This post was written by Nancy, who is a regular contributor. She also runs a blog Savingforadream and has an awesome YouTube channel!

Next summer, my family of five is going on our biggest vacation yet—a Disney Cruise to Alaska! I wrote about how we are saving for this trip and my thought process for booking a hotel on points, but I still had to conquer the biggest obstacle, finding award flights for all five of us.

Our cruise departs from Vancouver, British Columbia. If we were to buy five tickets to Vancouver in cash, it would cost us $2350 – $3000 depending on the airline and the number of connections. Oy! Not in the budget. We could fly to Seattle for around $1500 and take a bus or train to Vancouver, but that’s still money and time we’d rather not spend on this vacation.

Before we got close to the dates where we could book these tickets, my husband and I had a discussion about what we were willing to do in the name of “free” flights. We decided that we were willing to give up more points for business/first class tickets if that was all that was available and we had the miles. No overnight flights.

We really wanted to bypass Seattle and fly straight to Vancouver so we didn’t have to deal with the extra time, money and hassle of transportation between Seattle and Vancouver. I’ve been to Seattle once, and it’s a very lovely city that I’d like to visit again with my kids….but I’d rather explore Vancouver and save Seattle for a future trip.

The miles and points I had at my disposal included:

* ~25k Amex Membership Reward points

* ~130k American Airlines miles

* ~50k British Airways Avios

* ~40k SPG points

Before I reveal how we got our flights, keep in mind the following:

• Whoever said that earning miles is the easy part but using your miles is the hard part, is right! I’m used to booking flights on Southwest where award availability is not an issue.
• Trying to get five award tickets requires some compromise and flexibility, and once you see the choices I made you may think I’m crazy.

The airport after midnight—not as fun as it looks!

Getting to Vancouver

The time had finally come to start searching for our award tickets. I eagerly woke up each morning to check flights on various airlines, only to be disappointed that there was nothing available to Vancouver. Then one day, I found five seats on a United flight that stopped in San Francisco for a 15-hour overnight layover before going on to Vancouver the next morning.

The flight would give us only a day and a half in Vancouver before we would have to board our cruise, but it cost a mere 12.5k miles per ticket, and we could all fly together. I didn’t have United miles, but I could transfer my Amex and SPG points to a United partner.

I emailed Leana to ask her if it would be a wise idea to transfer my Amex or SPG points to Singapore Airlines (a partner of United) to book these tickets. Had I not been reading miles and points blogs, I never would have known it was even possible to do this.

Leana had a better idea—I could transfer SPG points to Air Canada Aeroplan instead because Air Canada is giving bonus miles for hotel transfers through August 15. I could transfer 40k SPG points and get 60k Aeroplan miles, and then top off the award by transferring 3,000 Amex points for a total of 63k miles, more than enough  for five one-way tickets. I could book United award flights through Aeroplan online, whereas with Singapore I could only book flights over the phone and the miles would expire in three years.

But there was a catch…SPG transfers are not instant, and the award seats could be gone by the time our transfers were complete. According to this post by The Points Guy, transfers from SPG to Aeroplan take about five days. If the award seats disappeared during that time, I would be stuck with Aeroplan miles since I couldn’t transfer them back to SPG. Was I willing to take that risk? I decided to sleep on it.

The next day, I wasn’t feeling good about taking the risk. Plus, I wasn’t ready to part with my SPG points. I had grown quite fond of their multiple uses, and I only wanted to let go of them if it was absolutely necessary.

A Better Option—Delta to the Rescue!

The next day, I woke up to my morning routine of checking award availability (and it reminded me of the movie Groundhog Day). I got lucky and found three award tickets on AA (15k miles each) to Vancouver five days before our cruise. What luck! Now I just needed to find two more tickets.

On a whim, I decided to check Delta. I don’t have a good impression of Delta because my husband and I had Delta Amex cards a few years ago and we were never able to use our miles. We ended up cashing out our points for Amex gift cards.

Surprisingly, I found two tickets on Delta (Alaska Air flights) for our preferred date! I noticed that Delta displayed some Alaska Air choices that AAdvantage  did not. I transferred 25k Amex points to Delta and booked those two seats for my husband and oldest son.

So the start of our vacation would involve me flying with my two younger kids to Vancouver two days before my husband and oldest son got there. A year ago, I would never have considered making the journey alone with my children without the help of my husband. I think my recent solo trip to Minneapolis has boosted my confidence of my ability to travel alone with kids…plus it helps that they are getting older and easier to handle.

While splitting up the family isn’t ideal, I liked this scenario better than flying into Seattle. I had the hotel points for the extra two nights, and the additional time in Vancouver would give my younger kids more time to adjust to the earlier time zone. Since AA allows free changes to award tickets if the origin and destination remain the same, there’s a chance I may be able to move our departure date to match the rest of the family if award seats become available.

Yay, we’re halfway there!

Getting Return Flights to Dallas

Award availability from Vancouver to Dallas was looking good in the weeks before our time frame, but as soon as we got into mid-June there were no decent award tickets to be found. Due to his work schedule, my husband really needed to fly home the day we disembarked from the cruise. I could always buy him a one-way cash ticket if necessary. Here were our options:

• Two coach tickets on AA three days after the cruise for connecting red-eye flights (yuck!) for 15k miles each
• Two first-class tickets on AA on disembarkment day for 30k each (and cash or red-eye Seattle award flights for the other three)
• Five red-eye connecting flights leaving from Seattle for 12.5k each
• Five AAnytime coach tickets direct to Dallas for 25k each
• Wait to see if better options became available at a later date

Taking the bus to Seattle and hopping on a red-eye flight did not sound like a fun option. We are always exhausted at the end of a cruise. Did I really want to put my family through such a long process to get home? I’m afraid the long and cumbersome commute to Texas could sour the end of an otherwise awesome vacation.

But the AAnytime tickets on a direct flight seemed like a great option! Sure, they cost 10k more than the MilesAAver flights, but it  was the exact direct flight we wanted and we could all be on the same flight. Other days had AAnytime tickets for 40k and 65k, so the 25k tickets seemed like a bargain comparatively. I didn’t have enough AA miles for all five tickets, but if I converted my 40k SPG points to 50k AA miles, I would have enough.

I put the flights on hold for five days to see if any better options surfaced, but we ended up booking the AAnytime flights. The SPG points took two days to transfer to AAdvantage. Speaking of, right now through September 14th, you can get a 20% bonus on transfers from SPG to AAdvantage. So, 20k SPG points will equal 30k AA miles. Thanks to DoC for breaking the news

An added bonus I didn’t realize until I booked the seats was that the flights included Main Cabin Extra seats (with 4-6 inches of extra legroom) for no additional charge. My husband will love this!

Bottom Line

We have five round-trip award flights to Vancouver for our cruise! We are splitting up and flying on different days to get to Vancouver, but we splurged on direct flights home with AAnytime awards.

We paid $5.60 per person in taxes to get to Vancouver and $42.36 per person in taxes to get back to Dallas. I feel relieved that we have our tickets secured and that we didn’t have to pay a few thousand dollars on top of our cruise expense in order to get to our destination. Yay for miles and points!

Would you consider splitting up your family for award flights, or splurging on AAnytime awards? Why or why not?

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