Serendipity in Travel: Our 2019 Kauai Trip


[ ser-uh n-dip-i-tee ]


an aptitude for making desirable discoveries by accident.

good fortune; luck:the serendipity of getting the first job she applied for.


happenstance, fluke, break, blessing, luck 


One of our Photographers in Focus, Craig Semetko, is big on serendipity, giving talks and workshops on finding and introducing serendipity in your photography and life.  Other than hearing Craig speak, I’d never thought much about serendipity in travel, until our April, 2019 trip to Kauai left me realizing Craig might just be onto something.

For years, I’ve passed along tips for traveling to Kauai, based on our many trips there since our 2001 honeymoon.  In January, I assembled them into a mammoth post. As we gathered information for the post and looked back at our Kauai photos, Keith and I kept saying we wished we were planning a trip there, and talking about how much we love Kauai.  The post went up January 31 and we moved on.

Just six days later, I was searching for plane tickets to attend a wedding in San Diego.  At exactly the moment when I was pricing the tickets late on February 5, I received an email about crazy low airfare prices to and from Hawaii.  I looked at the email and deleted it because the airfares were from places where I don’t live . .  including San Diego.  After a moment, I went back and reread the email, then quickly calculated that it was cheaper to go from San Diego to Kauai and then home to Chicago rather than returning directly to Chicago.  


Aloha Serendipity

Aloha Serendipity

Next I recalled a review of the Hilton Garden Inn Kauai that I had just read a few days earlier on  


A few clicks later and I realized we could travel from San Diego to Kauai on Hawaiian Airlines, spend 3.5 days in Kauai, use Hilton points to stay at the Hilton Garden Inn, and then fly back to Chicago using part of an American voucher we’d earned due to a flight snafu last summer.  After paying for just a rental car and meals, we would be back to Chicago by the following Friday night, in plenty of time for our Saturday career coaching clients.

I told Keith about all this, expecting him to say “that’s great, but . . .” and point out some obvious reason I’d overlooked that this plan wouldn’t work.  Instead, he said “that’s great.  Did you book it?”  So I did.

We arrived at the Hilton Garden Inn and instead of the regular room we’d booked, we were offered a complimentary upgrade to a cottage that was literally a 90 second walk to the beach.  


As we checked in, the employee helping us (also named Amy!) noted that the activities desk could help us with any bookings.  We generally avoid the activity desks (which usually take the place of concierge desks in Kauai) because we book things directly, but we hadn’t booked our luau tickets in time and it was sold out during our stay.  We headed to the desk, and they had exactly two tickets left for the luau we wanted (and the one you should attend if you’re in Kauai: Smith’s). 


Right before we left San Diego I had seen on Facebook that a friend who lives in LA was in Kauai.  We arranged to meet in Kauai during the few hours our stays overlapped, and got to catch up over a great breakfast at the Tip Top. 


While we were at the hotel, we had great free breakfasts, free mai tais, and enjoyed a Hawaiian sunrise ceremony.  We’d have experienced none of that if not for that Travel Codex blog post that made me think of staying at the Hilton Garden Inn, the kind waiter who realized we were missing our drink tickets (and made up for that with a big handful), or the benefits of Keith’s Hilton gold status.  


At that luau, we discovered that a former coworker who lives in Seattle was also attending the luau with her family.  Getting to attend the luau with Kate and her family (particularly because Keith was able to get her on stage to hula with him) made the luau even more fun.  


As we headed to the airport late Thursday night after a packed visit, we commented that we wished the flight would get cancelled.  And, to summarize a long saga, it was delayed overnight.  When we got our voucher for the hotel American Airlines put us up at, the Kauai Beach Resort, we discovered we were being sent to the same hotel we’d stayed at (several ownership changes ago) both for our honeymoon and on two other trips. 


Red Dot Blue Dot Reflective Jeep Selfie

Red Dot Blue Dot Reflective Jeep Selfie

How can you make yourself more open to serendipity in your own travels?  Here are some suggestions:

-      Read those airfare sale emails!  I subscribe to Scott’s Cheap Flights, Fare Deal Alert, and follow several airfare deal groups on Facebook.  If you don’t want to go crazy with junk email, pick one.    

-      Don’t delete information about hotels you may want to visit someday.  I couldn’t remember which blog had recently reviewed the Hilton Garden Inn, but because the email came up when I searched my email for Kauai, I could quickly scan it and remember that it seemed like a good place to stay on the East Side of Kauai (where we hadn’t stayed in several visits.) Normally I save reviews in Evernote notebooks for different destinations.  But if you don’t want to deal with that, just use the search in your email.  

-      Be nice to hotel staff and others.  One, it makes life better for everyone.  Two, the nice people at the Hilton Garden Inn – from check-in to bartenders to the activity desk to the man who did the sunrise ceremony – enhanced our trip in ways beyond their job descriptions.  (By contrast, the TSA and American Airlines staff proved that just because you live in paradise, doesn’t mean you’re pleasant.  So don’t take it for granted.)  

-      Give serendipity time to creep in.  Not overscheduling ourselves for our short visit meant we could switch gears when we realized we could get together with Brian for breakfast, get to the luau, etc. (Keith isn’t going to believe I wrote that.) (No, I don’t. - Keith).

-      Pay attention. In a luau of several hundred people, the odds of our realizing Kate and her family were there were low – we likely never would’ve known if she hadn’t been paying attention or if we had been looking down at our phones when she happened to walk by.  

-      Get out of your comfort zone.  As we’ll share in a future post, even though we’ve had many trips to Kauai totaling several months, we had a few new experiences on this quick trip that enriched our visit.  And one that will enliven cocktail parties for years to come. . . .

-      Look for the serendipity.  We, frankly, didn’t have time for a 24 hour flight delay, particularly one due not to weather but American’s maintenance issues and not having spare parts on Kauai. We had client commitments in Chicago and being “stuck” in Kauai was not ideal.  But we kept saying “of all the places to be stuck . . .”  Others in the same situation were not, shall we say, willing to find the serendipity in it all and spent their time pacing inside while we walked on the beach and enjoyed the pools. 

-      Be ready to handle travel complications.  We did what we always do when faced with a delay: call the airline 1-800 number while standing in line (program the numbers into your phone right now – finding them online doesn’t always work if many people are on the airport wifi), try to get the airline employees to follow the airline’s policy on vouchers, etc., and know that if they won’t, there’s always the credit card travel delay coverage/appealing to the airline to deal with it.  We also make back-up plans; sitting on the tarmac waiting to return to the gate, I checked the and Hotel Tonight apps and knew that even if the airline was difficult about covering hotel, we wouldn’t have to sleep in the airport.  And, when American’s many, many delays ultimately meant we would need to spend a night in Phoenix in addition to the extra night in Kauai, the airline staff in Kauai were adamant there was no other option.  I just smiled, knowing I had already rebooked us on better flights getting us back to Chicago a full 24 hours earlier, thanks to the 1-800 number. 

-      Remember that serendipity can’t find you if you’re sitting on the couch.  It’s often cheaper and safer to stay home.  But when was the last time you sat on the couch thinking “this is serendipity in action?”

Share your own examples of serendipity in your travels below.