Episode 73: Working on a Hawaiian farm for free food and housing

Because we just have to keep the plot moving forward

Oct 27, 2025

A few months ago, Brooke and I were backpacking through Oregon when it started pouring rain, and a few hours after getting soaking wet, she told me something along the lines of, “Dennis, after all this is over, I want to lie on a beach in a bikini and not do anything.” I very much echoed that sentiment (except I’d be wearing a swimsuit, not a bikini), so while we were still on trail we began thinking about a post-PCT trip. Somewhere with a beach. A vacation from a vacation, if you will.

A Quick Look at Google Flights revealed that out of the exotic beach travel destinations, Hawaii had the cheapest flights by far (only ~$350 round trip, compared to $800+ to the Caribbean, Central/South America, and I’m not trying to go to SD), so a Hawaii vacation it was. However, there was a little predicament about this: Even with cheap flights, Hawaii’s quite expensive, and the Dennis Gavrilenko Treasury was starting to run a bit low on funds after the 5-month PCT expedition. It reminded me of one of my sister’s wisdoms, paraphrased for you here: “When you’re young, you have time and energy, but no money. Middle-aged, you have energy and money, but no time. Old, and you got time and money, but no energy.” The key there is to figure out how to get the thing you don’t have at the moment.

A Google Search along the lines of “cheap places to stay in Hawaii” revealed a website called Worldpackers, which connected cash-strapped travelers with labor-strapped hosts, allowing travelers to adventure around and do odd jobs in exchange for food + lodging (this is the same thing as WOOFing, just a different website). Brooke and I were intrigued by this idea, so we made profiles on the website, paid the $60 membership fee, and applied to every single available work stay in Hawaii less than 2 weeks long.

We ended up choosing one in Maui, with these two guys, Ron and Shawn. They have a lovely property on the North Shore, and were looking for folks to help them landscape, garden, paint, etc. I happened to grow up landscaping, gardening, painting, etc., and found the idea of doing that in Hawaii tremendously exciting. So off to Maui we went!

The rest of this blog will be about the work stay, and the fun things we did all over the island. For starters, I must say that I didn’t do a day-by-day blogging like I normally do, mostly because I was completely burnt out from doing so for the 5 months on the PCT. Looking back now, that was an incredible decision in terms of properly relaxing. So, I’ll stick to the highlights here, and I figured that the most fun way to write this (and later reread myself, hi future Dennis!) would be in the form of an FAQ. Papa, if you’re reading this, you may recognize these questions; in fact, 90% of them are the ones you asked me when I got home, and since I liked them I decided to steal them here. Lol! (occasional embellishments are my own doing)

Q1: What even is a work stay? Why did you decide to do one?

A work stay is when a traveler does work for someone in exchange for something, usually free lodging and food. The scope and type of work varies tremendously; I first heard about work staying from my friend Jackson, who took a gap year after high school to travel around Europe and work stays all over. Some of his highlights included shepherding in Ireland, building a church organ in Germany, and working at a hostel in Budapest. Clearly, varied work. There are a ton of different websites to do this on (Worldpackers and WOOFing being the main two, to my knowledge), Worldpackers is the one we went with because… that was the one that showed up first on Google.

I decided to do a work stay because it’d be a great way to save tons of money on a Hawaiian vacation (Hawaiian food and lodging is eeeeeexpensive), plus it’d give a nice structure to the day: work in the morning, chillax and travel in the afternoon. Especially after an intense period of go-go-go hiking the past 5 months, having 10 days with absolutely nothing to do might’ve driven us both a little crazy.

Q2: How much did you work? What did you do for work?

We did a work stay with Ron and Shawn, and worked ~3-4 hours each morning, somewhere from 8:30 to noon each day. Some days we ended earlier, some later. Brooke and I stayed at their house for 9 days, and worked on 7 of them. We had two full days off; during the first day, we hitchhiked across the entire island to relax on some West Maui beaches; the second, we hitchhiked up to the top of Haleakala (the giant volcano on Maui) and hiked in the summit crater (technically an erosional valley, but whatevs). Both days were fantastic!

As for the work itself, it was mostly clearing land on their property. Ron and Shawn’s place gets a ton of rain, which means lushness and greenery like you’ve never seen… and tons of overgrown vines and plants. Over the course of 7 days, we cleared ~100 square meters of land (from complete overgrowth to a clear field!), where they’re planning to plant some citrus trees and breadfruit! It was my first time using both a sickle (the tool on the Soviet Union flag) and a gas-powered chainsaw, which was both extremely fun and time-saving. Chainsaws are great! Plus, over the course of the work stay, Ron explained the general principles about how a chainsaw works (2-stroke engine, baby!) and I learned how to get it started. Did I mention it was fun?

Clearing the land involved chopping down crazy amounts of vegetation, dragging it over to the driveway, and loading it into their pickup truck to drop off at the Central Maui Green Waste Dump. Some of those vines were crazy annoying, but we did some great work together and managed to clear the entire area. Plus! I took some timelapses of our work, which you can check out here, here, here, here, and here.

On the last day, Shawn gave me a propane-powered flamethrower to burn some weeds in their driveway. That was 100% the highlight.

Clearing the upper field, with some before and after photos!

Q3: Who were your hosts? Was your stay nice?

The stay was an absolute 11/10 experience. Ron and Shawn hosted us, both super friendly and fun. They’d met in Texas, lived all over the US, and now have a lovely house and property in Maui. Their place has one main house (where they live) and a guest house with three bedrooms; Brooke and I got one all to ourselves, with a PRIVATE BATH AND SHOWER. Everything was so comfy and cozy and altogether magical. I felt like I was hacking the system by staying there.

