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Italy Food and Wine Tour – Pilgrimage to Rome, Assisi, Siena, Florence

Faith Food and Wine Tour in Italy with Pilgrimage to Rome, Assisi, Siena and Florence

Visit a vineyard and taste the wines of Tuscany, discover local cheeses, and enjoy a cooking class in Florence.  This new Catholic Foodie Pilgrimage Tour visits Rome, Assisi, Siena, and Florence while sampling the best food and wines of Chianti and Tuscany. Perfect for Catholic Foodies!  Feed your body and soul on the premium food and faith pilgrimage tour to Rome, Assisi, Siena, and Florence.  Why don’t you book today’s Tour of Italy Food and Faith pilgrimage for 2024 or the Jubilee Year in 2025?

Food and Wine Tours in Italy – combined with a pilgrimage to Rome and Italy

Tour Details Italy Food and Wine Tours - Pilgrimage to Rome, Assisi, Siena and Florence

Departure & Return Location

Your local airport of choice —  Or you can choose land only and make your own flight arrangements.

Departure Time

Arrive for Check-in 3 Hours Before Flight Time

Price Includes

  • Air fares - Round trip airfare listed below Airfare is included for most major airports
  • 1 checked bag with the airlines
  • Hotel Accommodations - First Class Hotelswith Porterage
  • Meals - Breakfast and Dinner Daily; 3 lunchesWine & mineral water with dinners & 3 lunches
  • All transportation in destination locationAir conditioned Deluxe Motor Coach with Bottled Water and WiFi available onboard
  • Tour Guide - Professional Catholic English Speaking Guides
  • Entrance Fees - Sightseeing and admissions fees as per itineraryWhisper Headsets where needed
  • Priest with Daily Mass and Spiritual Activities Coordinated
  • Cooking class in Florence
  • Wine & Food tastings as indicated in the itinerary
  • Tour Escort Throughout Pilgrimage
  • 3 nights in Rome ~ 2 nights in Assisi  ~ 1 night in Siena ~ 3 nights in Florence

Price Excludes


  • Name and Luggage tags
  • Neck Wallet
  • Travel Bag
Itinerary Italy Food and Wine Tours - Pilgrimage to Rome, Assisi, Siena and Florence

Day 1Depart for Rome

italy flag pilgrimageDepart on your overnight flight(s) to Rome. Dinner and breakfast will be served on board the transatlantic segment.

Day 2Arrive Rome

ravioli rome italy food pilgrimage Welcome to Rome, “The Eternal City.” Upon arrival at Rome airport, collect your luggage in the baggage claim area, and continue to the arrival hall, where you will be greeted by a tour escort. Together you will make your way to the bus and transfer to your hotel. Following check-in, you will have free time to unpack and relax or explore Rome on your own. Breakfast will be served at your hotel.  Your tour escort may suggest places to visit. Later in the afternoon, your group will meet in the hotel lobby and depart for Mass. Following Mass, you will return to the hotel for your Welcome Dinner. 

After dinner, you will have the opportunity to walk to St. Peter’s Square as a group, for the Rosary.

Day 3Rome: Papal Audience - Basilica of St. John the Lateran - Holy Stairs - Basilica of St. Mary Major

pope france italy pilgrimage tourAfter a nice breakfast at your hotel, your first sightseeing day in Rome starts! The tour begins with attending the Papal Audience in St. Peter’s Square! The Audience is celebrated each Wednesday by His Holiness (pending the papal schedule). Following the Audience, there will be free time for lunch, or shop, or mailing a postcard from the Vatican Post Office. This afternoon you will visit the oldest of the four major Basilicas in Rome, and the home to the relics of Peter and Paul, the Basilica of St. John the Lateran. This Basilica is where the Pope is installed as Bishop of Rome, and where he officiates as the Bishop of Rome. Next, we will cross the street to visit the Holy Staircase. Tradition states that this staircase is from Pontius Pilate’s palace of Jerusalem during the time of Jesus. It is also said that this Staircase was brought to Rome by St. Helen in the 4th century. If time permits, you may climb the steps on your knees, in memory of Christ’s agonizing Passion. To conclude your day, we will proceed to the Basilica of St. Mary Major. This Basilica contains a relic from the Manger of the Infant Jesus. Return to the hotel with time to relax and freshen up before departing for dinner in a local restaurant. Overnight in Rome. 

