It’s a challenge.

There are so many options, so many parameters, and so many diverse opinions when it comes to what makes the perfect place to stay.

In the past, we’ve used VRBO, Airbnb, dealt with hotels directly, and used aggregate sites like Hotels.com and Booking.com – even occasionally TripAdvisor – but my favourite resource for this kind of trip, where there are already multiple flights, trains, and accommodations to keep track of, is our Expedia app. There I can store all our bookings, AND communicate directly with each hotel in the Inbox feature which allows both notifications (things like booking acknowledgment) and messages (things like requesting airport pickups).

Our first priority for this trip was balancing the types of accommodation we’d book: luxury vs. economy, apartment style places with kitchens (and maybe even their own laundry) vs. places without kitchens but with breakfast or half board (breakfast and dinner) included; boutique hotels and quaint independent B&Bs vs. reliable chains; city centres vs. waterfront. In the end, since we’ll be packing a lot into our five months, I’ve even thrown in an off-season all-inclusive resort on Crete.

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For each stay, I chose at least 5 or 6 possible options within our price range. Expedia has a 1-10 rating system; I decided that I wouldn’t even consider anything below an 8.5, or with fewer than 300 reviews. Even then, we’ve learned that there’s a secret to reading reviews: check the most recent ones first, and then check the lowest ratings to see what kinds of things people complained about. If it’s bad parking options, for instance, that isn’t an issue for us. If it’s cleanliness, and there are multiple comments, that’s a deal breaker. I also look for reviews in languages other than English. When a German review raves about the breakfast options, that’s much more meaningful to me than a North American review, because Germans expect hotel breakfasts to be much superior in both quality and variety to what is standard here.

Because not everyone who stays in a hotel uses Expedia, once I’ve narrowed down my favourite 2 or 3 places, I also look them up in Google Maps and check the ratings (on their 5 star scale) there. Again, I look at the most recent reviews and the lowest. The advantage to using a map app is that I can also look at real photos of the building’s exterior, and often see a 360° view of the neighbourhood. Plus, I can see how far the nearest grocer or market is!

The other thing we do is only book properties that are fully refundable up to a week before check-in, even if we have to pay a premium to do that. That not only helps avoid ending up out of pocket if something unforeseen happens during a long trip, but it also means that if we find out after booking that a hotel’s reputation has significantly changed, we’re not stuck.

So what’s our final schedule look like? Here are our Expedia summary pages, which show city views as opposed to our specific accommodations.

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It’s definitely the most pre-planning I’ve ever done for a single trip, and the most moving around we’ve ever done, with our longest single stay being 2 weeks, and our shortest (not counting overnights near an airport) just 4 days.

Not surprisingly, our least expensive accommodation is the 2-bedroom apartment in Kuala Lumpur, clocking in at just $108CAD/$78USD per night after all taxes and fees.

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Our most expensive is not the Greek all-inclusive, but the self-catering apartment in Sydney’s CBD (Central Business District) that will cost $331CAD/$240USD per night. I learned very quickly that location is everything, and that hotels close to airports – which is essential when we have early international flights – are relatively more expensive than their counterparts inside the city.

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Right in the middle at $224CAD/$162USD per night is Campbell House in Penang, built in 1903. It boasts a terrace, rooftop garden, library, and restaurant. Our “deluxe superior” room won’t have a kitchen or laundry for our 2 week stay, but there is guest laundry onsite and laundry service nearby, and this was one place where the photos absolutely enchanted me. It didn’t hurt that it came highly recommended by acquaintances who live part of every year in Penang.

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Our average cost per night over 137 nights that I booked for us (the hotels during the New Zealand train tour were chosen by Pounamu Tourism who created the tour) average $203CAD/$147USD per night inclusive of taxes and fees. We’re pretty satisfied with that.

We know we won’t always get it 100% right, but that’s not for lack of trying, and if occasionally we can stay in a place with an outdoor area like this one in our Rethymnos hotel on Crete, I think,we’ll be pretty happy.

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Plus, with all this done, maybe August will be my month to get a good night’s sleep, because in September we’re off to Europe!