• Direct In Italy: +39 375 823 5314
  • Toll Free: 1-866-779-2565
Umbria and Tuscany, Private Food & Wine Experience Umbria, Italy. Escorted Tours with Italy Vacation Specialists Private Tuscany and Umbria Food and Wine Experience

Semi-Private · Rome

Tuscany & Umbria: Exclusive Small Group Tour Including Florence

7 Days Umbria · Tuscany

The Overview

Overview

This deluxe small group tour through Tuscany and Umbria offers our guests the possibility to experience two of Italy's most beautiful wine regions as well as Florence.  There are many highlights on this tour including a private cooking class with a local Tuscan Chef as well as dinner at a farm in the heart of Chianti wine territory. 

This journey through Tuscany and Umbria begins in Rome and ends in Florence.  Gourmet meals including select wines are included in the package price.  

The properties where we stay in each location are some of the finest hotels each destination has to offer.  

Duration

7 days

6 nights

Starting From

EUR 3,820

Per person for two travelers

Tailored to your departure and group.

This deluxe small group (or private tour ) through Tuscany and Umbria in central Italy offers our guests the possibility to experience two of Italy's most beautiful wine regions as well as Florence. There are many highlights on this tour including a private farm to table cooking class with a local Tuscan Chef as well as lunch at a farm in the heart of Chianti wine territory.

Regions
Umbria · Tuscany
Tour Style
Semi-Private
Departs From
Rome
Included Meals
Daily breakfast · 3 dinners · 2 lunches · 1 wine tasting
Day by day

Itinerary

Follow the route as you read. The map traces each day of the journey, moving with you from place to place.

Umbria

Chapter 1 · Days 1–1

Welcome to Umbria

Umbria is one of the most beautiful regions in central Italy. South from Florence, north from Rome, it is often referred to as 'Italy's green heart', for it is the geographic center of the county.   it's lovely countryside and rolling sea of valleys and rolling hills are totally land-locked between the regions of Tuscany, Lazio and Marche .  Italy's capital…

Explore Umbria
Day 1

Umbria, Orvieto Tuscany, Cortona

Private Transfer from Rome Airport - Cortona with Stop in Orvieto

  • Dinner
Private Transfer from Rome Airport - Cortona with Stop in Orvieto — photo 1 Private Transfer from Rome Airport - Cortona with Stop in Orvieto — photo 2 Private Transfer from Rome Airport - Cortona with Stop in Orvieto — photo 3 Private Transfer from Rome Airport - Cortona with Stop in Orvieto — photo 4 Private Transfer from Rome Airport - Cortona with Stop in Orvieto — photo 5

Our journey today will begin from the Rome Airport Hotel Isola Sacra at 09:00 in the morning where our tour conductor will be there to met you and privately transfer you through the regions of Lazio and Umbria to Cortona. 

We will stop today en-route in the beautiful city of Orvieto where you will experience a privately guided tour of this remarkable cliff-top town and free time for lunch and shopping in Orvieto.

In the afternoon, we carry onto Cortona where you will enjoy time for relaxation by the pool or in the spa and a welcome dinner featuring some of this region's finest products.

Overnight at the hotel in Cortona. 

Tuscany

Chapter 2 · Days 2–7

Welcome to Tuscany

Tuscany is among the most beautiful regions of Italy. The gentle curves and slopes of the land will enchant you. Tuscany is as famous for its wine and cuisine as it is for its landscapes. Wine production focuses on red wines like Chianti, San Giovese, Rosso di Montalcino, Rosso di Montepulciano, Bolgheri, and others. Food is prepared with seasonal…

Explore Tuscany
Day 2

Tuscany, Cortona Tuscany, Castiglion Fiorentino

Private Tour of Cortona followed by Lunch & Olive Oil Tasting in an ancient Olive Mill

