Pilgrimage Trip to
Rome, Assisi and Florence

- Fall 2023 -


Disciples at Work:
Exploring the lives of St. Paul, St. Peter, St. Francis, St. Clare and the Church in Italy through the Renaissance
on a Pilgrimage Trip to Rome, Assisi and Florence
with the Church of the Good Shepherd
Cashiers, NC

11 nights / 12 days
from 20 October
to 31 October 2023

with optional Siena Extension:

3 nights / 4 days
from 31 October
to 3 November 2023

DAY 1 - Friday, October 20

In the air

Sit back and relax on your flights (arranged by participants directly), bursting with the anticipation of your time in Italy!  With some advance planning, participants can choose to be on the same flights and begin the camaraderie then.

DAY 2 - Saturday, October 21


Welcome to Italy! Benvenuto! Grab your bags and head to your accommodation independently by car or pre-arranged van transfer, taxi or train. (Groups of six people can pre-arrange a minivan at $175 per van.) 

After settling in, you can explore the city a bit on your own or choose to delight in an optional 3-hour Rome Welcome Walk starting at 3.00 PM in the afternoon to see the main sites of one of the most impressive cities in the world. (extra $45 fee).

Otherwise meet your fellow travelers and tour manager in the early evening as we welcome you in true Italian style – at the table! Enjoy a Welcome Reception & Dinner (included) before settling in for your overnight stay in a Double room at the Hotel Conciliazione.


DAY 3 - Sunday, October 22


After breakfast,  we set off in private mini-vans to tour some of the important sites relating to the beginning of Christianity. First, we will visit one of the Catacombs located on the outskirts of the city. 

Christians started burying their dead underground in the 2nd century. Catacombs began and developed around family tombs, whose owners, newly converted Christians, did not reserve them to the members of the family, but opened them to their brethren in the faith. With the passage of time, these burial areas grew larger. One complex in the area occupies an area of 90 acres, with a network of galleries about 12 miles long, occupying four levels! After exploring this unique space, enjoy a special Sunday service led by Fr. Rob. Lunch will be enjoyed as a group in the area. In the afternoon we will continue our explorations of the final resting place of the Evangelist Paul, in the Basilica of St. Paul Outside the Walls. Explorations then continue to San Clemente.  In this sacred space, one experiences different levels of Rome’s past. From the 12th century Basilica to the 1st century area with its Mithraic temple. Joining us for the day will be an expert guide. In the afternoon return to the hotel and enjoy dinner on your own tonight in one of the many lively restaurants in the neighborhood.

DAY 4 - Monday, October 23


Buongiorno! After a quick coffee at the hotel, it’s time to set off for an early-morning tour of the Vatican Museums, in the company of an expert guide to bring the extensive collection of artworks to life and share with you the fascinating history behind one of the most iconic and memorizing places in the world! Admire world-renowned works of art including Raphael’s School of Athens, the celebrated Apollo Belvedere, and Laocoön and His Sons.  Walk through the long Galleries before arriving to the famous Sistine Chapel where the famous figures of Michelangelo await. Next, it’s time for Brunch to recharge before setting off to continue seeing more of the museums such as the early Christian section.  

In the afternoon tour St. Peter’s Basilica, his burial site, where your guides will regale you with fascinating insights and enjoy a time of prayer. Enter the largest church in Christendom, built on the site where Saint Peter was martyred. In the evening, you have free time for dinner (on your own or in groups, and at your own expense) before turning in for the night. 


DAY 5 - Tuesday, October 24

Rome and Assisi

After breakfast at the hotel in Rome, it’s time for check-out and to set off on new adventures! Meet up with your driver and settle in for the drive to Umbria in a private coach. Along the way, we’ll stop to visit the Dionigi Winery (or similar) where you will learn about one of Italy’s most famous and enjoyable passions – wine! – and even savor in a typical lunch (included) at the estate. We then head to Assisi, arriving in the late afternoon in time for check-in for your 3-night stay at the Fontebella Palace HotelThis town is the birthplace of St Francis and St. Clare, and it retains a magical, mystical atmosphere. You then have time to stroll around the undulating streets of Assisi on your own or with the group and Fr. Rob.  Many great dining spots await (including bakeries and gelato shops, your choice and cost) before settling in for your first of three nights in Assisi.