Day 4Rome: St. Peter's basilica- Vatican Museum - Appian Way - Basilica of St. Paul Outside the Walls - Catacombs

pieta rome vaticanThis morning you will enjoy an early breakfast before making your way to the largest Church in Christendom, St. Peter’s Basilica. This Basilica was built on the site where St. Peter, the first Pope, and Bishop of Rome, was martyred. It is here that you will view Michelangelo’s Pieta. This stunning marble sculpture depicts the Virgin Mary holding Christ after His crucifixion, death, and removal of the cross before being placed in the tomb. Continue to proceed to the Vatican Museums. At the world-renowned museum, you will see the most impressive of edifices, galleries, and awe-inspiring relics. Additionally, you will observe the Tapestry Gallery, Raphael Rooms, the Sistine Chapel, and Michelangelo’s Masterpiece, the restored mural of the Last Judgment. The final stop on your Vatican tour is at the tomb of Saint John Paul II. Afterward, you will be transferred to the Fontana di Trevi (Trevi Fountain), where you may enjoy some free time on your own for lunch. Continue on your short journey down the Appian Way, the earliest road of Ancient Rome. This road leads to the Domino Quo Vadis Chapel, the Baths of Caracalla, the Arch of Drusus, the Tomb of Caecilia Metella, and the catacombs of St. Callixtus. The day concludes with a visit to the Basilica of St. Paul Outside the Walls. Originally founded by Emperor Constantine in the 4th Century, this Basilica is the burial place of Saint Paul the Apostle. We will make our way to a local restaurant for dinner. Following dinner, feel free to explore the streets of Rome, or return to the hotel overnight.

Day 5Rome: Orvieto - Assisi

Lunch with Umbrian fare and Orvieto Classico wines,

assisi italy pilgrimage tour basilicaAfter an early breakfast, you will head north through the Roman countryside of vineyards and villas. Throughout this bus ride, your tour escort will share very interesting information regarding the spiritual, historical, and cultural aspects of Italy. Arrive in Orvieto, a city known for its Duomo and considered one of the most architecturally important in Europe, for its Etruscan roots, and for the museums where one finds collections and displays that range over 2,500 years of history. During this tour, you will walk through Orvieto’s charming, narrow alleys, and small squares. Your tour will be a very memorable experience, perfect for reflecting while you enjoy an Umbrian meal and a glass of Orvieto Classico wine. After lunch, board the coach and continue to Assisi. Upon arrival, your group will enjoy a tour of the hometown of St. Francis. St. Francis is the “Patron Saint of Animals and the Environment.” Additionally, he is responsible for founding the Franciscan Order and, the inspiration for our Holy Father, Pope Francis. He chose his name in admiration of the Saint of Nature, and Servant to the Poor. Known for being a humble man himself, Pope Francis spent most of his life denying the luxuries of life. He preferred to live in simplicity and humility while giving up all other worldly possessions, just as St. Francis did. As your group visits the birthplace of St. Francis, you will become captivated as the atmosphere has not changed since St. Francis began his ministry, in the early 13th century. During the tour, your group will have the opportunity to visit the tomb of St. Francis in his Basilica. At the Basilica of St. Francis, you will have the opportunity to view a series of frescoes depicting his life, as well as, view a few of the saint’s possessions. Additionally, your group will visit the Church of San Damiano. At this modest, yet beautiful Holy Church, you will have the opportunity to kneel before the crucifix where Jesus asked St. Francis, “to rebuild His church.” As the tour continues, your group will visit St. Mary of the Angels Basilica. This Basilica is where St. Francis spent most of his life and is made up of two structures; both of which you will visit. The Porziuncola is where St. Francis founded his order of the Friar Minor (Franciscans), and the Capella del Transito, which is the place of St. Francis’ death. During this visit, your group will have the opportunity to visit the beautiful Rose Garden where St. Francis and other friars lived, as well as the cave where the Saint retired to pray. After visiting this beautiful Basilica, your group will enjoy some free time on your own. Feel free to take this time for additional prayer, or shop in the Gift Shop. The last stop on your tour will be the Church that honors St. Clare, the foundress of the Poor Clare Sisters. This Saint followed the teachings of St. Francis very closely by also living a life of poverty and humility. Lastly, your group will transfer to the hotel for dinner and overnight.

