Uncorked:
Tuscany
September 19-25th, 2027
ITINERARY
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![beautiful house in Italy with a pool]()
Day 1: Arrival
Welcome to Tuscany!
You will have a private transfer from the airport to the week’s luxury Tuscan Villa in the picturesque Chiusi.
Settle into your room and unpack, or explore the grounds and hang out by the pool, it’s your home for the week!
If you want to enjoy the massage that comes complementarily, it’s a great time to get the jet lag stretched out of your system.
Early evening will hold an Aperitivo hour and there will be a traditional Tuscan dinner at the villa. Spend the night relaxing or enjoying the Tuscan sky as the sun sets.
Meals Included: Aperitif Hour & Dinner
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![people cheering and celebrating with a glass of red wine.]()
Day 2: Brunello & Lunch
Wake up at leisure this morning and enjoy breakfast on the patio.
Specializing in Brunello, the first winery will take everyone on a journey through the vineyards and to the tasting rooms. You’ll taste signature offerings from their cellars.
For lunch, you’ll head to a farm to table experience. Enjoy views overlooking the vineyards and the rolling hills of the countryside. Lunch is locally produced and enjoyed at leisure. A second wine tasting accompanies this and tasting artisanal cheese made on site.
Free time spent relaxing at the villa will give you a chance to go over what you’ve experienced today before a pizza chef joins the villa for an exclusive pizza dinner made to order.
Meals Included: Breakfast, Lunch, Dinner
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![home made pasta and cooking class]()
Day 3: Sangiovese, Cooking Class
Sleep in and enjoy the patio breakfast as you wish today. You’ll visit an organic Tuscan winery today to start. Lean int the organic wine movement and taste what wine is like with nothing but sunshine and Mother Nature to help it along.
Lunch in a classic Tuscan town and some free time to explore and shopping time will follow for a few hours. Local wine shops can offer tastings, gelato vendors have treats to enjoy, and goods vendors have plenty to sell.
After you’ll head back to the villa and create your own Italian meal with the guidance of an experienced chef. Dinner will be served from your new found skills!
Meals Included: Breakfast, Dinner
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![walking a path around in Italy]()
Day 4: Dolce Far Niente
“The sweetness of doing nothing”
Spend the morning with a cup of coffee and a pastry before you begin.
Take a day trip to Siena or the train to Pisa. You can strike out on your own or schedule a tour through the villa to truffle hunt in the countryside or visit a cheese farm. Maybe there’s a winery you’ve wanted to check out and this is the day to do it!
Enjoy a complimentary massage during the afternoon (if you didn’t the first day!) or maybe a lounger by the pool and a book is what you want to do. (You’ll probably find a trip host or two sitting right beside you!)
Meals included: Breakfast
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![soft white beach sand with chairs and umbrellas]()
Day 5: Super Tuscans & the Beach
This morning we hit the road, and what a beautiful road it is! Enjoy breakfast a little earlier than usual and join the group as you embark on a drive which will see the hills transform into the coast. Home to the Super Tuscan wines.
Your first winery is a new kid on the block so to speak. Taking new ideas for old wines, they are a fresh take in the industry.
You’ll have free time in the historic town of Bulgheri to explore at your leisure, your hosts will be a local restaurant for lunch where you can meet them before heading to the next winery.
You’ll be given a time to meet back at the bus or you can take on a scenic walk to the next winery if you so wish.
The second winery holds significant value in the history of Super Tuscans. You’ll learn about the history of the wine style and how it differs from other wines in the region while tasting it.
The day concludes on the beach in a private cabana. Enjoy happy hour and drinks as you wish and enjoy the waves of the coast for a couple of hours before heading back for the night.
Meals Included: Breakfast
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![a beautiful home in Tuscan with a classic car]()
Day 6: Chianti
We round out the week with a Tuscan classic, the Chianti Classico. Another wake up and get breakfast morning awaits you before heading to your Masterclass for the day.
A renown Chianti winery will introduce you to their estate which houses an ancient castle, the vineyards, and their extensive collection of wines.
Following the tasting, a lunch featuring views of classic Tuscany, wine pairings, and food that has earned 2 Michelin stars rounds out the day. You’ll have the final chance to shop around and get last minute souvenirs or soak in the Tuscan towns before heading back to the villa.
The final night ends with the culmination of every food and wine you’ve tried. A classic Tuscan dinner and curated wine pairings await you as you spend the final night reminiscing about your adventures in the countryside and comparing notes with everyone else.
Meals Included: Breakfast, Lunch, Dinner
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![A car driving though the street of Italy]()
Day 7: Departure Day
A final slow morning as we say goodbye to the villa. One of two shuttles back to the airport will take you back as you continue on to home or explore more of Italy.
This is never goodbye, but always a presto!
Meals Included: Breakfast
Meet the Wines
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Produced exclusively around the hilltop town of Montalcino, Brunello di Montalcino is one of Italy's most prestigious wines. Made from 100% Sangiovese (locally called Brunello), it is known for its rich structure, dark fruit, elegant tannins, and remarkable aging potential. Strict production standards and years of cellar aging create a wine that is both powerful and refined, making Brunello one of Tuscany's true flagship wines.
