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Over the past two years, two of my close friends have gone on three one to two-week vacations to Italy. At first glance, their multiple European vacations made it look like they must have suddenly come into piles cash. As it turns out, the key was when they were travelling: during the off-season.
While trips to Florence and Rome could potentially run into the thousands, they had started booking package travel deals on Expedia that took the price of those trips to just a few hundred. I was super impressed, and my boyfriend and I ended up joining them in Florence in March. It was pretty fantastic.
Depending on where you're travelling, there's a reason why there's an "off" and a "peak" season people travel there. The weather is typically better in the peak season, and tours are easier to come by. However, travelling during the off-season can have its benefits as well. During our trip to Florence, our tour groups were just a handful of people, streets were easy to navigate so we could actually enjoy them, and we could literally just wander up to museums and churches and walk right in. In contrast, friends that went to the city a few months later reported spending hours in lines that for us were non-existent and having to deal with mobs of people at every landmark, train station, and restaurant. Yes, it was a little chilly while we were there, but I think we won.
If you want to travel during the off-season somewhere, a new site called Offpeak.io can help. The app looks at median hotel prices over the course of the year to determine what the "off-season" might be for that place. Then you can use that information to plan a trip.
Additionally, it takes into account events going on in town that might drive costs up or make places crowded and lets you know what those things are. For instance, next month in San Francisco, Salesforce is holding its annual Dreamforce conference. You can see where that is by that huge peak in the graph below.
Image credit: Offpeak.io
If I was planning a casual family vacation to the city, then I might use that knowledge to plan a trip a week (or even a few days) later when hotels are more readily available and a quarter of the price.
You can sort the information by the star level of a hotel, and look up to 11 months in advance. You'll still probably want to do a bit more research before booking (are Boston hotels that cheap because the city is typically buried in snow that week?), so you know what you're getting into. The site lists typically high/low temps for each day as well, so you can use the graphs to find the perfect mix of weather and price.
Unfortunately, as it currently stands in beta, the site doesn't offer prices in Australian dollars. You're only able to get prices in USD, EUR, GBP and CAD. It's worth using Google's conversion tool to get a better understanding of when you should be travelling.