An exclusive wine & food journey with



June 9-16, 2024

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8 / 7

Days / Nights



Come together and raise a glass to the irresistible heart of Tuscany. With its world-class wines, cultural treasures, and rolling countryside dotted with olive groves, cypress trees, and vineyards, Tuscany captivates the senses of all who visit. During our week together, meet proud artisan creators and savor their superb wines and regional specialties, discover medieval towns and marvel at the seamless blending of past and present, and learn the fascinating history of the region known as the cradle of the Renaissance.


the traditions of Tuscan cooking during a hands-on workshop


Chianti, Siena, Pienza, and more, tasting local specialties and wines along the way


ancient cathedrals and works of art while discovering beautiful Florence

Day 1


Land in the Florence Airport where an Experi representative will greet you and assist with a 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 a Welcome Dinner featuring local flavors.


Overnight at Monastero di Cortona

Day 2


This morning join our local guide for a walking tour of Cortona - your host town for the first part of your trip. Discover the city’s amazing Etruscan history and visit some of its most important sites. Enjoy some free time to lunch on your own in one of the many eateries.
In the afternoon, visit an olive oil mill — one of the few remaining mills to operate a traditional, cold-stone milling process. We’ll meet the family and taste fragrant, freshly pressed oils over wood-fired grilled bruschetta. After, roll up your sleeves and get ready to prepare a pizza dough at a lovely quaint pizzeria in the outskirts of town. Learn the local secrets and then sit down for a family dinner.

Breakfast, dinner

Overnight at Monastero di Cortona

Day 3

Val d’Orcia

This morning, head to the beautiful medieval and Renaissance town of Montepulciano for a very special winery visit. Taste one of the most sought-after Tuscan wines: Nobile di Montepulciano. Enjoy a light lunch and take a stroll among the cobblestone streets of this charming village located between the Valdichiana and Val d’Orcia.

After a short drive with breathtaking views of the Val d’Orcia, we’ll arrive in the picturesque hillside village of Pienza, a UNESCO World Heritage Site. Enjoy a walking tour of this Tuscan gem, famous - among other things - for the production of pecorino. Enjoy some free time to shop around Pienza’s gourmet and petite boutiques. Return to the property and unwind. Dinner is on your own tonight back in Cortona.

Breakfast, lunch

Overnight at Monastero di Cortona

Day 4


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. Back at the villa, we’ll have time to relax before heading out to a wine estate for a tasting followed by a wine-paired dinner.

Breakfast, dinner

Overnight at Monastero di Cortona

Day 5

Castiglion Fiorentino

Drive to the small, walled city of Castiglion Fiorentino and spend the morning with our Italian cheese expert at his workshop featuring two cheese caves. Learn techniques to taste, cut, and smell different cheese varieties. After, enjoy lunch at a quaint restaurant.

The afternoon is at your leisure. Spend time at the hotel or perhaps walk to the downtown area of Cortona for additional shopping and sightseeing. Dinner is on your own this evening.

Breakfast, lunch

Overnight at Monastero di Cortona

Day 6


After breakfast, we’ll check out of the hotel and travel to the Chianti region. En route, we’ll stop at one of the charming hilltop villages of Chianti for a stroll and free time for lunch. Afterward, we'll continue to our accommodations: a beautiful wine estate with views over the surrounding olive orchards and vineyards.

Check-in, relax, and explore the property. We'll meet up later for a wonderful in-depth tasting followed by dinner at the property.

Breakfast, lunch

Overnight at Torre a Cona Wine Estate

Day 7

Historic Florence

This morning, we'll head to Florence and join a local guide for a walking tour of the city’s famous sites, including the Duomo di Firenze, San Lorenzo Market, Ponte Vecchio, and more. End of our tour with a visit to the Accademia di Belle Arti, an art academy founded by Cosimo I de’ Medici in 1563, which now hosts the original statue of Michelangelo’s famous David. After the visit, enjoy free time to explore at your own pace before returning to the property.

This evening, we'll toast our journey with a festive Farewell Dinner at the property.

Breakfast, dinner

Overnight at Torre a Cona Wine Estate

Day 8


Enjoy breakfast at your hotel before transferring to the Florence Airport. Not ready to leave Italy behind? Continue your journey on an optional four-day extension in Cinque Terre. Arrivederci!


Extend your trip

+ 4 days in Portovenere & Cinque Terre

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.

Breakfast, lunch

Overnight at Grand Hotel Portovenere

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. 

Breakfast, lunch

Overnight at Grand Hotel Portovenere

Day 10

On your last day in the region, enjoy free time to explore at your own pace. Take a stroll along the harbor and the narrow pedestrian shopping street, Via Capellini, or check out one of the beautiful swimming spots near the hotel. If you feel like venturing further afield, you could return by boat or ferry to one of the Cinque Terre villages or travel by boat or kayak to nearby Palmaria Island where hiking trails, caves, and secluded beaches are waiting to be discovered.


Overnight at Grand Hotel Portovenere

Day 11

Say farewell to this spectacular corner of the Italian Riviera. A driver will transport you to Florence Airport for flights home. Arrivederci!



The Fine Print

Questions? Get in touch.



Program: June 9 - 16, 2024
Extension: June 16 - 19, 2024

Flight Information

If you would like assistance with reserving your flights, please contact us at, and we can refer you to an air ticket travel agency.

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

Note: Group maximum is based on double occupancy. The itinerary is subject to change or substitution at any time. You can learn more at


  • Seven nights accommodations, including all taxes and fees
  • Meals as listed on the itinerary: 7 breakfasts, 3 lunches, and 4 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
  • 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


Classic: $6,495
Deluxe: $6,995
Jr. Suite: $7,495
Suite: $8,295  SOLD OUT

Single Occupancy: $7,995

Extension Rates*

Classic: $2,995
Jr. Suite: $4,595

Single Occupancy: $3,995

*Rates are per person, double occupancy in US Dollars.


A $1,000 non-refundable deposit per person reserves your space for this program. Final payments are due no later than 90 days prior to departure. An additional $500 non-refundable deposit is required for extension reservations.

Travel Insurance

Learn more about travel insurance and how it can help you prepare for the unexpected at

Travel Terms & Conditions

View our complete terms and conditions here at

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