Hawaii: Living, Working & Exploring for 3 months (Recap)!

In the summer of 2021, we had the experience of a lifetime getting to live, work and play in Hawaii for 3 months! I (Whitney) had the opportunity to take a travel physical therapy contract on the Big Island, and Jared came along for the adventure! We had an amazing time, and I want to share some of our experiences!


Taking a contract in Hawaii was always a dream of ours (who wouldn’t want to take a job there?), albeit a distant one for most of our travel careers because we chose to take a lot of our contracts closer to home on the east coast. But when COVID kept us from traveling for most of 2020, and our prospects for being able to travel abroad were bleak for the foreseeable future, we started thinking more about taking a job in Hawaii as a “working vacation.” We figured it would be tough to find two Travel PT jobs together there due to high competition, so we just planned on me getting licensed there and searching for one job, since Jared is already financially independent and doesn’t need to take travel therapy contracts if he doesn’t want to.

So I started the licensing process in the summer of 2020, and just figured I’d wait until it got processed, then we would consider a job there sometime in the fall or winter. To our dismay, it actually ended up taking 9 months for my license to finally come in due to several delays, so we had already been making other plans to visit Central or South America by spring of 2021. But, once I “suddenly” got a notification that I received the license in May of 2021, we decided to put feelers out to see if there would be any potential contract opportunities.

Because of our connections with a lot of recruiters in the travel therapy industry, I lucked out on finding a perfect contract within days of asking around: a private practice outpatient PT clinic with 1-on-1 care on the Big Island. In addition, I was able to negotiate working only a part time schedule (3 days/wk) so that I would continue to have enough time to work on our online business, and get to explore the island with Jared on my days off! I also negotiated to only work for 8 weeks rather than the standard 13-weeks for typical travel contracts, so that we would have time to visit the other islands for a few weeks after I finished working, and still get back to the mainland by September to go on our cross-country road trip and make it to the Traveler’s Conference! So, after I had my contract in place, we quickly shifted gears and started making plans to move to Hawaii for a few months!

To learn more about the logistics and process for arranging housing, car, flights, etc. for Hawaii, check out this post!

Working & Living on the Big Island

This Travel PT contract was easily my best one yet, because of both my job and everything we got to see and do while we were in Hawaii. My coworkers and patients were all very welcoming and nice, and the work environment was laid back. I would often not have a full schedule, so the already easy caseload of seeing patients 1-on-1 for an hour was often even easier with only 4-6 patients per day sometimes. The clinic itself was located within walking distance to the beach, and you could see the ocean from the window, along with beautiful tropical plants and trees. Talk about a dream contract! Patients would often bring local fruits and veggies from their own trees, because lots of produce grows abundantly there and they can’t get rid of it fast enough! Patients would also bring local prepared dishes, Kona coffee, and baked goods which were awesome to try! On my last week of work, a few patients brought me hand made fresh flower leis, which was such a nice going away present!

My job was in Kailua-Kona, Hawaii, which is located on Hawaii Island (aka “The Big Island”). This was a great spot to live and work for a couple months. It’s not a big city like Honolulu, but there’s enough around with easy access to grocery stores, restaurants, and endless outdoor activities. During our 2 months there, we thoroughly explored the entire island. You can drive from one side to the other in 2 hours, so we went all over the island on my days off.

Below is a list of some of the many activities we enjoyed on the Big Island:

  • Scenic drives along the 3 different routes from Kona to Hilo
  • Night snorkeling with the manta rays at Keauhou Bay
  • Visiting Hawi town & hiking down to Pololu Valley
  • Trying local foods including Hawaiian BBQ, Lau Lau, Kalua Pig, and Poke
  • Visiting the farmer’s markets in Kona and Hilo
  • Coastal hikes such as: Onomea Bay near Hilo & Kaloko-Honokahau in Kona
  • Enjoying sunsets after work at the local beaches in Kona
  • Visiting & hiking at Volcanoes National Park (sadly there wasn’t active lava flow when we were there)
  • Watching sand volleyball while eating street tacos or ice cream at Coconut Grove Marketplace
  • Visiting Honokaa town, hiking down to Waipi’o Valley, & eating at Tex Drive-In (malasadas!)
  • Hiking to Captain Cook Monument for beautiful snorkeling
  • Eating & drinking at Kona Brewing & Ola Brewing
  • Visiting gorgeous Kona beaches including “A-Bay” (Anaeho’omalu Beach), Kukio, Kua Bay, Makalawena, Hapuna & more
  • Enjoying local restaurants such as: Jackie Rey’s, On the Rocks, Foster’s Kitchen, Umeke’s, Broke Da Mouth Grindz, Shaka Tacoz & many more!
  • Hiking at Pu’u Wa’awa’a Forest Reserve
  • Enjoying traditional Hawaiian music & dance at KeauHou Shopping Center & Coconut Grove
  • Drinking Mai Tais at sunset at Lava Lava Beach Club
  • Walking the trail at the Old Airport Beach
  • Catching the sunset & stargazing from the Mauna Kea Visitor’s Center
  • Going to Akaka Falls & Rainbow Falls in Hilo
  • Visiting the Punalu’u Black Sand Beach & eating at Punalu’u Bake Shop
  • Taking a coffee tour & trying local coffee at Heavenly Hawaiian Kona Coffee Farm
  • Going to South Point (the southernmost point in the United States) & Papakolea Green Sand Beach
  • Hiking the two large volcanoes on the island: Mauna Kea & Mauna Loa (these are both extremely challenging & not for inexperienced hikers!)

