An exclusive wine & food journey with

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Taste of Tuscany

April 12 - 19, 2026

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.

Dinner

Overnight at Monastero di Cortona

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.

Breakfast, Lunch

Overnight at Monastero di 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.

Breakfast, Lunch

Overnight at Monastero di Cortona

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.

Breakfast, Dinner

Overnight at Monastero di Cortona

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.

Breakfast, Lunch

Overnight at Monastero di Cortona

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. 

Breakfast, Lunch

Overnight at Torre a Cona Wine Estate

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.

Breakfast, Dinner

Overnight at Torre a Cona Wine Estate

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!

Breakfast

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.

Breakfast

Overnight at Grand Hotel Portovenere

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!

Breakfast

Accommodations

The Fine Print

Questions? Get in touch.


Details

Dates

Program: April 12 - 19, 2026
Extension: April 19 - 22, 2026

Flight Information

If you would like assistance with reserving your flights, please contact us at guestservices@experi.com, 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 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.


Deposits

A $1,500 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 $750 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 https://experi.com/travelinsurance/

Travel Terms & Conditions

View our complete terms and conditions here at https://experi.com/agreement.

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