2 Discoveries for How to Get Unpublished Hyatt Upgrades

Plus a Bigger Picture Lesson for How to Get Unpublished Upgrades at Other Hotel Chains as Well

I’ve recently discovered two tricks that have added value to my family’s Hyatt stays. One involves booking a standard room with points and then paying a cash supplement to upgrade the room to a better room or suite. The other involves using points to upgrade an award stay to allow club lounge access.

The view from my family’s upgraded suite at the Hyatt House Naples/5th Avenue

I’m not aware of either upgrade being an official part of Hyatt’s loyalty program offerings. But each trick has worked for me twice in a row now, so I think them worth sharing as my experiences may be more than a fluke.

In this post I share why I find these tricks valuable and how to pull them off. I also share how to find other such upgrades, whether at Hyatt or at other hotel chains. (more…)

Are Lie-flat Business Class Seats Worth It?

Thoughts After My First International Business Class Flights (Which Would Have Cost $17,461 Had I Paid Cash!)

If you read miles and points blogs, many make it seem as if the pinnacle of travel—if not of life itself—is flying in lie-flat business class or first-class seats. Your travel destination and what you might do there appear, by contrast, unworthy of the consideration of one who, in flight, is able to sample suboptimal caviar.

Sarah reading with her lie-flat business class seat reclined

My wife, Sarah, in our Frankfurt to Denver lie-flat business class seats

Having not flown in lie-flat seats myself, it’s been tough to judge whether such miles and points bloggers believe what they’re preaching or whether they just enjoy the commissions they receive from pushing the greater number of credit cards one must open to accrue enough miles and points to fly business class on an award redemption.

Too sassy?

Well, I finally had the chance to try it out. Here are my down-to-earth thoughts on luxury at 30,000 feet. (See what I did there?) (more…)

How to Save Big with Extreme Hotel Deals

I Booked a $25,680, 3-Bedroom Suite in the Bahamas for $2,210 (a 91% Savings)

Over the past couple of months, I’ve booked two extreme hotel deals. The first was an executive suite at the nearby Grand Hyatt in Denver—a family favorite—for a 1-night “staycation.” That room usually goes for about $380, including tax. I paid $114 after tax, a savings of $266 (70%).

The Grand Hyatt Baha Mar, Bahamas -- one of the extreme hotel deals I've recently booked

The Grand Hyatt Baha Mar, Bahamas

Saving 70% on a hotel is incredible. But my second booking made the first look like child’s play:

I booked 6 nights in a 2,500 sq. ft., 3-bedroom Ocean View Residence at The Grand Hyatt Baha Mar in the Bahamas. The 6-night, all-in price for this monster should have been a jaw-dropping $25,680. But I paid $2,210, a discount of $23,470 (91%).

The way I scored these deals is new to me. In this post I’ll show you how to do likewise. And I’ll show how you can sometimes do so using points instead of cash (if you prefer). (more…)

Beating the House on a Vegas Vacation

How to Vacation in Las Vegas Very Inexpensively

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.”

Vegas Strip showing several hotels including Paris and Planet Hollywood

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…)

Easiest Way Ever to Get the Southwest Companion Pass; But Is It a Good Deal?

As widely reported by travel bloggers, Southwest is offering an unprecedented signup bonus on the personal versions of the Southwest credit card. Specifically, from now through February 11, you can earn 30,000 Southwest miles and the Companion Pass by opening just one credit card.

The Southwest Companion Pass is arguably the best deal in travel. It allows a companion to fly for free with you on any Southwest flights you book. This version of the pass is good from the time you earn it until the end of 2019.

Knowing that I love the Companion Pass, a reader reached out to ask my thoughts.

Although it has never been possible in the past to earn the Companion Pass with such ease, is it a good deal? That depends. For some, it’s a terrific deal. For others, it’s not. Here’s how to decide if it’s a good deal for you:

(more…)

Party of Five? Don’t Double Your Hotel Costs by Booking Two Rooms.

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…)

My Top 10 Posts of 2017

Get Outsized Value from These 10 Most Popular Posts

As 2017 draws to a close, I wanted to recap for you the 10 most popular posts on my blog this year. You should be able to get outsized value from these posts, especially the #1 most popular.

Here are the top 10 posts, starting with the most popular: (more…)

How to Get the Best Seat on a Southwest Flight [Complete Guide, 2019]

Whenever you fly, you want to get the best seat on the plane for your money. With Southwest, getting the seat you want is more complicated. That’s because there are no assigned seats on Southwest flights. Rather, as passengers board the plane, they may choose any unoccupied seat.

I'm holding my son Michael on a Southwest flight

My son Michael and I on a Southwest flight last summer

Over time, I’ve given an inordinate amount of thought to how to get the seat you want on a Southwest flight. Here’s a complete guide to scoring your desired seat, whether that be an exit row, an aisle, or a window. (If you prefer the middle seat in the back row near the lavatories, you can stop reading now.) (more…)

How to Get a Spectacular Hotel Room Upgrade for Free

This Approach Has Worked for Me 9 out of 9 Times

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.

View from the balcony of our hotel room upgrade

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 to Get 23 Months of Free Flights with the Southwest Companion Pass

Act by 10/4 (ideally *on* 10/3) to Maximize the Best Deal in Travel, Worth More than $1,800

The Southwest Companion Pass is arguably the best deal in travel. It allows a companion to fly for free with you on any Southwest flights you book. The pass is good from the time you earn it until the end of the following calendar year. The opportunity has arisen to enable a companion to fly for free with you for 23 months: most of 2018 and all of 2019. But you have to act by October 4, 2017 (and, ideally, on 10/3) to take advantage of this opportunity.

The Southwest Companion Pass works on all Southwest flights.

Following is more about the Companion Pass and exactly what you need to do by October 4th in order to score 23 months of free flights for your companion (and a lot of free flights for you as well): (more…)