Developing a Trip Outline

Perhaps the best way to explain our approach to developing a trip outline is to take you through a working example.

While on a European cruise we were inspired to take another cruise the following year – 3 weeks exploring the fjords of Iceland and Norway. I always try to get maximum value from long-haul flights so I figured that we should arrive in Europe a bit early and spend time sightseeing before joining the cruise.   The cruise departs from Amsterdam so our pre-cruise travels must finish in Amsterdam by the sailing date.

Singapore Airlines were favoured because they have one of the best lie flat beds in business class and I could use points for our flights. I started by looking at what cities we could land in (from the Singapore hub). Friends of ours spoke enthusiastically of their time in Switzerland so we decided that flying into Zurich would be a great start. It didn’t take long to work out that it was considerably cheaper to book a return flight than to fly into and out of different cities (open jaw) so our challenge distilled to start and finish in Zurich and do a cruise out of Amsterdam in the middle!

Looking at Google Maps quickly suggested that a nice trip outline would be to travel to Amsterdam via Switzerland, Austria, Budapest and Prague. How long would we need for a trip like this? Trains were quickly identified as a great way of getting around and even some especially scenic routes to try and catch. We used the price of a Rail Pass for budget purposes, planning to compare price options later.

The Viator website is a great help for deciding how long you need in each place. Viator is an excellent tour-booking site for pretty much any place in the world. If a place has oodles of tours that sound interesting then you know you need two or three days. If the list is shorter you can plan on just one or two nights.

At this outline planning stage we aren’t necessarily planning to actually book the tours. Rather we simply use them as inspiration on what is worth seeing. After all, if a business can make money taking people somewhere, then it is probably worth seeing or doing (if it appeals). Later, when we get into detail we’ll weigh up tours vs self-guided discovery.

Every city has multiple websites extolling their virtues. Google for these to expand on what you have quickly learned on Viator. After a week or two, with lots of discussions in between, you’ll have a pretty solid outline of where to go, how long to spend in each place and what you’ll probably do when you get there.

For our trip we even figured out that after the cruise finished in Amsterdam we would take a few nights in Germany working back to Zurich before flying home with a stopover in Singapore to lounge by a pool and decompress.

That’s it! Trip outline complete! Time to jump onto some hotel websites and see how much accommodation is going to cost. Add up the accommodation, the airfares and a daily living allowance. If the total is something you are comfortable with then lock it in. Flights can be safely booked a long way ahead to get the best rates and hotels reservations can be made.

Book hotels at fully flexible rates so that plans can be tweaked (or even cancelled) if needed. Aim for bookings that only require a credit card guarantee not actual payment. But by doing it nearly a year in advance you will usually get flexible rates that are as cheap or cheaper than “advance saver” rates booked two months out. And if you want to use points for flights and/or hotels, doing it a long way in advance is highly recommended.

With the trip outline complete and the flights and accommodation booked, filling in the detail at each destination is a delightful task that can be done at leisure.

In case you’re wondering, the trip outline in this example became 52 days. Three weeks before the cruise, three weeks on the cruise and a week after.


Photo: Arc de Triomphe from the highest viewing platform on the Eiffel Tower, Paris, France