October in Italy

October 17th – 27th, 2022
$3,800 (plus air)
Priest: Father Christopher Smith
Sold Out! Email me to be on the waitlist.

Some of you may know the story of Father Christopher Smith as the guy who traveled with me in 2011 while working as a pharmacist and then traveled with me again in 2021 as a priest. If not, you’ll love when he tells the story of his calling.

October is my favorite month in Italy. The weather is usually perfect. The days are warm, the mornings are cool. The leaves are changing. And the olives are being pressed.

Italy is currently open to anyone vaccinated, anyone recovered in the last six months, and to anyone passing a negative test. As of this writing, the only restriction for unvaccinated is indoor dining, but that should be dropped in three weeks. Keep in mind, this is Italy and things 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 or if they change the requirements for entry. You can read the cancellation policy below – it’s very generous. 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 getting back to normal, but the world is still a bit uncertain. While everything is going well so far, we have be able to adjust our plans if needed.

That said, all my pilgrimages since Italy has reopened have been great.

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. 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. We don’t not have porters and the two story hotel we use in Rome does not have an elevator. I will provide a thorough packing list to help you pack lightly and efficiently.


You’ll get the full itinerary once Masses are confirmed, but…

We will start with two nights in Rome at the lovely Bramante Hotel in the Borgo neighborhood – with lots of great food and shopping just outside the door, and Saint Peter’s Basilica a 60 second walk away. We will get a great intro to Rome with visits to the Appian Way, the Colosseum, Roman Forum, and some of Rome’s oldest churches.

Then we travel to Tuscany. We are staying three nights in a beautiful hotel converted from a monastery built in the 1500s. Our local guide will walk us through the history of this Renaissance town, where we will visit Michelangelo’s David, the Duomo, the Ponte Vecchio, and more. Over the next few days we will visit Tuscan wineries, and, if the harvest is good this year, an olive mill. We will also make a stop in Siena to see the hometown of Saint Catherine.

Next we head into Umbria to Assisi. We will be staying two nights in Hotel Umbra, just off the main piazza. We will have a local guide take us on tour of the shrines, including San Damiano, the Hermitage, and the Porziuncola. We will visit the nearby town of Montefalco so we can compare Tuscan wine to Umbrian wine, and have lunch at a family farm.

We return to Rome for three nights, stopping for lunch in the hill town of Orvieto, known for the Eucharistic Miracle that led to the Feast Corpus Christi. In Rome we will tour the Vatican, see the pope, visit some amazing churches, and have some excellent meals.

Of course Mass will be celebrated daily in some of the most beautiful churches in Italy.


$3,800 per person – ground only.

$1,000 deposit secures your spot.

Final payment of $2,800 is due September 17th, 2022.

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

Traveling alone?
I match singles with other traveling singles (of the same sex) and that always works out great. If you are uncomfortable sharing a room with a stranger, you can request a single room for an additional $900. Single rooms are limited.

Included in the price

Accommodations for 10 nights
We are staying 5 nights at the lovely Hotel Bramante located in the Borgo neighborhood.

We are staying 3 nights at the Renaissance era hotel of Loggiato dei Serviti in Florence.

We are staying 2 nights at Hotel Umbra in Assisi, just off the main piazza.

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.

Two lunches at wineries, one in Tuscany and one in Umbria

Coffee and pastry breakfast at my favorite cafe, Sant’Eustachio

Traditional aperitivi one evening

Airport transfers
Airport transfers both ways 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.

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 October 17th, we will begin at 3 PM on October 17th. If you want to arrive early, let me know and I can arrange the extra nights.

You should depart no earlier than October 27th, our last group activity will be dinner on the October 27th. If you want to stay longer, let me know and I can arrange the extra nights.

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.


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 at all up to 60 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 at all within 60 days of departure, you’ll get everything back minus the deposit.

Trip insurance is a wise investment in case something comes up while you are in Italy. 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.

Entry & Exit Requirements

Currently Italy allows anyone fully vaccinated, recovered in the last six months, or with a negative COVID test (rapid or PCR) taken within 72 hours before arrival to enter the country. If you need to test, you are responsible for getting tested according to your airline’s instructions. I recommend you make an appointment well in advance.

It’s possible these rules drop before October. I will keep you updated on Italy’s requirements to make this as easy as possible for you.

To go home: The US currently requires everyone, regardless of vaccination status, returning from Europe to pass a COVID test within 48 hours before departure. You are responsible for getting tested. I will include time for testing and we have a few testing locations near the hotel. The test is around €19 and takes 10 – 20 minutes, no appointment needed.

Green Pass

As of this writing, a Green Pass is required to dine inside restaurants only. That is expected to drop on May 1st.

For non-Europeans, a Green Pass is simply:

  • proof of vaccination (such as a paper CDC card),
  • or proof of a negative test (valid for 48 hours),
  • or a letter of recovery within the last six months from your doctor.


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.


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.

These rules are set to change on May 1st, but it’s possible they could decide to extend the indoor mask mandate.

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.

Openings and Closings

Currently, everything in Rome 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.

Sign up

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

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