Planning a family trip for my mother’s first time In Italy.

Yes. My mother and Aunt are 78 and 80 years old.
Maybe we can stick to three or two places.

Teramo is where my Mom and Aunts father was born.

I am not an expert on Italy although I have been to Venice, Florence and Rome in 2023 but just helped plan a family trip which we took in Portugal for 12 adults ages 19-82 years old this past June. I would say narrow down the cities that are important to 2-3 depending on where you fly in and out of trying to get non stops if you can. Book hotels so everyone can be together and then let everyone do their own research on what they want to see in each city. We just booked accordingly on who wanted to do the same thing. There were times were my mom just needed to rest and couldn’t keep up with the younger crew. Plus the younger crew wanted to sleep in more and not do early tours. Everyone has there on style so better to have each family unit plan activities for themselves especially the one with the 2 year old. Dinners together were a challenge but we booked weeks ahead of time a special dinner to celebrate my parents 60th wedding anniversary. Sitting at 2-3 tables works good as a table for 12 was challenging.

I am not an expert on Italy although I have been to Venice, Florence
and Rome in 2023 but just helped plan a family trip which we took in
Portugal for 12 adults ages 19-82 years old this past June. I would
say narrow down the cities that are important to 2-3 depending on
where you fly in and out of trying to get non stops if you can. Book
hotels so everyone can be together and then let everyone do their own
research on what they want to see in each city. We just booked
accordingly on who wanted to do the same thing. There were times were
my mom just needed to rest and couldn’t keep up with the younger crew.
Plus the younger crew wanted to sleep in more and not do early tours.
Everyone has there on style so better to have each family unit plan
activities for themselves especially the one with the 2 year old.
Dinners together were a challenge but we booked weeks ahead of time a
special dinner to celebrate my parents 60th wedding anniversary.
Sitting at 2-3 tables works good as a table for 12 was challenging.

^^Really good advice for a group your size.

Finding an apartment for 10-16 people would be really difficult I think. You need a very large kitchen with plenty of seating, a good number of bathrooms and real beds for all, except maybe the 2 yo. And you'd have to be sure that all those people can handle so much togetherness.

I have a very large family- 8 siblings. We love each other very much and all get along but we would all want our own space/hotel room on a trip of that length.

All excellent advice.
It sounds as if you are the one being landed with all the planning.
Have you had a group meeting to figure it all out?
If others don’t want an actual tour, but they want you to organize everyone, it won’t be easy at all and you will be frustrated and exhausted.
It won’t be a holiday for you!
The plan of taking Mum and Aunt to near their ancestral village and staying there for a while is a really good one…..after all, the whole point of the trip is all about your Mum and her wishes.
Best of luck, and I hope you get the whole group involved in the planning!

Just a thought…if this huge group is made up of a few different families, get each family group to plan and book their own airfares and hotels, but all of you plan to stay in the same areas of each town.
That takes the heat off you as master planner.

Know that this is a huge undertaking for you, not impossible, however. But before you take miuccia's advice, which IMO is spot on with the raison d'etre for the trip being the pilgrimage to Teramo, you must set planning guidelines with the others.

Starting with...and an idea of a group meeting (EMail back and forth is better, I think, to limit fisticuffs!) is good...a logistics come-to-Jesus discussion. Teramo is probably gorgeous, but decidedly out of the way. You only have 10-14 days. Assuming you're an Italian family like mine, you're going to have a certain number of your group that like everything set for them, go-along folks, and then a few whose attitude is 'I've never been to Italy, I wanna go where I wanna go!', with no regard or knowledge as to how to get around or whether it makes sense or not. And you have a big crowd...

If you're the lead dog here, you have to set a plan forth and when (not if) they question it, have your logistical reasons at hand. Personally, I think a week on the Adriatic, visiting Teramo and exploring nearby areas...then a week in Rome--especially if you're flying in and out of Fiumicino--in a big apartment (or series of close-by smaller apartments) is the way to go. When you're in the Eternal City--my favorite place on the planet--one can easily take a daytrip to Florence, 90 minutes each way by fast train, Naples/Pompeii is a longer daytrip but doable. But day tours within Rome itself--for those who want to participate, give everyone that option--are great. Roma is also the best wandering/sitting & people-watching city I've ever seen.

I've been to Italy three times, just with my wife, and through my love of planning we've had great times, basically a self-styled tour--not flawless but pretty good. This next April, we're taking two of my cousins and possibly another couple with us, and the planning dynamics change for sure. FYI we were able to just book a 3 BR, 2 bath apartment in Rome for $650/night. Know this--it's difficult to say 'I've checked and re-checked the logistics on this, and this is the best way' without being labelled a control freak! HA!

What’s the nicest upscale area clean clear beautiful beach, town/cute shops, cultural beach area close to Teramo?

Check a good map, please. Teramo isn't close to a beach. At least a 45 minute drive to either San Benedetto del Tronto to the north or Pescara to the south. Haven't been to either, you can search to get an idea of what's there. To the north--but inland--there is Ascoli Piceno, which is the country's biggest producer of travertine natural stone, and pictures show that it is a beautiful place.

I did just that last year with my mom. Like you I have visited Italy before but not my mom. She is 74 years old. It was great!! But you need to plan ahead.

First thing: buy one of the Stevens books. I started with the book.

We arrived in Milan, then moved around: Milan- Verona (with a day trip to Venice)- Florence- Rome - Amalfi coast for one night- Rome and flew back to US out of Rome. 14 days total. We went late May (weather was great and Amalfi was not super crowded)

We were in 6 people. I reserve Airbnb apartments in all locations expect Amalfi . In Amalfi I reserved the hotel recommended by Rick Stevens (Palazzo Starase bed and breakfast), and they helped me booking a private transportation. It was WONDERFUL!!! Great and most friendly people ever!!

All the apartments were right in the center of the locations close to the attraction so it would be easy for my mom to move around. The only thing you need to be aware it is very difficult to get a taxi around or Ubber. In Roma was a little easier. I Milan I had a private service too. I bought all the train tickets and museums online from home, so we did not have to spent time at the train stations or lines.

In Florence my sister and her husband did not want to see Michelangelo so I wasted two tickets.

I did not book with any travel agency or tours because I wanted the freedom to enjoy at our own pace.
You can definitely can do it without a travel agency. I also binged on the Rick Stevens Italy episodes for several weeks during my planning phase. It took me about 3 months of planning. It was so worthy!!!! A memory that will have forever!! I just wished I had done it earlier while my dad was alive.

P.S.: I just loved Sorrento and Verona. It was a such surprise for me. I cant wait to return and spent more time on those cities.
Good Luck

I

I love the idea of the wedding planner. Brilliant!