As you can see, there was no shortage of things to do, see, eat, drink & experience on the Big Island! This was such a special time in our lives that we’ll never forget!

While we were on the Big Island, we even had the opportunity to meet up with some fellow healthcare travelers, and even one of our recruiters who was visiting family there! At the end of my 8-week contract, my mom joined us to vacation in Hawaii for two weeks, starting with a few days on the Big Island! We were excited to show her around and take her to some off the beaten path places she probably wouldn’t have normally gone on her own when she imagined a “Hawaii Vacation.”

When it was time to leave, we were sad to say goodbye to the Big Island, but excited to explore the other islands! We had about 3.5 weeks (2 of those with my mom) to explore the other 3 major islands (Oahu, Maui, and Kauai). We were able to use our Southwest Airlines points and Companion Pass to fly between islands which was an awesome perk. But even if you don’t have SW points, flying between the islands is pretty cheap and very fast. Some people even take weekend trips to the other islands and back!

First time in Oahu

My mom has been dreaming of going to Hawaii for decades, and of course at the top of her list was Waikiki Beach in Honolulu! We were able to use some of our Hilton points to give her the ocean-front view she’d been dreaming of at the Hilton Hawaiian Village Waikiki Resort. This isn’t typically how Jared and I would travel, but it was everything she wanted and more so we were happy we could make it happen! We enjoyed our few days of relaxation at the beautiful oceanfront resort with many pools, a lagoon, restaurants, and a nice gym. This was a great central location to be able to explore Waikiki a bit.

While in Waikiki, we did some touristy activities with my mom which we all enjoyed, including going to a Luau and visiting the Pearl Harbor Memorial! One day, Jared and I ventured off to do some hiking at Diamond Head and another nearby hike while my mom relaxed at the resort. We also rented a car for one day and drove around the island to the north shore and back.

Because we had to fly out of Honolulu once my and Jared’s Hawaii adventures ended, we were planning to circle back to Oahu for a few extra days at the end of our trip. So we saved some activities in Oahu for that part of the trip!

Here’s a list of some of the activities we did on this part of the trip in Oahu:

  • Chief’s Luau – of course this is touristy but we still loved the experience!
  • Trolley tour + trip to Pearl Harbor Memorial
  • Hiked to the top of Diamond Head
  • Enjoyed food & drinks at Waikiki Brewing
  • Scenic drive around the island from Waikiki, going east along Route 72 to Sandy Beach, up to Waimanalo Beach, up through Kaneohe, Kahaluu, past Kualoa Ranch, to the North Shore, and back to Waikiki
  • Stopped for shrimp trucks in North Shore (to be honest, this was completely over-rated and over-priced in our opinions with long lines and wait times for decent but certainly not life changing food)
  • Watched the sunset at Kawela Bay (North Shore)
  • Walked along the strip (oceanfront, shops, restaurants) at Waikiki Beach

Visiting Maui

Our next stop with my mom was Maui! Here we stayed the first few days at an Airbnb condo with a pool that was near the ocean in Kihei. My mom’s favorite thing to do on vacation is relax by the pool or ocean and read a book, so we enjoyed some more relaxation with her on this part of the trip in Maui. We did drive around the island a bit with her, including visiting the town of Lahaina, and some beautiful beaches near Lahaina and Kihei.

When it was time for my mom to head back home after her two weeks in Hawaii, we stayed a few extra days in Maui to do some hiking and exploring on our own. We moved over to a private room in a hostel (which was more like a 2-star motel since we had our own private little room and bathroom) in Wailuku. This was a more affordable option since we’d already splurged a bit on accommodations in Waikiki and Kihei, and we knew we’d be busy going out to explore so we didn’t need anything fancy for those few days.

While on our own in Maui, we drove the Road to Hana with its many gorgeous stops, including one of our favorite places: the stunning Waiʻānapanapa State Park. The Road to Hana was getting extremely busy with tourists during the time we were there (more on this later) so we unfortunately didn’t make too many stops because we didn’t want to crowd the side of the road. But we still very much enjoyed it!

We also got to meet up with some more healthcare travelers for dinner while we were in Maui! We love meeting people from our travel community in person all over the world!

