Jubilee of Hope Pilgrimage

Rome, Metropolitan City of Rome Capital, Italy

CT
Captivating Tours & Pilgrimages
  • Email address verified
12 reviews
Nov 6 - 15, 2025
Group size: 1 - 20
Jubilee of Hope Pilgrimage
Rome, Metropolitan City of Rome Capital, Italy

Captivating Tours & Pilgrimages
  • Email address verified
12 reviews

Nov 6 - 15, 2025
Group size: 1 - 20

About this trip

Jubilee of Hope Pilgrimage:

We are deeply honored and filled with gratitude to share that we will be part of a  Papal Audience with Pope Leo XIV on November 8, 2025, a special occasion recently added to the Holy Father's schedule.

Rome, Orvieto, Assisi, Loreto & Cascia | November 6 – November 15, 2025.

"Let us go rejoicing to the house of the Lord." (Psalm 122:1).

This pilgrimage is a sacred journey through the holy places where saints walked, miracles happened, and the beauty of God’s creation reveals His majesty. As we travel through ancient cities, hilltop villages, and quiet mountain sanctuaries, we allow grace and beauty to transform our hearts.

Day 1 | November 6: Departure from New York

With our hearts set on pilgrimage, we entrust this journey to Our Lady and the saints who will accompany us along the way. We depart, open to the miracles and mercies the Lord has prepared.

Day 2 | November 7: Arrival in Rome 

Upon arrival in Rome—timeless, golden, and crowned with domes—we are welcomed by the city's grandeur that cradles the Church’s beginnings. 

Day 3 | November 8: St. Peter’s Basilica – St. Paul Outside the Walls, Tre Fontane

Standing on the sacred ground of St. Paul Outside the Walls, we enter through the Holy Door into a place of deep spiritual power. Beneath the grand arches and glowing mosaics lies the tomb of St. Paul, the Apostle to the Gentiles. The vast basilica echoes with the strength of his witness and the unbroken line of faith stretching from the early Church to today. It is a place of silence, strength, and surrender—where faith meets eternity. We visit the Basilica of St. Agnes Outside the Walls, where the beauty of Roman architecture meets the purity of a young virgin martyr who laid down her life for Christ. In the catacombs, surrounded by silence and stone, we sense the faith of the early Christians who carved out hope in the darkness.

Mass today opens our pilgrimage in prayerful unity, Tre Fontane (Three Fountains)

A short walk away, Tre Fontane marks the solemn site of St. Paul’s martyrdom. Tradition holds that his head struck the ground thrice, and a spring of water flowed from each point. Surrounded by quiet and monks' prayer, this place speaks of sacrifice, transformation, and the triumph of love over death.

Day 4 | November 9:  The Sunday Blessing (Angelus)  - Pope Leo XIV– St. John Lateran – Scala Sancta – St. Mary Major

We gather in St. Peter’s Square, filled with the voices of the nations, to receive the blessing of the Holy Father, Pope Leo XIV. Later, in the Basilica of St. John Lateran, sunlight streams through centuries-old windows onto the high altar—the cathedral of the Pope. Across the street, pilgrims kneel upon the Scala Sancta, ascending the same stairs once wet with Christ’s Precious Blood. We end the day in the tender arms of Our Lady at St. Mary Major, where the relics of Christ’s crib whisper the mystery of the Incarnation.

Day 5 | November 10: Bolsena – Orvieto – Eucharistic Miracle

As we leave Rome, the landscape begins to change. Rolling hills, scattered cypress trees, and vineyards begin to greet us. We stop in Bolsena, nestled by a deep-blue volcanic lake, where a miracle once unfolded at the altar. We ascend to Orvieto, a majestic town perched atop a cliff of golden tufa stone. The winding streets lead us to its breathtaking Cathedral, a Gothic jewel shimmering with mosaics. Inside, we venerate the blood-stained corporal, an eternal testimony to the Real Presence of Christ in the Eucharist. Holy Mass is celebrated in profound thanksgiving. As the sun sets, we descend through the green Umbrian countryside to Assisi.

