Italy Tour 2023

Art, Culture, Food, & Wine Tour of Italy

June 20 – June 30, 2023


With Dr. Brad Franco, Dr. Gary Malecha, and Fr. Ed Obermiller, CSC as your guides, you will visit iconic destinations while also venturing off the beaten path during this one-of-a-kind travel experience for UP alumni, family, and friends. 

In Rome, you will explore the Colosseum, Pantheon, and ancient catacombs, attend a private Mass at St. Peter’s in Rome, and ponder Michelangelo’s Sistine Chapel; in Siena, you’ll marvel at the Gothic churches, admire medieval architecture and art, and explore the Tuscan countryside; then in Florence, you’ll be able to contemplate the artistic achievements of the Renaissance. All the while, you will stay in luxury accommodations and enjoying the best food and wine that Italy has to offer with fellow UP alums!

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. Fr. Obermiller will hold an optional mass for participants daily. 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 Pilots with a one-of-a-kind experience.

A Few Practical Matters

  • As the best way to see the towns of Rome and Tuscany is on foot, participants should expect to walk 6-8 miles each day, often on hilly, cobblestone streets.
  • We are still finalizing hotel reservations and this information will be available by the end of summer. We will be staying in 3- and 4-star well reviewed hotels. 
  • Flights and trip insurance are not included in the cost of the trip, though we will provide information on how to get to Rome from nearby airports.
  • The tour cost assumes double occupancy for lodging. Single occupancy is available for an extra $1000.
  • Participants will have free time in each city that we visit. We will happily provide suggestions on sites, restaurants, shopping, or anything else of interest to participants.
  • Please note that this itinerary is subject to change, if necessary. If any sites are closed for renovation, they will be replaced by comparable options.

Trip Details

  • Early Bird Special: Reserve your spot by September 1, 2022 and receive $100 off the cost of your trip!
  • 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.



Tuesday, June 20
Arrival in Rome

  • Meet in Hotel dei Mellini lobby at 3 p.m. for walking tour (sites include Piazza Navona, Pantheon, Trevi Fountain, and Spanish Steps).
  • Dinner at 7:30 p.m. (meet at 7:15 in hotel lobby)

Wednesday, June 21

  • Visit Colosseum and Forum.
  • Lunch on own (11:30 a.m. – 1:30 p.m.).
  • Tour of the Church of San Clemente.
  • Return to hotel at 4 p.m.
  • Free time.
  • Group dinner.

Thursday, June 22

  • Walk to St. Peters. While there, we will visit the basilica, have Mass at St. Peter’s, and visit the Vatican Museums, including the Sistine Chapel.
  • Lunch break.
  • 3 p.m. – Take a chartered bus to the catacombs of San Priscilla for a tour.
  • Dinner on own.

Friday, June 23
Rome – Assisi – Siena

  • Take a chartered bus to Assisi. Visit upper and lower church in Assisi with guided tour. Mass at the tomb of St. Francis. Arrive in Siena by 6 p.m., check into Hotel Athena.
  • Group dinner at Papei.

Saturday, June 24

  • Walking tour of Siena, a UNESCO world heritage site, with visits to sites of local interest, including the Palazzo Pubblico.
  • Lunch and free time on own.
  • Group dinner at Il Gatto.

Sunday, June 25
Wine Tasting in Chianti

  • Wine tasting and group lunch at local wineries.
  • Farm/butcher visit in the afternoon.
  • Return to Siena by 6 p.m.
  • Free evening and dinner on own.

Monday, June 26

  • Guided tour in Siena of the cathedral, museo del Duomo, and other local sites.
  • Lunch and free time (noon – 3 p.m.).
  • Visit the museum of the Sienese neighborhood of Onda (if open).
  • Local cheese and wine tasting.
  • Group dinner (Contrada dinner).

Tuesday, June 27
Siena – San Gimignano – Florence

  • Depart Siena and visit the hilltop town of San Gimignano. While there, we will visit the Collegiata, Museo del Comune, and the Church of San Agostino.
  • Lunch and free time to explore San Gimignano on own.
  • 3 p.m. – Depart San Gimignano for Florence.
  • Arrive at hotel in Florence around 5 p.m.
  • Group dinner in Florence.

Wednesday, June 28

  • Walking tour of Florence, with visits to Santa Croce and several other sites of interest.
  • Afternoon guided tour of Italy’s most famous art gallery, the Uffizi.

Friday, June 29

  • Visit the Churches of Santa Maria Novella and Santa Trinita.
  • Visit Mercato Centrale, the celebrated food market of Florence.
  • Lunch and free time on own (cooking class?).
  • Final dinner at local restaurant in Florence.

Saturday, June 30
Departure from Florence

  • All participants must check out of hotel by noon.