Loyalty pays … or does it?

Shopping around is one of THE cornerstones of frugality. Taking a little time to do your research in order to get the best deal … it’s a no-brainer.

But when do you draw the line?

I wasted far too much time early on in Europe trying to save money on accommodation. Hostels and hotels were so expensive in Brussels and Amsterdam that frankly, I may have saved a few euros, but it was a poor payoff in proportion to how much time I spent searching countless websites looking for the best price.

My go-to sites for booking accommodation are Agoda (in Asia) and Booking (Europe/North America). I also used Hotwire, Priceline and Expedia once each in the US, but by and large, Booking.com is where it’s at for me. Unlike other sites, it’s always upfront about taxes and other charges that individual places levy. And while I don’t ALWAYS check against other sites, I can’t think of any instance where I’ve found the same room for cheaper elsewhere.

(As for hostels, I always play off both Hostelworld and Hostelbookers against each other, though Booking also includes some hostels in its database.)

The convenience of booking through the same site can’t be understated, particularly if there’s a good mobile app. All your details are saved, so you don’t need to enter them every time. You know how to navigate your way around instinctively to get the information you need. And your loyalty starts to pay off – you start to get emails with special subscriber deals and exclusive discounts. I’ve booked through Booking.com so many times I now have a 10% Genius lifetime discount, although it applies to certain hotel deals only.

Loyalty pays in other areas, too. You’re more likely to get fees waived if you’re a long-time customer. You get discounts for staying with the same insurance provider after a certain number of years. You get a free coffee if you rack up enough stamps at your favourite cafe. And so on and so forth.

Personally, I’m pretty loyal when it comes to banking and insurance, but I’m a personal finance nerd. Nothing is totally sacred.

When do you go with the easier option, and when do you hunt down the best possible deal?