  • Breakfast
Private Tour of Cortona followed by Lunch & Olive Oil Tasting in an ancient Olive Mill — photo 1 Private Tour of Cortona followed by Lunch & Olive Oil Tasting in an ancient Olive Mill — photo 2 Private Tour of Cortona followed by Lunch & Olive Oil Tasting in an ancient Olive Mill — photo 3 Private Tour of Cortona followed by Lunch & Olive Oil Tasting in an ancient Olive Mill — photo 4 Private Tour of Cortona followed by Lunch & Olive Oil Tasting in an ancient Olive Mill — photo 5

This morning, following a delectable buffet breakfast at your hotel, you will begin a guided walking tour of Cortona with one of our top local guides who will introduce you to how Cortona has played an important role in Tuscany's history as one of the twelve major Etruscan cities.  The town is home to rich in archaeological sites, including the remains of Etruscan walls and artifacts that provide insights into ancient Etruscan culture.

You will learn about its Roman Influence Following the Etruscans and about how Cortona came under Roman control, further enhancing its importance as a strategic military and commercial center. The Romans established roads and trade routes that contributed to its growth and throughout the Renaissance, the art and culture which grew up in Cortona was incredible and Cortona became a rich created center for Renaissance art and culture, home to notable figures like the painter and architect Andrea Vasari. The town boasts beautiful architecture and art, seen in its churches and palaces.

Following our guided we will transport you to the Buccelletti wine and olive estate where you will be served a gourmet farm to table lunch complete with wine and olive oil tastings presented by our local hosts at this marvelous estate.  

Return to Cortona in the evening for free time for shopping and dinner at leisure. 

Day 3

Tuscany, Val D'Orcia Tuscany, Montepulciano Tuscany, Pienza

The Spectacular Orcia Valley including: Montepulciano, Pienza and Bagnovignoni

  • Breakfast
  • Lunch
The Spectacular Orcia Valley including: Montepulciano, Pienza and Bagnovignoni — photo 1 The Spectacular Orcia Valley including: Montepulciano, Pienza and Bagnovignoni — photo 2 The Spectacular Orcia Valley including: Montepulciano, Pienza and Bagnovignoni — photo 3 The Spectacular Orcia Valley including: Montepulciano, Pienza and Bagnovignoni — photo 4 The Spectacular Orcia Valley including: Montepulciano, Pienza and Bagnovignoni — photo 5

We depart this morning for the beautiful Tuscan town of Montepulciano known around the world for the 'Vino Nobile' or Noble Wine that is produced here.

This is a spectacular town surrounded by 365 degree views of valleys laced with vineyards and here you will have a chance to explore the town before we begin our morning visit to one of the most impressive wineries in Tuscany which is completely underground 'Cantina De Ricci'.   Here, you will explore not only the history of wine production in this area but the incredible infrastructure of the Etruscans and incredible engineering that enabled many of these towns and cities to flourish.

You will enjoy wine tasting and lunch in Montepulciano before we head onto some of the other towns in the area like Pienza and Bagnovignoni.   

In the afternoon we return to Cortona for dinner at leisure and time for relaxation.  

Day 4

Tuscany, Pisa

Discovering the Legacy of Saint Francis in Assisi & the Power of the Etruscans in Perugia

  • Breakfast
  • Dinner
Discovering the Legacy of Saint Francis in Assisi & the Power of the Etruscans in Perugia — photo 1 Discovering the Legacy of Saint Francis in Assisi & the Power of the Etruscans in Perugia — photo 2 Discovering the Legacy of Saint Francis in Assisi & the Power of the Etruscans in Perugia — photo 3 Discovering the Legacy of Saint Francis in Assisi & the Power of the Etruscans in Perugia — photo 4 Discovering the Legacy of Saint Francis in Assisi & the Power of the Etruscans in Perugia — photo 5

This morning following breakfast in Cortona we depart for Assisi where we will be met by our local expert guide who will be taking us on a unique deep dive into Assisi and the legacy of Saint Francis who is one of the most revered figures in Christian history and is known for his profound commitment to poverty, humility, and service to others.

