5-Day Tuscany Combo Tour of Florence, Siena & Val d’Orcia with Wine Tastings & Cooking Class
- Instant confirmation
- Guided tour in English
About this experience
Experience the best of Florence and Tuscany over five unforgettable days of guided tours and activities. Explore historic Florence, wander charming Tuscan towns, and savor local wines and cuisine. This itinerary includes tours and experiences only, giving you the flexibility to choose your own accommodation.
Next available dates
What’s included
- Food and drinks
- Entry / admission fee
- Orientation walk of Florence
- Activities : Share group tour to Tuscany with wine and olive oil tasting in 2 wineries, hands on cooking course, share group tour to Siena, Montepulciano and Cortona with food & wine tasting
- Transport: Transfers between Florence & the Chianti region
- Professional tour leader providing insider knowledge and assistance
- Office Assistance pre departure
- Full Time office support during your stay
Not included
- Tips and gratuities
- Accommodation ( we recommend booking 2 nights in central Florence and 2 nights inside San Gimignano)
- Meals
- Transport where not specified in the program
Itinerary
- 1
Explore Florence’s Iconic Sights & Evening Freedom
Begin your adventure in Florence, checking into your accommodation of your own preference and joining your guide for a welcome walk through the historic center. Admire landmarks like the Duomo, Piazza della Signoria, and the Ponte Vecchio. Spend the evening discovering Florence at your own pace, dining in a traditional trattoria, sipping wine in a cozy café, or exploring hidden corners of the city. Meeting Point: Central Florence, TBC Meeting Time: 3.00 pm Duration: 2h
- 2
Florence Free Day: Customize Your Experience
Spend the next day exploring Florence at your own pace. Choose from optional activities like a day trip to Pisa and Cinque Terre or a walking tour of the Accademia and Uffizi museums.
- 3
Iconic Tuscan Towns, Siena, Cortona & Montepulciano and Val D'Orcia
On day three, depart Florence for a full full-day journey through some of Tuscany’s most iconic towns. Stop in Siena, a city of medieval splendor, and stroll through the atmospheric streets to reach the breathtaking Piazza del Campo. Continue to the hilltop town of Cortona, made famous by "Under the Tuscan Sun." Enjoy sweeping views of the surrounding valleys, browse artisan boutiques, and experience the timeless charm of a traditional Tuscan town. Pause for a local food tasting at a countryside farm. In the afternoon, visit Montepulciano, celebrated for its medieval streets and the renowned Vino Nobile di Montepulciano. Explore the town at a leisurely pace, taking in the views over the Val d’Orcia while learning about its rich history and wine culture. In the evening, return to Chianti. The day will end in the UNESCO-listed town of San Gimignano, where we recommend booking the 2 nights. Meeting Point: Piazza della Calza, Firenze. Meeting Time: 8:00 am Duration: 12h
- 4
Tuscany Countryside & San Gimignano Wine Experience
On day four, set off on a wine tour around the hills of San Gimignano. Stop at a boutique Chianti winery for a guided tasting of Chianti wines paired with regional specialties. Continue to a family-run estate in Chianti for more wine tasting. By mid-afternoon, arrive back to San Gimignano. Wander its winding cobbled streets, admire the medieval towers, and take in sweeping views of the countryside. Meeting Point: Bivio Volterra San Gimignano Meeting Time: 11:30 am Duration: 4h30'
- 5
Hands-On Tuscan Cooking & Farewell to Florence
On the final day, take part in a hands-on Tuscan cooking class, learning authentic recipes from a local chef. Sit down to enjoy the meal you’ve prepared, accompanied by a glass of local wine. Return to Florence by 5:00 PM, marking the conclusion of your Tuscan adventure. Meeting Point: Bivio Volterra Bus Stop, Via S. Gimignano, San Gimignano Meeting Time: 11:00 am Duration: 7h
Good to know
- Duration
- 5 days
- How you meet
- Meet on location
- Confirmation
- Instant confirmation
- Cancellation policy
- This booking is non-refundable once confirmed.
- Difficulty
- Easy
- Guide
- Guided tour in English
- Start times
- 15:00
Know before you go
- Public transportation nearby
- This is a partially guided, pre-booked adventure, designed for travelers who want the perfect balance of structure and freedom. Your major transfers, and key activities are arranged in advance, while you have flexibility to book your own accommodation and explore each city at your own pace.
- On-trip assistance is available whenever you need it, ensuring a smooth, stress-free Italian experience.
- The tour is ideal for:
- Couples or friends seeking a romantic, slow-paced immersion in Tuscany’s culture, food, and landscapes
- First-time visitors wanting a curated blend of Florence highlights, countryside charm, and iconic hilltop towns
- Wine lovers and food enthusiasts eager to enjoy tastings, local specialties, and a hands-on cooking class
- Travelers who enjoy small-group experiences, stress-free logistics, and authentic Tuscan traditions
Cancellation policy
This booking is non-refundable once confirmed.
24h Cancellation Policy
Meeting point
View on map
Central Florence -TBC
- Address
- Piazza di Santa Maria Novella, Firenze, 50123, IT
- How you meet
- Meet on location
- Coordinates
- 43.77363, 11.24985
Illustrative map. Open it in Maps for the exact spot and live directions.
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Frequently asked questions
How long does this experience last?
It lasts 5 days.
Can I cancel this booking?
This booking is non-refundable once confirmed.
Is this experience guided, and in what language?
Guided tour in English
Is hotel pickup included?
No — you make your own way to the meeting point.
Where does this experience start?
It starts at Central Florence -TBC, Piazza di Santa Maria Novella, Firenze, 50123, IT.
Still have a question?
Message our team on WhatsApp — we can help with dates, group bookings and anything else before you book.
From AED 3,876 per person
