Italy Tour 2023 | University of Portland

Italy Tour 2023

Art, Culture, Food, & Wine Tour of Italy

June 21 – July 1, 2023


While the 2023 excursion is fully booked, we encourage you to read about it–we will reach out when the next trip is planned.

Dr. Franco, an expert of medieval and Renaissance Italian art, religion, and history, and Dr. Gary Malecha, an expert in American and European food politics and policy, and Rev. Ed Obermiller, CSC, invite you to come explore the best food and art that Italy has to offer. Each day, we will be visiting iconic destinations while also making time to venture off the beaten path. Our goal is to bring Italy’s culture, history, and traditions alive and to provide UP alums with a one of a kind experience.

What is included in the cost?

The $4,395 cost of the tour includes lodging, most meals, chartered bus transportation for our excursions, and guided visits to numerous churches, museums, and other points of interest. We will be staying in charming boutique hotels located in the heart of Rome, Siena, and Florence. The tour includes seven group dinners at some of the best restaurants in Rome and Tuscany, expertly selected by your guides, as well as all breakfasts. Our goal is to bring Italy’s culture, history, and traditions alive and to provide UP Pilots with a one-of-a-kind experience.

A Few Practical Matters

  • Participants must be able to walk up to 8 miles a day, as each day will involve a significant amount of walking, as we’ve found that this is the best way to experience Italian culture.
  • We will be staying in carefully chosen and well-reviewed 3 and 4 star hotels. Breakfast will be included each day.
  • As getting to experience authentic local Italian cuisine is one of the features of this trip, we are pleased to announce that we will be eating at some of the best restaurants that Rome, Siena, and Florence have to offer. Most dinners (except where noted in the itinerary below) are included in the cost of the trip.
  • Participants will have ample free time in each city that we visit. We will be happy provide suggestions on sites, restaurants, shopping or anything else of interest to participants.
  • Please note that this itinerary is subject to change, as necessary. If any sites are closed for renovation or other reasons, they will be replaced by comparable options.
  • Please note that flights are not included in the tour price.
  • Daily Mass led by Fr. Ed will be open to all who would like to attend.

Trip Details

  • For more information or to reserve your spot, contact Dr. Brad Franco at
  • A $500, non-refundable deposit secures each spot. Deposits are due by November 1, 2022. 
  • Full payment is due February 10, 2023.

About Our Guides

Dr. Bradley Franco is a historian of medieval and Renaissance Italy at the University of Portland who has lived in Siena and published extensively on the city, its religious history, and its culture. Most recently, he published A History of Siena From Its Origins to the Present Day (Routledge 2019).

Dr. Gary Malecha is Professor of Political Science at the University of Portland and the recipient of the Spirit of Holy Cross Award, among many other honors. He is an expert in European culture and food politics, and is a connoisseur of Italian food, wine, and olive oil. 

Father Ed Obermiller, CSC is a gifted, compassionate leader who has served the University of Portland and the Congregation of Holy Cross in many capacities for over twenty six years. He received his undergraduate education at Pontifical College Josephinum in Columbus, Ohio and his Master of Divinity from the Graduate Theological Union in Berkeley, California.


Wednesday, June 21: Rome
Afternoon: Group will meet at our hotel in Rome for introductions. We will then take a walking tour of Piazza Navona, the Pantheon, and the Trevi Fountain. Group will return to hotel before dinner. 

Evening: The group will gather at approximately 7:30 p.m. for a group dinner (included in program costs) at a local restaurant to enjoy traditional Roman cuisine. 

Thursday, June 22: Rome
Morning: Walk to the Vatican for a guided tour of the Basilica, visit the Vatican scavi (underground crypts) with the tomb of St. Peter, and attend private Mass at St. Peter’s Basilica. 

Afternoon: Take a chartered bus and visit the ancient Roman catacombs of St. Priscilla, containing some of the earliest surviving Christian art in Europe. 

Evening: Group will gather in hotel lobby at approximately 7:30 p.m. and proceed to a local restaurant for group dinner (included in program costs) featuring traditional Roman cuisine. 

Friday, June 23: Rome
Morning: Group will meet in lobby after breakfast to take a chartered bus to the Coliseum and the Forum for guided tours of both ancient sites. Free time and lunch on own after tour. 

