Florida: From St. Augustine to Miami & the Keys
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A Catholic Pilgrimage Through the Spanish Missions, Marian Shrines & Living Faith of Florida
7 Days / 6 Nights | St. Augustine, Orlando & Miami | Optional Key West Extension | Available for Parish and Catholic Groups
Discover Where Catholicism Took Root in North America
Long before the foundation of the United States, Catholic missionaries, explorers and settlers were already celebrating the Eucharist on the shores of Florida.
In 1565, Pedro Menéndez de Avilés arrived at what would become St. Augustine accompanied by Father Francisco López de Mendoza Grajales.
One of their first acts was the celebration of Holy Mass.
More than four and a half centuries later, that same ground remains a place of Catholic pilgrimage.
The Mission Nombre de Dios and National Shrine of Our Lady of La Leche preserve the memory of these beginnings and of one of America’s oldest Marian devotions. The shrine stands on the site associated with the first parish Mass in St. Augustine and the beginnings of the oldest continuously existing Catholic parish community in the continental United States.
From St. Augustine, our pilgrimage travels south through Florida.
Groups may stop in Central Florida for an entirely different experience — exploring the American space program at Kennedy Space Center or adding one of Orlando’s world-famous theme parks.
We then arrive in Miami, where another remarkable Catholic story awaits.
Here we discover historic Gesù Church, the arrival and experience of Cuban exiles, Little Havana and, above all, the National Shrine of Our Lady of Charity, La Ermita de la Caridad.
And groups wishing to continue even farther south can travel along the spectacular Overseas Highway through the Florida Keys to Key West, where Catholic history, Cuban heritage and devotion to Mary Star of the Sea provide a fitting conclusion to the journey.
This pilgrimage connects two extraordinary chapters of Catholic history:
the arrival of Catholicism in Florida from Spain and the Caribbean — and the generations of Catholics who continued arriving centuries later carrying their faith with them.
Pilgrimage Highlights
- National Shrine of Our Lady of La Leche — pray at America’s historic Marian shrine in St. Augustine.
- Mission Nombre de Dios — stand on the ground associated with the first parish Mass celebrated at the founding of St. Augustine in 1565.
- Cathedral Basilica of St. Augustine — discover the historic heart of the oldest Catholic parish community in the continental United States.
- Historic St. Augustine — explore America’s oldest continuously occupied European-founded city and its extraordinary Spanish heritage.
- Castillo de San Marcos — encounter the Spanish colonial world in which the early Catholic Church of Florida developed.
- Orlando or Space Coast Option — choose between Kennedy Space Center, a theme park experience or additional time exploring Central Florida.
- Miami Catholic Heritage Tour — discover a side of Miami many visitors never encounter.
- Historic Gesù Catholic Church — encounter the beginnings of Catholic life in Miami and its later connection with the Cuban exile community.
- National Shrine of Our Lady of Charity — pilgrimage to Miami’s beloved Ermita de la Caridad.
- Freedom Tower — discover one of the great symbols of the Cuban exile experience.
- Little Havana & Calle Ocho — experience the cultural heart of Cuban Miami.
- American Museum of the Cuban Diaspora — explore the history and memory of the Cuban community.
- Optional Florida Keys & Key West Extension — travel across the Overseas Highway to the southernmost city in the continental United States.
- Basilica of St. Mary Star of the Sea — discover Key West’s historic Catholic community.
- Our Lady of Lourdes Grotto — pray at Key West’s beloved Marian grotto, built in 1922 and traditionally associated with prayers for protection from hurricanes.
- Opportunities for Holy Mass, prayer and spiritual reflection throughout the pilgrimage.
From La Leche to La Caridad
Florida’s Catholic history is intimately connected with the sea.
Catholicism arrived on these shores from Spain.
Spanish settlers brought with them their devotion to Mary.
At St. Augustine, Our Lady of La Leche became one of the earliest Marian devotions established in what is now the United States.
Centuries later, another Spanish-speaking Catholic population crossed those same waters.
This time they came largely from Cuba.
And they too brought Mary with them.
In Miami, Our Lady of Charity became a symbol of faith, homeland and hope.
More Than a Florida Tour
Florida is often associated with beaches, theme parks, cruise ships and sunshine.
But beneath that familiar image lies one of the oldest Catholic stories in the United States.
At St. Augustine, we stand where Catholics celebrated Mass at the beginning of the permanent Spanish settlement in 1565.
At Our Lady of La Leche, we encounter a Marian devotion carried across the Atlantic.