DAY 6 - Wednesday, October 25


After a Continental/Italian breakfast at the hotel (included), it’s time for a Morning Tour of Assisi: Life of St. Francis including churches, the home of St. Francis, the Basilica di San Francesco in Assisi with its  frescoes and more … all in the company of an expert Assisi guide.  

Afterwards comes free time to have lunch (your choice and cost) and rest up in preparation for an afternoon visit as a group to the San Damiano Church and Eremo delle Carer hermitage complex, again led by your private guide. 

In the evening gather for a group reflection and dinner (included) before your overnight stay in Assisi.


DAY 7 - Thursday, October 26


After breakfast at the hotel, we turn our attention to Assisi: Life of St Clare on a 3-hour guided tour. We go to the Church of St Clare to see the saint’s incorrupt body. 

We then gather for a nice traditional lunch in the city (included) before you have free time in the afternoon for spiritual reflection or to explore the city and then go for dinner (on your own) on what will be your last night in Assisi (for this trip at least!).

DAY 8 - Friday, October 27

Assisi, Cortona & Florence

After breakfast at the hotel and check-out, it’s time to say goodbye to Assisi and head in St. Francis’ footsteps.

First stop is to see Santa Maria degli Angeli where we visit the Chapel, the Porziuncola, the rose bush and the cave where the saint retired for prayer. We will then drive to Cortona for lunch together (included) and to see the sites in the company of your very own private tour guide. Time permitting, visit Le Celle di Saint Francis before reaching Florence!  What a great city for culture, walking, and spiritual reflection.  

After check-in at the NH Palazzo Gaddi, you can choose to rest up in your comfortable room or hit the city streets and have dinner in one of the many amazing eateries in the historic city center (on your own) before your first of four overnight stays in Florence.


DAY 9 - Saturday, October 28


Following breakfast in the hotel, head off on a guided tour of Florence including a visit of the San Marco Monastery with frescoed cells by 15th century master Beato Angelico and the Accademia Gallery (home to Michelangelo’s David) in the company of a private tour guide.

Afterwards enjoy a delicious lunch in a typical Florence trattoria (included).  In the afternoon transfer to one of the city’s most spectacular gardens, found on private grounds and visited by special arrangement. Afterwards there is free time for dinner (at your own expense) before an overnight stay in Florence.

DAY 10 - Sunday, October 29


This morning, after breakfast, enjoy a Sunday service by special arrangement.

The day is then dedicated to exploring one of the most impressive collections of art in the world as a private guide leads you through the Uffizi Gallery. Admire masterpieces by Botticelli, Leonardo da Vinci, Raphael and Michelangelo.

You then have free time in the afternoon for lunch and individual activities – feel free to ask us to make some recommendations or arrange additional activities for you – then time for dinner in Florence (at your own expense) before spending the night in Florence.

DAY 11 - Monday, October 30


On our last full day in Florence together, we will spend time exploring together the Religious Center, together with your private guide. Concentrating on the magnificent Cathedral (Duomo) and Baptistry see sites dating back through the ages, even as old as the sixth and seventh centuries.  Lunch on your own.  

There is free time in the afternoon for spiritual reflection or perhaps for some shopping or to rest up before a group farewell aperitif (included) before the last overnight stay in Florence.

DAY 12 - Tuesday, October 31


After breakfast, it’s time to check-out of the hotel in Florence in time for final transfers (not included and to be arranged separately) before the end of the Rome, Assisi and Florence program.  

The airport in Florence is nearby and a good point of departure.  Florence also has a convenient train station for onward travel.  The Rome airport is 3 ½ hours away, so transfers there are more involved, but possible.

