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Best Bolgheri Winery

5-Nights Bolgheri and Val d'Orcia 

2026 Dates

Coming Soon!!!

Price

$5200

All Inclusive package including accommodation, transportation, food, wine tastings, expert led tours and a photographer capturing the experience.
 

*Price per person
*Flights not included

Itinerary

Day 1: Super Tuscan Discovery of Bolgheri 8:30am: Meeting and Pickup in Florence 10:30am: Exclusive Winery tasting/lunch and tour at Tenuta Fratini 3:00pm: Check into Accommodation and Villa 4:00pm: Winery tasting and tour at Tenuta Pakravan-Papi 6:00pm: Free time and aperitivo at Tenuta Pakravan-Papi 8:00pm: Dinner with local chef

Day 3: Historic Dive Into Montepulciano 8:00am: Breakfast at Tenuta Pakravan-Papi 11:00am: Visit to Tempio San Biagio 12:00pm: Winery tasting and tour at Salcheto* 3:00pm: Winery tasting and tour at Contucci 5:00pm: Free time Montepulciano/Check in at Agriturismo Pescaia 8:00pm: Dinner at Ristorante L’Oliveto

Day 2: Free day or Exploration 8:00am: Breakfast at Tenuta Pakravan-Papi Free day to relax at the villa, on the Tuscan coast, or on an excursion to Pisa or Volterra 8:00pm: Dinner with a local chef

Day 4: Hidden Gems of Val d'Orcia 8:00am: Breakfast Agriturismo Pescaia 9:00am: Visit to Montichiello, a small medieval village 11:00am: Winery tasting and tour at La Nascosta 2:00pm: Cheesemaking, wine tasting, Lunch, and Pecorino farm tour at Caseficio Piu 6:00pm: Free time around Montepulciano and Agriturismo 8:00pm: Dinner at Osteria del Conte

Day 5: Breathtaking Val d’Orcia and Montalcino’s Identity 8:00am: Breakfast Agriturismo Pescaia 9:00am: Visit to Pienza 11:00am: Winery tasting and tour at La Fornace in Montalcino 1:30pm: Lunch in Montalcino 3:30pm: Winery tasting and tour at Colle Mattoni 5:30pm: Golden hour drive and aperitivo in Val d'Orcia 8:00pm: Dinner at Ristorante Daria

Day 6: 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!

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Highlights:

6 Winery Visits - tastings/tours with the producers

Experience the ever changing Terroir of Tuscany like never before. Indulge in different expressions of numerous grape varietals as we travel across multiple microclimates and Italian wine denominations of Bolgheri, Montalcino, Orcia, and Montepulciano. Learn about the stories and history of 3 different families of the Chiana and Val d'Orcia valleys while you quench your wine thirst.

Cheese Making Classes and Cozy, Authentic Dinners

Enjoy Italian food like never before. Satisfy your need for cheese as we explore Val d'Orcia and Val di Chiana, two valleys famous for pecorino. Get your hands dirty and stain your apron as we learn how to make cheeses in an authentic Tuscan style. In the evening, we will be eating the true Italian way, local and seasonal. Cuisine in Val d'Orcia is every sense of the word, rustic.

Visits to 5 towns across Val d'Orcia and Bolgheri

On a ride through Tuscany, you will quickly discover that straight lines hardly exist. Roads whip back and forth, up and down, whilst passing through farmland, forests, medieval towns, olive groves and of course, vines. It is so easy to fall deeply in love with Tuscany, as this stunning landscape is not only one of the most romantic destinations on Earth, but one of the most diverse.

Professional Photographers Capturing your experience

We are professional photographers and love to capture the moment, so we want you to live in it. Don't worry about spending too much time taking a selfie, we would rather do it for you. Our tours include professional photographers following along to help best capture your experience and provide you with your very own memory book to show off to friends and family.

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Book the Bolgheri and Val D'Orcia Tour

Click below to reserve your spot(s) on our exclusive tour of Bolgheri and Val d'Orcia. You will be required to pay a deposit of $750 per person upon reservation (If you are reserving for a group of 2, you will select 2 deposits totaling $1,500). We will send an invoice with the remaining amount ($4,450 per person), due six weeks before the tour.

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SPRING 2026 TOUR DATEs: 

Coming Soon!!!​

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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.

Must be 21 or older to purchase:

This tour includes wine tastings and experiences that involve alcohol.

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What's Included

Accommodation in two gorgeous Tuscan agriturismos/villas.

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All transportation throughout the duration of the tour.

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Six winery visits and tastings.

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All meals as detailed in the itinerary.

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Cheesemaking class and other activities as detailed in the itinerary.

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Professional photographer capturing the experience.

Not Included

Flights/transportation to and from the starting/ending point of the tour.​

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Travel insurance.

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Free time activities/activities not detailed in the tour itinerary.

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Additional drinks/wine at meals

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Personal purchases and services such as souvenirs, laundry, phone calls, Internet, etc.

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