Why and How I Went on a Solo Trip to Hawaii for my 40th Birthday (In a Pandemic)

I celebrated my 40th birthday with a solo trip earlier this month to the Big Island of Hawaii. It was fantastic and the best thing I could have done. Here’s how that decision-making process took place, how I planned for the trip, and some ideas that might inspire you to travel now or in the future.

A Party Wasn’t Feasible
I start thinking about what to do for my birthday around the turn of the year, and in late December, it was clear the pandemic would still be raging by early February. Some years, like this one, I also have to plan around the Super Bowl – yay sports! If I had a party this year, it would have been an outdoor brunch at a private venue early enough in the day to allow people to watch the game in the evening. And I would have had to plan it and pay for it myself, and stress over: a.) who would be willing to attend a gathering in a pandemic b.) any judgement I would have to face for having said gathering c.) limiting the party to 10 people and d.) God forbid, someone getting sick as a result. It was enough to short-circuit my brain. The more I thought about it, the better a solo trip seemed.

It Was Safer There
I thought, “What’s the farthest I can go and stay in the United States? Where can I do outdoor activities and not be  freezing cold? Where haven’t I been that’s on my list?” All signs pointed to Hawaii, which I had visited fifteen years ago, but not the Big Island, so I started investigating what it would take to go there. I learned that Hawaii had stringent restrictions and closures for many months, but recently implemented its Safe Travels program, which allows visitors from the mainland U.S. to bypass a mandatory quarantine. For me, this meant taking a test at Walgreens after 4:30 p.m. on Wednesday knowing my flight from LAX to KOA was departing at 1:30 p.m. on Saturday. The restrictions aren’t an overreaction so much as ensuring that the island-chain state has the capacity to manage an outbreak with its limited resources. Kauai, as of this writing, still has a 10-day quarantine, because it simply doesn’t have the medical infrastructure to deal with large-scale hospitalizations. I read that 25 percent of mainland Big Island visitors were subject to an additional rapid test at the airport, and it was actually all of us who were tested on arrival. At times on the flights and in the airports on the way to Hawaii, I wore two masks and a face shield – taking no chances. I saw the COVID case numbers during my trip, and there were three new cases on the island one particular day. Three. Total.

My own sister called me a safety dork.

The Price Was Right
I knew I might not have an opportunity soon to travel to Hawaii so affordably. One of the first things you purchase for a trip is a flight, which can be an indicator of how expensive or affordable the trip will be. I searched and found I could use points on Delta accrued from opening a Skymiles credit card for my 2019 Russia trip, or I could just shell out about $500 for the flight to Hawaii. Seeing that, it seemed crazy NOT to go on this trip, just for the free/cheap flight. Then I started looking at accommodations. Eight nights, two of which were at a four-star resort and the rest were at very nice private AirBnBs, cost around $1,200. I also booked my favorite tour of the trip, sunset and stargazing on Maunakea (not a referral link just really liked this tour/company) using Chase (referral link) points I got from opening a card to use for end-of-year spending, and also got my rental car using Chase points.

A Rabbit-Hole of Research
I planned this trip over the course of a month. One bonus of pandemic times is that I have been really laying low on weeknights and weekends. This has enabled me to listen to a ton of podcasts and audiobooks as well as given me time to do research on many topics. I spent one solid weekend doing nothing but searching for things to do, places to go and food to eat on the Big Island. A big shoutout to the blog, Love Big Island, which had a lot of useful information. I made the mother of all travel documents (side note: the sample travel doc in the linked article was from TrekSimple co-author Caren’s trip to the Big Island in 2019, and helped me get a jump on my own planning, too) and pinned all of my “must dos” on a Google map so I could determine where to stay and how long, based on what I wanted to do and the days and hours of operation. Most of these were outdoor activities that are open every day, so it wasn’t too hard logistically to plan. The most stressful part was picking and booking my two AirBnBs and deciding on a resort. There were some early closures due to the pandemic, and some of the restaurants I wanted to try were takeout-only, so when I got there, I ate a handful of meals in the car, usually parked in front of some gorgeous ocean vista. While planning, I searched my library app for Hawaii and listened to two books that gave me a lot of perspective: James A. Michener’s Hawaii and Hawaii’s Story by Hawaii’s Queen, by Queen Liliuokalani, the last queen of the Hawaiian Kingdom. Michener’s book is historical fiction but meticulously researched, so after listening to the 50+ hour audiobook I went down another rabbit hole googling the real people the characters were based on. I learned about how Hawaii was first inhabited by Polynesian islanders, then waves of immigrants from the mainland U.S. and Asia, and how it was subsequently annexed and made a state by the U.S. Little details like seeing a giant trunk that accompanied Queen Liliuokalani on her trip to London for Queen Victoria’s Jubilee – described in her book – helped bring Hawaii’s history to life for me.

One of many takeout only meals from great restaurants eaten in the car.

I Love Solo Travel
There are so many reasons to travel solo, it warrants a standalone article. One major plus is the only person you have to consult with when making plans is yourself. Do this enough and you get more comfortable with breaking perceived norms. I wasn’t held back from taking a solo trip to places like Hawaii or Paris, universally known as romantic honeymoon destinations, just because I don’t have a date to go with. I’m happy for people who have “their person,” but since that’s not currently me, and life is short, I’m going to do things alone or with friends. On this trip in particular, but typically everywhere I’ve traveled solo, I find the interactions I have with people I meet are meaningful. My docent at the Hulihe’e Palace, a native Hawaiian who happened to be very funny in addition to a knowledgeable guide, had the exact same birthday as me. We joked about turning 40. At the luau I attended, I sat with two women who had both lived in Orlando, one of whom went to my university (Go Knights!) and shared their own Big Island travel stories with me. I got a restaurant recommendation from my Waipi’o Valley tour guide, and ended up running into his cousin at that restaurant a little later that day. The cousin had hitched a ride out of the Valley at the end of the tour and took one of my favorite photos of me from the trip (seen below – he made me do the shaka sign). Because of a Facebook connection, I visited the home of a fellow Florida Circle K International alumnus and his wife, who lived near the resort I stayed at. My AirBnB host near remote Hawaii Volcanoes National Park had lived in Fort Lauderdale at one point. If you’re willing to talk to strangers, even just a little bit, you’ll never feel alone traveling solo. If you’re willing to share your photos and experiences while on your trip, you’ll probably hear from friends back home, too.

I Had the Time
Even being an evangelist for using one’s PTO, I carried over a week of vacation from 2020 to 2021 and I suspect most people have extra time to take this year. I normally do not take much or any time off, or go anywhere too far for my birthday, because typically the weather here in Florida is glorious in early February. In normal times, it’s great to stay put and do something in town, but it is not normal times. 

If you read this entire rambling article, you deserve a malasada (hot, filled donut), a cup of smooth Kona coffee or a delicious poke bowl, maybe all three. I’m very thankful for the strange set of circumstances and timing that enabled this trip and made it so special, and I’m really glad I didn’t sit around at home being irritated that I couldn’t throw an epic party.  I hope everyone who reads this will be inspired to make the best of any circumstance, and if you can, give yourself the gift of travel now, or soon.


7 thoughts on “Why and How I Went on a Solo Trip to Hawaii for my 40th Birthday (In a Pandemic)

  1. I can totally relate. Traveled quite a bit with Madelyn and now with Miranda. It’s great to have travel days where you do only the things you want, when you want. I’ve never traveled solo but I would have no reservations in doing so. Luckily, I have (had) the best travel companions ever. Looking forward to your next journey 🙂


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s