Chesterton Italy Trip


Our experienced staff can help you customize an itinerary that will best suit your group travel needs.


You will be accompanied by experienced and knowledgeable tour guides for the duration of travel.


Your tour will include all transfers between airports, hotels, and attractions for your convenience.


Enjoy a good night’s sleep in comfort with our top rated hotel accommodations for the duration of travel.


Your tour includes round trip transportation from local departure cities to any destination worldwide. 

TICKETS AND ADMISSIONSAll admission tickets to top attractions will be secured in advance to ensure your trip goes smoothly.



Highschool Custom Tours - Rome and Around Tour

Discovering Rome, Assisi, & Florence


  1. Round Trip International Airfare 

  2. Nine Days eight Nights

  3. Hotels - 3 nights in Rome,  2 nights in Assisi, and 2 nights in Florence

  4. All Breakfasts

  5. Eight Dinners

  6. Private Transportation. We will have our own private motorcoach every day until we arrive in Florence

  7. Local Tour Guides in Rome, Assisi, and Florence

  8. Lorna Holland, 24/7 Tour Director with you from beginning to end 

  9. Entrance fees: Coliseum, Roman Forum, Vatican Museums and Sistine Chapel, The Scavi at St Peter's Basilica, The Catacombs, entrances to churches and basilicas as listed, The Accademia in Florence. (The David)

Total cost per passenger including airfare:


Includes 3 Free Chaperones

Not Included:

  1. Travel Insurance 

  2. Tips

Sample Itinerary - Rome and Around Tour

Day 1 

Depart from Pittsburgh - Fly through the night

Day 2

Upon arrival in Rome, we meet Lorna, our 24/7 Tour Director as we clear security. Today we visit the Pantheon with a guide followed by an orientation tour of Navona Square, Trevi Fountain and the Spanish Steps. We then have free time in the area. Tonight we enjoy dinner at a local restaurant! B, D

Day 3

Today we will attend one of the following, depending on the travel dates we decide on.  This day will be moved around as needed!  Some events are dependent on availability. For the Scavi, all students must be over 15 years of age that day.   

This afternoon we meet our local guide to tour the Vatican Museum with its magnificent art collection and the Sistine Chapel with Michelangelo’s masterpiece and deeply moving interpretation of Christianity. We tour St. Peter’s Basilica and have quiet time for reflection.  B,D


Day 4

This morning we see the catacombs along the Appian Way, the traditional pilgrims’ route followed by Peter and Paul.  After lunch, we explore ancient Rome with the Colosseum and a walking tour with a local guide of the Palatine and Capitoline Hills areas. We walk through the Roman Forum and the ruins of 2000 years ago imagining what it must have been like as we see the tracks the chariot wheels left. B,D


Day 5

ORVIETO – ASSISI – Today the focus will be on the ancient history of the Italian people. We will make our way to the magnificent city of Orvieto, an ancient city of the Etruscans, home to a Eucharistic miracle, and the unforgettable frescoes of Signorelli’s chapel in the Duomo. For lunch we will eat at Da Maurizio, voted the 2nd best restaurant in all of Italy! We will then depart for Assisi. B, D


Day 6

After breakfast, our day begins with a local guide joining us as we explore the basilica with its wonderful frescoes by Cimabue and Giotto. We visit the Basilica of St. Clare, Francis’ friend and foundress of the Poor Clare nuns, and see the crucifix that spoke to St. Francis in San Damiano. We also visit the Basilica of Santa Maria degli Angeli built to enclose the tiny Church of the Porziuncola. The church is St. Francis’ first retreat and place of prayer, where he consecrated Clare as the Bride of Christ. Later we go to San Damiano to pray in the place where Francis wrote the “Canticle of the Sun.” B,D 


Day 7

We depart his morning for Florence, “the Cradle of the Renaissance.” En route we stop at the American Cemetery of Florence. Here we see the graves of thousands of GI’s who fell while fighting their way “up the boot” of Italy. Next we stop for a photographic moment and a beautiful view of Florence on Piazza Michelangelo. A local guide joins us for a walking tour and explains the history of this colorful city to us as we walk. We learn of the Duomo with its famed Baptistry, Giotto's Tower, the Pitti Palace, and Ponte Vecchio. We see the magnificent bronze doors of the Baptistery and explore the treasures inside the Duomo. We overnight in Florence tonight. B,D

Day 8

We leave from Florence this morning, we stop for a visit to the Accademia with Michelangelo's incomparable "David." The afternoon is free to explore all the great treasures of the city or go shopping! B, D

Day 9

Our journey draws to a close as we transfer to a Milan airport for our return flight home. We return home moved by the Spirit with enduring memories of early Christianity, historic sites and cities, and a host of new friends. B

Abbreviations for included meals: B = Breakfast   L = Lunch D = Dinner

Supplemental charges for inflight meals are not included in the tour cost.