Day 6 | November 10- 11: Assisi – Blessed Carlo Acutis – First Encounters

We journey north, through the Umbrian valley framed by soft mountains and olive groves, until we reach Assisi, a city that seems to float in light. Its pink stone glows in the sun, and silence lingers in the narrow streets. We begin at the Sanctuary of the Spogliazione, where Blessed Carlo Acutis—young, joyful, and radiant in love for the Eucharist—rests. In a modern glass tomb, his peaceful body invites our own renewal in holiness. We celebrate Mass and begin to walk the town, embraced by Saint Francis and Saint Clare—two lives of radiant poverty and boundless joy.

Day 7 | November  12: Assisi – St. Francis and St. Clare – Carceri – Porziuncola

We begin the day at the Basilica of St. Francis, whose majestic frescoes speak of a saint who imitated Christ in suffering and love. His tomb, simple and luminous, is a place of tears and thanksgiving. At the Basilica of St. Clare, we encounter her resting body and the crucifix that spoke to Francis: “Rebuild My Church.” We then ascend through forests and narrow paths to the Hermitage of the Carceri, carved into the mountain rocks—a place where birdsong and silence speak of God. In the valley below lies Santa Maria degli Angeli, where the Porziuncola is nestled within a basilica. Here, we celebrate Mass in the same humble chapel where Francis died.

Day 8 | November 13: Loreto – The Holy House

Driving east, we cross rolling hills and flowering fields to reach Loreto, perched above the Adriatic Sea. The Basilica of the Holy House, rising like a crown, encloses the sacred stones of Nazareth, carried by tradition through divine intervention. Within those stone walls, the Word became flesh.

While at the Holy House, we whisper our “yes” to God beside Our Lady, asking for the grace to imitate her surrender. The views from the hilltop sanctuary offer a glimpse of heaven.

Day 9 | November 14: Cascia – St. Rita of the Impossible

Winding through the Umbrian mountains, our final full day brings us to Cascia, a quiet jewel nestled between peaks and wildflower-filled valleys. Here we encounter St. Rita, the bride of Christ who bore His wounds and loved beyond all human strength. We venerate her incorrupt body and the Eucharistic miracle preserved in the monastery. Mass is offered in the sanctuary. In this peaceful town wrapped in green hills, we surrender our deepest intentions to God through the intercession of this powerful saint of forgiveness and impossible causes.

A farewell dinner closes our time in joy and gratitude. Overnight Albergo delle Rose.

Day 10 | November 15: Return Home

We return home filled with grace, our hearts renewed by the beauty of creation and the power of holiness. We carry with us the light of Rome’s basilicas, the quiet of Assisi, the miracles of Orvieto and Cascia, and the tenderness of Mary’s Holy House in Loreto.

"You will show me the path of life, the fullness of joy in Your presence." (Psalm 16:11)

Available Packages

Jubilee Pilgrimage of Hope
Deposit: $600
Available until August 1, 2025

Package Includes:  

  • Round-trip airfare - NY - Rome/Rome-NY - Airport taxes and fuel surcharges 
  • Overnight Accommodations - double occupancy -city taxes accommodations in the hotels 
  • Breakfast and dinner daily - wine and mineral water with dinner  
  • Deluxe private motorcoach for all the transfers according to the above program - Baggage allowed on the motorcoach: 1 big suitcase per pax in the motorcoach trunk + 1 small carry-on hand luggage.
  • Road taxes, parking fees, and special permissions (ZTL) to enter the cities  
  • English-speaking local guide in Rome (1FD+1HD), Orvieto (1HD) and Assisi (1HD+1FD);  
  • Entrances to: Catacombs of St. Callixtus in Rome & Orvieto Cathedral.  
  • Sightseeing and admission fees as per the itinerary.
  • 24-hour assistance - Tour Director
  • Ticket for the Taxi to reach Eremo delle Carceri in Assisi;  
  • Daily Mass and spiritual activities at sacred sites.  