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Tuscany has become a leader in organic winemaking, with many estates choosing to farm without synthetic pesticides or herbicides. By working in harmony with the land, organic producers aim to create healthier vineyards while allowing each wine to express its unique sense of place. The result is a growing movement that blends centuries-old Tuscan traditions with a modern commitment to sustainability and quality.
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Super Tuscans are bold, innovative wines that broke from traditional Italian winemaking rules. Beginning in the 1970s, pioneering producers blended Sangiovese with international grapes like Cabernet Sauvignon, Merlot, and Cabernet Franc, creating wines that earned worldwide acclaim. Today, Super Tuscans represent the perfect balance of Tuscan heritage and modern winemaking, producing some of Italy's most sought-after bottles.
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Nestled between Florence and Siena, Chianti is one of Italy's most celebrated wine regions. Made primarily from the Sangiovese grape, Chianti is known for bright cherry flavors, lively acidity, and exceptional food pairing. At the heart of the region lies Chianti Classico, the original growing area, identified by its famous Black Rooster emblem—a symbol of centuries of Tuscan winemaking tradition.
What you’ll get
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✺Accommodations
Enjoy yourself in your solo occupancy room in a classic Tuscan villa!
Terraces overlooking the countryside, a full sized pool, lounging patios, and charming walkways give you the feeling that you aren’t just visiting Tuscany, you’re calling it home.
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✺Meals
Breakfast every day is included at the villa. Meals curated with the ultimate Tuscan experience in mind are arranged and taken care of for you. Farm to table lunches, personal pizza chefs, a Michelin star rated restaurant, and more are included in the cost of the experience.
You will have a few opportunities to personally explore a new option or go back to your favorite spot you already found.
*reference the timeline above for information on which meals are included.
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✺Transportation
Private transportation to and from the airport in Rome, and shuttles during experience activities are included in the cost of the trip.
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✺Wine Tastings
All wine tastings are included. They will range from short, limited edition tastings, to a wide variety of what a production vineyard offers in their collection.
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✺ Activities
Beach club access and rentals, in villa massages, Cooking classes, and tours of wineries.
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✺Trip Hosts
You’ll have 2 hosts available to you 24/7 during the trip. They’ll serve as a resource for the area, your guiding light on when to show up and when to get going, and people to hang out with. Anything you need, they are there for you!
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✺Transaction Fees
Transaction fees for your deposit and final payments are included!
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✺Unique Swag
All trips feature a unique piece of “swag” for the trip.
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✺Villa Wine
A selection of wine will be stocked in the villa for you to enjoy.
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✺Professional Photographer
A professional photographer will accompany the trip throughout the week. He will be capturing both scenic photos and candid photography of the group, as well as pictures on request. Each day will give you limited access to the best photos to have and to share, and all photos will be available after the trip is concluded. You won’t have to worry about caputuring the trip, it will be captured for you!
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✺Portal Access
Exclusive access to packing lists, trip details, and preparation guides for the trip, created specifically for this guided experience.
✺ Frequently Asked Questions ✺
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Dates: September 19th-25th 2027
Yes that is more than a year from now. Plenty of time to find the perfect outfit to match this occasion.
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Air fare to and from Tuscany.
Meals not mentioned as being included in the itinerary.
Travel Insurance for the duration of the trip is not included in the listed price.
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This trip is a little different and it is wrapped around the culture of wine in Italy.
Guest are still welcome to join the trip even if they do not like wine. (Men, setting down the bourbon for 1 week will be worth it)
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Dietary restrictions can be accommodated for the most part. Please make sure to reach out with any that you have to make sure we have enough time to make any adjustments for you!
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You can! We can customize a payment plane for you if needed.
*Please note that final payments are due in full by the deadline, so any payment plans will have to fit before that date.
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The drivers to the villa will be picking up from Rome Fiumicino Airport. There will be 2 drivers there to take you to the villa, and we ask that everyone arrive by 2pm the first day of the trip.
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We are taking 10 people on this trip! You’ll have 2 trip hosts with you as well. Making the total group number 12.
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Everything listed for $5,696.40 USD
Currently only a “Spot Deposit” ( $500) is necessary to lock in your spot.
The full deposit amount is due on or before 01/01/2027 (20% of total amount)
Final payment is due 100 days before trip begins.
* Please note deposits are non-refundable unless the trip is filled and someone takes your spot.
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The first 30 days of the trip launching, we are giving an early bird discount that takes $100 off of the trip. You’ll see this reflected on your final invoice for the trip.
There is also a cash discount.
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Absolutely! This trip is designed to be a great time whether you’ve traveled before or are in possession of an empty passport. Trip hosts will always be with you and available so you are never navigating alone if you aren’t comfortable.
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Daily highs start near 96°F at the beginning of the month and gradually taper down to about 91°F by the end of September. Overnight lows typically range from 73°F early in the month down to 65°F at night's end.
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Entry requirement for US citizens are the following:
Passport must be valid 3 months after the date you plan to leave.
You must obtain an ETIAS travel authorization before entering the Schengen zone (this can be done online)
Not have been in the Schengen zone fore more than 90 days out of the last 180.