I wasn’t particularly looking forward to my 30th birthday. I felt old. (cue derisive laughs from anyone older and the sympathetic nods from anyone younger) We didn’t have a big party planned (my fault: work, projects, blah blah), and I had been extremely vague about any gift desires.
When Mary handed me a gift bag from across our wonderfully romantic table at the Cliff House on the evening of my 30th, I had no idea what could be inside. I tore into the artistically arranged tissue paper and let out a carefully-manufactured gasp of delight as I pulled out a chic denim-and-leather toiletries kit.
Expressing my admiration, I turned it in my hands a few times before setting it to the side and going back to the menu.
“Aren’t you going to open it?” she asked dryly.
Confused, I unzipped the bag. Inside was a bright green envelope. My “I’m thankful I got anything at all” gratitude quickly turned into authentic excitement as I pulled out two thick pieces of cardstock. Mary had a smug smile on as I looked them over, each one printed with bright tropical patterns. They looked like something you’d get from winning a game show.
After a few stunned seconds, I had to ask. “Uhh… this is amazing, but how…? Can we afford this?”
Can we afford this?
We managed to get both of these tickets for $213 all-in, not including the further portion paid for by credit card points. There are a few layered discounts here, I’ll go through each one point-by-point.
We’re based in the Bay Area, and we flew on Southwest. They had just started flying to Hawaii and were running some promotional rates. Further, we were flying in October which is off-season for Hawaii. Even today you can get a single round-trip ticket to Maui (OGG) for about $300 if you can fly weekday in February.
On top of that, we’d gone all-in on the Southwest Companion Pass via their credit card offer. I was skeptical that this was worth the effort, but boy was I wrong. Over the year we saved a few thousand dollars on flights. Shaving a full ticket price off the top made a spur-of-the-moment trip like this a possibility.
Finally, we paid for part of the ticket with points from the initial sign-up bonus that the Southwest credit card had given us.
We also were able to grab a pretty affordable AirBnb in Kihei. Ground floor with no ocean view, but within walking distance of the beach checked all of the boxes we needed. All-in, flight and lodging ran us $954 for the 5 night trip – not nothing, but a real steal for the vacation we ended up getting, and an amazing way to celebrate my 30th.
So what did we do?
Mary and I are not the most organized travelers. Our very best vacation we’ve ever had was our honeymoon, where we sat on a beach outside a resort in St. Lucia with no plans at all for a whole week, and just… relaxed. It was incredible. Soaking up the sun, swimming with tropical fish, deciding what to do as we felt like it and without any of the pressures of planning or research was so… rejuvenating.
So, we tried not to plan too much for Hawaii. We looked over some beaches, flipped through a travel guide, and did a little reading about the food scene but we made no reservations or other advance preparations.
The one thing that really stood out from a casual perusing of TripAdvisor and the travel guide was that the Road to Hana was well-reviewed. We weren’t totally sold, but it was high on the list of “things to do if we felt motivated to do anything”.
The Beaches
This may come as a surprise to some of you, but the beaches on Maui are amazing. Like, really really cool.
We saw so many different kinds of fish, turtles, crabs, and birds. We didn’t see dolphins or whales, but I’ll never get tired of being able to put on a mask and look through the window into the incredible undersea world of reefs. Below is a description of each of the beaches we visited.
Charlie Young Beach
Our most frequented beach and Mary’s favorite was the beach right across the street from our AirBnb Rental. Expansive and calm, this was the perfect beach for relaxation and light swimming.
Wailea Beach
Beautiful but crowded, Wailea Beach is a resort beach that is also open to the public. With soft sands and easy waves this beach is perfect for leisure but comes at the cost of sharing it with others. When the water is calm (which is often) there are outcroppings of rocks that are perfect for snorkeling, even for more inexperienced ocean swimmers. Mary and I both got to see schools of fish and sea turtles napping here!
Secret Cove Beach in Makena
Nicknamed “Wedding Beach” and also not much of a secret at all, this picturesque beach is known for its hard to find entrance and for being a popular wedding location.
While this beach was truly beautiful and a cool spot to photograph and explore, we wouldn’t recommend setting up camp here for long. The beach is not large at all and conducive to getting busy and packed very quickly. It’s also not a particularly great place for swimming… [more here about getting in the water]
Big Beach
Another picturesque beach with a long shoreline and nice sand, this beach is great for getting away from the tourist crowds but not great for inexperienced swimmers. Also known as Break-Neck Beach the waves here are powerful and the shore break can be very rough.
If you did nothing but explore a new beach every day you were on Maui, that would be a vacation (or a life) well spent.
