with every purchase of their Canaiolo, labeled with a greyhound, 20% of the value of each bottle is donated to the Animalist Project for Life Association After walking around the vines, olive grove, and cellar, we will be treated to what we love most about Italy, a lovely lunch with family. We will share a homemade feast, enjoying Podere la Botta’s wines, and the freshest ingredients from their very own land. It doesn’t get much better than a post tasting lunch with family. Next stop, the Chianti Colli Fiorentini region, where the Poggio al Chiuso brothers will be waiting for us. The Corti family has been making wine in the area for four generations, with Marco, Matteo, and Andrea running the business now. This fun bunch of brothers take their winemaking seriously, and for good reason. They are always looking for new wine-making and viticultural techniques to grow with the change in market and climate. Younger generations of Italian wine-making are adapting quickly to change, and you will have the opportunity to see it first hand with the Corti brothers. After our stomachs once again full of wine and laughs, we are back to Fattoria di Fugnano for our last evening in the area. You will have free time for a couple of hours to rest, explore, or drink more if you so desire. Our last dinner at Fugnano is up to Laura who always has something special up her sleeve.
Day 7: Under the Cortona Sun A quick breakfast and we are off! But take it lightly, we are about to make and eat A LOT of cheese. This day will take us through Val di Chiana, with Cortona as our main focus. Cortona is a gem of a town, perched on the edges of a vast hill side, overlooking the Val di Chiana. The town is most famously known for its role and setting in the early 2000’s Rom-Com, Under the Tuscan Sun. If you want to catapult yourself out of the van and buy a villa somewhere, we get it. First stop, Fattoria Bistecca. We know you have been eating a lot of cheese, but you haven’t made it yet. The staff at Fattoria Bistecca will guide us through a 3-hour experience of making three different kinds of cheeses; raveggiolo, pecorino, and ricotta. Fattoria Bistecca will train us through the traditional method of production and aging, using raw milk. The experience will be accompanied by bruschetta, pasta, pecorino, ricotta, and of course, wine. Keep your hands dirty and get to work, our cameras will make sure to document it for you. Next, a few minutes down the road to our next winery. We will spend a beautiful and light afternoon with Elisa and Luca of Iviti. We will learn everything organic as Iviti specializes in natural techniques in the field and production. They use some very rare and difficult techniques in both the vineyard and cellar that are hard to find elsewhere. This area of Tuscany doesn’t revolve around the classic and rustic Sangiovese as most zones, rather more internationally famed varieties like Cabernet Sauvignon and especially, Syrah. Cortona continues to become more and more internationally recognized for its high quality production of the finicky Syrah. The bold wines of this area are making a massive push as some of the best in Tuscany, with Iviti producing outstanding expressions of Syrah, Cabernet Sauvignon and Cabernet Franc We know, you’re stuffed again, but you have some time to recover before a big, rustic farm dinner. We will ride about 30 minutes to our last accommodation of the trip, tucked away nicely, just below Montepulciano. Sabrina will be waiting to check us in at Agriturismo Pescaia where you will have some time to relax with this stunning view and natural ambience before we make our way out to dinner, only a minute or two down the road. Around 7:30 pm, we will make our way down the road to Ristorante L’Oliveto, another family run Agriturismo in the area. Oliveto specializes in local ingredients and specialty dishes in this extremely cozy and rustic setting. An incredible dinner to end another incredible day.
Day 8: Historic Dive Into Montepulciano Morning in Montepulciano is often accompanied by the cockling sounds of roosters and a gorgeous glowing hue, waking up the valley. Today is potentially our most laid back as we don’t have an organized tasting until 3:00pm, but we want to show you around the area and town a little bit. We want to leave a lot of the morning up to you, because we know how addicting Montepulciano can be. Our day begins with some breakfast in the Agriturismo before heading out for some views and exploration of town. Just up the hill from our Agriturismo is Templo San Biagio, what many consider to be one of the most important pieces from the Renaissance. After a little walk around and inside of this masterpiece, we will make our way up the hill and into town for a day of walking, shopping, and exploring. We will start in town as a group, so that we can share some of our favorite spots with you. Montepulciano is an incredible spot for local artists as well, so If you’re looking for uniquely hand made ceramics or true paintings/mosaics, you will find it here. We will take you on a walk through town, but if you want some free time, we understand! Andrea Contucci, one of the family members and owners of the historic Contucci winery, will meet up with us in Piazza Grande to take us through one of the most memorable tastings and tours. Visiting Montepulciano and the Contucci cellar/home is always special. The history of winemaking in the Contucci family goes back 40 generations and a little bit over 1000 years. To this day, they are the last remaining, historic family of Vino Nobile di Montepulciano that continues the production of the wine within the walls of the stunning hilltop town. Spending a few hours with Andrea really puts the history of winemaking, especially Tuscan, in perspective. Andrea will share stories and history of Montepulciano in the Piazza before he takes us inside his amazing home, Palazzo Contucci. Inside, you will be blown away by the art and history of the Sala de Feste, a family party room, and down to one of the most extraordinarily beautiful cellars in all of Italy. History and art aside, we need a drink. Andrea will take us into the tasting room where we will sample 6 different styles of wine, starting from small and simple drinking, making our way to elegant, bold, and long aging potential. You will feel like a tru pro after this tasting. After an incredible and educational day in Montepulciano and Cantina Contucci, we will make our way back down the hill to allow for some time to rest and freshen up before dinner. For dinner, we will meet up with Andrea for a traditional dinner at Osteria del Conte. Montepulciano is known as the birth place of one of Tuscany’s most famous styles of pasta, Pici, and Osteria del Conte specializes in it. A meal of local specialties and drinking house wine with the producer himself. A well deserved evening in Tuscany.