Day 6Umbria Touring - Bevagna - Trevi - Montefalco Olive Oil Tasting and Lunch in Trevi at an Oil Mill, Afternoon Wine tasting of the local Sagrantino grapes

trevi olive oil italy food and faith pilgrimage tourToday you’ll discover the Umbria region, also called “Italy’s green heart”. Drive to the town of Bevagna, where ancient Roman monuments date back to the 1st century B.C. Just a few steps from the Forum, see the remains of a temple and check out the thermal baths which are still decorated with frescoes. Explore the medieval heart of the city, including the 13th-century Palazzo dei Consoli, and the 19th-century theater with decorations by Domenico Bruschi, and a ceiling of dancing muses by Mariano Piervittori. After the visit to Bevagna, transfer to Trevi, the town famous for its olive oil, and enjoy a guided visit with light lunch at an oil mill. You will then visit the medieval city of Montefalco, with its Romanesque, Renaissance, and Gothic monuments: tour the Museo di San Francesco (Museum of St. Francis), a former Franciscan church with frescoes that tell the story of one of Italy’s most famous patron saints. Admire the 13th to 14th-century Palazzo Comunale (Town Hall), and the former church of San Filippo Neri, now a town theater. Other historic churches include Sant’ Agostino and Santa Illuminata. See handsome 16th-century residences in Santa Maria di Piazza. Then, visit a local wine producer, to taste the local wines, and especially the deep red Sagrantino wines, made from an Italian grape variety mainly found in the area. Return to the hotel in Assisi for dinner and overnight.

Day 7Assisi - Siena and San Gimignano


Siena Cathedral

After an early breakfast, celebrate Mass and depart Assisi for Siena, stopping at the walled medieval city of San Gimignano. Resting on the top of a hill, explore the area’s impressive Romanesque and Gothic architecture, frescoes, towers, and more. Upon arrival, meet your local guide who will show you first to the medieval city of Siena. Siena is also the city of Saint Catherine of Siena: she is one of the two patron saints of Italy, together with St. Francis of Assisi. Begin with a private tour of the Siena Cathedral, admiring the unique marble stripes of its interior as well as the Piccolomini Library, which hosts illuminated choir books and frescoes. Your tour will continue to the Piazza del Campo, the famed site of the Palio di Siena, the horse races held twice a year. Afterward, soak up some free time to continue exploring independently or to purchase lunch. Continue to Siena for dinner at a local restaurant and overnight.


Day 8Montalcino - Orcia Valley - Pienza & Montepulciano Wine Tastings (2) - Food Tasting - Wine Tour - Cheese Tasting

pienza tuscan cheese italy food and faith pilgrimage tourAfter breakfast, you will depart for a full day’s Tuscan tour. The tour begins with a drive through the rolling, grape-clad scenery leading you to Montalcino. Once here, you can breathe in the timeless character of this hill town with its narrow and winding alleyways and squares. The town is also the home of the world-famous Brunello wines. Visit a famous and renowned wine cellar/museum set on an estate with a rich history. Here you can taste these rich and aged wines and receive expert advice and suggestions from a connoisseur. Go up to the top of the town along alleys and streets lined with flower-covered houses and peeks of the plains spreading out before you. Here you can feast your eyes and breath in the history and culture of the place. The next stop is one of the hidden gems of Tuscany – the Orcia Valley. Stop at San Quirico d’Orcia and use your free time to visit the Romanesque Collegiate with its dragons and mermaids on its portals or the Horti Leonini – a beautiful box garden. Having spent some time here you will understand why UNESCO has put the area on its list. Continue on to the perfect Renaissance model of a city: Pienza. Perched on a hilltop, the town seeps history and also offers one of the best cheeses in the world: Pecorino. You’ll be given the chance to taste the best of the cheeses and then you’ll have free time to look at the palaces and piazzas of this Florence in miniature. The last stop is the elegant and refined hill town of Montepulciano. It stands 605 meters above sea level, encircled by massive fortifications. It really is like walking into the past. Later, it’s home to the highly esteemed Vino Nobile, where you will take part in your second wine-tasting session whilst visiting the cellar where the wine is stored. A perfectly tasteful way to explore one of the regions most loved by true and discerning Tuscans. Transfer to Florence for dinner in a local restaurant and overnight.

