12-24
Guests
8 / 7
Days / Nights
14
Meals
Join Rex Hill and raise a glass to the irresistible heart of Tuscany. Celebrated for its world-class wines, rich cultural heritage, and rolling landscapes dotted with olive groves, cypress trees, and vineyards, Tuscany is a place that captivates the senses of all who visit. Throughout our week together, meet passionate artisan creators, savor their exceptional wines and regional specialties, and explore medieval towns where history seamlessly blends with modern life. Discover the fascinating stories and timeless beauty of a region known as the cradle of the Renaissance.
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
Florence’s ancient cathedrals and iconic art, from the Duomo to Michelangelo’s David
Day 1
ARRIVE CORTONA
Land in the Florence Airport and take a private transfer to our accommodations in a renovated 17th-century monastery situated in the heart of the ancient hilltop town of Cortona.
Unwind at the property and take time to explore your new surroundings. This evening, we'll gather for introductions and a Welcome Dinner featuring local flavors.
Day 2
CORTONA
This morning, join our local guide for a walking tour of Cortona, where we’ll uncover the city’s rich Etruscan history and visit its significant sites. Afterward, we’ll immerse ourselves in the art of Tuscan cuisine during an interactive cooking class led by a local chef. Savor the dishes we prepare together for lunch, paired with a glass of local wine, and then enjoy the rest of the day relaxing, checking out the spa, or further exploring the charming streets of Cortona.
Day 3
Val d’Orcia
This morning, head southwest to the picturesque hillside village of Pienza, a UNESCO World Heritage Site. Enjoy a walking tour of this Tuscan gem, known for its stunning Renaissance architecture and the production of pecorino cheese. After some free time to explore at your own pace, we’ll take a scenic drive with breathtaking views of the Val d’Orcia to the beautiful Renaissance town of Montepulciano. Here, we’ll 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 second winery in the countryside. Afterward, we’ll return to our accommodations for an open evening.
Day 4
Siena
Discover the medieval city of Siena on a guided walking tour with a local expert. Visit the Siena Duomo and the art-filled Casa di Santa Caterina. Take time to explore at your own pace and enjoy lunch at your leisure. We’ll return to Cortona this afternoon and have time to relax before heading out to a wine estate for a tasting followed by a wine-paired dinner.
Day 5
Castiglion Fiorentino
Drive to the charming, walled city of Castiglion Fiorentino and spend the morning with our expert Italian cheesemaker at his workshop, which features two cheese caves. Learn the art of tasting, cutting, and smelling a variety of cheeses, gaining insights into traditional Italian cheesemaking techniques. Afterward, enjoy lunch at a quaint local restaurant.
In the afternoon, visit a traditional olive mill to discover the process of Tuscan olive oil production. Learn about its history and cultural significance and sample freshly pressed extra virgin olive oil. After returning to the hotel, take some time to relax, or perhaps stroll into town for 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. En route, we’ll stop at a wine estate in the heart of Chianti Classico for a tour, tasting, and wine-paired lunch.
This afternoon, we’ll continue to our hotel— a historic estate in the Tuscan countryside. After some time to relax, we’ll meet for a tasting of the estate’s wines followed by free time for dinner.
Day 7
Historic Florence
This morning, join our local guide for a walking tour of Florence’s most iconic landmarks, including the majestic Duomo di Firenze, the Ponte Vecchio, and more. Conclude the tour with a visit to the Accademia di Belle Arti, established by Cosimo I de’ Medici in 1563, where we’ll see Michelangelo’s original statue of David. 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, raising a glass to our shared experiences.
Day 8
DEPART FLORENCE
Enjoy breakfast at your hotel before taking a private transfer to the Florence Airport. Not ready to leave Italy behind? Continue your journey on an optional four-day extension in Portovenere & Cinque Terre. Arrivederci!
Day 8
Depart the city this morning and head west to the charming seaside village of Portovenere, nestled between the famous Cinque Terre and Gulf of Poets on the beautiful Ligurian coast. Enjoy lunch at a quaint restaurant that will treat you to a traditional pasta al pesto— the iconic dish of the area.
Afterward, meet a local guide for a walking tour of the highlights of this town: the church of San Pietro, which sits atop a cliff jutting out on the sea, the Doria Castle, and the carrugi— the iconic narrow alleys of eastern Liguria. Later, have some time to unwind and settle into your accommodations, located in the heart of Portovenere’s historic center with the evening open for your exploration.
Day 9
Join a local guide this morning and board the ferry that runs to the Cinque Terre— a UNESCO World Heritage group of remote villages perched dramatically on the cliffs. Stop first in the small fishing village of Vernazza for a cappuccino or a piece focaccia. Continue on to the lovely town of Monterosso to visit a winery nestled among the vineyards and lemon groves. Savor the local cuisine during a wine-paired lunch and let your palate be surprised by the deliciousness of the Sciacchetra— one of the best passito wines of Italy that hardly ever leaves the boot.
Afterward, return to Portovenere for an open evening.
Day 10
Day 11
Say farewell to this spectacular corner of the Italian Riviera. A private driver will transport you to Pisa International Airport for flights home. Arrivederci!
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.

Grand Hotel Portovenere (Cinque Terre Extension)
Grand Hotel Portovenere is nestled between the famous Cinque Terre and the inspirational Gulf of Poets in eastern Liguria. Once upon a time, the building hosted the XVII-century Convent of San Francesco. This boutique hotel overlooks the marina and the historic center of Porto Venere. It is just steps away from the boats that take you to the Cinque Terre and the Bay of La Spezia, which inspired poets such as Lord Byron and Mary and Percy Bysshe Shelley.
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, 5 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: $7,295
Deluxe: $7,895
Junior Suite: $8,495
Suite: $8,995
Single Occupancy:
Classic: $9,395
Deluxe: $10,295
Junior Suite: $11,395
Suite: $13,295
Extension Rates*
Classic: $ TBD
Single Occupancy: $ TBD
*Rates are per person in US Dollars.