Bem-vindo to The Azores

8/23/25, AirFrance Lounge at JFK Airport, NYC

It’s time for my next big adventure, to the Azores!

It has been delightful telling people where I’m going on my next trip – they always ask; I’ve garnered a travel reputation. Some know and express sincere excitement; but about half hesitate for a micro-second before expressing enthusiasm, leading me to ask “do you know where that is?” and leading them to admit that they’ve never heard of the Azores.

And I love telling people about it! The Azores are a set of nine islands in the middle of the Atlantic Ocean, part of Portugal. They’re not near the Canary Islands, as many ask; they’re not really near anything. The islands developed into a major maritime stopover for intercontinental travelers. They’re known as the Hawaii of Europe. I’m looking forward to learning more.

So why did I choose this random, little-known spot for my next big solo trip? I guess I got influenced, because two years ago I was catching up with my friend Maia who shared about her Azorean adventure, and she sold it so much that I added it to my list. I like to say that some places call to me, and that’s definitely what happened here as I made the trip a reality. The technical selling points include beautiful landscapes with waterfalls, volcanoes, and epic hiking, affordable prices, the ease of a European destination, not yet over-touristed, and a 5-hour direct flight from NYC. Sold!

The logistics: I planned early, knowing the limited lodgings and automatic car rentals on the island book up many months in advance. I’ll be traveling between three islands (Sao Miguel, Flores, and Faial) over two weeks, plus some day trips to a few other islands (Pico and Corvo and maybe Sao Jorge). Inter-island travel will be by plane; except for the day trips which will be by ferry. I’ll rent cars the whole time to get around. I’ll be staying in hostels, in dorm beds, to save money and meet fellow travelers. I booked a few activities like canyoning, whale watching, and island tours. I’m planning some hikes, hot spring visits, and learning about the local culture and food, including wine, cheese, and pineapples. I’m very excited to explore and adventure!

As I’ve been telling people, I haven’t left the country since Trump was inaugurated. I’m eager to see the attitude toward Americans in Europe. And mostly I’m just so excited to leave this hellscape of a country for a while, as I prepare for more international trips over the coming months and contemplate how I can incorporate travel even more into my lifestyle. My brain has been swirling a lot the last few months, in a period of contemplating change. This summer work finally slowed down after a bruising 6-month busy season, and I started to really take stock and put some plans into motion. I’ve been feeling good and sad and scared and deep in some big emotions for the last few months. My intention for this trip is to try and let go of all that a little bit, and just explore, enjoy, and live in the moment. We’ll see where the next two weeks take me.

So far, the trip is progressing nicely. Transit got me to JFK quickly but sweaty, check in was smooth, and I cut the security line through the VIP One lounge. I landed in the Air France lounge right next to my gate, where I’ve had about two hours to enjoy the delicious food and free champagne. Cheers!


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