Jerry Seinfeld once said about Las Vegas, “If you were not losing, this would not be a very nice place to be, would it? They wouldn’t have beautiful carpeting and restaurants and wonderful shows. It would be like a POW bunker. . . . The losing pays for the nice hotels.”

You can benefit from the countless billions lost every year in Vegas by using some simple tips to vacation there for a fraction of what other people pay. (more…)

When our third child was born almost ten years ago, I was so excited. Another healthy baby boy to round out my future golf foursomes! We were now only one short of our own basketball team and could play two on two in soccer whenever we wanted. There was only one problem (besides the need for a minivan). I thought we would be stuck booking two hotel rooms whenever we went on vacation. That would seriously strain the travel budget.

My Party of Five

But necessity is the mother of invention. I have spent the last nine years perfecting the art of travelling with a family of five. Arguably the most important skill I’ve learned is how to find hotel rooms that will comfortably fit our whole crew. By booking one hotel room we save tons of money. Plus, we get the memorable experiences that only come from sharing a room.

Every major hotel chain has a brand that will sleep five people. I will focus on the three brands I know and love the most: (more…)

The weekend before last, my wife and I stayed 2 nights at the historic Hotel Del Coronado, just south of San Diego, CA. Using Hilton points, I booked a free stay for us in a standard room, which sells for around $350/night. I wasn’t excited about the room. It wasn’t on the ocean, didn’t have a view, etc. But we were upgraded for free to an Oceanfront Tower Resort Suite on the top floor of the hotel. That room sells for over $1,500/night. It was 900 sq. ft. large. And it had the two features that I wanted: a spectacular ocean view and a balcony to enjoy it from.

The view from our upgraded room’s balcony at Hotel Del Coronado

The upgrade was a gratuitous gift from the hotel. That said, I took certain steps to ask for the gift. I’ve now taken those steps to try to secure an upgrade on 9 separate occasions in three different countries. In all 9 cases, I succeeded in receiving a free room upgrade. Some of the upgrades, such as the one my wife and I just received, have been jaw-dropping. Others have been more modest, but still extremely meaningful to me, providing larger rooms, connecting rooms, better views, etc. Each upgrade has added substantial value to my family’s trip without costing a penny.

In all 9 cases, I booked the rooms for free using points prior to asking for, and receiving, an upgrade. Most people might be hesitant to ask for an upgrade on a paid stay and would be downright embarrassed to ask for an upgrade on a free room. But I have no shame in asking. And neither should you. Worst the hotels can say is “no.” But that’s not what they say.

Here’s how to get hotel room upgrades—sometimes incredible ones—for free: (more…)

How would you like to save 46% on a hotel stay as I recently did? The trick is to play Priceline off of Hotwire. Let me explain through the lens of my recent booking.

I needed to stay in Estes Park, CO for one night. Searching on Orbitz.com, the cheapest rate I found was $90 for a 2-star hotel.

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