-  Not Included:  Lunches and drinks; - Tips for our driver; - All that is not specifically mentioned in "Included in the Price". 

$3,690
Deposit: $600

Your Organizer


CT
Captivating Tours & Pilgrimages
12 reviews
Anna is the founder and managing director of Captivating Tours and Pilgrimages in New York City, a Boutique Pilgrimage company that offers a unique and transformative experience, she has been a restauranteur and entrepreneur in the hospitality industry in New York City, owning and operating a Hotel, Restaurants and working with Tour Operators and Travel Agencies for more than 30 years, but above all, her deep faith and love for Christ. "Be Captivated by the Beauty of God in your Journey"

Reviews

It was a great trip. Well organized, marvellous people, incredible spiritual experience. Thank You.
By Alfredo T for Medjugorje - Holy Week on Apr 23, 2025
Travel has always been a pillar and tenet in my life since I was a small girl. Having been blessed with parents who took very seriously the opportunity to expose me to didactic lessons of life by way of experiencing at a deep level that which is all around us, the gratitude I have for having been shaped into one with a nomadic soul, is never lost on me. For, I was given a gift from the beginning. That said, I have always ventured forth with an open heart and have known these opportunities for my vision to be broadened by the grand vistas around me to be those I am most thankful for. To reiterate: I have never been in poverty of understanding the inheritance I was given of making my travel adventures tailored to allowing magnificent moments to be created. It was all that I aimed for by way of memories made, new friends who may have once been strangers gathered, photos of frozen moments captured, stories acquired…I spent these former journeys in pursuit of future tales I could one day tell. For, even after over a decade of a career in aviation, traversing the globe on my own personal trips for work or play, international jaunts and domestic excursions having taken place within the timeline of my life, it wasn’t until my divine Pilgrimage with Anna and her legacy Captivating Tours where my entire thought process of stepping aboard for a new adventure became redirected. No longer is my pursuit about the experiences I could tally, the epoch-making moments I would have in my back pocket as future riddles to share, nor is even the idea of being open to what lay ahead, paramount … My heart and soul fundamentally shifted after my premiere journey with Anna and Captivating Tours & the fellow pilgrims only she has the gift of assembling ….For, the time spent with Anna reenvisioned all that I now believe travel can be and most importantly IS, as I presently understand the purpose it plays in the delicate balance of my life. At once, after being granted the fortune of a Captivating Tours Pilgrimage, the only desire of my life, heart & soul is: WHO will I become? The immediate answer is simple: someone who is never quite the same after their passport has been stamped…..the second answer is something I look forward to learning should you and I find ourselves seated side by side on my next life-altering journey with Anna and Captivating Tours & Pilgrimages: who will YOU become? (And dare I say this begs an even deeper and more intimate question: who then by the graces and miracles of what you have become, will your family, friends, neighbors and all those you come in contact with have the chance to transform into as well? Thus, the continuation of your own life legacy can begin anew on a Captivating Pilgrimage with beloved Anna!)
By Carla B for Pilgrimage Retreat to Medjugorje from Greenwich on Nov 05, 2024
The pilgrimage was a success for Anna and captivating Tours! It was truly a blessed and grace-filled time with all who said yes to Our Blessed Mother's invitation. Everything was beautiful and well-planned. Thank you Anna for making it a memorable experience. God bless!!
By Miriam A for Pilgrimage to Medjugorje on Jun 19, 2024
PT
It was wonderful! Food was good. Accommodation was very nice and close to St. James Church.
By Pauline T for Pilgrimage to Medjugorje on Jun 19, 2024
Este viaje fue maravilloso;lleno de muchas bendiciones y memorias que Dios permita permanezcan en mi mente por siempre. Agradecida totalmente por tan excelente trabajo de Ana para coordinar que todo saliera acorde a lo planeado.Tiene un A+ SU amabilidad y dulzura para con todo el grupo fue muy especial. Por siempre agradecida a todo el equipo de trabajo de este viaje. Liliana
By Liliana Y for Pilgrimage to Medjugorje on Jun 18, 2024
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