Tech needed

All you need is a plug adapter - a 99 cent adapter you can buy on Amazon or ebay or a tourist store in Europe, probably (or from the Rick Steves online travel store - whatever it's called.) Not a "converter" - you need something like that only for a hair dryer. Europe uses a different voltage and power cycle frequency than the US, but modern charges can switch between them automatically. (at least for phones and tablets.) All you need is the physical plug adapter.

Otherwise, to protect your information, set a PIN lock code on each device to be safe. In the old days, web transactions were not encrypted, so people used a Virtual Private Network (VPN) to protect their internet browsing from snooping bad guys, but these days a VPN isn't necessary for the average person. I don't bother connecting to my VPN at home anymore unless I need to connect to my home network.

Just connect your charger to the electric source via a standard adapter plug, you plug into the adapter, and then the adapter to your source. Note that if you also go to the UK, they use different outlets than the continent, and you need a UK adapter there.Not trying to, plug rock Steves online store, but go here, and you will see what you need, explained: https://store.ricksteves.com/shop/travel-accessories/travel-gear
Note also that Apple devices and all modern computer or communication devices have transformers in their chargers that accept 50 or 60 HZ, and 11 to 240 V on the current., so you are fine with them wherever you are.
You likely also can charge from any USB outlet, too, though likely slower.

You need a plug adaptor with two pins, very inexpensive, buy a handful of them to take to Europe. You use the chargers that came with your devices but add the plug adapter to their plugs. You do not need a converter as they are dual voltage.
We always buy an international plan for one of our phones to be able to call back to the US, especially needed if you have an emergency which we have many times.
We buy a European SIM card for the other phone to easily and cheaply make local calls. Keep your US provider’s SIM card safe when you take it out to put European one in it’s place. I usually put the US SIM back in my phone on the flight home.
Does your iPad Have internet roaming? Or just rely on WiFi? If WiFi only, leave it in your hotel room when out and about. Use it while in the hotel room. Not difficult and it’s a bonus to have these devices along.

I changed my Lock Screen to show my full name, my wife's phone number and my wife's email, in case I lose my phone or my Ipad. Some people may be too paranoid to put that information is such a visible place. But how many people on a cruise ship or in a fancy hotel or art museum are really there to steal tech? Besides, if they sell the device, my whole address book is possibly compromised!

Although a simple little plug adapter will work--Rick sells them here, and they're widely available, I recommend a device with a single plug and multiple ports for the cords of all your devices. I suggest that because in my experience many hotel rooms have only one available outlet. I assume that's less of an issue if you stay in expensive, business-oriented hotels.

I do not own Apple devices, so I cannot recommend a specific multi-device adapter. I'd expect something suitable to be available from Amazon, but it's possible you'll need to buy from Apple because of proprietary connectors.

The iPad will take more power to charge than an iPhone. When you pack be sure to pack the iPad charger because a phone one (they both fit) will take ages to charge the iPad. You can use an iPad charger for the phones, no problem... You may also find that standard USB wall ports may struggle with the iPad.

This extension cord was recommended a couple years ago on the forum. I bought it and used it on my Italy trip. Very handy for charging multiple devices. You will need a plug adapter to plug it into the wall. Since most of our hotel rooms had hard to reach electrical plugs, the extension cord came in handy.
Tip: the electrical sockets have child proof protectors which makes plugging cords in almost impossible. My husband popped the protectors off so it was easy to use.

https://www.amazon.com/UPWADE-Protector-Charging-Multi-Port-Portable/dp/B06XFZPQSM/ref=mp_s_a_1_140?dchild=1&keywords=extension+cord+usb+and+plug&qid=1596749999&sr=8-140

You need charging (already covered), you need service (WiFi or European cell network/roaming on your US network) and maybe a VPN. For service it is handy to not always have to depend on wifi. Many unlocked iPhones can now adapt to two SIM cards or a "virtual SIM card" so that you can connect to a European cell network as well as to your US network once you get the European SIM information. Check on the capabilities of your phone to be sure how to do it best. On our old unlocked iPhone 6's we just swapped in an Aldi SIM card when we got to our first destination which came with a cheap standard monthly fee and a European phone number. We haven't tried the Virtual SIM option yet on our new SE's.

Ok..first thing you need is to order the Euro to USA plug converter from Amazon - in fact order 3.
I made a mistake of assuming my Airbnb would have the converter in Barcelona. I had to buy one near La Ramblas and they charged me 10Euros.
Second thing you need to is to decide whether you'll need an international phone data plan in Europe. Verizon charges $10/day in roaming fee to use my phone internationally. I usually can get by using my phone on airplane mode and able to make wifi calls to USA without problems.
Download offline google map to where you are going. Or use "Citymap2go" app. Free. It's very intuitive map of all the cities I downloaded with tourist must see sites. It gives gps directions while on airplane mode. - I never need to use international roaming using my smartphone.
Third - watch out for pickpockets.... they are notorious for pickpocketing iphones. Somebody almost tried to pickpocket my iphone in Barcelona.. Yichhes. I almost called the cops..we had a big fight with the thief in the rain...

