Travel Sites you should know

It's starting to finally show signs of summer in the United States, and you might be getting those itchy vacation feet.  You might have some travel sites that you use regularly, but we wanted to run a couple more by you to make sure you're getting all the best options for your travels.


There's no shortage of search engines for your flights, hotels, rental cars, etc. but Hipmunk has both a special category and a visual presentation that makes decisions easier.

The special category is called the "agony index" and is scored based on how long a flight is, how much it costs, how many layovers (if any), etc.  It allows you to see, for example, that while a flight is slightly more expensive, it's going to be lower on the agony index, and as a result, you may decide to purchase it because you value your time lost on a layover more than the price savings for that flight.

Your search results are also presented visually, so you can see colored indicators for how long a journey is.  In addition to searching all the airlines, Hipmunk also searches the engines of other travel aggregators, and even adds in options like Amtrak to your travel (where applicable) or even links to Southwest in a guess of their price range (which doesn't permit searching of its results).  You can also set "alerts" for target pricing.  But that's the particular specialty of...


Hopper doesn't function as a website, but only as an app for both Apple and Android.  Once you download it you can search for a flight.  Hopper has a color coded calendar to tell you when it will be cheapest for you to fly (this is most helpful if your dates are more flexible or further out).  The continuously updated machine-learning algorithm will then tell you WAIT or BUY based on what the database has "learned" over time.  You can then either buy or set a notification to be told when the price drops to a level you want.

Hopper boasts a 95% accuracy via its predictions, and has no hidden fees, and has a real customer service team to help you, not solely email and voice mail jail!


Most travel sites (as with online dating, interestingly) are owned by a few big players who control dozens of sites.  Booking.com is owned by the Priceline Group (which owns Kayak, CheapFlights, and OpenTable, just to name a few) and accounts for upwards of 60% of the parent company's annual revenue.

Unlike many sites that only search hotels and motels, Booking also takes into account smaller bed and breakfast or simple "private" listings in the mode of Airbnb.  It also has some of the most extensive filters offered by any of the travel sites, as well as an internal rating system so that you can rely on your fellow travelers for intelligence about the property before booking.

Do you have any favorite travel sites?  Share them with us in the comments below!

Ben Davis

About Ben Davis

A serial entrepreneur, Ben Davis is founder of The Gents Place and a leading investor in gentlemen's refinement and confidence.

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