Family Travel Hacking Guide Archives

Feb 15 2017

Daddy, daughter, delays!

I had an amazing time at #DisneySMMC but I’ll post about that another day. Instead, I’m writing about my trip home while it’s still fresh in my mind. On Saturday, while I enjoyed some much needed rest and relaxation on Disney’s private island Castaway Cay, a cloud still loomed in my mind.

My four year old daughter and I scheduled a flight home for 12 noon the next day. I figured that was enough time to get to the airport (it was) but had a growing concern about the potential blizzard moving into Boston, our destination. As the title would indicate, we ended up delayed. Here’s how we made our decisions and dealt with the interruption.

Debarking the Disney Wonder

Just a quick note, a 12 noon flight would have been no problem getting off the Disney Wonder. It’s a small ship and even though it was mostly full, we were off by 8 AM and on a bus by 8:10.

On board airline check in rules: you put your checked baggage out with tags by 10:30 PM the night before and then pick them up in your home airport. We had nothing to declare so pretty much walked straight through customs. We were at the airport before 9:00 AM and I joked that it was the earliest I’ve ever been at the airport for a flight (it is, as far as I can remember).

Going to be three hours early for a flight for the first time in my life thanks to @DisneyCruise transportation
— Joe Cheung (@asthejoeflies) February 12, 2017

One final point, the checkout checklist said that for flights before 12 noon you need to be off the boat by 8 AM or else they’ll pull your bags. Didn’t stick around long enough to find out but it’s something worth noting.

Delay 1: IRROPS

Being three hours early for a flight was a very foreign experience for me. Luckily we ran into Leslie from Trips with Tykes – her daughter V and M had bonded quite a bit on the trip. Everything seemed all good as the two kids celebrated their favorite part of the cruise:

View this post on Instagram

A post shared by Joe Cheung (@asthejoeflies)

Then at around 10 AM I got a text from Delta saying our flight had been delayed by one hour. Uh oh. It looked to be because of delays at Logan, but now the total time I had to kill at the airport had ballooned to four hours! Let me give Delta credit here: sometimes with American I don’t hear about the delay until, you know, after departure time. It helped to get the text before we went through security.

We ate an early lunch and ended up going through security around 11:45 AM. Boarding was a piece of cake and M was happily watching Peppa Pig as the cabin doors closed. All good, until…

Delay 2: Mechanical

So we taxied onto the runway. I heard the engines spin up and then…nothing. After a bit of a delay, the pilot came on the intercom to say there was an equipment issue and he was waiting for advisement from the powers that be. Ten minutes later he announced what we all knew: we were headed back to the gate.

How my four year old and I dealt with a bunch of travel delays thanks to Delta and Disney — Get me out of here!

We soon found out the number 2 engine starter had an issue. The pilot said that if MCO had the part, the delay would be about an hour. If the part had to be flown in, all bets were off. Well, by the time we got back into the terminal: all bets were off.

Again, Delta did the best they could – there were sodas and water within minutes of us deplaning. Sandwiches arrived about 10-15 minutes later. But at this point it was 2 PM, we were only scheduled to get an update at 6:00 PM, and I had been at the airport for five hours. Decision time.

Making alternate plans

At times like these, I generally like to utilize all avenues available to me: humans, phone, internet. So I started waiting in line at the gate counter while on hold with Delta. Thankfully, I can surf the internet while on a call so I checked my Delta app too. They were offering a free flight change but worried about my two checked bags I stayed in line.

Eventually I realized that there was a Delta assist station. This was a bank of phones that put you in contact with an agent immediately: agents who had as much power as the gate agents. This was pretty clutch. At this point I figured I had two decisions:

Wait until 6 PM and hope the flight got out that night despite the blizzard
Find a hotel and fly out the next day

I still had one day left on my SMMC Disney ticket, but I wanted to do whatever was easiest for my daughter. Ultimately I decided that spending another four hours at the airport for the chance to go home that night was probably too much to ask of her.

