The Itinerary: The Systematic Escape

If you had told me a few years ago that I’d be booking a solo trip to the middle of the Atlantic, I would have laughed. Then I would have created a spreadsheet. Approaching 40 has brought a lot of 'heavy and light' reflections, but it has also brought the realization that choosing myself is a system worth investing in. Here is the literal 'cents and sense' of how I mapped out my Azores escape, even without my normal level of advanced planning.

Let's map out the approach I take when planning most of my trips. Usually, I use Google Flights to hone in on cost-effective options 4–6 months in advance. Because I was "behind the ball" on this one, I moved away from my usual scouring for award seats and focused on a cash strategy.

The Flight Strategy

When using Google Flights, I factor in more than just the ticket price: I balance timing, connections, and multiple airports (TYS, ATL, BNA, CHA, AVL). I calculate if the drive time and a potential hotel stay are worth a cheaper and/or more direct flight. I always book directly with the airline for better customer service and mile-earning potential.

💡 System Tool: I use the Points Path extension to automatically calculate if I should pay cash or use miles. And then utilize several points and miles sites to find award seats.

I booked directly with Azores Airlines using my Capital One Venture X. Booking closer to departure meant a higher cost than I’d like, but I earned miles on the $1,188.33 fare. My flight was in the evening, so I was able to drive down to Atlanta that morning and have time to park in a remote lot to reduce the cost of parking. Once I've secured the flight, I'll scope out the lounge situation and determine if my route will allow me to utilize Priority Pass or Capital One Lounges for some bougie on a budget travel. I also set a reminder to use my quarterly $50 flight credit on my Hilton Business card for both the departure and return flights. I can then indulge a bit in an in-flight cocktail or snack.

Lodging & Island Transportation

I bypassed AirBnBs (no "murder-doc" vibes for this solo traveler) and leveraged my Hilton Diamond Status at the DoubleTree Lagoa Azores. I had looked into staying local but this was one component where I could maximize savings.

• The Perk: Free room upgrade, breakfast, spa, and gym access.

• The Win: I applied a $200 resort credit to the stay.

Another reminder is scheduled to send my hotel an email about my upcoming stay, hotel loyalty status, reason for the trip, and the shameless request for an upgrade and a little welcome gift. The hotel concierge or customer service email is usually available on the hotel's website, and if not, a quick chat with the hotel chain can remedy that. A huge shoutout to GeoBreeze Travel for this tip - its one of my favorite things to do and it's had a high success rate!

I also opted for a bit more freedom, since I read that the island's public transportation might cramp my exploration. I've previously rented from Sixt and chose to use them for this trip as well. Rakuten had a 15% cash-back offer that definitely influenced my decision; I chose a Nissan Juke for its familiarity and to ensure I had enough space.

My final night of travel back home consisted of an overnight layover at JFK, and I begrudgingly chose to pay for the luxury of a bed—despite the fact that one night there cost almost half of what I spent for an entire week on the island.

The "No-Thinking" Itinerary

Once I have the skeleton of my trip scheduled (hotel, flight, and car), I spend several hours researching tourist spots, hidden gems, 'not-to-miss' dining options, and key souvenirs. I plug everything into a working document so I have confirmation numbers, costs, and routes mapped in Google Maps ready to go. My findings, URLs, and notes are layered in so I have a comprehensive resource to reference. On the day of, there is zero mental load—I just pull it up and enjoy. Go into this document below, but be prepared for how Sam's brain works...

Azores Itinerary.docx

Download DOCX • 37KB

Excursion Breakdown

By using the Capital One portal, I secured 35x miles back on these island experiences with GetYourGuide:

• 2-Day Van Tour (with lunch): $187.57

• Whale Watching & Islet Boat: $73.61

• Beekeeping & Honey Tasting: $56.99

Item	Cost	Strategy/Hacks	Savings
Flight	$1,188.33	Capital One Venture X (earned miles)
ATL Parking	$70.81	Peachy Parking + Coupon	upgraded to covered
Doubletree Hilton	$601.77	Hilton Diamond + $200 Resort Credit	$200 + 22,332 pts
JFK Layover Hotel	$281.80	Necessary bookend for the flight schedule	7,850 pts
Car Rental	$387.00	Sixt + 15% Rakuten Cash Back	pending
Excursions	$331.78	GetYourGuide + 35x Capital One Miles	11,135 miles
Hot Springs	$13.00	Pre-booked entrance and locker
TOTAL	$2,874.49	(Before final cash-back rebates)

Prepping for Content

Since sharing this journey is new to me, I planned in some unique ways. I traditionally use a packing and five-day lead-up checklist to prepare the kids, the pup, and the house before departure. I’m someone who likes to come home to a clean house and hit the ground running, so the days leading up to a trip are usually pretty packed. For this trip, I also crafted a content checklist and reminders to check in and journal about the process. Since I was solo, capturing pictures of myself was new territory—I’m definitely not a selfie pro, but I wanted to document the experience. I packed a tripod/selfie stick and a microphone, which I purchased through Walmart using a cash-back extension to save even more.

🐶 The Grandparent Resort: A huge thanks to my parents for taking the pup. She was included in my "Weekly Ledger" prep to ensure all her items were packed and she was ready for her own vacation.

This trip wasn't just about the destination; it was about proving that the systems I use to organize the chaos of daily life work just as well for international solo travel. Next up, I’m diving into the ROI—what actually happens when an 'overplanner' finally hits the ground in a foreign country alone.

xoxo Sam