DONALD WOODARD

Woodard Luxury Travel

Faith Food and Wine: Jubilee Year Italy Pilgrimage

Sep 15, 2025 to Sep 26, 2025
Rome, Tuscany, Florence
FOOD, FAITH, AND WINE: JUBILEE YEAR PILGRIMAGE IN ITALY
 

In September 2025, join Woodard Luxury Travel and Father John Putnam on pilgrimage to Italy for the Jubilee Year!! Start in Rome for the Jubilee festivities, then head to Assisi, Orvieto, Siena, the Tuscany Region, then finally end in Florence. Along the way we will visit amazing Catholic sites, sample great Italian cuisine, and sip on the fantastic wines of the region! You won’t want to miss this opportunity!

Price of the 11 day pilgrimage is $5,950 per person which includes transfers to/from the airport, 9 nights’ land accommodations, breakfast and dinners, and much more!

 


 
 
 
 
 

What's included in this trip:

  • Airport transfers 
  • 9 nights accommodations at centrally located 4 and 5 star hotels
  • Breakfast and Dinner daily
  • Some lunches
  • Olive Oil, Vinegar, and Wine Tastings
  • Air-conditioned Motorcoach transportation during trip
  • Sightseeing and admission fees
  • Mass daily and spiritual events
  • Professional local guides
  • Whisper headsets
  • Tips to hotel staff, restaurants, and porters
 
 

What's not included:

  • Airfare (added upon request)
  • Travel protection (Highly recommended)
  • Tips to tour guides and driver
  • Some lunches
 
 

Itinerary (Subject to change):

Day 1: Depart for Rome

Make your way to your local airport, where you will board your overnight flight(s). Your meals will be served on board.

Day 2: Arrival in Rome

Welcome to Rome, also known as, “The Eternal City”. Upon arrival at Rome airport, collect your luggage in the baggage claim area, and continue to the arrival’s hall, where you will be greeted by a tour escort and/or driver. 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. Your tour escort may suggest places to visit. Later in the afternoon, your group will meet in the hotel lobby for a “Meet and Greet” with your fellow pilgrims and depart for Mass. Following Mass, you will attend a welcome dinner at a local restaurant. After dinner, you will have the opportunity to walk to St. Peter’s Square as a group, for the Rosary (optional). 

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

After 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 mail 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 for dinner and overnight.

Day 4: Rome: St. Peter's Basilica - Sistine Chapel - Scavi Tour - Appian Way - Basilica of St. Paul Outside the Walls - Catacombs 

This morning you will enjoy an early breakfast before making your way to the largest Christendom Church, 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 off the cross before being placed in the tomb. Here we will also go on the Scavi tour. We then continue to proceed to the Vatican Museum where we will visit 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 Cecilia 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 for overnight. 

Day 5: Rome: Orvieto - Assisi 

Today you’ll discover the Umbria region, also called “Italy’s green heart”
After 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 over while you enjoy an Umbrian meal and a glass of Orvieto Classico wine.

Day 6: Assisi and Cascia

Assisi, 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 at 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 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 to 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. This beautiful pilgrimage continues to Cascia, following on the footsteps of St Rita of Cascia, visiting the Santuario di Saint Rita, a sanctuary dedicated to the Saint.
Upon return, a delicious wine and oil tasting will await you!

Day 7: Montalcino - Orcia Valley - Pienza & Montepulciano 

After 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 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. 

Day 8: Assisi - Siena and San Gimignano 

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.
You'll visit the Tenuta Torgiano winery, and meet our dear friend Pierluigi the world's most enchanting sommelier.
You'll learn about the grape, the nose, food pairings and most importantly- which glass to use with each wine! You'll also get to experience an olive oil and truffle oil tasting...and of course have some fresh bread with it!

Siena. 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 9: Florence

After breakfast, meet your local tour guide, 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 you will participate in a very interesting and private demonstration of leather and gold and how they are worked.

Day 10: Lucca & Pisa 

After breakfast, we drive to Lucca, also known as "the city of 100 churches".
The churches are protected against Medieval invasions with huge, fortified walls.
We visit the Duomo, the Amphitheater and the impressive Church of San Frediano.
This afternoon we visit Pisa! The Piazza dei Miracoli (Square of Miracles) is recognized as one of the main centers for medieval art in the world, with four great religious edifices: the Cathedral, the Campanile( the famous leaning tower ) the Baptistery and the Camposanto.
We'll enter the Cathedral dedicated to St.Mary of the Assumption. The big candelabrum near the altar is where Galileo Galilei tested his laws of pendulum physics!
Next we enter the marble Baptistery, the largest in all of Italy. Dedicated to St. John the Baptist, the building took 211 years to construct. The acoustics are amazing! You can whisper to a person 30-feet away and they'll hear you clearly.

Day 11: Return Home 

Transfer to the airport in Florence for our return flights home! After breakfast, board the coach and transfer to Florence International airport for your return flight. Be sure to tell everyone how much you enjoyed this trip and get prepared for the next pilgrimage with Woodard Luxury Travel! Arrivederci, Italia! Grazie mille!!!  

 
 

Cancellation policy:

All itineraries are subject to the cancellation policy of the trip insurance you purchase. If you would prefer to purchase trip insurance, please let Woodard Luxury Travel know prior to booking and we will adjust the pricing to include the insurance.

Available Packages

Pilgrimage Package
Available until June 1, 2025

$5,950.00
Deposit: $1,190.00 per person

9 nights accommodations
Motorcoach Transportation for tours
Breakfast and Dinners and some lunches
Tips for hotel staff, restaurants, and porters
20% Deposit at booking
 

Extra Options

Travel Protection - Allianz
Available until June 1, 2025

$599.00

 
 
More Information:
 
 

Single Supplement
Available until June 1, 2025

$850.00

Addition if you want a private room