So I rented a car ($35) and a room at the Doubletree at Disney Springs ($110). The helpful “gate agent” on the phone rebooked us for the 740 PM flight the next day, the only flight free.

In the end, my flight did end up taking off around 8 PM, but as my dad told me, I made the decision based on the knowledge I had at the time. While I was out ~$150, I know I made the right decision. It was just too big of a risk to stay. I was still worried about my bags but Delta assured me that they would be automatically moved to the flight.

Disney Springs, Take 2

Our first night in Orlando, we didn’t have the greatest time at Disney Springs. But due to Doubletree proximity (15 min walk), M and I decided to give it another shot. We weren’t disappointed. This time, we happened upon the World of Disney, aka the largest retail Disney store in the world. That place was a LOT of fun for a Disney fan. I managed to get out of there only buying two items, but it was pretty difficult!

We also enjoyed our return visit because we had some “magical”, unplanned moments. First, on our way down from the pedestrian bridge, we got a great view of a set of floor lights shaped like a Mickey. M was so excited to run down there and just walk around in circles, tracing Mickey with her path and I just marveled at how much fun a 4 year old can have doing the simplest things.

We also ran into a “fairy” who sprinkled pixie dust on M’s head. Honestly, if I had known it was going to be glitter I probably would have passed! But M was so excited to have the pixie dust PLUS the fairy was from “the kingdom of Burlington, MA” so we had a nice chat about Boston’s Frozen Ever After situation. Moral of the story? Extended daddy daughter time is rarely a bad thing.

One final flight change

Before we left for Hollywood Studios on our final morning (M loves the Disney Jr. Live! show), I decided to see if we could get on an earlier flight. The logistics of getting home at 930 PM are pretty difficult!

For this, I tried out Delta’s Twitter account, @Delta. This Twitter account houses the true wizards. They confirmed me (not standby) on an earlier flight and made sure my bags got rerouted for the second time. It turned out to be a lifesaver because the 740 PM got pushed to 930 PM (still due to Boston weather).

I can’t say enough about Delta’s entire customer service team through this whole experience – while I wish their plane didn’t break down they did such a great job accommodating us. We got one extra day of magic with the least amount of stress thanks to them.

Final Thoughts

Flight delays are tough. Day long flight delays are tougher. Making decisions with a 4 year old might be the most stressful part of all. Still, thanks to my Fairy Godmother (my wife, helping me make the right decisions from afar), the seven dwarves (Delta’s Customer Service team), and Minnie Mouse (my surprisingly non melted down daughter), we had one extra magical day in Orlando!

Update: Delta is even giving us $150 for our trouble, yay!

Aug 19 2016

Surveying Scotland: What to do on the Isle of Skye (Part 2)

We spent four nights in Skye, but I would have happily spent more. It really is the type of place where one can just enjoy taking their time and exploring. I covered the first half of our time there in my last post; here are a few other things we found worthwhile.

Random walks and hikes

There are a lot of well known hikes on the Isle of Skye. One of the most famous ones cuts from the Fairy Pools through the Black Hills and ends at the Sligachan Hotel. That looks like an amazing hike and the only reason why I regretted (for a split second) bringing my kids on the trip. It takes 4-6 hours and there is cold beer waiting for you at the end if you stop by the hotel restaurant. I plan to return someday.

Skye holds many other shorter hikes and walks, including one that we were able to take from our house. We took about an hour walk behind the house and along a hillside with picturesque views of Fiskavaig Bay. We were looking for a lighthouse but were not able to find it. There must be hundreds of similar walks all over the island – the Scots love their walks so if you love walking in nature you’ll love Skye. Here are some pictures from our little walk.

Sights on the Trotternish Peninsula

Skye’s largest peninsula is called Trotternish. It hosts the main town, Portree, and a host of other sites. There is a single lane road running around the entire peninsula with plenty to do and see along the way.