In Miami, we discover another community that crossed the sea centuries later carrying its Catholic faith and devotion to Mary.
At La Ermita, we encounter Our Lady of Charity as Mother of a people separated from their homeland.
And if we continue to Key West, we discover that Cuban Catholics were already building a chapel to La Caridad there in the 19th century.
Along the way, we also experience everything that makes Florida such an extraordinary destination — St. Augustine’s colonial streets, the Space Coast, Orlando, Miami, Cuban culture, tropical landscapes and the Florida Keys.
This is not simply a Florida vacation with Catholic churches added along the way.
It is a journey through more than four centuries of Catholic faith in Florida — from the first Spanish missionaries to the living Catholic communities of Miami and the Keys.
Important Information and Terms and Conditions
The published program is a general description and may be adjusted due to availability, operational requirements, local conditions, or the group’s needs. By registering, each traveler confirms that they have reviewed and accepted our Terms and Conditions.
Confirmed trip details, payment information, official meetings and presentations, updates, and final travel documentation will be provided through the official WeTravel page, the final itinerary, and other communications from Pilgrim Groups Travel. Travelers are responsible for reviewing all documents, insurance provisions, entry requirements, and travel instructions provided.
Proposed Itinerary
Day 1 — Arrival in Florida – St. Augustine
Welcome to America’s Oldest City
Arrival at the appropriate Florida airport and meeting with our local team.
We travel to historic St. Augustine, founded by Spanish admiral Pedro Menéndez de Avilés in 1565 and named for St. Augustine of Hippo.
Depending on arrival times, we may enjoy an introductory walk through the historic center before checking into our hotel.
Tonight we gather for our welcome dinner and introduce the remarkable story that will accompany the first part of our pilgrimage:
the arrival and establishment of Catholicism in Spanish Florida.
Dinner and overnight: St. Augustine
Day 2 — St. Augustine
Where the Catholic Faith Took Root
Today we visit one of the most important Catholic historical sites in the United States.
We begin at the Mission Nombre de Dios and National Shrine of Our Lady of La Leche.
It was here, on September 8, 1565, that Pedro Menéndez de Avilés and the first settlers came ashore. Father Francisco López de Mendoza Grajales celebrated a Mass of thanksgiving, marking the beginning of Catholic parish life in the new settlement.
We will have time to explore these sacred grounds, dominated by the Great Cross rising above the Matanzas River.
Particularly important is the historic chapel of Nuestra Señora de La Leche y Buen Parto — Our Lady of the Milk and Happy Delivery.
Spanish settlers brought this Marian devotion to Florida, and a shrine dedicated to Our Lady of La Leche was established here in the 17th century. Today the devotion remains especially associated with couples praying for children, expectant mothers and families.
Time will be provided for prayer and, subject to arrangements, Holy Mass.
We then continue into historic St. Augustine.
Our visits may include the Cathedral Basilica of St. Augustine, together with the city’s historic streets, colonial buildings and the impressive Castillo de San Marcos.
The combination is particularly valuable for pilgrims: we are not simply visiting old churches but seeing the Spanish colonial world in which the Catholic faith first took permanent root here.
Dinner and overnight.
Overnight: St. Augustine
Day 3 — St. Augustine – Central Florida
From Spanish Florida to the Space Age
After breakfast, we leave St. Augustine and travel south.
Today can be customized according to the interests of each group.
Option A — Kennedy Space Center
We travel toward Florida’s Space Coast for a visit to Kennedy Space Center, discovering the extraordinary story of the American space program.
From the early Mercury and Apollo missions to the Space Shuttle and the continuing exploration of space, this provides a completely different but fascinating dimension to our journey through Florida.
Option B — Orlando Theme Parks
Groups particularly suited to families, youth ministries or multigenerational parish travel may instead continue toward Orlando and include a day or afternoon at one of the major theme parks.
Option C — More Florida, Less Theme Park
For groups wanting to preserve a more traditional pilgrimage atmosphere, this day can instead be used for a more relaxed journey through Central Florida, additional Catholic visits or free time before continuing south.
Dinner and overnight in the Orlando/Central Florida area.
Overnight: Central Florida
Day 4 — Central Florida – Miami
Journey to South Florida
After breakfast, we continue south toward Miami.
The landscape and atmosphere gradually change as we approach South Florida and the cultural crossroads between the United States, the Caribbean and Latin America.
Upon arrival, we begin our introduction to Miami.
