Pilgrimage to Italy

Under The Spiritual Direction Of Fr. Martin Gillespie
FROM $4,999


May 13 - 25, 2025

Activity Level

Moderate – High

Book By

1 / 31 / 2024

Group Limit


Pilgrimage Overview

My Dear Brothers and Sisters in Christ, it is with great excitement and anticipation that I invite you to travel with me on the pilgrimage of a lifetime!  In May of 2025, we will travel to Italy to visit some of the holiest places on Earth and enjoy each other’s company as we are drawn closer to Our Lord!  It is good for us to step away from our daily routines, as Jesus Himself invited His Disciples to “Come away for a while and be refreshed” and to enter into a more spiritual realm.  It is on just such a pilgrimage where we begin to not only appreciate the places where the saints once walked, but to also, and perhaps more importantly, to see Christ more clearly in the people we meet.  It is with these very thoughts that I look forward with great glee the opportunity for all of us to share a most special journey together!

On a personal note, on May 20th, 2025, I will be celebrating my 25th anniversary of ordination to the Roman Catholic Priesthood, a very special milestone indeed.  On that day, I will honor my commitment and promise to Our Lord and His Mother, to be a good and faithful steward of the souls in my care.  As per Christ’s command, I have placed my hands on the plow and never looked back.  I have served joyfully in the vineyard of God, and would like nothing more than to share this momentous occasion with all y’all!  What’s more, I will be celebrating my Mass of Thanksgiving in the Basilica of St Clare in Assisi.  I have had a tremendous devotion to St Clare after having served as pastor of St Clare Catholic Church before, during, and after Hurricane Katrina.  We placed our lives in Her care, and she kept everyone safe.

So please, I ask that you prayerfully consider joining me on this pilgrimage.  I can assure you that it will not only be a spiritual journey, but also a fun and exciting one, too!  Be safe and be well, and may Almighty God bless you!

Fr.  G

Travel Insurance Group Name/ID: CA112

Depart USA

Our Pilgrimage begins today as we depart on our flight to Milan. Meals and drinks served aloft.

Arrival in Milan

Upon arrival in Milan we are welcomed by our HLTC Guide and Driver. We will then enjoy a brief panoramic city tour before arriving at our hotel for a special welcome dinner and overnight.


After a good night’s rest and a delicious breakfast we’re ready to explore Milan! We begin with what is perhaps the city’s most famous structure. Standing as the centerpiece of Milan for over six centuries, the Duomo is an architectural marvel and is sure to both awe and inspire us as we experience our in-depth tour. Afterwards, we will be free to indulge in a meal at one of the many restaurants that surround the Cathedral Square. We then continue with a short walk to the nearby Church of Holy Mary of Grace.  Here, we will see one of the world’s most iconic and recognizable works of art – Leonardo da Vinci’s The Last Supper. Before returning to our hotel for dinner we will enjoy a private Mass at a local Church.  


We greet the day with a smile and bid farewell to Milan as we depart for Florence (5hrs). Upon our arrival, we check in to our hotel and enjoy the balance of the day to explore Florence and rest after our long journey. 


Today we enjoy a comprehensive tour of Florence with visits to the Piazza della Signoria, Palazzo Vecchio, Ponte Vecchio, the Duomo and the Academia to see Michelangelo’s “David.” Get those cameras ready! Later, we return to our hotel for dinner and overnight. 


Today we depart Florence for Assisi (2.5hrs), birthplace of St. Francis. Assisi holds a special place in the hearts of every faithful Catholic the world over. Upon arrival, In Assisi, we will visit the Basilica of St. Francis, the upper Basilica with Giotto’s frescoes representing the life of St. Francis, then the lower Basilica and the Tomb of St. Francis. After lunch, we will transfer to the Convent of San Damiano, where St. Francis received his call to rebuild the Church and where St. Clare lived and died. Here we celebrate Mass before continuing for our hotel for dinner and overnight.


After breakfast, we begin our day with Mass at the Basilica of Santa Chiara followed by a group tour. We then have the balance of the day to explore Assisi at our own pace. To facilitate your exploration, our bus will offer limited transportation to the town’s Piazzas. In the evening, we will gather for our group dinner at the hotel to share stories of our wonderful time in Assisi!


Today we depart Assisi for Rome. Before our departure, however, we will celebrate a special Mass at the Basilica of St. Clare to mark Fr. G’s Silver Jubilee! Afterward, we’ll enjoy a tour of this magnificent Basilica before transferring to Rome (2 hrs). Upon our arrival in Rome, we will visit Saint Paul Outside the Walls, one of the four major basilicas in Rome, where we will visit the tomb of St. Paul before enjoying lunch and some free time to stretch our legs. We then close the day by checking in to our hotel for dinner and overnight.


Today, we will share in the truly unique experience of attending a Papal Audience. An early morning start ensures the best possible view of the Holy Father as he personally greets and addresses the faithful. In the afternoon, we visit the Basilica of St. John Lateran, the oldest basilica of the Western World. We then visit the Basilica of St. Mary Major, one the most important shrines in the world dedicated to the Blessed Virgin Mary. At the close of the day, we will return to our hotel for a peaceful night of rest.

DAY 10

Our day begins with an exploration of Vatican City. We begin with a tour of the magnificent St. Peter’s Basilica. We will then discover the Vatican Museums which house many of the Western world’s most important collections of art. Our experience culminates in a visit to The Sistine Chapel, a place where our minds and hearts will surely linger for many years to come. After lunch, we will continue to a tour of the Catacombs of St. Callixtus. Later, we return to our hotel for dinner and overnight.  

DAY 11

Today we bid a brief farewell to Rome as we make our way to Orvieto (1.5hrs) just North of the city. Here, where we visit the Gothic Cathedral built to house the holy relics of the Eucharistic Miracle of Orvieto. It was this miracle that occasioned the proclamation of the Feast of Corpus Christi and inspired St. Thomas Aquinas to write the famous hymn “Tantum Ergo.” Here we celebrate Mass. We enjoy lunch in a local restaurant with tasting of the Orvieto and Orvieto Classico wine that this region is famous for. Afterwards, we board our bus and return to our hotel in Rome for dinner and overnight.

DAY 12

Our pilgrimage is nearly at an end. After breakfast, our group will enjoy a special Mass at St. Peter’s Basilica. We then proceed to the Piazza Navona for a walking tour that visits the Trevi Fountain and Spanish Steps among other interesting finds. The group will then be given the balance of the day to explore Rome at their own pace. Later, we will reconvene at the hotel for a farewell dinner to celebrate our shared pilgrimage.

DAY 13
Return Home

Our hearts and minds fortified by faith and fellowship, we now begin the long journey home.


  • 4-5 Star Hotels
  • Roundtrip Flights
  • One Checked Bag
  • Air-conditioned Motor Coach
  • Professional Licensed Tour Guide
  • Gratuities
  • Accommodations (based on double occupancy)
  • Entrance Fees as per itinerary
  • Meals (per itinerary)


  • Passport and Visas (Refer to the section below for Passports or Visas help)


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