Afternoon: Visit to the Basilica San Clemente where Dr. Franco will give a tour of eleventh-century church, the fourth-century basilica underneath it, and the first-century pagan temple below! 

Evening: Early dinner (on own), followed by group excursion to the Vatican museums (including the Sistine chapel and Rafael rooms) at night.
Saturday, June 24: Rome – Assisi – Siena
Morning: After breakfast, check out of hotel and board chartered bus to Assisi (about a 90-minute trip north of Rome). Group will arrive in Assisi mid-morning and visit the lower church (and tomb of St. Francis). Dr. Franco will lead the tour of the lower church. Free time and lunch on own in Assisi. 

Afternoon: After break for lunch, Dr. Franco will lead a tour of the upper church with the famous Giotto frescoes in the afternoon. The group will depart Assisi and take chartered bus to Siena (approximately 90 minutes) and arrive at hotel around 5:30 p.m.

Evening: Group will walk to neighborhood restaurant, Papei, which features typical Tuscan Cuisine (included in program costs). After dinner, participants will be free to explore the city and return to the hotel on their own.

Sunday, June 25: Siena
Morning: After breakfast, group will meet in hotel lobby to take a walking tour of Siena, a UNESCO world heritage site. We will visit Santa Maria dei Servi, San Domenico (with relics of St. Catherine of Siena), the Piazza del Campo, and the frescoes of the Palazzo Pubblico. After tour, participants will have free time to explore the city. Lunch on own.

Afternoon: Optional visit to the Pinacoteca Nazionale (Siena’s world-class art museum).

Evening:  Group will walk to Il Gatto for a Tuscan feast in a local osteria (included in program costs).  After dinner, participants are free to explore the city and return to the hotel on their own.

Monday, June 26: Sant’Antimo, Montalcino, and Pienza
Morning: Breakfast in hotel (included in program costs).  Group will meet in lobby of hotel at 9 a.m. to board a bus to the Tuscan Countryside. We will visit the Romanesque monastery of Sant’Antimo and the hilltop town of Montalcino for wine tasting.

Afternoon: After a wine-soaked picnic lunch (included in program costs), we will explore the quaint Renaissance hamlet of Pienza.  

Evening: Return to hotel around 6 p.m. Free evening and dinner on own.

Tuesday, June 27: Siena
Morning: After Breakfast, group will visit Siena’s gothic cathedral, as well as the Museo del Duomo. Participants will have the opportunity to climb to the top of the unfinished cathedral façade for an unrivaled view of the city.

Afternoon: Group will gather at designated meeting place for local wine and cheese tasting. This will be followed by a visit to the museum of one of Siena’s local contradas (or neighborhoods) and further explanation of Siena’s famous Palio and the contrada system.

Evening: Group will gather at 7:30 p.m. and walk to a dinner party in one of Siena’s famous contradas with locals (included in program costs).  

Wednesday, June 28: Siena – Monteriggioni – San Gimignano – Florence
Morning and Afternoon: After breakfast, check out of hotel and board bus for Monteriggioni, a small medieval garrisoned village. We will then continue on to San Gimignano, a picturesque Tuscan hill town and UNESCO world heritage site famous for its medieval towers. Dr. Franco will lead a tour of the town’s iconic Renaissance art and architecture found in the Collegiata, museo del comune, and the church of San Agostino.

Late Afternoon: Board bus for trip to Florence (about 90 minutes) and check into hotel in Florence by 5 p.m.

Evening: Meet in hotel lobby and walk to local restaurant for group dinner featuring local Florentine cuisine (included in program costs). Free to return to hotel on own.

Thursday, June 29: Florence
MorningAfter breakfast, meet in hotel lobby to visit the churches (and Renaissance art) of Santa Maria Novella, Santa Trinita, and Santa Croce.

Afternoon: Lunch on own in the Mercato. Guided tour of the Uffizi, the greatest museum of Renaissance art in the world.

Evening: Free time to explore Florence and dinner on own.

Friday, June 30: Florence
Morning: After breakfast, visit Accademia (with Michelangelo’s David) and the convent of San Marco.

Afternoon: Lunch and afternoon on own. 

Evening: Meet in hotel lobby for final dinner at local restaurant in Florence (included in program costs).

Saturday, July 1: Departure from Florence
Morning: Breakfast in hotel (included in program costs). Check out of hotel by noon.