The World is Waiting

Or why this blog is starting a subscribers-only travel agency👇🏼

Friends,

One of my favorite parts of writing these posts is picking out the thumbnail image.

It’s fun to search back through old photos and find something from a previous trip that semi-fits the topic. And, of course, I’ve got a pretty solid inventory of random airplane wing shots that will do in a pinch.

Today’s photo comes from Milford Sound on New Zealand’s South Island. My family spent a week in the Southland Region last year, and our adventures there truly changed my life. More on that another time.

For now, I just want to highlight again that travel is good because it is transformational. There’s a lot that goes into traveling well — I talked about this last night while recording the podcast.

One of the reasons I started this blog was to share my love of travel in a way that could be (hopefully) useful. The mission here is simple: to inspire and help others travel well — both for our subscribers and onward. Because good travel begets good travel.

My hope is that one day we’ll help lots of people travel well — every day, all around the world.

And so today, the next step of that pursuit is the launch of a dedicated, subscribers-only travel agency. It’s going to be great because we’re going live with three active services:

Hotel portal: a self-serve booking tool soon available to subscribers. Functionally, it feels like Expedia, Andrew Harper, and Amex Fine Hotels & Resorts had a baby. Practically, it’s going to be a strong tool in your kit when you need a great hotel room with VIP perks at special, negotiated pricing. The portal will go live soon, and will be included at no extra cost to subscribers.

Trip planning: a done-for-you, old-school travel advisor service. We’ll meet, and I’ll plan and book your trip for you. While there may be a fee component in the future, for now I want to offer it free to subscribers.

Points audit: a reinvention of the popular “book time with Tommy” call-outs from my original emails, helping you define and implement a great earn-and-burn strategy for your points. This will continue as a chargeable, one-off service.

While this is all plain text for now, expect a prettier menu soon — along with a section on the website to get started. I’ll keep you posted here.

What isn’t online yet is what I’m calling our “air desk” — a white-glove flight booking service to make sure you get the best fares, seats, and support when flying commercially. This is on the roadmap, but it requires infrastructure that takes time to build.

And what about AI? This question (rightly) gets a lot of airtime, and I want to address it since a travel agency is, at its heart, an old-fashioned service business. We’re using AI to support our workflows — surfacing the best deals and helping us plan more intuitively. But it’s not replacing the human element, which is the heart of great travel (and great travel planning). I expect to write more on this soon.

Are you dreaming about an upcoming trip? Reply and I’ll share how we can specifically help. And know I’m grateful you’re here — on this travel-passion-project with me — and I’m excited for your adventures ahead.

Fly well.