Should you wish to extend your time in Italy, there is, however, the Optional Siena / Tuscany Tour Extension for an additional 3 nights/4 days.

Extension Program

DAY 12 - Tuesday, October 31


After check-out from your hotel in Florence, take advantage of the private transfer to Siena, stopping along the way to savor the sites and tastes of Tuscany. 

Visit a Chianti winery and see the spectacular countryside. Delight in a typical Tuscan lunch  (included) before going to San Gimignano for an afternoon visit of the city of medieval towers.


Arrive in Siena (a great walking town) in the late afternoon for check-in at the hotel NH SIENA where you will stay in a Double Standard room (or Superior room on request with supplement). This evening, you will have free time for dinner (at your own expense) before an overnight stay in Siena.


DAY 13 - Wednesday, November 1


After your Continental/Italian breakfast (included) at the hotel, set off on a fascinating private tour of religious Siena with a focus on St Catherine, the patron saint of Europe.   In the company of your local expert, on hand for the next 6 hours, enter the famous Cathedral and view relics of St. Catherine at the Basilica of St. Dominic. Stroll the Piazza Del Campo, one of Italy’s finest squares. If possible visit the Basilica of St. Francis, containing the miraculous consecrated hosts that remained intact since 1730.

Next comes a traditional lunch in local restaurant (included) before free time to stroll the cobbled streets and go for dinner (at your own expense) in one of the many traditional eateries within the ancient walls.

You then have an overnight stay in Siena.

DAY 14 - Thursday, November 2


Today is dedicated to you and your interests, with time available for individual activities – visit the museums, enjoy some shopping, go on a DIY tasting adventure or have us organize an alternative activity of your choosing (with any costs to be paid separately).

One such option is a winery excursion to Montalcino or Pienza/Montepulciano. Hiking and bike rentals are also options to explore the countryside. Participants will discuss options and pre-plan the day—as a group, as smaller groups, or as individuals.  Dinner is on your own before your overnight stay in Siena.

DAY 15 - Friday, November 3


On the final day of the tour, check-out of the Siena hotel after breakfast. A private transfer to Florence airport or Florence train station will be arranged (with 2 fixed departure times possible).

Alternative departure points can also be organized upon request, possibility at extra cost.

The Siena Tour Extension ends and it’s time to say arrivederci!

Pilgrimage Dates

From October 20 to October 31, 2023


The Pilgrimage Trip Rome, Assisi and Florence program includes:
  • 4* Accommodation in a double room for 10 nights including bed and breakfast
  • Whispers (audio devices to hear the guide/chaperone) for 10 days
  • Tour manager at your disposal for 12 days
  • Tips for group meals, activities and hotels
  • Porterage to and from the 3 hotels throughout the program
  • Activities with local guides and entry costs to the included venues (as indicated)
  • Transportation via luxury coach or mini-vans (as indicated)
  • Multi-course meals (2 dinners, 4 lunches, 2 reception dinners, 1 winery visit)
  • My Italian Treasures assistance in Italy
  • City Taxes (from 3–6 euro per person per day) imposed in each city by law

Extension Dates

From October 31 to November 3, 2023


The Siena Extension package includes:
  • 4* Accommodations in a double room for 3 nights including breakfast
  • A local guide for one full day
  • Entry costs to sites included in the itinerary
  • Full-day arrival transfer excursion from Florence to Siena in a private minivan with stops along the way
  • Winery visit and countryside lunch
  • Time in San Gimignano
  • 2 final transfers in private minivan to Florence airport or Florence train station
  • 1 meal in a local establishment
  • City Taxes (from 3–6 euro per person per day) imposed by law


The Pilgrimage Trip Rome, Assisi and Florence program and Siena Extension do not include:
  • Trip Insurance
  • Airport transfers outside of group travel times
  • Porterage to beginning hotel and from ending hotel
  • Gratuities for tour manager
  • Costs for optional extras

We look forward to sharing our love for Italy with you!