Depending on timing, we may enjoy a panoramic drive through some of the city’s most recognizable areas, followed by Holy Mass and our first opportunity to experience Miami’s extraordinary multicultural Catholic community.
Dinner and overnight.
Overnight: Miami
Day 5 — Catholic Miami
Faith, Exile & a New Home
Today we discover a side of Miami that many visitors never see.
Our guided Miami tour introduces us to the city’s history, neighborhoods and cultural transformation.
In Downtown Miami, we visit historic Gesù Catholic Church, whose origins date to 1896 — the same year Miami was officially incorporated.
Gesù takes us back to the beginnings of organized Catholic life in the city.
But its story later became intertwined with another decisive chapter in Miami history: the arrival of thousands of Cubans following the Cuban Revolution.
We continue to the Freedom Tower, one of the great symbols of the Cuban exile experience, before traveling into Little Havana and Calle Ocho.
Here we experience the community that grew from those successive waves of immigration: its restaurants, businesses, music, traditions and unmistakably Cuban identity.
Depending on the final program, our day may also include the American Museum of the Cuban Diaspora.
Our visits allow us to understand the historical background before tomorrow’s spiritual culmination.
Dinner and overnight: Miami
Day 6 — Miami
Our Lady of Charity
La Virgen de la Caridad
Today we make our pilgrimage to one of the most beloved Catholic places in South Florida:
the National Shrine of Our Lady of Charity — La Ermita de la Caridad.
Beautifully situated beside Biscayne Bay, the Shrine has become a spiritual home for generations of Cuban Catholics.
Here, devotion to Nuestra Señora de la Caridad del Cobre, Patroness of Cuba, became intertwined with the experience of exile.
We will discover the story of the Shrine, its remarkable Cuban historical mural and the generations of families who have come here to pray, give thanks and entrust their hopes to Our Lady.
Time will be reserved for Holy Mass, prayer and contemplation.
For our own family, La Ermita is also a place for which we have developed a very special affection through our many years working with Catholic parishes and communities in Miami.
It is somewhere we have visited and prayed on numerous occasions, and a sanctuary we are particularly happy to share with our pilgrims.
Depending on the group’s interests, the afternoon may include additional Miami sightseeing or free time.
Tonight we gather for our farewell dinner.
Overnight: Miami
Day 7 — Miami – Home
Return Home
After breakfast, at the appropriate time, transfer to Miami International Airport for our return journey.
Those choosing the Key West extension instead begin a spectacular journey south through the Florida Keys.
End of the main pilgrimage services.
Optional Extension
The Florida Keys & Key West
Day 7 — Miami – Florida Keys – Key West
The Road Across the Sea
After breakfast, we leave Miami and begin one of America’s great scenic journeys.
The Overseas Highway carries us through the Florida Keys, crossing bridges and small islands surrounded by the waters of the Atlantic and Gulf.
Stops can be incorporated along the route before reaching Key West.
Upon arrival, we explore the historic center, with time around famous Duval Street, Mallory Square and the colorful architecture of the island.
But Key West also adds another fascinating Catholic chapter to our journey.
Overnight: Key West
Day 8 — Key West
Mary, Star of the Sea
We begin at the historic Basilica of St. Mary Star of the Sea.
The present church dates from 1905, but Catholic activity in the Keys reaches much further back. Particularly interesting for the narrative of this pilgrimage is that Key West itself became home to a substantial Cuban population in the 19th century.
In 1879, a Cuban chapel dedicated to Our Lady of Charity of El Cobre was established in Key West for Cubans who had come to the island seeking freedom from Spanish rule.
This creates a remarkable connection with what we have just encountered in Miami.
The Cuban Catholic story of Florida did not begin in Miami.
Key West was already experiencing it generations earlier.
On the Basilica grounds we will also visit the Our Lady of Lourdes Grotto, constructed from natural rock collected around the island and dedicated in 1922.
Its creator, Sister Louis Gabriel, had experienced several devastating hurricanes and built the grotto seeking Mary’s protection for the people of Key West. A beloved local tradition maintains that as long as the grotto stands, Key West will be protected from the full force of a hurricane.
We will have time for Holy Mass and prayer before continuing our exploration of Key West.
The remainder of the day may include the historic district, Southernmost Point and other cultural sites before our farewell dinner.
Overnight: Key West
Day 9 — Key West – Home
Return Home
After breakfast, our pilgrimage comes to an end.
Depending on flight arrangements, departure may be from Key West International Airport or transportation can be arranged back toward Miami.
End of our pilgrimage services.
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