An exclusive wine & food journey with
Taste of Tuscany
May 15 - 22, 2026
12-24
Guests
8 / 7
Days / Nights
14
Meals
Join us as we raise a glass to the irresistible heart of Tuscany. Celebrated for its world-class wines, rich cultural heritage, and rolling landscapes of olive groves, cypress trees, and vineyard-covered hills, Tuscany captivates the senses of all who visit. Throughout our week together, meet passionate artisan creators and savor their exceptional wines and regional specialties. Explore medieval towns where history blends seamlessly with modern life. Uncover the legendary art and architecture that have shaped the spirit and identity of this storied region.
Taste
the essence of Tuscany in a hands-on cooking workshop, crafting authentic dishes with expert guidance
Explore
the charming towns of Cortona, Siena, and Pienza, savoring local wines and specialties at each stop
Discover
the region's ancient cathedrals, historic piazzas, and awe-inspring art, including Michelangelo’s David
Day 1
ARRIVE CORTONA
Land at the Florence Airport and take a private transfer south to our accommodations in a renovated 17th-century monastery in the ancient hilltown of Cortona.
Unwind at the hotel and take time to explore your new surroundings. We'll gather this evening for introductions and a Welcome Dinner featuring local flavors.
Day 2
CORTONA
Start the day with a walk through the historic center of Cortona, where a local guide will introduce us to the town’s rich Etruscan roots and notable highlights. Next, we’ll roll up our sleeves and dive into the art of Tuscan cuisine during a hands-on cooking class led by a local chef. Afterward, we’ll gather at the table to savor our creations for lunch, paired with a glass of local wine. The rest of the day is open to relax, enjoy the spa area at the hotel, and further explore the charming streets of Cortona.
Day 3
Val d’Orcia
This morning, head southwest to the picturesque village of Pienza, a UNESCO World Heritage Site. Enjoy a walking tour of this Tuscan gem, known for its Renaissance architecture, as well as the production of pecorino cheese. After some free time to explore, we’ll continue through the scenic Val d’Orcia to the Renaissance town of Montepulciano. Visit a historic winery and taste the prestigious Vino Nobile di Montepulciano, one of Tuscany’s most sought-after wines. Enjoy a light lunch and stroll through the cobblestone streets of this charming town before continuing to a nearby olive farm. Learn about the longstanding Tuscan olive oil traditions as we walk through the olive groves and sample freshly pressed extra virgin olive oil produced onsite.
Day 4
Siena
After breakfast, we’ll venture west to the stunning medieval city of Siena, where a local guide will bring the city’s rich history and traditions to life. Visit the magnificent Siena Cathedral, and learn about the city's contrade (neighborhood districts) and the thrilling Palio di Siena horse race in the city’s Piazza del Campo. Afterward, enjoy free time to find a spot for lunch and explore at your own pace. On our return to Cortona, we will stop at a family-run winery overlooking the Tuscan hills for a dinner featuring traditional regional dishes paired with the estate’s Cortona DOC wines.
Day 5
Castiglion Fiorentino
This morning, we’ll meet a passionate cheese expert who will share insights into traditional Italian cheesemaking techniques and enlighten us on the art of tasting, cutting, and smelling a variety of cheeses. Afterward, head to a quaint local restaurant famous for its steak Fiorentina and enjoy lunch paired with minimal-intervention red wines from a local producer.
In the afternoon, visit a small, traditional olive mill to experience another aspect of Tuscan olive oil production. After returning to the hotel, enjoy time to relax or do some shopping and sightseeing. Dinner this evening is on your own. Our Travel Director is happy to provide recommendations.
Day 6
Chianti
After breakfast, we’ll check out of the hotel and travel northwest to the Chianti region. Along the way, we’ll stop at a farm in the heart of Chianti Classico for a guided truffle hunt through the woods. Learn about the tradition of truffle hunting and how skilled dogs are trained to detect these prized ingredients. Afterwards, enjoy a truffle-themed lunch paired with local wines.
In the afternoon, we’ll continue to our hotel — a historic estate nestled in the beautiful Tuscan countryside. After some time to settle in, we’ll gather for a tasting of the estate’s wines followed by an open evening.
Day 7
Historic Florence
This morning, we’ll head into the Renaissance city of Florence and join a local guide for a walking tour of the city’s most iconic landmarks, including the majestic Duomo di Firenze, the Ponte Vecchio, and more. Along the way, we’ll stop into a few specialty shops to sample local artisanal products and get a taste of Florence’s culinary traditions. Afterward, enjoy some free time to shop and explore Florence at your own pace before we return to our accommodations. This evening, we’ll celebrate our journey with a festive Farewell Dinner at the property.
