September Pilgrimage to Italy

In October 2020 Joannie and I started The Catholic Traveler Podcast. We’ve uploaded a new episode every week, and during Lent we temporarily switched to a daily format, with a new episode each day covering the Lenten Station Churches. We now have thousands of amazing listeners.

Through Joannie’s Diocesan work, we’ve been working on pilgrimages together for years.

So it only made sense to offer a pilgrimage for our podcast listeners.

Along the way we plan to record a few episodes live and on location and visit some of the most popular places we’ve discussed on the show.

Dates: September 7th – 16th, 2021

Price: $3,400 (plus air)

Visiting: Rome, Orvieto, Assisi

My first post-pandemic sold out in just a few days. I’m keeping all my 2021 pilgrimages small, so this one will surely sell out quickly as well.

As of May 16th, Italy has reopened to US tourists! A negative test, or proof of vaccine, or proof of recent recovery is all that is required. But keep in mind, this is Italy and anything can change at any moment. This pilgrimage comes with the risk that it could be cancelled if Italy decides the reopening isn’t going well of if they change the requirements for entry. You can read the cancellation policy below as well as what Italy is planning to require for entry. Should you have any questions, email me.

Is this pilgrimage trip for you?

You need to be flexible.
This pilgrimage is not for grumpy people or those unable to be joyfully flexible. Italy is just getting back to tourism. While everything is going great so far, we have be able to adjust our plans if needed.

That’s said, my June pilgrimage, The First Post-Pandemic Pilgrimage to Italy, was a huge success with absolutely no issues.

So if you are easy-going and excited to travel, even with some uncertainties mixed in, this could be the trip for you!

If this pilgrimage doesn’t work for you, no worries, I’ve been doing this for nearly 17 years and plan to do many, many more.

You should be in good physical shape.
We will do a lot of walking, much of it outside, and much of it on uneven ground – and remember that this is in the summer heat. We average around 5 miles per day. Please do consider this before signing up.

You need to be able to carry your own luggage.
You are responsible for your luggage and getting it from the plane to the bus and the bus to your hotel rooms. I will provide a thorough packing list to help you pack lightly and efficiently.


I want you to feel comfortable signing up for one of the first post-pandemic pilgrimages to Italy, so I am offering you 100% refunds for any reason you may wish to cancel.

I offered 100% refunds for all my cancelled/postponed pilgrimages for 2020, and I’m offering that here as well. It’s the right thing to do.

If for any reason I need to cancel or postpone the trip, you will be refunded 100% of the cost of the pilgrimage.

If Italy changes their requirements for entry, and you decide that doesn’t work for you, you will be refunded 100% of the cost of the pilgrimage.

If you need to cancel for any reason up to 21 days before the start of the trip, you will be refunded 100% of the cost of the pilgrimage.

If you need to cancel for any reason after that date, you’ll get everything back minus $500.

Trip insurance is a wise investment in case something comes up while you are in Italy. I can recommend places for that, if you are interested.

Entry Requirements

As of May 16th, Italy is allowing US tourists back. A negative test, or proof of vaccine, or proof of recent recovery is all that is required. But keep in mind, this is Italy and anything can change at any moment.

You are responsible for getting tested according to your airline’s instructions.

I will keep you updated on Italy’s requirements to make this as easy as possible.

Should anything change, remember, I am allowing you to cancel for any reason with a 100% refund up 21 days before departure.


As of this writing, masks are only required inside public places, with a few outdoor museums also requiring them. No exceptions are made for vaccinated people. No exceptions are made for those who are unable to wear masks for medical or personal reasons. We are all visitors to a foreign country, so we must be willing to follow their laws.

We will follow the local laws and the request of our bus driver. That means if masks are required while outside and/or on buses, we will comply. But it also means that if masks are not required outside and/or on buses, then it will be up to the individual to wear a mask or not.

If you are uncomfortable around those who do wear masks, or those who do *not* wear masks when not required by law, this is not the trip for you.


Since Italy is allowing anyone passing a negative test, know that we could have people who are vaccinated on the trip and some who are not.

Keep in mind that some of the Italians we interact with here will not be vaccinated.

If you are uncomfortable around those who are not vaccinated, or those who are vaccinated, this is not the trip for you.

Openings and Closings

Currently, everything is open, including churches, museums, restaurants, cafes, and bars. But keep in mind that things can change. Again, we need to be flexible. If something unexpectedly closes, we will look for a good alternative. And while I don’t expect this to happen, even the Vatican Museums, Colosseum, or Papal Audience could close or be cancelled without warning.

