I’ve gotten so much help from this Forum that I thought I’d share my experiences for others. Hit me up with questions!
Itinerary:
Four adults (my husband M63, me F55, and the ‘kids’ F24 and M20). 14 days of travel, 12 nights in Italy. 3 nights in Rome to start, 8 nights in Puglia, 1 final night in Rome. Flew from West Coast US to FCO with one stop each direction. The kids’ first trip to Europe, my husband’s 2nd and my 4th. We strongly disliked our connection on the return through EWR — you had to go through TSA security again in the US and, as our flight was delayed leaving FCO by an hour, we only had 1.5 hours to make the connection. Next time I’ll try to route through ORD where you don’t have to go through security again on a connection.
Took Frecciarosa high speed train from Rome to Lecce and back again (5.5 hour trip each way). Because I bought our tickets so early I got us all business class, which was nice to have the legroom for the long trip. Our trip from Rome to Lecce was delayed also by 1.5 hours so we got a 25% refund on that travel. It was a bummer because we would have liked more time in Lecce, but what can you do?
Took the local train from Lecce to Gagliano di Leuca. It was like a Disney train (or a bus) — so small, so slow. No a/c but it wasn’t very warm that day so just having open windows was just fine. No annoucements or anything — you needed to know where you were going and where to get off :)
Tech Stuff:
Spouse and I used Airalo e-sims (data only) which worked really well for all that we needed. The kids’ just used Wi-Fi at our lodgings and had pre-downloaded Google maps. If we split up we made sure each group had a data phone with them so we could WhatsApp if needed.
Used the Trenitalia app for all of our train travel — it was easy to use, could buy tickets 5 min before departure if needed, etc.
Used Google Pay or Garmin Pay (my watch) for the majority of our transactions, especially in nearly all the cities and towns. Used cash for hotel taxes mostly.
Packing & Bags:
Given that this was a big splurge for all of us and us ‘rents were covering a lot of the costs, our plane tickets were super economy (no checked bag allowance). We each had a personal item (that most likely exceeded the airline dimensions for a personal item, but no one even blinked) and a carryon duffle/backpack. The kids each had Deuter Pro-40 duffles, I had a bargain basement Hyeagle 38L backpack, and spouse had a somewhat better but still bargain basement 40 L backpack. My personal item was an Osprey Daylight plus and then I also had a Fjallraven High Coast Pocket inside of that which I used “around town”. I packed: 1 pair flip-flops, 1 pair trail shoes, 1 jumper (Title 9), 2 tanks, 2 merino t-shirts (Bombas), 1 pair shorts, 1 hiking pants, rain poncho, 6 underwear, 6 socks, 2 bras, sleep shorts, sunshirt, lightweight hoodie, sun hat, swimsuit, power adaptor, clothesline, pack towel. Also included hiking notes, maps, copies of travel insurance/passports, and printed out tickets to colosseum and Borghese gallery. My daypack had a pashmina, travel pillow, kindle, water bottle, charging cords (in a BlueQ pouch), makeup (another BlueQ pouch), wireless earbuds and wired earbuds, etc. I have a “bra purse” where I kept my passport and cards — I pinned this with a diaper pin to the inside of my Fjallraven rather than keeping it under my clothes — even if someone had opened the Fjallraven they could not have just pulled out the pouch with the passport/cards. On the plane I wore lightweight hiking pants, compression socks, Adidas town shoes, a tech polo, bralet.