Overcoming Holiday Travel for a Rewarding Trip

A long-distance relationship.

Courtney lives in Washington, DC. Alex lives in New York. They’re GF and BF, both Shop Your Way members, and travel frequently to spend time together. Including holidays.

Sometimes travel + holidays isn’t as ‘merry’ as it sounds, and it’s challenging to be ‘thankful.’

Here’s Alex’s travel log demonstrating just that.


Oct. 23: Booked our flights through Travelocity (got $10 CASHBACK in points) to see Courtney’s parents/attend her old roommate’s wedding. She has a stop-over in Chicago, I have one in Denver. We should arrive in Seattle within an hour of each other. Should. Rent a car and quickly up to Vancouver.

Oct. 24: Called airlines and re-booked Courtney’s flight – my original had her flying out of BWI on November 21, 2019. She caught the date.

Oct. 27: Looked to book hotel for wedding – used Shop Your Way Hotels so I could be rewarded with CASHBACK in points. Getting $115 back after we return – literally a free night. Sweet. Wonder what I’ll redeem those on…

Oct. 28: …clearly, I’ll be redeeming those on bigger luggage – C just let me know we have a formal rehearsal dinner, then the wedding, then a post-reception brunch. All requiring formal dress. #dufflebagnotenough

Nov. 1: Rented car through Avis and Shop Your Way and saved 30%! Asked Courtney if we had to drive on the wrong side of the road in Canada. She wasn’t amused.

Nov. 12: Just realized that even though it’s Thanksgiving next week here, Canada had their Thanksgiving two months ago (okay, C corrected me when I asked if her mom was preparing a turkey). We’ll have dinner out, probably Chinese or Thai. #nostuffingthisyear

Nov. 14: One week out til trip. Weather app says clear skies expected on the 21st.

Nov. 21:Travel day. Weather apps wrong. Storms in the Great Plains have some flights delayed; we’ll see what C’s flight does.


Nov. 21: Ubered to airport, forgot passport. Ubered back home, got passport. Took third Uber of day back to airport, thankful my flight delayed, made just in time. At least I got $2 CASHBACK in points per ride. Texted C – she didn’t forget her passport, and her flight’s on time. #memoryfail

Nov. 22: Happy Thanksgiving…from the air. Re-routed around Denver after leaving an hour late from NY. Now we’re circling Seattle….be thankful, be thankful, be thankful….

Patient Courtney met me at gate…bags took a while but 3 am rental car still there. 3 hours to her folks’ place outside Vancouver. Nice sunrise as we snuck in quietly.

5 hours sleep on the couch, awoke to smells of coffee and pumpkin bread (nice of her mom). Watched streaming NFL games (nice of her dad) on their fuboTV before heading out to dinner. #canadiannice

Nov. 23: Rehearsal and dinner tonight in San Juan Island, WA. Ubered (another $2 CASHBACK in points) to port area in Victoria in crazy fog. Ferries closed! Now we can either head back stateside via a different ferry southbound to risk even more fog-closed ferries north or drive the 5+ hours around the peninsula to get there. We drive. Thankful (hey, it’s the season!) that Budget had a car available. Super-slow going and we missed rehearsal but made the dinner. Half the wedding party ended up watching the Canucks game afterwards.

Nov. 24: Wedding day – all fog gone and just beautiful. Ubered to and from the reception ($4 more CASHBACK in points). Good thing, reception stocked with Canadian brews…

Nov. 25: Beautiful weather, all ferries operating, so after the brunch, a slow but enjoyable trip all the way back to Victoria area. Another Uber (and another $2 CASHBACK in points) back to her folks’ house. The four of us had dinner (my treat, used my Sears Mastercard with Shop Your Way and got 3% back in points. And I ordered turkey. With stuffing.

Nov. 26: Flights out of Seattle not until evening, so we had time to get down to airport. Stopped just inside Washington state and gassed up using my Pay with GasBuddy card – got 15 cents per gallon CASHBACK in points through Shop Your Way. Nice.

Decided to switch my flight so we could go together back to D.C. Yes, we ended up in last row of plane, but holding hands while we slept worth it. Got to C’s apartment in the wee hours, but slept in.

Nov. 27: Took Acela back to NY. Back at work tomorrow after a week-long, sometimes-challenging, (nearly) turkey-free Thanksgiving holiday. Think I earned around $150 CASHBACK in points for the whole shebang. Now, to use on a holiday gift for C…or a little something-something for me. Or both.

Nov. 28: 24 hours later to think about the trip as a whole, while there were all sorts of hurdles, being rewarded all along the way made those hiccups bearable.

Now, where to in December?

Whether your travel is over the river and through the woods, or planes/trains/automobiles, let Shop Your Way help you make your holiday trip a rewarding one.

Above view shot of accessories fashion lifestyle to travel and Merry Christmas & Happy new year concept.Passport & clothes with many essential winter season background.Several objects on brown plank.

Share your most challenging travel story, and how it was ultimately a rewarding one!

LifeYourWay Editor