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Building WhenToTravel: My 2026 plan for learning and monetization.

  • Writer: Mark Waldron
    Mark Waldron
  • Feb 2
  • 3 min read

I’ve set myself a few clear aims for 2026:

  • Make something useful

  • Learn something new

  • Make some money doing it — ideally passive income


On the learning side, I want to focus on:

  • Productivity enhancement using AI

  • Stronger, hands-on experience with modern UI technologies

  • Getting much more familiar with embedding AI into a real product or tool


I’ve owned whentotravel.com for quite a long time. When I bought it, the motivation was fairly simple: travel content has highly profitable keywords and a huge audience. The idea was to build a content-driven site, target those keywords, and generate income through ads.

I never actually built the site. That’s bothered me for a while. But my current aims now line up surprisingly well with my original reasons for buying the domain, so it feels like the right time to dust it off and finally put it to work.


Hmm, I need to add an image to this blog post otherwise it's just a bit flat. I asked ChatGpt for a prompt and then fed that back into the wix ai image generator. It's a little odd, but I like the attempt.
Hmm, I need to add an image to this blog post otherwise it's just a bit flat. I asked ChatGpt for a prompt and then fed that back into the wix ai image generator. It's a little odd, but I like the attempt.

Why this project makes sense now

It’s useful At its core, this can be a genuinely helpful tool: something that allows people to optimise their travel plans around their own personal criteria — weather, cost, crowds, events, and so on.


It’s targeted The domain itself implies a very specific intent: discovering the best time to travel. That makes it easier to understand for both humans and search engines. By focusing tightly on that intent, I can aim for a smaller, more focused niche and go after longer-tail searches, rather than competing head-on with huge, generic travel sites from day one.

That focus should also make the site simpler to build and easier to evolve.


How to monetise it

ChatGPT has been helpful here, suggesting ideas that partly align with my own experience from previous attempts at passive-income sites, and partly push me into new territory.

  • Ad placements Straightforward, content-driven ads such as Google AdSense. Easy to add and a sensible baseline.

  • Ad management / publishing Using something like Google Ad Manager for more control: auctioning ad slots, inserting my own content where appropriate, or working directly with advertisers or content publishers.

  • Affiliate links and partnerships Travel is full of purchase opportunities. If someone is searching for the best time to travel, they’re either close to — or already at — the buying stage. If my site helps them reach that point, then partnerships with hotels, experiences, insurance providers, flights, travel gear, and related products could work well.

  • Email lists This is newer territory for me. It’s a little outside my comfort zone, but ChatGPT is adamant that this is extremely monetisable. The basic mechanics are still ads and affiliate partnerships, but with a more focused, opted-in audience. Longer term, that could also open the door to paid subscriptions, exclusive content, or even my own products. That all feels a bit fanciful right now, but I’m open to it — at the very least, I want to start experimenting with building an email list and see where it leads.


Traffic, SEO, and discoverability

All of this only works with traffic. SEO is going to be a major part of the project and needs deliberate attention from the start.

I don’t have a marketing budget. I mostly just have me (and maybe a bot — note to self: look into that). That means the site needs to be inherently discoverable. Search engines effectively become a primary user alongside actual humans, and the site has to be built with both in mind.

I also want to do something slightly different by aiming beyond just English-speaking users. I’d like to target other languages that are less well served by similar tools and sites. That adds complexity — especially around SEO — but if I can get this right, it could significantly multiply the potential audience beyond the usual UK/US focus.


Target endpoint

What I’m aiming for, ultimately:

Obviously this will change as I progress the idea, but here is my current vision.


  • An SEO-focused, multinational website

  • Multi-channel marketing across social networks

  • Personalised travel recommendations and discovery tools

  • Travel guides targeting key SEO areas and keywords

  • Subscribed users receiving tailored content


Phased approach

MVP (now)

  • SEO-focused multinational website

  • Travel guides targeting key SEO areas and keywords

Next

  • Multi-channel marketing across social networks

  • Personalised recommendations and discovery tools

Later (once traffic and engagement are proven)

  • Subscribed users receiving tailored content


For now, the priority is simple: build something useful, learn as I go, and see whether this long-ignored domain can finally earn its keep.

 
 
 

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