Saint Francis was the son of a wealthy merchant and in his youth, he lived a life of luxury and indulgence, however after a series of personal and spiritual experiences, including a period of illness and imprisonment during a conflict, Francis underwent a profound conversion. He renounced his wealth and dedicated himself to living a life of poverty and serving the poor.   In 1209, he founded the Order of Friars Minor (Franciscans) with a group of followers. The Franciscans emphasized simplicity, fraternity, and a deep connection to nature and all living things.  His teachings and the Franciscan Order have had a lasting impact on Christianity, inspiring countless individuals to live lives of service, compassion, and simplicity

Francis is often celebrated for his love of animals and nature, famously giving a sermon to birds and being the patron saint of animals and the environment. He is venerated in various Christian denominations, including the Roman Catholic Church. Saint Francis' message of peace, care for creation, and love for all living creatures continues to resonate with many around the world today.

It is a truly remarkable and beautiful thing to walk the same streets fo Saint Francis in Assisi and discover his legacy first hand with one of our best guides. 

Following our break for lunch in Assisi (on your own), we head north to Perugia where you will enjoy an afternoon walk through the town and enjoy time for shopping and learning about one of Italy's most impressive university towns, before we return back to Cortona for dinner and overnight.

Day 5

Tuscany, Siena Tuscany, San Gimignano

Siena & San Gimignano en-route to Florence

  • Breakfast
  • Lunch
  • Wine Tasting
Siena & San Gimignano en-route to Florence — photo 1 Siena & San Gimignano en-route to Florence — photo 2 Siena & San Gimignano en-route to Florence — photo 3 Siena & San Gimignano en-route to Florence — photo 4 Siena & San Gimignano en-route to Florence — photo 5

This morning following breakfast at the hotel we will head north to the incredible towns of Siena and San Gimignano located in the heart of Italy's Chianti region.

Siena is home to one of Italy's largest piazzas and highest bell-towers.  One of our top guides will showcase the best of what this city has to offer before we break for lunch and head to San Gimignano where you will enjoy a sumptuous Tuscan lunch complete with elaborate wine tasting.

After lunch, we will stop in San Gimignano itself to explore this town which is known as the Manhattan of Tuscany where you will have time to shop the fine assortment of leather wears this city is famous for.

It's about a 1 hour drive to Florence from here and upon checking into your hotel in Florence you will have time to settle in and enjoy an evening walking the divine streets of Florence's city center. 

Overnight at the hotel in Florence.  

Day 6

Tuscany, Florence

Full Day Florence including the Accademmia Gallery & Farewell Dinner

  • Breakfast
  • Dinner
Full Day Florence including the Accademmia Gallery & Farewell Dinner — photo 1 Full Day Florence including the Accademmia Gallery & Farewell Dinner — photo 2 Full Day Florence including the Accademmia Gallery & Farewell Dinner — photo 3 Full Day Florence including the Accademmia Gallery & Farewell Dinner — photo 4 Full Day Florence including the Accademmia Gallery & Farewell Dinner — photo 5

Following breakfast at the hotel today, our local expert guide will be there to meet you at the hotel to begin your private walking tour of this enchanting capital city.

Your guide will be able to bring the history of Florence to life and showcase many of the city's finest historical and artistic treasures.

Around 13:00 PM we will conclude at the Accademmia gallery where you will enjoy Michelangelo's David and then break for lunch and free time for shopping in the afternoon.

At approximately 19:30 PM this evening we will begin our farewell dinner.

Overnight in Florence.  

Day 7

Tuscany, Florence

Time to Say Arrivaderci!

