The Itinerary...Solo in the Azores (Part I)
- 4 days ago
- 4 min read
The Lead Up
This Bingo card keeps coming into play as I write, and I am so glad I actually made it. What started as a New Year’s Eve craft with my boys has served as an anchor for my year. It’s a pulse-check for daily life. Sometimes I get so bogged down in the "daily grind" that I don’t reflect on what I’ve actually accomplished. I have a habit of raising the bar—stretching myself to grow but then getting upset because I don't feel like I'm where I thought I was "supposed to be." This card and my tracking sheets have allowed me to monitor my progress and celebrate my successes.
But...back to the trip. This was on the Bingo card, and it was the one item that scared me the most. I caught the travel bug; I love seeing the touristy things, but I also love taking the path less traveled to see what the locals experience. I dive into the culture, the food, and the local vibes. However, travel was always something I did with a "unit"—first with my family growing up, then my husband, then our boys. Even when I traveled with just the kids, I had them to lean on or, at the very least, they provided a distraction from being truly alone.
I had solo-traveled for work. I’ve gone to movies and eaten at restaurants alone. But the thought of doing all of it solo —the navigating, the deciding, the being—was "piss my pants" nerve-wracking.
Passenger Princess No More
I was always the planner, not the executer. I can work through logistical hoops, scour the net for deals, stack points and miles, and research every hidden gem. But in the past, once the legwork was done, I was able to switch hats to "Passenger Princess." I wasn't responsible for leading the day, navigating directions, or driving the car. Everything was printed, packed, and ready so I could just "be mom."
Like this website (noticing a theme of me dragging my feet on things that aren't perfectly mapped out?), I hesitated. I abandoned the thought of a solo trip for Summer 2025—I just didn't have the bandwidth. But through late fall, I played the "Google Flights: Let's Go Anywhere" game for Spring Break 2026.
Now, if we’re talking strategy, a cash ticket should have been bought in December. That was not the case here. In mid-February, I finally pulled the trigger on a non-refundable ticket to Ponta Delgada. This isn't a case study on the "best bang for your buck" in terms of points and miles; this was a "if I don't buy this while the kids are with their dad, I'm never going" situation. Plus, I had the ultimate travel hack in my back pocket: a looming 40th birthday. ✈️🏨💝 Let the planning begin.
The Systems Tie-In
I’ll be covering the specific resources I used—the credits, portals, and savings—in a separate post. I want to be as transparent as possible about the all-in costs and where I found discounts. I recognize that being able to take this trip was and is a privilege, but I hope my strategies can help you map out your own "stretch" trip. It all started with Google Flights, the Hilton and Hyatt apps, and a clear list of credit card benefits to navigate lodging and logistics with safety emphasized (especially as a solo woman traveler).
To the People We Meet on Vacation
Traveling solo after being part of a unit required some intentional adjustments. I didn't even know what I’d enjoy doing when it was just me. I had to get comfortable with my own company, and if I wasn't, then that meant... gasp... engaging with other travelers.
I learned that when you aren't sheltered by your family unit, you open yourself up to the most precious opportunities. Through Get Your Guide, I met people from Toronto, Romania, and even good ol' Chattanooga. A highlight was the day I spent with another woman traveling solo; sharing our different stages of life and commiserating over being "out there" alone. Another woman was testing the solo waters for the first time after her husband passed. We hiked a trail to an abandoned factory and talked about our kids and past lives. If I had been with my family, it's very likely I would have missed those conversations and interactions.
Steal My Itinerary
I love to map out trips, the timeline and routes, so I don't have to think through logistics while on the trip. Despite having it all mapped out, I even learned to "go with the flow" a few days in and stray a bit from my plans. Here is the birds-eye view of how I squeezed the most out of the Azores:
🛫 Travel Day: Atlanta to Boston with a red-eye to Ponta Delgada.
🏨 Hotel & Jet-Lag Day: Checked into the DoubleTree by Hilton Lagoa Azores, visited the Caldeira Velha hot springs, and crashed early.
🚐 Island Tour Day 1: Pineapple plantation, Sete Cidades, Mosteiros, Santa Barbara beach, and Rio de Quesa.
🚐 Island Tour Day 2: Furnas, Ribeira dos Caldeiros, Gorreana tea plantation, Santa Iria viewpoint, and Nossa Senhora das Vitorias.
🐋 Sea & Surf: Whale watching tour, waterfall hike, and dinner at Cais20.
📷 Self-Guided Drive: Explored Vulcana and Azores Breweries, grabbed a smashburger, and hit another waterfall hike.
🐝 The "Organista" Special: Beekeeping and honey tasting, horseback riding, and a massive local grocery score.
🌲 The Grand Finale: One final hike, Ponta Delgada city center, and steak sandwiches before the flight to JFK.
I promised myself a solo trip, and successfully pulling it off as an early 40th birthday celebration was the ultimate win. The Azores became the place where the chaos finally went quiet; I was fully immersed, present, and at peace.
My departing flight—apropos to the sentiment of this past year—left the islands to the sight of a perfect rainbow. It reminded me of one of my favorite books I read to the boys, Rain Brings Frogs. We may hate the rain and the mud it leaves behind, but we know the sun is waiting behind the clouds—and if we’re lucky, we may even see a rainbow.
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