Planning our Family of Five (Adults) Trip to Italy in May 2025

Assisi is a bit over 2 hours from Rome by train, and I'd guess it will be busier than usual next May because of Holy Year. I enjoyed my day trip to Assisi a lot, but I wished for more time there. I was very glad I had started at the blessedly quiet upper part of the city and gradually walked down to the area around the (fabulous) basilica, which is unfortunately awash in really tacky souvenir stands.

I know nothing about Montecassino (not sure how you get to the monastery, which is massively uphill from the train station), but the rest of your potential itinerary doesn't say "rental car" to me; quite the contrary. Other than Montecassino, the trickiest part will be the Amalfi Coast, where you'll be depending on ferries, buses and (expensive) taxis if necessary. But driving in that area is reportedly not for the fainthearted, because the roads are jammed and parking is a serious challenge.

Hopefully you know that the Jubilee will be bringing thousands if not millions more visitors to Rome next year?
And even without any spillover from the Jubilee, that the crowding in Sorrento and the AC is already bad in May, that the infrastructure in the area has been sadly neglected, and that there is no fast nor efficient mode for moving about the AC? I bring this up as it is not relaxing to explore the AC. Sitting on a veranda and looking at the ocean is relaxing, and the area is beautiful. I'm wishing you a great trip, but one must be prepared for the realities on the ground.

Regarding guides, Mondo tours does shared tours and transportation in the area. RS recommends them in his guidebook, and they have a website.

It will difficult finding hotels for five adults. You would need two rooms and hope the third bed in the second room is a real bed, and not a pullout sofa bed.

Driving in Italy can present challenges with ZTL zones, parking, speed cameras, and the tickets which arrive about nine months later. I would only recommend driving in the Tuscany countryside.

There are several helpful Trip Reports and posts here on the Forum under the Italy section. Join some city-specific Facebook groups for real-time, on the ground info.
You have alot of time to plan, enjoy the process, and have a wonderful family adventure! Safe travels.

Train vs car - for 5 adults with luggage, even carryon, you would need to rent a larger car which besides being more expensive, presents serious parking issues. We were 6 adults in Croatia one summer and had to rent a minivan. We couldn’t finish our car part of the trip fast enough for me.

AirB&B vs hotel vs monastery - we don’t ever use AirB&B so no help there. You would need two hotel rooms which can be very expensive. Many forum members have stayed at monasteries with good reviews. Do a search on the forum.

We always hire guides, they add so much to your travel experience and with 5 people is very economical. We hire private guides with just 4 of us. Some guides on Toursbylocals, have a limit of 4-8 people. If you hire them you could be the only ones on the tour.

Montecassino is almost 2 hour train ride from Rome. IMO- too far for a day trip. Same for Assisi.
It is closer to Naples- about an hour. Maybe slot that in on your way to Naples?

There are dozens of threads here about the AC- mostly about how to get around and deal with the chaotic transportation! I would not drive anywhere near there.
If your flight home is from Rome you will need to be in Rome night before. If so it's often a good idea to travel onwards to Naples on arrival and do that part if trip first, then back to Rome so all Rome nights are at end of trip (eliminating a split stay/1 night).

Booking . com is a good place to research lodgings. Use the filters for budget, location, # beds etc. They do list a lot of apartments as well as hotels. Monastery stays are often recommended here- a search will bring that info up

We are all fluent in Spanish

That's great but please don't expect Italians to speak or understand Spanish. Some may- but some/most will speak/understand English.

Lots of great advice already!
May is very much high season in much of Italy so time is of the essence to get accommodations booked; lots of folks have those wrapped up for 2025 high season already. I might suggest apartments over hotels so that you can all be together but you'll need to be cautious about what's advertised as a 'bed' as that might include a foldout in the living area. As well, you're going to want more than one bathroom. On the plus side, an apartment would provide the ability to have easy breakfasts "in" with supplies from a market.

Apartments are usually better for longer-term stays versus, say, one or two nighters to spread the cleaning fees over more nights. One drawback is not being able to store your luggage as you usually can when arriving at a hotel before check-in.

Car versus train: For your itinerary, definitely trains. You do want or need a car in Rome nor drive and try to deal with parking in the Naples/Amalfi Coast region.

Guides: that's very much up to personal preference and/or budget. My husband and I tend to prefer to explore on our own when possible although that involves lots of dedicated research. It can also depend on the place/venue and how complex it might be to do solo. in any case, if not booking a tour you're going to need advance, timed-entry tickets to the most visited attractions in Rome, specifically Colosseum, Vatican museums and Borghese Gallery, if any/all of those 3 are on your list. They're going to sell very quickly once available so be ready to jump on them when that happens, and you have the added challenge of needing 5 tickets.

A note about Rome: you could very, very easily spend the entire week there without running out of things to do. It's not clear if your two weeks includes the travel days on each end so it's possible that you'll realistically have 12 full days or less on the ground In Italy, and you'll lose at least part of a day in transfer to Campania. So, go easy on planning day trips? Orvieto is fine but IMHO, Assisi and Monte Cassino are too far.