  • Breakfast
Time to Say Arrivaderci! — photo 1 Time to Say Arrivaderci! — photo 2 Time to Say Arrivaderci! — photo 3 Time to Say Arrivaderci! — photo 4 Time to Say Arrivaderci! — photo 5

Following breakfast at the hotel this morning it will be time to say Arrivaderci and we can assist you in organizing private transportation to the Florence Airport or Rail Station or making other arrangements for your time here in Italy.

The details

Inclusions & Exclusions

What's Included

  • 24-hour emergency service
  • Accommodation in Centrally Located, Four Star Hotels
  • Cooking class
  • Detailed explanation of sites
  • English speaking tour escort for the duration of the tour
  • Excellent Photo Opportunities
  • Friendly and Professional Service
  • Siena and San Gimignano
  • Specialized and Personal Service
  • Wine and Olive Oil Tastings in Chianti and Montepulciano
  • Winery Visits

What's Not Included

  • Optional excursions during your tour
  • Travel Insurance
  • Arrival transfer
  • Porterage at airport on arrival
  • City Tax( 4€ per person per night, to be paid locally. The amount may change according to local policy ) Tips
  • Beverages and meals not mentioned in the program
Your rooms

Where You'll Stay

Hotels are subject to availability and may be replaced with a property of similar standard.

Hotel Berchielli

Hotel Berchielli

Tuscany, Florence

Hotel Berchielli is a luxurious 4-star establishment nestled in the heart of Florence. Situated on the picturesque riverfront, the hotel boasts breath...

Discover Property
Hotel San Michele

Hotel San Michele

Tuscany, Cortona

Hotel San Michele is located inside of one of the oldest buildings of Cortona, the ancient Baldelli Palace, strategically located right in the heart o...

Discover Property
Hotel Villa Marsili

Hotel Villa Marsili

Tuscany, Cortona

Hotel Villa Marsili, nestled in the heart of Cortona, welcomes you with a blend of historical elegance and modern comfort. This exquisitely restored v...

Discover Property
In their words

Traveler Reviews

Emily and David Davison Travelled with us

My husband and I just took a two week trip to Italy that was planned for us by Eleanor Kinchin-Smith. It was a fantastic trip and we could not have been more thrilled. We worked together with Ele to let her know about our interests and our style of travel. She planned the perfect trip with excellent private guides at all of our sites, professional drivers and lovely hotels. We arrived in Italy with all of our train and ferry reservations made by Ele, with tickets in hand. She was in touch with us daily throughout our trip to make sure that things were going smoothly. She was able to make a few changes to our itinerary as needed. We look forward to working with Ele again on our next trip and have put her in touch with another family member to help plan their trip as well.

Ron and Deb Crosby Travelled with us

Dear Guiseppe and Jesse,

We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future.

Hotels

1. Hotel Sovestro in San Gimignano was wonderful. The staff were very friendly and helpful and made the first portion of our journey very stress free. They made us feel like we were part of their family. I would recommend it to anyone and would specifically ask for it if we were to make a return visit.

2. Hotel La Baia in Monterosso was nice and it's location was very good especially for us older folks humping luggage from/to the train station.

3. Hotel Lucchesi in Florence- what can I say expect FANTASTIC. The rooftop view at sunset is well worth it. Again very friendly and helpful staff. Would recommend it to everyone.

Wine Tour

Money well spent. We had a great time overall. The driver Mario was OUTSTANDING. He had lots of local knowledge as well as about winemaking. USE HIM AGAIN!!!

The various wineries we visited on tour:

Altesino- fantastic and they were not cheap on their pouring. Great experience.

Azienda Agricola Patrizia Cencion Sloaria- Again a great tour by one of the owner's daughters. We felt like we were the only thing on their mind although there were other customers there. A great way to complete the day.

Again we had a fantastic time and are very appreciative of everything you booked for us. We wish you continued success and if our travels should bring us back to Italy, we know who to call.

Leon and Michele Travelled with us

The trip was great we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details in particular Giuseppe spending the time and the focus with us on the road and as we were exploring your great country.