One of many views on the Trotternich Peninsula — One of many views on the Trotternish Peninsula

We started our day at the Isle of Skye Baking Company and then proceeded to drive clockwise around the peninsula. We stopped at the Museum of Life, which provides a picture of what life was like on the island back in the day. That actually proved more interesting than I expected, though it’s not must see by any means.

At some point we had to yield for sheep:

The Quiraing

To me, one of the true highlights of the Trotternish Peninsula is the Quiraing. Up on the top of the hills is an area that just looks breathtakingly carved out. There are weird cliffs, plateaus, you name it. It’s a rough drive on a steep one lane road on the way up, or you can hike it. Either way the views are fairly dramatic.

There are hours of hiking trails to be found on the Trotternish Peninsula: if you’re up for hiking, make sure the footpaths of the Quiraing are on your list.

The Old Man of Storr

One of the most famous sights on the Trotternish Peninsula is the Old Man of Storr. The best views are found by, you guessed it, hiking. Jess and I visited with H on a day when my parents took M, so we managed to hike quite a bit with H in a carrier. It was tough work but the views were worth it.

The Oyster Shed

There supposedly are great places to eat in Skye, but we didn’t get a chance to try many (plus we cooked a lot). We did make it to the Oyster Shed which deserves special mention. Freshly shucked oyster and some great lobster bakes. It gets crowded and closes at 5, but worth scheduling around!

Final Thoughts

Hopefully the last three posts have convinced you the Isle of Skye is worth visiting. When we were done, we still had over a week left in Scotland, and found there was still a ton the country had to offer. Stay tuned!

Family Travel Hacking Guide 13: The four different types of credit card rewards

To do: Examine the credit cards in your wallet and try to determine which type of rewards they earn.

One thing I’ve noticed writing this guide is that beginner’s guides are difficult to write! How best to cover the plethora of information? I guess the options are write briefly or try to cover everything and have people use it like an encyclopedia of sorts. I’ve chosen the latter :P.

But I digress…

Before we get to applying for credit cards, we need to understand the four types of credit card rewards out there that are relevant to travel hackers. Each reward type deserves a place in your overall strategy when utilized correctly.

Cash Back

The saying “cash is king” applies in the miles and points world as it does in the rest of the world. It’s easy to get enamored with where miles and points can take you, but if you ignore cash you ignore it at your own peril.

Cash back credit card rewards are simple. Sign up for a card and they will give you $X in cash if you spend a certain amount of money in a certain amount of time. Generally, the best cash back cards offer you 2% cash back on all of your purchases (e.g., Fidelity Visa). While that’s not sexy, that’s the only thing that will help you if you ever need money in the real world.

Some other cards have special bonus categories where you can get up to 5 or even 6% cash back in certain categories. Those are cards worth looking out for, though most of them have a cap on cash back these days (like the AMEX Blue Cash).

Cash Back Equivalents

Jennifer Garner loves talking about all the “miles” she earns with her Capital One card, but it’s important to understand those aren’t actually “miles” in the traditional sense of the word. They are a term that Capital One uses to describe the rewards that you earn that can be applied towards travel. These rewards are essentially cash back – if you use them for travel.

Capital One calls them “miles” because you use them for statement credits to offset your travel expenses. The card earns 2X miles per dollar spent, so you are essentially earning 2% cash back rewards if used on travel.

If you want to redeem these points for cash back, however, they are only worth half as much. That’s why I differentiate between cash back credit card rewards and cash back equivalents – if at some point I need the cold hard cash form of my reward, sometimes cash back equivalents might not be worth as much, so it’s important to do your research.

Frequent Flyer Program miles

Way back when, airlines came up with an incentive program to keep people traveling with them. Fly a certain airline, earn miles, use those miles to redeem for free flights.

While much has changed, the frequent flyer programs still remain intact. Almost every airline has a co-branded credit card that can help you to earn miles. These miles can be used only on that particular airline and its partners (which are important to learn, subject of Part 3 of the guide).

