An exclusive wine & food journey with


Umbria & Chianti

May 5 - 12, 2025



8 / 7

Days / Nights



Join Dobbes Family Winery on a captivating journey through the green heart of Italy on this wine and culinary adventure. From the tucked-away villages of Umbria to the wineries and vineyard-clad hills of Chianti, experience the local traditions and gastronomy, historic sites, and striking medieval architecture that permeate these regions. This unforgettable journey is sure to satisfy all your senses.


the ancient basilicas of San Francis and San Pietro and the medieval walled cities of Perugia and Siena


a variety of wines including Assisi DOC, Trebbiano, Super Tuscan,  and Chianti DOCG


the tranquil shoreline villages of Lake Trasimeno, inhabited since the age of the Etruscans and Romans

Day 1


Land at the Rome/Fiumicino Airport where a driver will be waiting to greet you and transport you to our accommodations nestled among the vineyards and olive groves of the Umbrian countryside. Upon arrival, have time to relax, get settled, and explore the sprawling grounds of the property. This evening, we’ll kick things off with introductions and a wine-paired welcome dinner featuring traditional regional dishes.


Overnight at Valle di Assisi Hotel

Day 2


Today, we begin our exploration of the region with a visit to a local estate for a wine tasting, culinary class, and lunch featuring a variety of local wines including Assisi DOC, Sangiovese, Merlot, Cabernet, Greghetto, and Trebbiano. After lunch, we’ll travel west to Lake Trasimeno, where we’ll embark on a scenic boat tour, taking in the historic shoreline villages. We’ll conclude the day with a visit to the fishing village of Passignano sul Trasimeno, on the northern shore of the lake, where we’ll have free time for dinner and a stroll through the ancient streets.

Breakfast, Lunch

Overnight at Valle di Assisi Hotel

Day 3


After breakfast, we’ll take a short drive south to the small medieval town of Bevagna where a local guide will share stories of the town’s rich history during a walking tour through ancient cobblestone streets. We’ll have some free time to explore before continuing on to the lovely village of Spello for an open lunch and free time. This afternoon, we’ll visit Tenuta Castelbuono, the Lunelli family’s Umbrian estate, devoted to the production of Montefalco Sagrantino where we’ll enjoy a tour and tasting at the family’s unique Carapace winery, designed by Italian sculptor Arnaldo Pomodoro. Dinner tonight will be at the property.

Breakfast, Dinner

Overnight at Valle di Assisi Hotel

Day 4


After breakfast, a short drive will take us to Eremo delle Carceri, a peaceful retreat located in the hills outside of Assisi. Enjoy a guided visit of the hermitage, founded by Saint Francis, and learn about its history and significance. For those feeling adventurous, there may be an opportunity to hike in the area and take in the stunning views. After the visit, stop for lunch in an authentic rustic venue featuring traditional simple dishes before continuing on to the hill town of Assisi, a UNESCO World Heritage Site known for its medieval architecture, churches, and spectacular views of the countryside. We’ll visit the Basilica San Francis, famous for its frescoes and enjoy a free evening in town to shop, have dinner, and wander at our own pace.

Breakfast, Lunch

Overnight at Valle di Assisi Hotel

Day 5


This morning, we head to Perugia, capital of the Umbria region. The town has been celebrated for its beautifully preserved historic center and cultural riches, and we’ll have some free time to explore before heading up the hill to visit the Basilica di San Pietro, known for its art collection and medieval gardens. We’ll experience “lunch of the Benedictine monks” with ingredients cultivated from the gardens and an exclusive wine tasting. Next we’ll head to Torgiano to visit the Lungarotti Winery and Wine Museum, where we’ll enjoy a tour and tasting of the Torgiano DOC wines. The evening will be open to enjoy dinner at the property or in one of the nearby towns.

Breakfast, Lunch

Overnight at Valle di Assisi Hotel

Day 6


We’ll check out this morning and make our way west to the beautiful medieval city of Siena where we’ll join an expert local guide for a walking tour of the city’s highlights, including a visit to the Duomo. After, enjoy some free time to have lunch and explore the city at your own pace. Later in the afternoon, we’ll drive north to our accommodations nestled in the heart of the Chianti countryside. Relax and walk around this gorgeous estate, home to olive trees and vineyards before gathering for dinner.

Breakfast, Dinner

Overnight at Torre a Cona Wine Estate

Day 7


Today, we’ll have a relaxing morning before heading out to visit a winery producing Super Tuscan wines. Our visit will include a wine tasting and tour of the property, providing a unique insight into the history of the denomination and production methods. Afterwards, we’ll venture to the hilltown of Panzano where we’ll have time for a stroll before sitting down to a festive Farewell Dinner at the infamous Antica Macelleria Cecchini.

Breakfast, Dinner

Overnight at Torre a Cona Wine Estate

Day 8


After breakfast, we'll be transported to the Florence Airport for departure flights home. Not ready to say farewell? Extend your travels with 4 days in Bolgheri and the Etruscan Coast.


Extend your trip

+ 4 days in Bolgheri
and the Etruscan Coast

Day 8


We extend our exploration of Tuscan culture and wine, journeying west toward the Etruscan Coast, known for its natural beauty, seaside resorts, archaeological sites, and good food and wine. Enjoy a stop en route in the medieval town of Volterra, the city of Alabaster. We will have an open lunch in downtown Volterra before continuing our journey to our beautiful seaside accommodations. The remainder of the day is free to relax and unwind at the property.


Overnight at The Sense Resort or similar

Day 9

Massa Marittima

After a relaxing morning and free time for lunch, we'll head northeast to the hilltop town of Massa Marittima where a local guide will take us on a walking tour within the walls of the town's historic center. Enjoy some free time to stroll through the town's cobbled streets before taking a short drive into the countryside to a biodynamic vineyard and winery where we'll be introduced to this natural method of winemaking and farming. A tour of the vineyards will be followed by a tasting of the estate's wines and dinner at the Villa.

Breakfast, Dinner

Overnight at The Sense Resort or similar

Day 10


Today we visit Antinori’s Tenuta Guado al Tasso estate in the small but prestigious Bolgheri DOC, the birthplace of the Super Tuscan movement. The estate, where porcupines wander the roads at night and wild boar roam in the woods, contains a home where the Antinori family spends weekends and holidays. Discover the historic vineyards of the estate, learn about the unique microclimate, and enjoy a memorable lunch at the Osteria del Tasso, overlooking the Via Bolgherese “wine road.” Afterward, we’ll stop for a stroll in the lovely village of Bolgheri before returning to the property.

Breakfast, Lunch

Overnight at The Sense Resort or similar

Day 11


After breakfast, a transfer will take you to Pisa or Florence Airport for flights home. Arrivederci!



The Fine Print

Questions? Get in touch.



Program: May 5 - 12, 2025
Extension: May 12 - 15, 2025

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
  • 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


Classic: $5,795
Superior: $6,095
Junior Suite: $6,595

Single Occupancy: $6,795

Extension Rates*

Classic: $3,395
Single Occupancy: $4,195

*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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