I wouldn't call the Naples/Sorrentine/Amalfi Coast area 'laid back" either. it's going to be very busy in May so unless planning just to hang out at a hotel pool or whatnot, you'll find transport around the region to be packed. Ferries are a fun way to get around the AC- but tickets won't be inexpensive for 5. As an example, tickets for Sorrento> Capri, one way, are currently running a minimum of € 18,90 pp. SITA buses (which of course you couldn't use for Capri) are much less expensive but boarding lines can be long in certain locations and you'll be trying to keep 5 people together. I have terrible motion sickness too so ferries work better for me than road transport.

Circumvesuviana commuter train is also inexpensive - can use for trips between Naples, Pompeii and Sorrento - but is a battered unlovely thing with no creature comforts. It works fine but may be crowded and hot, and you'll want a tight hand on your valuables but that applies to virtually ALL public transit anywhere at all.

Monte Cassino: if you do try and do it - maybe from Naples as suggested - the website for the abbey states this (translated from Italian) if arriving in Cassino by train.

"A bus that leaves from the (Cassino) train station at 10:00, 12:35 and 15:20 (indicative time)
He then leaves the monastery at 10:20, 12:50 and 17:10. Check the departure times from the terminus at this link Autolinee Mastrantoni"

https://abbaziamontecassino.it/visita-montecassino/come-raggiungerci/

Great responses so far...
My wife would definitely prefer doing the first half of the trip further away from Rome, so as to not rush at the end when its closer to the date of departure.
We understand the Jubilee Year is going to be at times insane, but that is one of the highlights of this trip.

When in Rome, since we'd be there a week, what are the recommended attractions that are a MUST besides the Vatican?
When in the Naples/Pompeii/AC area, same things that should be a MUST?

We can't decide a MUST for you. One person's can't miss is a pass for someone else. Perhaps if you share some interests? It might help if you get an RS Guide book, watch some RS or u-tube videos, Search topics here, read the related posts under Italy, and/ or join some city-specific face book groups.
Have fun planning. Safe travels !

Besides pilgrimages to the Vatican and related churches and basilicas in Rome, our family is interested in dining, and shopping for authentic Italian crafts, as one finds in other European cities, such as bazaars, fine flea markets, etc. We may even want to see an outside concert if available.

Rome is just full of interesting/beautiful churches. And I say that as someone who is not at all religious. Any guidebook will identify more worthwhile churches in Rome than you'll have time for. The cathedral in Orvieto is an obvious must-see if you get to Orvieto at all.

Someone mentioned in an earlier thread that there's a tour offered at Santa Maria Maggiore. I was sorry I hadn't known about it before my winter 2023 trip. You might like to check that out.

It's useful to have 1-euro coins on hand when you visit Italian churches. Sometimes there's a coin-fed meter controlling the lights on mosaics, statures or frescoes.

Lots of great advice already.
I will try not to repeat.

Rome deserves 6-7 by itself.
My wife and I don't do Airbnb since it is just the two of us, but you may do better with five. Still, research both.
Hotels near the Pantheon are a great location. Still, I stayed once at a Church run place near the Vatican that was good.

Don't recommend renting a vehicle. Many people get very expensive tickets, sometimes months after returning home. Trains in Italy are great.

Check out some paid tours and compare prices and quality.
Gate 1 Travel for entire tours
TripAdvisor.com for day tours or multiway tours.

You can do some touring without a guide, but some places deserve a tour guide, like the Forum/Colliseum. Do not miss the Sistine Chapel.

As for the Naples area, we stayed in Sorrento and it was nice.

When in Rome, since we'd be there a week, what are the recommended
attractions that are a MUST besides the Vatican? When in the
Naples/Pompeii/AC area, same things that should be a MUST?

There's no such thing as a MUST unless it matches your personal interests. Mine run heavily to art, architecture and history so are very different than the preferences you've listed. I do have a thing for old Italian churches but like acraven, I'm not religious so I enjoy them for other reasons, such as having been built upon Roman ruins that are still visible in subterraneous levels. LOL, the list of fascinating churches in Rome is longer than my arm and I still have many to see!

I do think you should explore more of the ancient city as the Roman Empire once encompassed a VAST area with Rome at the center of it.
https://en.wikipedia.org/wiki/Roman_Empire#/media/File:Roman_Empire_Trajan_117AD.png

Top of the list would be Colosseum/Forum/Palatine. I'll strongly recommend a tour which includes all 3 so if interested, we can provide some resources.