Day 9Florence & Cooking class with dinner

florence duomo italy pilgrimageAfter breakfast, meet your local guide and travel first to the neighborhood of San Lorenzo, a popular spot with visitors and locals alike for its open-air market, which sells a wide array of leather goods, clothing, and more. As you go, your guide will discuss the rule of the Medici family and their significant impact on the city’s politics and art during the Renaissance. Head past the Medici Chapels, designed by Michelangelo and Matteo Nigetti, and check out the Basilica of San Lorenzo, where members of the Medici family are buried. Next, wander over to one of Florence’s most iconic landmarks, the Duomo, where Brunelleschi’s Dome famously sits. Visit the Baptistery and Giotto’s Bell Tower while learning the history of the architecture. Continue through the bustling square of Piazza Della Signoria, home to the Palazzo Vecchio, outdoor cafes, and a collection of famous sculptures, including Giambologna’s Rape of the Sabine Women. Visit Il Porcellino, the bronze piglet statue that offers luck to those who rub his nose. Visit the Academia and experience this world-renowned museum. In the afternoon, meet your Chef and get ready for a traditional Tuscan cooking lesson: prepare a delicious, full meal. Learn the principles of Tuscan produce, tips on how best to prepare it, and the fine art of creating pasta from scratch. Reward your efforts afterward by sitting down to feast on your dishes, complemented by local wine. After dinner, return to the hotel overnight.

Day 10Chianti Region and the Tuscan Countryside - Greve – Castellina - Wine tasting and lunch in Tuscany

chianti wine italy food and faith pilgrimage tourJourney through the beautiful Tuscan countryside, viewing the olive groves, vineyards, and rolling hills of one of the most prestigious winemaking regions in the world before arriving in Chianti Fiorentino. Stop for the visit to a distinguished castle and wine estate, where you’ll tour the historical cellars. Learn the winemaker’s secrets as you see where the grapes are crushed, and where the wine is matured and bottled. Then, get to tasting! Enjoy a glass of Chianti Classico, Chianti Reserve, Tuscan dessert wine, or a prominent white wine. Learn the complex character of each from your expert guide while you taste. Later, enjoy a typical Tuscan lunch, and afterward, head to the medieval village of Greve, where the most important wine fair of the Chianti region is held each year. Explore the main square and pursue the local artisan shops. Then make your way to Castellina, a hilltop village characterized by its large fortress and Etruscan settlements. Stroll past the medieval street of Via Delle Volte and explore the local shops and squares before returning to Florence. Farewell dinner at a local restaurant in Florence, before returning to your hotel for overnight.


Day 11Return to the USA

After breakfast transfer to the airport in Florence for our return flights home! 


Map Italy Food and Wine Tours - Pilgrimage to Rome, Assisi, Siena and Florence
Dates, Pricing, Booking Italy Food and Wine Tours - Pilgrimage to Rome, Assisi, Siena, Florence
Make a Deposit to reserve your place. Prices start at $4,959 for Land Only

pilgrims of hope 2025 larger rome vaticanPrices vary from $5,899 – $6,099 per person in 2024, based on a minimum of 15 pilgrims.

Available in 2024 or 2025 for the Jubilee Year!

At this time, we are only accepting group bookings.  If you are interested and have about 10 interested persons, don’t hesitate to contact Jimmy or Fr. Paul.

Photos Italy Food and Wine Tours - Pilgrimage to Rome, Assisi, Siena and Florence
Travel Insurance Italy Food and Wine Tours - Pilgrimage to Rome, Assisi, Siena, Florence

Travel Insurance is available for Italy and – is recommended!

Click here for information on insurance plans!


FAQ for Italy Food and Wine Tours - Pilgrimage to Rome, Assisi, Siena and Florence


Do you have hotel information? Coming soon.

Do I need an electrical adapter in Italy?  Yes, you will need an adapter in Italy.

Are your guides Catholic?  All of our guides are Roman Catholic!  Absolutely!  We are the only pilgrimage tour agency with a Roman Catholic priest on staff!

Do you have other tours to Italy?  Yes. See our other pilgrimage tours to Italy.

Would you like to lead your parish or group on this Italy Food and Wine Tour and Pilgrimage to Rome?  Click Here to get started.


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