Day 9: Breathtaking Val d’Orcia and Montalcino’s Hidden Gem It’s hard to not be extremely excited for a day riding around Val d’Orcia, but this is truly the quintessential experience of Tuscany. The valley, a UNESCO Heritage Site, is one of the most stunning settings in the world, no wonder it is so often associated with romance. We will spend our morning, quietly riding around to some of our favorite spots to take in the scenery. Stops along the way include the stunning towns of Montichiello and Pienza, along with view points of Monte Amiata (the regions’ extinct volcano), Cappella della Madonna di Vitaleta, Cipressi di San Quirico, Gladiator Road and other spectacular lookouts upon winding roads, hilltop towns, and colorful valleys. We will take a brief stroll through Montichiello, a Tuscan gem, to enjoy the tranquil streets and one of the best panoramic views of Italy. In Pienza, we will explore shops, particularly those with cheese. Pienza is not only famous for its outstanding viewpoints and beautiful architecture, but it is home to one of the best cheeses of Italy, Pecorino di Pienza. This town will be a perfect spot for a little bit of free time and to have a class Tuscan lunch, a panino. When it comes to Sangiovese, Montalcino is the King. There are many remarkable small producers in this region, but we will have the privilege to spend our time with none other than Fabio at La Fornace. The property was once upon a time a furnace in the late 1500’s, before transitioning to a farm for the production of olive oil and grapes in the 1960’s. It has been a family business ever since, producing their first Brunello di Montalcino vintage in 1988. Fabio took over the full management in 1998 and the rest is history! Fabio will walk us through the vineyards and show us his impressive production of his elegant Brunello. Fabio makes four different wines, all different in method and character, but they all exemplify their terroir. Rosso di Montalcino, Brunello di Montalcino, Brunello di Montalcino Origine, and Riserva Brunello di Montalcino. The entire process is done hands on as Fabio himself does the work in the vines, in the cellar, and in the marketing. There is something extremely romantic about a traditional style wine being done with every ounce of love and passion from a producer. A tasting with Fabio is always full of laughs as he truly has a one of kind personality. After finishing up a lovely tasting of some of Italy’s most famous style of wines, Golden Hour has begun. On our way to Montichiello for dinner, we will stop to enjoy the sunset the right way, with a blanket, a bottle of wine, and some snacks. The last sunset of the trip needs to be done right! Dinner will be a sad farewell, but your tastebuds will be extremely happy. We are finishing up our Tuscan adventure in style at Ristorante Daria in Monticchiello. This restaurant is tucked away down a side street of the tiny town of Monticchiello. The late and great Daria Cappelli poured her love and charm into this incredible property. Today, the restaurant is run by her daughter, Deborah, and still embodies an atmosphere showcasing the style and flair of Daria. The food is always to die for and the wine list is sensationally extensive. Ristorante Daria personifies comfort, elegance, and authenticity. Get ready to clink glasses and enjoy mouth watering foods one last time!
Day 10: Arrivederci. Departure from Florence Sadly, our time together has come to an end, but the memories will last forever! We will make our way back to Florence after one final breakfast together. We will arrive back in Florence around 11 am. We can help you organize any transfers or plans that you need to make. Thank you for an unforgettable adventure!
Highlights:
Book the Della Botte Wine Club Tour
Click below to reserve your spot(s) on our Grand Tour of Tuscany. You will be required to pay a deposit of $1000 per person upon reservation (If you are reserving for a group of 2, you will select 2 deposits totaling $2,000). We will send an invoice with the remaining amount ($4500 per person), due six weeks before the tour.
SPRING TOUR DATES: May 13-22, 2025 Launch Special: Save $500pp
AUTUMN TOUR DATES: September 30-October 9
Our small group tours require at least 4 people to run (with a maximum of 8). If the tour gets canceled due to insufficient group size, you will receive your deposit back.
What's Included
Accommodation in three gorgeous Tuscan agriturismos.
All transportation throughout the duration of the tour.
Eight winery visits and tastings.
All meals as detailed in the itinerary.
All cooking classes and other activities as detailed in the itinerary.
Professional photographer capturing the experience.
Not Included
Flights/transportation to and from the starting/ending point of the tour.
Travel insurance.
Free time activities/activities not detailed in the tour itinerary.
Additional drinks/wine at meals
Personal purchases and services such as souvenirs, laundry, phone calls, Internet, etc.