I'm Off to Italy for the Month of May!! (Planning for Rome & Sicily)

As an Amazon Associate, I earn from qualifying purchases. 

Mr. Bear reviewing the official flight itinerary to Rome (FCO)
and checking the guidebook for our 10-day tour of Sicily!

I'm Off to Italy for the Month of May!! (Planning for Rome & Sicily)

Well, here we are again. The blog rises from the digital dust, and this time I'm actually writing about what happened today instead of what I meant to write about three weeks ago.
So what happened today? I dove headfirst into planning mode for my May trip to Italy, and to satisfy my nagging friends: the rabbit hole is deep and wonderful.

The Plan (So Far)

Flying into Rome, because all roads lead there and all that. But I'm not lingering long in the Eternal City—at least not at first. The real adventure starts when I head south to catch a ferry over to Sicily, where I plan to plant myself for a solid 10 days. Ten days! Time to actually be somewhere instead of just seeing it.
After Sicily works its magic on me (and let's be honest, it will), I'll head back north to visit friends and relatives in Cisterna, Grosseto, and then circle back to Rome. It's going to be that perfect mix of explorer mode and reconnecting with people who matter.
I have a confession to make: I've been using AI to brainstorm this trip, and it has been interesting: offering a different perspective I might say. Look, I usually do all my itinerary planning myself—it's part of the joy—but there's something fun about bouncing ideas off an AI that doesn't judge you for asking "What if I just spent all 10 days eating arancini in Palermo?" They've offered suggestions I hadn't considered and helped me think through logistics in ways that actually make sense. Who knew the machines would be so good at helping me plan me la dolce vita? Especially since I am ITMI certified in tour management, I appreciate tools that actually save time on logistics!

The Tech Situation

Here's where things get real: I just bought a Samsung Galaxy S25+ and a amsung Tab S10 FE. 

Yes, both. Because apparently I've decided to enter my "fully equipped traveler" era.

My Travel Essentials

To manage these itineraries and keep my travel-ready plans moving smoothly, I rely on two vital pieces of gear:

Samsung Galaxy S25+ (#ad) - My ultimate travel companion for snapping crisp photos,
tracking live street maps, and instantly accessing my Airbnb check-in addresses on the go.

Samsung Galaxy Tab S10 FE (#ad) - My portable, lightweight workstation
for deep itinerary planning, mapping logistics, keeping our route organized,
and writing my travel stories. 

Reading my blog, you come to know my trip was fantastic. Everything I wanted and then some. There were some a bit tense at times, then there was the "How am I getting out of this mess!!" Stay tuned for Mr Bear's and my adventure what turned out to be 3 weeks in Sicily.

Now comes the fun part—figuring out chargers, cords, and power packs. How many adapters does one person need? How many USB-C cables is too many? (Trick question: there's no such thing.) And do I really need that portable power bank, or do I just want it because it looks cool? Yes, I do!!

These are the questions that keep me up at night. Well, these and streamlining my vitamin situation, which is a whole other organizational challenge I'm tackling simultaneously.

Stay tuned. This time I mean it.

Ciao for now!

Sandy