Bob & Sandy Travelled with us

Jesse & Giuseppe,

Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever.

Where you are

Location

Italy Rome

Rome and beyond

7 days through Italy, with every stop chosen by the people who live here.

Where it starts

Rome

Nearby Experiences

Roman Street Food Tour
Roman Street Food Tour
Milan - Lake Como & Lugano Switzerland
Milan - Lake Como & Lugano Switzerland
Tour On Board The Legendary Fiat 500
Tour On Board The Legendary Fiat 500
Treasures of Tuscany & Gourmet Delights of Emilia Romagna Educational Trip
Treasures of Tuscany & Gourmet Delights of Emilia Romagna Educational Trip
Rome Mini Stay - Ideal for Cruise Ship Passengers - Includes transfers from Airport to Hotel & Civitavecchia, tour of Vatican City and Ancient Rome with VIP tickets included
Rome Mini Stay - Ideal for Cruise Ship Passengers - Includes transfers from Airport to Hotel & Civitavecchia, tour of Vatican City and Ancient Rome with VIP tickets included
The Vatican For Children
The Vatican For Children
Venice Mini-Stay: 3 days/2 nights
Venice Mini-Stay: 3 days/2 nights
Rome & the Amalfi Coast including Vatican City, Island of Capri, Pompeii and the Wineries of Mt. Vesuvius
Rome & the Amalfi Coast including Vatican City, Island of Capri, Pompeii and the Wineries of Mt. Vesuvius
Best Life Ever Tuscany: A continuation of Best Life Ever Amalfi Coast - Almost All Inclusive October 16-22, 2024
Best Life Ever Tuscany: A continuation of Best Life Ever Amalfi Coast - Almost All Inclusive October 16-22, 2024
Private Full Day Tour of Tuscany from Rome
Private Full Day Tour of Tuscany from Rome
Good to know

Frequently Asked Questions

Is this a private tour, or will we join a group?

Private. You travel with your own guide and driver, and the only people on the itinerary are the ones you bring with you. Nothing is shared with strangers, and the pace of each day is yours to set.

Can the itinerary be changed to suit us?

Yes. What you see here is a starting point, not a fixed departure. Tell us how long you have, what you love and what you would rather skip, and we will reshape it around you. A slower morning, an extra night somewhere you fell for, a different region entirely.

How do we start planning?

Send us a note using the form on this page, or call us on 1-866-779-2565. A travel specialist replies within one business day, usually with a few questions of their own. There is no cost and no obligation in asking.

Are the hotels shown the ones we will stay in?

Usually, yes. Hotels are subject to availability, and if one is full on your dates we will replace it with a property of a similar standard and tell you before you book. Never a surprise on arrival.

When should we book?

The earlier the better, particularly for travel between May and September, when the best small hotels and the guides worth having are taken first. That said, we have put together beautiful trips at short notice, so ask and we will tell you honestly what is still possible for your dates.

Plan your journey

Start the Conversation

Quick Enquiry

Our travel specialists reply within one business day.

Handpicked

Our Featured Properties

From the journal

Our Recent Blog

Visiting Rome During a Heat Wave? Read This Before You Go Latest

Visiting Rome During a Heat Wave? Read This Before You Go

Read article
Visit the journal
Keep exploring

Explore More of Italy

Curated Italy journeys and travel inspirations.

Weddings & Honeymoons Custom Group Tours Family Vacations Guaranteed Departure Small Group Tours Health & Wellness Retreats
Cinque Terre, Italy

Ready to plan your journey?

Connect directly with a member of our team for expert guidance and fully customized travel across Italy and the Mediterranean.

Start Planning Your Trip

7 days from EUR 3,820 per person

1-866-779-2565 Enquire Now
Direct In Italy: +39 375 823 5314 Toll Free: 1-866-779-2565
Home About Italy About Us Travel Agents Contact Us Book Consultation Trip Planning Customizable Tour