Day 8
VOLTERRA
We extend our exploration of Tuscan culture as we head west toward the Etruscan Coast. Our first stop is the medieval town of Volterra, known for its alabaster craftsmanship. After a demonstration by local artisans, we’ll have lunch at a nearby restaurant and continue driving to our destination overlooking the Tyrrhenian Sea. The remainder of the day is free to relax and unwind at the property.
Day 9
ELBA ISLAND
Depart for the coastal town of Piombino, where we’ll board a ferry to the island of Elba. Situated between the Ligurian and Tyrrhenian Seas, Elba is a natural paradise with a rich history dating back to the Etruscans and Romans. Upon arrival, we’ll make our way to Porto Azzurro, a seaside town known for its picturesque waterfront, lively piazza, and Spanish fortifications. Take time to stroll along the harbor, browse artisan shops, or relax in a cafe overlooking the bay before we sit down for lunch at a local restaurant. Afterward, we’ll board the ferry to return to the mainland.
Day 10
BOLGHERI
Enjoy a leisurely breakfast and free time to explore the offerings at the property. This afternoon, we’ll head to the lovely medieval village of Bolgheri, where we’ll have time for a walk before continuing to the small but prestigious Bolgheri DOC, known as the birthplace of the Super Tuscan movement. Visit a prestigious local estate to discover the historic vineyards, learn about the unique microclimate, and enjoy a delicious dinner.
Accommodations
Monastero di Cortona Hotel & Spa
Monastero di Cortona Hotel & Spa is a renovated 17th-century monastery situated inside the ancient walls of the town of Cortona. The location of the property provides easy access to the shops and restaurants in the historic town and a lovely setting with views of the Tuscan countryside. Hotel amenities include a terrace and garden, bar, complimentary WiFi, and health & wellness facilities. Distinctive and charming guest rooms feature minibar, safe, toiletries, hair dryer, bathrobe, and slippers.
Torre a Cona Wine Estate
This historic villa in the Tuscan countryside is also a working wine estate, surrounded by picturesque vineyards, olive groves, and gardens. The property features a restaurant, bar, outdoor pool, and complimentary WiFi. Rooms are equipped with air conditioning, electric kettle, minibar, toiletries, bathrobe, and hairdryer.
The Sense Resort (Bolgheri Extension)
Situated in the heart of the Tuscan Maremma, this resort property is nestled in a pine forest with beautiful views overlooking the Tyrrhenian Sea. The property features multiple dining options, bar/lounge, private beach club, seasonal heated pool, walking trails, complimentary bicycles, and fitness classes. Spacious rooms offer a terrace with sea view, air conditioning, coffee/tea maker, complimentary WiFi, and bathroom equipped with bathrobes, slippers, toiletries, and hairdryer.
The Fine Print
Questions? Get in touch.
Details
Dates
Flight Information
Activity Level
This trip has been designed to include daily exploratory walks that range from one to three hours. Each day, whether touring a city or winery, guests should be prepared to be on their feet for multiple continuous hours. Guests should feel comfortable strolling along cobbled surfaces, walking up and down stairs, and sauntering down uneven nature paths. Europe tends to have Old World infrastructure (narrow cobblestone streets, lack of elevators, etc.), which can leave some areas inaccessible. Typically, our more invigorating walks are included as optional activities. If your mobility is limited in any way, or if you have questions, please contact our Guest Services team at guestservices@experi.com.
Note: The itinerary is subject to change or substitution at any time. You can learn more at experi.com/agreement.
Included
- Seven nights accommodations, including all taxes and fees
- Meals as listed on the itinerary: 7 breakfasts, 4 lunches, and 3 dinners, plus wine pairings with most major meals
- All private excursions described in the itinerary along with services of local speakers, guides, entrance fees, and transportation
- Gratuities for travel director, local guides, drivers, porters, and included meals
- Full guiding services of a dedicated Travel Director
- Private airport transfers with porterage on the first and last scheduled days of the program
Not Included
- Pre-and post-trip accommodations and associated expenses
- Air and land transportation to/from host cities
- All types of personal insurance
- Personal expenses
- Additional alcoholic beverages beyond what has been arranged by Experi to pair with the included major meals
Rates*
Double Occupancy:
Classic: $7,895
Deluxe: $8,595
Junior Suite: $9,395
Suite: $10,495
Single Occupancy:
Classic: $10,395
Deluxe: $11,195
Junior Suite: $12,695
Suite: $14,995
Extension Rates*
Double Occupancy:
Classic: $2,995
Deluxe: $3,395
Junior Suite: $3,895
Single Occupancy:
Classic: $3,795
Deluxe: $4,295
Junior Suite: $5,195
*Rates are per person in US Dollars.
Deposits
Travel Insurance
Travel Terms & Conditions
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