The important thing to understand about frequent flyer miles for airlines is that they have no cash value. They are earned by the airline and the airline can choose to cancel it’s loyalty program at any time (Alitalia just did this recently).

Frequent flyer miles can be leveraged into great redemptions that will stretch your miles far beyond their cash values. They also can be used to gain more value than you would if you paid in cash. You just have to know how to use them well (Part 3!).

Transferable miles and points

The most powerful credit card rewards are generally transferable miles and points. Ultimate Rewards, Membership Rewards, and other transferable currencies can be used in multiple ways.

1) They often can be used as cash equivalents to pay for travel, often at rates higher than 1 cent per point (like 1.25, for example). This squeezes a bit more extra value out of the points.

2) They can be redeemed for cash or gift cards, though sometimes at reduced rates like cash equivalent cards

3) They can be transferred to frequent flyer programs.

That last point is what generally makes transferable credit card rewards the most powerful tool in a travel hacker’s arsenal. As you earn your points, you can transfer them to various frequent flyer programs as needed. That means you can build an entire award ticket with them or just top off an account if you’re a few miles short. Or you can use the points as cash equivalents if necessary.

Flexibility is key, and transferable points offer the most.

Final Thoughts

If you want to maximize credit card rewards, it’s important to understand the different types available to you. You need to combine that knowledge with your travel goals to come up with the best possible strategy for your credit card applications. As always, be sure to avoid ALL credit card debt, otherwise your rewards will be meaningless.

To do: Examine the credit cards in your wallet and try to determine which type of rewards they earn.

Jul 27 2016

Family Travel Hacking Guide 11: The power of miles and points

We’ve completed the first part of the Family Travel Hacking Guide series: how to save money on booking flights with cash. For many, the savings might stop there, and that’s fine. As parents we have limited time; just make sure you know your travel goals before you go about trying to save money.

The Family Travel Hacking Guide will now pivot. We are going to get into the more significant savings that can be achieved through earning as many miles and points as possible. In Part 2, our posts will look at how credit card sign up bonuses can power your family’s travel at a significant cost reduction. How can we earn miles efficiently and cheaply? (Part 3 will address how to use them properly). I’ll never claim that you will fly for free, but if you execute proper strategies you should be able to travel at a major discount.

This first post is here to illustrate what you can do.

Let’s say you are a family of four (two adults) living in a major city on the East Coast and you are hoping to fly to the West Coast next spring break. If you use some of the techniques from Part 1, you probably can easily find tickets for $250-$300 per person. If each ticket for your family costs $250, you are looking at an out of pocket cost of $1000.

You’d like to stay out there for four nights, so you’ll be needing four nights of hotels. Since you need a bigger room for your family, maybe you need to spend $175 per night – so $700 total. That means just getting out there for vacation will cost you $1700.

You could save a lot of that money by signing up for four credit cards (two per person). If each adult in the family signs up for the Hyatt credit card and the Citi AA Platinum Select credit card, you will have enough miles and free nights to cover the entire trip.

How?

Well, the Citi AA card gives you 50,000 bonus miles after $3000 of spending on the card within three months. If both parents get one card, the family will have over 100,000 miles to play with (50,000 X 2 plus miles earned from meeting the spend requirement). Since domestic AA saver tickets cost 25,000 miles round trip, that’s enough miles for your flights.

The Hyatt credit card gives 2 free nights after spending $1000 in three months. 2 X 2 = 4 free nights between the two adults. As you can see, credit card bonuses can easily subsidize a vacation. As long as a family puts $1000/month on their credit card regularly, they can earn all those sign up bonuses in 8 months. The average family spends more.

At this point most beginners have a litany of questions, which I’ll address in the next few posts. But it should be stated here and forevermore: if you are not paying off your credit cards in full, the interest you pay will cost way more than any potential savings!

In the next few posts we’ll address how applying for credit cards affects your credit score, the best strategies for applying for credit cards, some of the best cards out at the moment, and how to avoid bad advice.

