We’ve got a good partnership when it comes to itinerary planning and booking. GMac will create itineraries with options for travel, accommodations and activities and CMac will book once we refine the itinerary. We like to have an idea of where we’re going and where we will stay at each step of the journey but try to keep our schedule in a location reasonably flexible. We prefer to take our time in a location and hit some tourist sites but often we just enjoy experience the culture and people.

When building an itinerary we like to rough out a schedule which includes dates, travel (when needed), accommodations and activities. Often we’ll have a couple of draft itineraries when travelling somewhere so we can debate what we want. There is nothing complex about the itineraries and they’re drafted in a spreadsheet program – right now we’re using Google Sheets which works well for us.

For the initial research we use a range of travel sites, but most notably Tripadvisor and Google a lot in our planning. We try to identify interesting places and activities as well as accommodations. On Tripadvisor and other sites we prefer to sort by ‘Traveller Ranked’ since it gives you the best view of what other travellers think. We’ll take the rankings roughly at face value but always double check using a couple of techniques:

The Curve – As far as we can tell Tripadvisor and other sites use a combination of the number of reviews and the distribution of those reviews. For obvious reasons the ratio of reviews impacts rating with higher numbers of top reviews being associated with top rated hotels and restaurants. However, newer entries or smaller hotels can be lower ranked because the total number of reviews is lower. We’ve found some great spots for both accommodations and eating further down the lists because they weren’t as well known.

The Worst Reviews – We also sort traveller reviews to see if there is a theme in the worst reviews. There are very few places that don’t have poor reviews. You can’t make everyone happy all the time. With the best places the worst reviews don’t have a consistent theme which is a good sign. As you get further down the rankings you’ll start to see themes in the ‘worst’ reviews which helps us understand what we’re getting into if we can’t get into one of the top ranked places.

The techniques used in building an itinerary are similar to what we use when we’re in location and trying to find something to eat. Tripadvisor and Google are good for restaurants and depending on where you are Yelp can also be helpful.

Another key question when planning is when to use a tour company and when to go it by yourself. There are some activities and tours that are great and sometimes mandatory, for example food tours or the Inca Trail. We’ve found through experience that we like to have control over the ‘macro’ elements of our trip – specifically the travel, accommodations and food. However, we do like using tour companies for select activities such as food tours (we recommend these in almost every place we go) and specific excursions.

Once we’ve got our plan we try to book. We try to find the best deal but also try to balance paying in advance which gets you lower rates and keeping our itinerary flexible. Flexible itineraries are the best as long as the premium isn’t significant and if you have time to make adjustments. With our work commitments it’s hard to have full flexibility on timing since we have to be back home and at work at a specific time.

Due to our business travel we often have both airline and hotel point options when booking. We’re Marriott Rewards Members and for transparency we don’t have any sponsorship from Marriott. It’s just a program that works well for us in our business travel. If you’re travelling a lot join a hotel rewards program and when possible stay in that chain of hotels. We find that when you’re in big cities and well known locations (i.e. London) we’ll use Marriott properties and points if it makes sense. In smaller or more touristy destinations we like to target boutique hotels. Similarly for airline travel, make sure you join a rewards program so that you can accumulate miles. We’re with Star Alliance since we fly a lot with Air Canada. We can’t compare Air Canada’s program with others since we really haven’t used other point programs. Star Alliance has also been good for us but CMac has some pretty good status so that helps. We’d also recommend a travel rewards credit card and we’ve had a few different ones, there are better sources for picking a card than us though so we’ll leave that to others.