Here is a helpful link to the tips section here on the Rick Steves website about electricity. Note the differences in Switzerland and Italy. https://www.ricksteves.com/travel-tips/phones-tech/electric-adapters-converters.

As he notes, sometimes the outlet can be recessed so that the prongs may be the right size but if the plastic housing is too big you can't get a close connection. Here's one from Amazon that will fit the sockets and let's you plug in 2 devices at once. https://www.amazon.com/Ceptics-European-Adapter-Adaptor-Charger/dp/B01NCZJ5UN/ref=sr_1_9?dchild=1&hvadid=78408974153653&hvbmt=bb&hvdev=t&hvqmt=b&keywords=adapter+for+european+plug&qid=1596753273&sr=8-9&tag=mh0b-20

Also be prepared for a hunt to find available outlets in the rooms. We've had to crawl around on the floor, peer behind furniture, etc to find one. That's where having multiple adapters or charging strips can be handy.

If you're not already aware of the need to have an international data plan or a country-specific SIM card, you also need to research those possibilities. I won't go into it until you tell us to need to know those things.

You can get something like this and charge all three devices at a time.

https://www.amazon.com/Unidapt-Universal-European-Worldwide-International/dp/B077XRXRZR/ref=sr_1_4?dchild=1&keywords=usb+international+charger&qid=1596755831&sr=8-4

One important thing I would note here is you are CARRYING way too much tech.
Keep it simple rule applies here.
You only need iphone 8plus and iphone 11 for your wife and yourself.
Leave rest of it home... You are going to realize how much hinderance that is.. and you'll always worry about something being stolen.
You'll thank me later.

I really like those adapters with 2-3 USB ports for charging- I find I use them more than the regular 2 prong model although I still take a couple of those, too.
Nobody has mentioned downloading WhatsApp yet, both for communication with each other if you separate on the trip and in addition to a data plan.
I used to, pre-Covid when we could travel, get a cheap SIM card upon arrival at the airport. I keep a paper clip in my wallet that, when open, exactly fits the teensy hole to access the teensy tray it's in- not sure about Apple phones, though.

We always carry several adapters, an extension cord (have always needed it!), our phones, and a tablet. Besides the usb cables I carry a 6 port charger so I can charge up to six devices at once. I like reading at night, playing games, researching for the next day, etc and it is easier for me to see to do that on a tablet so it is worth it to me to carry the tablet. I have my visa credit card set up for email alerts although we mostly use cash when traveling except for very expensive things.

When I travel, I carry a good camera (battery to be charged), a computer (charge needed), and 2 cell phones (charge needed). Thus, I have come to the point of carrying a small power strip so that everything can be plugged in. One thing that is ESSENTIAL is a carrying case for cables. It's completely annoying when the cables get all out of control. We also have found that an external speaker is helpful. This charges on the same cord as a phone. It also needs a second cable to connect to the computer.

I really don’t know how anybody enjoys traveling carrying so much “stuff” around. My wife and I each have backpacks. That’s it. We have a rule, if it doesn’t fit into our backpack, we leave it home. My iPhone 11 has camera as good as my large expensive DSL camera - all my trip research is via my iphone. I carry 7 T shirts, 1 cargo pants, 1 shorts, 5 underwears and one sneaker onto my backpack, even on 16 day trips (making sure my Airbnb have washers). Any toiletries, Italy has plenty of supermarkets - so that has never been an issue.
Packing light saved us so many times including walking in Venice, not to mention numerous times trying to get on and off trains.

Or to confuse you further, you could also buy a European SIM card here in the U.S. I got a Vodafone card on eBay for under $10, added a 1-month "bundel" plan for data and topped it up online as needed in several countries -- cheap in-country calls, data connectivity when away from the hotel Wifi, and a number to give out to family and dogsitter for emergencies (not needed -- they sent emails and WhatsApp texts) We have used the same Vodafone number on two trips so far, just keep it current by sending a text every 6 months and switch the U.S. SIM back in between trips.

And what others have said about having multiple adapters. Very easy to forget in the hotel wall plug! We also carry a standard extension cord. Some hotels have USB outlets in lamp bases so you can just plug in your charging cable.

A portable (pocket-size) rechargeable power source is useful, too.

I would echo previous poster about portable charger. They can be life savers, especially if you are taking pictures a lot which runs the battery down.

We used ours almost every day we were in the UK last year.

He may not need a different SIM card or special plan. Depends on who his service provider is. We have Tmobile Unlimited 55+ plan. In Europe we get free text and data without anything extra needed. Calls are 25 cents a minute. We have Samsung phones but family members with IPhones have the same plan and the same benefits.

CJ... Does T Mobile have decent coverage overseas?? they have killer deals in regard to the 55+ plan. We will be primarily in Italy
Gene from Penn.....we too travel light... 2 packs 35L..so our goal is the same as yours. We have just added a new tablet and now a phone....so I hear you. People take what they want.
Thanks to everyone that has contributed. I think it is great all the input. I have a plana dn will look into the Sim card....
THANK YOU ALL!! Be safe and here is to getting thru this "stuff!"

