Reclaiming the Dream: How I Survived a PayPal Scam and Planned a 38-Day Solo Odyssey to Sicily
I started working on this magical dream back in June 2025. Then, the universe threw a diabolical curveball: I got scammed on PayPal.
Recouping from a financial disaster like that can break your spirit, or it can sharpen your focus. I chose the latter. I needed something massive, beautiful, and healing to look forward to. I became utterly hyper-focused on Italy. I’d been before, but I had never been to Sicily.
Why not Sicily for a whole month? I thought.
By January 2026, I took the leap and booked my ticket to Rome using my Delta SkyMiles (we will get into that absolute fiasco in a later post, believe me). By February, with some loving probing from friends, the blueprint began to take shape.
As an ITMI Certified tour guide, I have professional experience planning travel, but doing it for yourself as a solo female traveler hits differently. My trip was set: April 27 to June 3. Thirty-eight days to decide the where, the how, and the what.
Here is the 20-point master checklist I used to pull myself out of the scam aftermath and get my boots on Italian soil.
The Solo Traveler’s Pre-Trip Master Checklist
The Dates: April 27 – June 3. Why? It just felt right at the time. (Spoiler: Spring in Italy is spectacular).
The Ticket: Secured via Delta Miles (despite the drama). The Delta ticket agent misinformed me: Delta Comfort Class is NOT Delta's new classification for Delta Business Class.
Current Passport: Double-checked expiration dates. A valid passport is non-negotiable.
Driver’s License: Up to date, just in case.
Cell Phone Connections: Learned this the hard way. My eSim failed in Rome, so I switched to a TIM SIM with an Italian phone number. Problem solved.
Wall Plugs: More than one. You can never have too many outlets in a centuries-old building.
The Tech Sync: Getting a tablet completely compatible with my phone. If you are taking one, making sure they talk to each other seamlessly is a massive priority.
Credit Cards: Zero foreign transaction fees, and no need for stressful overseas notifications.
ATM: Double check your pin, and that it works. Also, check if there are transaction fees.
Health Provider: Checked in advance to see what my domestic plan covered overseas.
Travel Insurance: Absolutely non-negotiable. Check the prices, read the fine print, and get covered. Check with your insurance company first!
The First-Aid Kit: Not just prescriptions. Think ahead: pain relievers, stomach meds, blister bandages, and eye drops. Think!
The Big Question: Where are you going, and how long are you staying?
The Wardrobe Reality Check: Citizens all over the world look just like you. Yes, Europeans wear white sneakers and jeans!
The Capsule Wardrobe: Pack outfits, not closets. Remember: no one knows you, and absolutely no one will notice if you wear the same outfit twice. You are the one who is going to be hauling those suitcases and knap-sack up train station stairs, and rental apartments with no elevator. Remember, Italian towns are thousands of years old!
The Comfy Pivot: Always pack something lightweight and cozy to change into at the end of a long day of exploring.
Laundry Plan: Know where and how you’re washing clothes before you pack weeks of gear.
Shoes: One solid pair for heavy walking, one pair "for maybe," and sandals if necessary. These Taos Sneakers were the MVPs of my Italian adventure. For 38 days they carried me through airports, train stations, ancient streets, archaeological sites, and more staircases I care to count. If you're packing for a long trip, invest in one comfortable pair of shoes for walking and trust them. FYI, both Italian men and women wear sneakers, espeically white. Bonus tip: Don't forget lightweight slippers for the rental. Your toes will thank you.
Emergency Contact List: Written down, printed out, and shared.
The Budget: Oh yes, last but definitely not least—keeping the finances tight and secure.
The Strategy: Friends, Family, and Finding Safety
Safety is my top priority as a solo female traveler. For more than nine years, I've almost exclusively used Airbnb because I value how carefully they vet their hosts. It gives me peace of mind when I'm navigating a new city alone.
The logistics of this 38-day trip lined up beautifully. I’m lucky enough to have a cousin in Rome, and dear friends in Grosseto and the Rieti Valley. But because Sicily was uncharted territory for me, I built the ultimate itinerary: a heartwarming reunion in Lazio followed by a deep, slow dive into the football at the toe of Italy.
I divided my trip into distinct travel hubs:
The Reunion: Rome, catching up with family.
Ionian Coast: Catania for Mt Etna, Taormina for Ancient Greek Theatre (too crowded for me), and Messina for Torre Faro and The Astronomical Clock.
Syracuse and Southeast - Ortigia a small walkable island with Greek ruins and the Museo dei Pupi.
Palermo: The vibrant, high-energy capital of Sicily.
Tyrrhenian Coast: Cefalù for a La Rocca hike, and Capo d' Orlando for a view of the Aeolian Islands.
The Journey Home: Ferry crossing the Strait of Messina, train to Pizzo, then Tropea and Tivoli before returning home.
Getting scammed might have delayed my stride, but it didn't stop my journey. It proved to me that a setback is often just the prologue to an unforgettable adventure.
Fellow travelers, have you ever had to rebuild a dream trip after a major financial setback? What does your non-negotiable packing list look like? Let me know in the comments below!