6-Night Grand Tour of Tuscany

2026 Dates

May 1-7

Price

$5250

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

*Price per person
*Flights not included
*Times on itinerary subject to change

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Itinerary

Day 1: San Gimignano’s Towers, Hills, and Vines 9:00am: Pickup in Florence 10:30am: Walking tour in San Gimignano 11:30am: Freetime in San Gimignano 1:00pm: Winery tasting/tour/lunch at Fattoria di Fugnano   4:00pm: Check into accommodation in San Gimignano and free time *Subject to change 7:00pm - Aperitivo and dinner in San Gimignano

Day 2: Lesser Known Chianti Classico/Chianti 8:30am: Breakfast in San Gimignano 10:00am: Winery tasting and tour at Podere Bucine 11:30am: Cooking class and Lunch at Alcanto del Forno  3:00pm: Photo stops in Montefioralle and Badia a Passignano 4:00pm: Winery tour and tasting at Poggio al Chiuso 6:30pm: Free time at accommodation or San Gimignano 8:00pm: Aperitivo and dinner in San Gimignano with the group or on your own!

Day 3: Under the Cortona Sun 8:30am: Meeting and Pickup in Florence 10:30am: Cooking Class with chef Giada Mattioli 2:00pm: Winery tasting and vineyard walk @ Colle Acacia 4:30pm: Winery tasting @ Colle Acacia 7:00pm: Check in and Aperitivo at Agriturismo Pescaia 8:30pm: Dinner at Ristorante L'Oliveto

Day 4: Historic Dive Into Montepulciano 9:00am: Breakfast at Agriturismo Pescaia 9:30am: Visit to Tempio San Biagio or free time 12:00pm: Lunch and walking tour of Montepulciano 3:00pm: Winery tasting and tour at Contucci 6:00pm: Free time Montepulciano/Aperitivo at Agriturismo Pescaia 8:00pm: Dinner at Osteria del Conte

Day 5: 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 8:00pm: Dinner at Ristorante L'Oliveto

Day 4: Breathtaking Val d’Orcia and Montalcino’s Identity 8:00am: Breakfast Agriturismo Pescaia 9:00am: Visit to Pienza 11:30am: Winery tasting and tour at Colle Mattoni 1:30pm: Lunch in Montalcino 3:30pm: Winery tasting and tour at La Fornace 6:00pm: Golden hour drive and aperitivo in Val d'Orcia 8:30pm: Dinner at Ristorante L'Oliveto

Day 7: 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:

10 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. Learn about the stories and history of 10 different families spread across the Tuscany wine region as you quench your wine thirst.

Cooking Classes and Personal Chef Dinners

Enjoy Italian food like never before. Embark on market tours and choose your ingredients for handcrafted meals with local chefs. Get your hands dirty and stain your apron as we learn how to make pastas, cheeses, risottos, and other dishes in an authentic Tuscan style. We will be eating the true Italian way, local and seasonal.

Visits to 10 towns across 5 micro-regions of Tuscany

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 Grand Tour of Tuscany

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 ($4250 per person), due six weeks before the tour.

SPRING 2026 TOUR DATES: May 1-7, 2026

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.

What's Included

Accommodation in two gorgeous Tuscan agriturismos.

All transportation throughout the duration of the tour.

Ten winery visits and tastings.

All meals as detailed in the itinerary.

All cooking/cheesemaking 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.