Family Travel Hacking Guide Index

Introduction

Set a Travel Goal

Using and Tracking Frequent Flyer Programs

Who to Follow on Social Media

Part 1: Saving Money on Cash Flights

Saving Money on Cash Flights

How to find cheap airfare with airfarewatchdog

Finding cheap airfare with The Flight Deal

Finding the cheapest airfare using Kayak alerts

Using Hopper to monitor flight prices

Using Google Flights to search airfare

Jul 25 2016

Family Travel Hacking Guide 10: Using Google Flights to search airfare

As we reach the end of our “find cheap flights phase”, it’s finally time to look at one of the most flexible flight aggregators out there. Before we get into that, a note: a lot of “travel hacking” is about avoiding spending cash on flights and hotels. We’ve spent the last few weeks on saving money on cash flights because these ideas apply to the majority of travelers, not just travel hackers.

But rest assured, there are ways to avoid spending a lot of cash on flights – that section of the Family Travel Hacking Guide will commence after this post! Digression over.

I decided to write about Google Flights since I think it will be the best option for the average end user. Here are some ideas how to get the most out of your searches.

1 – Keep your dates flexible to find the best prices

If you’re not 100% locked in to your travel dates, you can often save a little bit of money. Let’s go back to those flights I was looking at between Boston and Syracuse. I started my search from Sept 9-11 (2 nights). Results appear instantly AND Google Flights helpfully tells me how much money I can save by adjusting the dates by a day or two:

If I click either my departure or return date, a calendar of dates with the cheapest prices for 2 night trips pops up:

I can also click on “Flexible dates” to see a matrix of departure and return dates around my original search:

Finally, I can click on “Price graph” to see how prices have been fluctuating:

While other websites can do all this for you, the nice thing is how snappy Google Flights is – there is virtually no wait time.

One key to saving money on flights is being flexible whenever possible, especially when looking for multiple seats for a family!

2 – Explore the cheapest destinations to visit that fit your schedule

If you want to take a trip but aren’t sure where you want to go, use the Google Flights map feature. Basically, you can give Google your dates and you’ll get a map of fares. As you move the map around it populates with different fares: pretty neat.

You can refine the map by continent, interest (like beaches vs. cities), times, airline alliances, and almost anything you can think of. So for example, you could search for two tickets from August 9-13 to beach destinations in South America on Oneworld with any number of stops.

The map is a simple visual aid to look at prices, and as you zoom in some of the smaller cities will appear. It’s fun to play with and dream about where you can go, but it also can provide some great deals to places you never would have thought of visiting.

Although a feature like this isn’t for every family, I find that it’s a good tool to use just to research destinations.

3 – Refine your results to find the best deal or most convenient option

A lot of family travel is about finding the best balance between price and convenience. Most families of four or more will pay a little extra to avoid two connections (this of course applies to many people).

Google Flights can help you quickly sort through the various options to find that balance. When you specify number of stops, airline alliance, departure times, etc., you can really drill down to find the flights you want. Best of all the results load quickly, saving valuable time. Most search engines offer the same functionality but I find Google Flights the most efficient.

Be aware, however, that Google Flights may sometimes miss the cheapest flights. Some low cost carriers like Southwest won’t share their data with Google (or anyone). In addition, Google preloads results, meaning it doesn’t perform a new search every single time you refine a parameter. That can sometimes leave to paying a little more but you can always use Google Flights to perform your initial searches and then switch over to something else when it’s time to book if you’re worried (I generally don’t bother).

4 – Automatically monitor flights you are interested in

Like Kayak and Hopper, Google Flights will track flights you are interested in and send you updates. Just in case you don’t want to use multiple services.

Final Thoughts

This is just the tip of the iceberg of what you can do with Google Flights. If you poke around there are a lot more features to play with. But the goal of travel hacking is to avoid spending money on flights! Looking forward to finally starting down that road in the next post in the series.