Basilica di San Clemente: similar to an iceberg, there's more underneath than visible on top.
https://www.basilicasanclemente.com/eng/

Santa Sabina: a very old and important church shaped from a repurposed Roman basilica and pieces scrounged from older ruins. Of particular interest for you, it has one of the earliest images of the crucifixion yet discovered carved into an entry door. There is a delightful orange garden next door with a fine view of city.
https://en.wikipedia.org/wiki/Santa_Sabina

I'd visit one of the catacombs: subterranean burial places for both Christians and non-Christians starting around the 2nd century until somewhere around the 6th century. Some of them can extend for miles, and a tour (tours are mandatory and can be booked right at the sites) will provide some interesting background. They were not used to hide Christians or their worship services as they were well-known locations, operated largely after Christianity had been de-criminalized, and at least some were employed by persons of various religious beliefs. They can also have some very, very old Christian decoration you might find personally interesting. Links to a few:
https://www.catacombesancallisto.it/en/index.php
https://www.catacombe.org
https://catacombepriscilla.com/en/home-en/

This ruin of a Roman bath will give you some idea how enormous they could be, and how important they were to the culture at the time.
https://www.turismoroma.it/en/places/baths-caracalla

Not ancient Rome but for a wonderful collection of art (although sadly some of stolen) in a villa created expressly for that purpose, here's Galleria Borghese.
https://galleriaborghese.beniculturali.it/en/
Pre-purchased tickets are mandatory and visit are in 2-hour slots. Their excellent crowd control made the the experience so much better than dealing with the mob at the Vatican!

Just a start....

I think your best bet for reasonable accommodations for your group is monastery stays. We stayed at Il Rosario near the Colosseum and our then-middle school daughter had her own room. I also think San Clemente is a must-see.

Great ideas from the forum.
I have been checking the Monastery Stays...but they're not always cheap for a family of 5 adults.

We have decided we will stay in Rome night one, then take most likely the train to the Naples area (not sure if we should make Sorrento our base of travel for that segment, or to stay in the AC proper...or Naples...or Pompeii)
We will have Rome be the second week of the trip.
Hoping to focus on just those two areas given the long distance to other places like Assissi and Monte Cassino.

We are hoping to take a winery tour and a cooking class. Where would it be the most authentic...in Rome or outside of Rome? I am taking some Italian lessons right now, but not sure how well I will make myself understood within the next few months

Depending on the time of your arrival in Rome, you can train to Naples your first night, and have a couple of nights there. I think hotels in Naples tend to be less expensive than Rome. With 5 of you, could look for a double and a triple room. It will add up of course. Sorrento otherwise is a good base for Pompeii, and maybe for the Amalfi coast. You could also consider Salerno, for a more budget friendly option for the AC. I have not been, but Paestum looks intriguing to me, ( and quieter) as does Ischia. They are on our next trip list!
Orvieto can be done as a day trip from Rome, but frankly is so charming that I would try to overnight there. Your best bet if not a monastery is probably an apartment. We stayed years ago at Suore di Santa elisabetta in Rome, with our 3 kids, in a family room, but they were younger. It was a large room with 5 single beds. Great location, but I'm not sure if I would do the same room with them as adults!
And if someone has not said yet. Train! no need for a car with the spots you prefer.

Regarding train vs. car, it sort of depends on your need for flexibility and your desire to embrace / avoid cities. You could take the high speed train to Naples, stay there and take trains to Pompeii / Vesuvius, then take a train or ferry to Sorrento and do a guided tour of the Amalfi Coast. Or you could rent a car on the outskirts of Rome, drive to Pompeii and base there, then drive to Sorrento or Amalfi Coast and stay at places out in the country if you want. My family planned to do the latter last summer because we really love to explore the countryside and the small towns. A day trip by train to Naples for the museum and some pizza would be plenty! Unfortunately that trip fell through but we’ll try it again. Good luck!

We have decided we will stay in Rome night one, then take most likely
the train to the Naples area (not sure if we should make Sorrento our
base of travel for that segment, or to stay in the AC proper...or
Naples...or Pompeii)

My choice would be Naples and the AC, but read through the forum to get a sense of the differences and pros/cons of various itineraries. If you fly in in the morning, I'd head straight to Naples area regardless, then return for the second week in Rome.

I found that while I am not fluent in either, studying Spanish as a child really helped me pick up some Italian--I think you'll make quicker progress than you may expect!

So...currently I am on the plans for the Rome leg of our trip. I have read different options on where to stay. An Arbnb will be more economical and practical than a hotel. A friend told me to stay by the Spanish steps, but my family is worried about the busyness and the crowds. We still want to enjoy the sites, but if we stay in an area close to the metro station or with ease of finding a cab that'd be great. Is it recommendable to stay closer to the Vatican? to the Coliseum? to the Pantheon?

We just got back from Italy. In Rome we stayed in between Piazza Navona and Campo d’Fiore. The location was right in the middle of all the sights we wanted to visit. There’s no metro station close by but there's a taxi stand at Piazza di San Pantaleo that was very convenient. Good luck with the trip!

unless one or more of you is mobility challenged, if you stay in the general central area - we like it around Piazza Navona / Campo de' Fiori but there are other equally good areas nearby - your primary methods of moving around will be your feet. If you're going too far to walk there are plenty of buses.

Of course you will have taken pickpocket precautions whenever out from your lodging, especially when travelling in a distractible spread out group.