Basic Itinerary

I’ll have the detailed itinerary once Masses and tour times are confirmed. But if you have specific questions, let me know.

We are going to take things easy. This is, hopefully, a once in a lifetime opportunity to visit Italy in the summer months before crowds fully return.

Expect some slow walks, long coffee breaks, relaxing meals, and plenty of time for prayer in each place we visit.

We will start with two nights in Rome, then head to Assisi for three relaxing nights, and then return to Rome for four more nights.

In Rome
We will visit lots of amazing churches, including Saint Peter’s Basilica, Saint Mary Major, Saint Paul Outside the Walls, Saint John Lateran, Scala Santa, Santa Croce in Gerusalemme, and many more.

We will attend the Papal Audience.

We will visit the Vatican Museums, including the Sistine Chapel, the Colosseum, the Spanish Steps, the Trevi Fountain, the Pantheon, and Piazza Navona.

We will also visit some favorite off the beaten places we’ve discussed on the podcast, including several of the Lenten Station Churches and the Roman Canon Churches.

In Assisi
Will will visit San Damiano, San Francesco, Santa Chiara, and the Hermitage.

We will have a winery tour with lunch at a farm.


$3,400 per person – ground only.

$1,000 deposit secures your spot.

Final payment of $2,400 is due August 6th, 2021.

The cost is per person, in double occupancy, meaning two people to a room.

Traveling alone?
Usually I match singles with other traveling singles and that always works out great. This time, I’m not sure how many are willing to share rooms with strangers. So, if you are traveling alone, there will be a single supplement of $800. However, you’ll have a chance to virtually meet any other singles before the trip, so you could always agree to share, and then there would be no single supplement.

Included in the price

Accommodations for 10 nights
Rome: Seven nights at Residenza San Paolo VI
Assisi: Three nights at Hotel Umbra

Breakfast daily plus 7 additional meals in some of my favorite restaurants, never hotels!
Drinks, including unlimited wine, is included in all our lunches and dinners.

Coffee / Pastry breakfast at my favorite cafe

Happy Hour one evening

Airport transfers
Airport transfers between FCO and our Rome hotel. Send me your flight info and my driver will pick you up. Easy.

All group ground transportation
We’ll be traveling in a private motor coach.

Full time service of a tour director
I’ll be with you at all times.

Local guides
We will have local experts with us for some tours.

No hidden costs
If we do it as a group, it’s included in the price! You are responsible only for the meals you have on your own, souvenirs you wish to buy, and anything you want to do in your free time.

Guaranteed price
Once I receive your deposit, your tour price will not go up!

All tips for group meals, guides, and drivers
Would you believe that many tour companies require you to tip as you go? Not only does that add to the advertised sticker price of a tour, it’s also a huge hassle to you! No need to worry about that here. Tips are already included.

Entry fees and tours
All entry fees and tours to our included group activities.

Social planning
Plan your trip with your traveling companions before you leave! I’ll set up private Facebook groups for each tour to give you a chance to meet before you meet!

You time
We have a lot planned, but time on your own is important. We take our time in churches to give you the opportunity for prayer and reflection. We also include free time for you to explore, shop, and relax on your own.

Not Included

Your flights.

You should arrive in Rome no later than September 7th, we will begin at 3 PM on September 7th.

You should depart no earlier than September 17th, our last group activity will be dinner on the September 16th.

Most airlines are offering free changes should anything happen to the trip. Most airlines are not offering refunds, but rather a credit.

If you need to cancel your trip for any reason, if the situation in Italy changes and we need to cancel or postpone the trip, it’s your responsibility to work with your airline to cancel, reschedule, or request refunds.

Sign up

Use the form below to sign up for this pilgrimage. If you have any questions, email me at

Optional Trip Insurance
If you think there is any chance you may need to cancel, I recommend you purchase travel insurance. A “Cancel for Any Reason” plan will let you, well, cancel for ‘most’ any reason. Most plans should allow for at least a 75% refund should you need to cancel at any time before departure. I have a friend who specializes in trip insurance, you can contact him directly, but you are under no obligation to use him and I don’t get any sort of kick backs, so shop around and find what is best for you.

Deposit Info
You’ll be able to pay by credit card or check. Payment info will be emailed to you once you sign up.