Here are some of the activities we enjoyed while in Maui:

  • Visited Lahaina town (walked around, tried Dole Whip, saw the incredible Banyan tree, and ate dinner at a diner)
  • Hiked the Lahaina Pali (windmill) trail
  • Visited beautiful beaches in Lahaina and Kihei
  • Enjoyed dinner & beers at Maui Brewing Company
  • Drove to the top of Haleakala volcano for sunset (we chose not to do the sunrise which requires reservations, and also getting up in the middle of the night which isn’t our thing, ha)
  • Hiked the “13 Crossings” trail
  • Drove the Road to Hana starting fairly early in the morning (we chose to drive all the way around the south side instead of turning around halfway- both are pretty sketchy choices but the south is a pretty rough road so be cautious)
  • Visitied Waiʻānapanapa State Park: hiked along the gorgeous coast and enjoyed the black sand beach
  • Hiked the Pipiwai Trail to enjoy the beautiful bamboo trees and waterfall
  • Took in the stunning mountain views at Iao Valley State Monument

Exploring Kauai

After Maui, we headed to the “Garden Island” of Kauai! While we had already seen some amazing sights on the other islands, we were itching to see the stunning views of the Na’Pali Coast and the jaw-dropping ridge trails on Kauai for ourselves. And let me tell you, it did not disappoint! Kauai ended up being our favorite of all the islands! It’s smaller and more laid back than the other islands, and there’s lots of nature to enjoy.

We did a lot of hiking in Kauai, visited the state park including a beautiful waterfall, and took a boat tour along the Na’Pali coast! We loved the cute Airbnb cottage where we stayed, and we enjoyed being close to everything in the town of Lihue.

Here are some of the activities we enjoyed in Kauai:

  • Boat tour of the amazing Na’Pali Coast which included dinner & drinks!
  • Driving to Waimea Canyon, “The Grand Canyon of Hawaii” & stopping at different overlooks
  • Daring ridge-line hikes with the most epic views, including Nu’alolo & Honopu (we also heard great things about Awa’awapuhi & Kalepa trails but didn’t get a chance to do those)
  • Beautiful coastal views from the Maha’ulepa Heritage Trail (Shipwreck Beach)
  • Visited Ha’ena State Park (reservations required) & hiked the first part of the Kalalau Trail to Hanakapi’ai Falls
  • Enjoyed dinner and drinks at Rob’s Good Times Grill and Kauai Beer Company

Second Time in Oahu

We were sad to leave Kauai after only a few days there (we felt like we could’ve spent months there exploring!) — but we were excited to see more of the nature that Oahu had to offer on our return trip there before we headed back to the mainland. Initially, we thought of Oahu as only the Honolulu area, which is very urban. But, during this part of the trip, we stayed with a friend who lived in Kaneohe, and we got to experience a much different side of Oahu.

We discovered some incredible mountain views and hikes in central Oahu that really blew us away! While we had to work hard to get some of the hiking views (especially Stairway to Heaven!) we also loved the amazing views you can find right from your car at the Ho’omaluhia Botanical Garden.

We loved getting to spend time with my friend from undergrad who now lives there, as well as meet up with yet another fellow healthcare traveler on Oahu! This was an awesome way to end our three month tour around the Hawaiian Islands!

Here are some of the highlights from our second visit in Oahu:

  • Hiking the “back way” (the legal way) to the top of the Haiku Stairs (Stairway to Heaven) via the Moanalua/Kamananui Valley Trail: This was one of the toughest and scariest, but also most rewarding, hikes I’ve ever done. I was shocked I convinced my friend who’s afraid of heights to go with us. But it was such a memorable hike with jaw-dropping views.
  • Driving around the Ho’omaluhia Botanical Garden & having a stunning photoshoot
  • Hiking to the Lanikai Pillboxes to take in the views, and going to gorgeous Lanikai Beach afterwards
  • Hiking the Kuliouou Ridge Trail with stunning ocean views all around
  • Climbing to the top of Kokohead via the 1000+ steps. Sadly it was POURING rain which added an additional challenge and made the views not so great, but it was still a cool experience!
  • Kinda silly, but on our last day we went to the Oahu location of Kona Brewing because I was feeling nostalgic about our times there on the Big Island and wanted to get a tshirt since I never got one when we were in Kona (also they have great food & beer, plus the Oahu location is really pretty, so why not!)


We loved the three months we spent in Hawaii, and we made memories that will last a lifetime! This was the most unique Travel PT contract experience we’ve ever had, and also a great vacation!

I should point out that tourism in Hawaii increased a lot in 2020-2021, as we weren’t the only ones who had the bright idea to travel to this domestic paradise when the rest of the world had its borders closed. There has been quite a bit of over-crowding happening in Hawaii, and we know that certain sites had to implement new policies to limit the number of visitors (such as Waiʻānapanapa State Park in Maui), and some have had to completely stop allowing visitors (such as Waipi’o Valley on the Big Island). So when you’re planning your trip, be sure to look into current regulations and what is currently open to visitors. And of course, always be respectful to the local people and the land.

We don’t have any immediate plans to return to Hawaii because we have many other places we hope to visit in the near future. But I do plan to keep my Hawaii PT license active for a while in case we want to return there for work. We would love to spend some more time on Kauai and Oahu particularly because of the incredible hiking on those islands. We would also love to visit the lesser known island of Molokai.

Have you been to Hawaii before? What were some of your favorite parts? Would you like to visit Hawaii in the future? Let us know in the comments! Please feel free to send us a message if you have questions about working as a healthcare traveler in Hawaii or visiting for vacation!

2 thoughts on “Hawaii: Living, Working & Exploring for 3 months (Recap)!

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