Q4: What… did you do all day? Did you just work? Where did you even go after work?

A typical day went like this: Wake up around 7:15, jump into their swimming pool just outside our room. Dry off, say hi to the wild geckos (they live all over), then have breakfast with Brooke, Ron, and Shawn. They make their own jam! We’d have delicious toast, eggs, coffee, and fruit (papaya yum yum yum), chatting for about half an hour. Then, Brooke and I’d get dressed in work clothes (our PCT sun hoodies and shoes + cheap Costco pants), start working around 8:30/9, and end around noon-ish.

After we were done, we’d shower, jump into the pool again, have a delicious sandwich lunch with Ron and Shawn, and then have the rest of the day off! About half of the days we stayed at the house, reading, hanging out, and walking around the neighborhood. Ron and Shawn would sometimes go into town to do chores/assorted adult things, and would drop Brooke and I off to explore! We spent a few days checking out Paia (the fun beach town 30 minutes from their house) and the nearby beaches, and then would hitchhike back home. One day after work, we hitchhiked 2 hours to the Black Sand Beach near Hana, which was super fun and surprisingly easy to get to (one hitch there with a German couple, one hitch back with a North Dakota couple; note to self: don’t move to North Dakota). We also went to a ukulele festival.

On our two full days off, Brooke and I went to 1) the beach, and 2) the top of the Haleakala volcano for some hiking. The beach experience was great; Ron and Shawn were driving to Lahaina, dropped us off at the beach, and we spent the day hanging out there before hitchhiking 1.5 hours back to their house in 4 separate cars (rock climbers do multi-pitch traversals, but we had a multi-HITCH traversal!). The snorkeling on the beach was amazing (I saw my first ever needlefish and lots of turtles!), and the hitchhiking experience was so fun; on that trip across Maui, we got picked up by 1) a local high school canoeing coach, who told us about her husband’s canoe race last week from the island of Molokai to Oahu, a distance of 44 miles. His crew didn’t win because “the Tahitians came and they’re really good at this sort of thing”, 2) a pickup-truck-driving painter, who let us sit in the back of the pickup truck with all the crusty paint cans (it’s legal to sit in the back of pickup trucks in Maui!), 3) an upcountry local, and 4) Stan, a super chill Hawaiian dude who ALSO let us sit in the back of his pickup truck! An amazing hitchhiking experience! Across the entire island is 1.5 hours, when a bus would’ve taken 2.5 hours to go half the distance!

On the second full day off, we hitchhiked up to the top of Haleakala, the 10000-foot-tall volcano that is huge af. It took 4 hitches to get up there; 3 to get to upcountry, then 2 miles of walking through a neighborhood (lol), before getting picked up by Xiaohui and Christie, who drove us all the way to the top! Thanks! We checked out the summit hut, then went on an AWESOME 13-mile hike down the Sliding Sands Trail to the Halemauu Trailhead. The highlight of this hike by far WAS THE NENE GEESE WE SAW OMG I LOVE THEM!!! We got to the trailhead in the pitch black darkness, and hitched down with an Israeli couple WHO SPENT $40,000 USD ON AN ANNIVERSARY VACATION. What a budget. The last hitch home was in the back of a pickup truck, which had the best stargazing experience… ever.

Q5: Can you tell me more about the nene geese you saw in Haleakala National Park? I wish I saw a nene goose, they look so fun and cute and awesome!

Nene geese are the state bird of Hawaii, endemic to Hawaii (they only live there), and are, in fact, the rarest goose on Earth (~3500 in existence). This trip was my first time seeing them, they were so cute and fuzzy and cuddlesome I love them. We saw a few on the park road driving up to the summit, and two more in the Haleakala Crater on our hike. There are three wilderness cabins in the crater, and upon reaching one and turning on the water faucet, the two geese ran over to me and began drinking out of my cupped hands. Brooke reported that after this happened, “you were the happiest I’ve ever seen you”, and I subsequently and promptly edited the Wikipedia article on the nene goose to include a Gallery Section. Perhaps you’ll even recognize the human tourist:

I love nene, they’re the best birds ever.

Q6: Was your trip cheaper because of the work stay? What did you spend money on?

OMG THIS TRIP WAS UNIMAGINABLY CHEAP! Between the two of us, Brooke and I spent about $1200 combined, INCLUDING FLIGHTS!!! ~$350 for round trip flights (each, I bought mine with Chase Points so they felt free), ~$500 for groceries (ingredients for dinner and snacks for the stay; we went to Costco and Safeway; we don’t have a Costco membership, but my dad got us Costco gift cards and those let you in), ~$150 for a one-day car rental on the last day. That last one made me cry a little, but you gotta splurge sometimes. All the other days, we just hitchhiked around (we’re pros at this after the PCT!) or got rides from Ron and Shawn. Not bad for a 10-day trip to Hawaii!

(Side note, but I learned that a big reason everything’s so expensive in Hawaii is that everything has to be shipped from the US West Coast. An old American law protecting US shipping requires shipping between US ports to be done by a more-expensive US ship with a more-expensive US crew, so unless a cargo ship comes to Hawaii from Asia directly (rare except for car shipments, because Hawaii doesn’t have a huge population and its ports are quite shallow for giant cargo ships), they have to import everything from the mainland and that’s… expensive)

All in all, the work stay trip was a fantastic trip, and I’ll definitely be doing another work stay sometime in the future. Thank you, Ron and Shawn, for being the best hosts ever!