This may have been mentioned earlier, but when is this trip taking place?

A few comments.....

As others have mentioned, you'll need to look into the cost of international roaming plans with your home cell network. Given my home location I don't use T-Mobile but have heard good things on the forum from those who have.

On the topic of plug adaptors and chargers, I prefer to travel with more than one as it's always a good idea to have a backup. I normally use a multi-device charger most of the time, and keep the Apple chargers for backup. Many European hotel rooms only have a few outlets, so a multi-charger is a practical solution to charge all devices at the same time.

Finally, I'd suggest being cautious with free Wi-Fi as there could be some risk if you use it for sensitive tasks like online banking, without using a Virtual Private Network (VPN). You'll probably find a variety of Wi-Fi quality in Europe. Some will work well and some will be slow. Many hotel systems require a password.

On Tmobile coverage in Italy - I know they have agreements with Italian service providers but can't say for sure how complete it is. The networks in Europe aren't T-Mobile owned. It's just that they use the same technology the Europeans use so if they have an agreement with that country's provider(s) then your phone will work. We have used our phones in Ireland and on a Budapest to Amsterdam river cruise with no problems. I'd recommend checking out Tmobiles website or speak to one of their reps directly. In the U.S. we've only once had a problem with coverage and that was in a rural area camping in Colorado.

We have used T-mobile in UK, Greece and Italy. You have 3 G at best for data when roaming which can be slow and clunky. However, I have been able to use GPS on my iPhone without difficulty. Every place we have stayed has had wi fi though so did most internet searching in evening. Great for texting as it is free and fast. We had to make several local and to US calls when on a Greek island and reception was good.
I actually have had many more issues with reception in US with T-Mobile than in Europe. T-Mobile doesn’t do remote US communities very well so was surprised at coverage in Europe.

If you are thinking of switching to T-mobile, consider where you live. I live in an urban area, and have been happy.

I'd strongly advise installing as many apps as possible that you will use while you are still at home in a controlled environment with known wifi.

Many apps are available in many counties but some are not available until you arrive.

If you have iCloud set up right you can mirror the apps across the phone and the iPad. Some apps are iPad specific but most will install automatically on both the iPhone and the iPad.

The iPad works a little differently than the iPhone - there is definitely a learning curve, and an iPhone works differently than other smart phones, and there are big differences between smart phones and old phones.

Getting all this under your belt well before you go will make dealing with the new SIM or international plan once you arrive much easier.

Do you have any idea of what sorts of apps you would like advice about?

I'd also strongly agree with Laura B with the suggestion to take a pocket power source. They aren't too big, recharge with a standard USB/micro USB cable and your charger and give plenty of peace of mind.

We have always taken our phones. However, we do not want to pay the overseas surcharge. So, we keep airplane mode on. But we can still use wifi. Many cafes have wifi. This enables us to send emails without the data usage.

We seldom, that is never, actually make phone calls in Europe. We make reservations, check for status updates, etc, on email. This has worked fine, plus keeps a record.

About a year ago, I published my method for tracking expenses using a spreadsheet. It's located at:

https://community.ricksteves.com/travel-forum/general-europe/tracking-expenses-on-our-trips

Take a gander if you like to keep your expenses and total by category.

You do not need a converter as they are dual voltage.

Back in the 1980s, I had a hair dryer that could accept either 115V (or 120V, what ever voltage was provided by the power company in the US) or 220V (continent) or 240V (UK) in Europe. You selected one of the two voltage options via a slide switch. The switch put the heating (resistance) elements in either series or parallel configuration. It was truly dual voltage, that is, by sliding the switch you selected one of two voltage ranges.

Today's USP power sources are actually "multi-voltage", that is, they accept any incoming voltage between 100V and 240V (the range may actually be greater, but that covers about everything provided from household wall receptacles in the world today). They work by clamping the incoming voltage at 5VAC, then rectifying it to 5VDC. And, they are essentially "converters"; they convert the incoming power from 115VAC or 230VAC, or whatever, to 5 VDC for your electronic devices. So when someone says, "you don't need a converter", that's wrong. You are using a converter; your USB power supply is a converter.

What you don't need is a dual voltage converter. Again, back in the 80s, converters were heavy transformers that cut the voltage in half, from 220V to 110V or 240V to 120V, but they didn't change the frequency; it was still 50 Hz. So certain motors would run slow.

By the way, unlike transformers, solid state power supplies cannot increase the voltage, so people with 220V - 240V appliances still have to use heavy transformers to run them over here.

We use T-Mobile 55+ and were in Italy and Slovenia last year for three months. It was great. Never had any problems with texts, emails or phone calls. While there my bank account was hacked and we were on the phone with our bank for almost two hours. No extra phone charges just the great flat rate T-Mobile charges. I would recommend downloading What's app. Used by almost everyone there. Also great to use when you return home to stay in touch with friends in Italy and other parts of the world.