NOTE -> This trip occurred pre-COVID-19 and feels like 100 years ago

The kids get a week in February from school. In 2019 we went on a n epic and memorable trip to Dubai. This year we weren’t looking to go quite as far but didn’t have any specific destinations. Our bucket list is long so we figured we’d find a destination based on a cheap airfare or a specific hotel or destination.

Search for a Destination

Knowing the dates we wanted to travel was a good start. I ended up plugging in the dates into my old friend Google Flights with Boston as the starting airport with no destination. This shows a world map showing the cost of tickets to all the destinations visible in the map. It’s a fun way to explore and I do it quite often.

I spent some time looking at Spain, originally looking at Christmas for 2019 when our Far East adventure fell apart. I had seen decent rates to Barcelona and was thinking of maybe doing a Mediterranean cruise for the holidays, but those plans ended up not being as inspiring as they first sounded once I dug in to more details.

We had talked about Spain for years, but had held back thinking we might make it a family trip with my wife’s family since they love Spain and especially Barcelona. For fun, I checked flights from Boston to Barcelona. The price was pretty low, but I then entered Madrid as a second destination. It’s a feature in Google Flights that you can enter multiple departure and destination airports and it will find the cheapest routings between all the options you entered.

When I did this, I saw the price drop dramatically. Initially I thought it was because Madrid was a lot cheaper the fly to/from than Barcelona, but when I checked closer the itinerary flew into Barcelona and out of Madrid. This is known as an open jaw itinerary. This requires you to find your own transportation between the two locations but that would not be a problem.

Based on the price of less than $300 per person round trip, we decided to make Spain our destination!