The Food (and drinks)
The food was great. I think I ate four different types of fish taco. Some standouts were the coconut shave ice from Gus’, the poke from South Maui Fish Company, and every single thing on the menu at Kihei Caffee.
I’d say the best meals that we had came from the trucks around Kihei. The sit-down food was good, but the poke, tacos, and ramen were on another level.
Because we’re just basic-ass Americans, we also go for those Trader Vics Polynesian cocktails that everyone loves. We drank a really respectable number of mai tais (invented in San Francisco!) and piña coladas.
The best colada was for sure at the Grand Wailea Maui’s Botero Lounge. Not too sweet, blended smooth, and served in a coconut, just the way it should be.
Mary’s favorite mai tai was at the 5 Palms restaurant. Sweet, juicy, and with a helluva kick! They also had an excellent happy hour, with cheap, delicious sushi.
The road to Hana
After four days cooking in the sun, swimming with fish, and drinking different combinations of ice, juice, and rum, we decided that we should take on the road to Hana. For the unaware, the road to Hana is a windy one-and-a-half lane highway that circles around Maui’s resident volcano, Haleakalā. It goes through the wet side of the island, and is known for having a preponderance of waterfalls, hiking trails, spectacular beaches, vistas, and history.
It’s a full day out-and-back adventure, and definitely the most popular tourist destination on Maui. We decided to get an early start, and to do the sights in reverse, in an attempt to beat the crowds. We ended up hitting the road at 5:30 in the morning. Our goal would be to go straight to the end of the road, hike the Pipiwai trail, and then see all the best waterfalls, beaches, and views on our way back.
We decided to get an audio guide to keep us company and point out the best spots to stop at. We went with Shaka Guide, which was a great choice. Just having someone point out the landmarks. parking spots, and places to use the restroom was useful enough to pay for. We got a lot more than that, though – the narrator was fun, talked us through treating the sites we were visiting with respect, and had loads of interesting stories to keep us company though the windy and challenging drive.
I could write a whole post about the things we saw on that day, but I’ll keep it brief.
Bamboo forest hike
The Pipiwai trail had an incredible hike through a bamboo forest. Because we got there fairly early, we had it mostly to ourselves. The sound the bamboo makes as the wind blows through it is soothing and a little otherworldly.
Waimoku falls
After a good hike through the humid jungle, you get to a spectacular scene – a 400 foot tall waterfall. It felt so good to cool off in the mist at its base and marvel at its height.
Seven Sacred Pools
At the bottom of Pipiwai trail, there is another spectacular view. Just a short hike brings you to the Seven Sacred Pools. This gorgeous overlook into the roiling sea is backed by a set of stepping-stone pools and falls. While you can’t swim in the pools anymore, just the view, the breeze, and the ocean spray is enough to refresh and revitalize you after a good morning’s hike.
Food trucks at Hana
Sweaty, and with an appetite worked up from a long morning hiking, we headed back to Hana to grab some lunch. The food trucks here all looked incredible, and we got our favorite curry of the trip here. Just delicious!
Wainapanapa state park
You could almost spend a whole day just here. This historic site features lava flows, black sand beaches, natural arches, and dramatic blowholes. You can swim, camp, and sun yourself. We couldn’t get enough of this spot, but at this point we were racing the sun so we had to hustle onwards after a quick hike and swim.
Lava tube cave
Definitely our favorite hidden gem of the drive. Off to the side of the road, with no obvious signage or parking, is a little lava tube cave. You have to duck into a small hole, but inside it opens up and for a few minutes you’re surrounded by nothing but darkness and gently dripping water. Then, you spot a light and clamber out and you’re right beside the road you started from, tucked away on a hidden path. Just a little moment of magic that we would have completely missed if it wasn’t for our audio guide.
Three Bears fall and others
The Road to Hana is absolutely littered with waterfalls. You can’t go twenty feet without hitting another fall in places. There’s something about the waterfalls that is simultaneously soothing and awe-inspiring. We saw as many as we could before we lost the light.
If you travel to Maui, you absolutely must do the Road to Hana, no questions asked. It is one of my all-time favorite travel memories. There’s so much to see and do, it’s exhausting but a once-in-a-lifetime experience.
Farewell, aloha!
We saw a few more things on our trip – some more beach time, a really nice evening in Lahina, but nothing could top the epic road trip to Hana.
With that, we hopped back on the plane and bid Maui a fond farewell. We couldn’t stop talking about what it would take to get a vacation rental there (quite a lot, it turns out).
It captured our hearts, and we can’t wait to go back to those sunny beaches, tasy drinks, bright fish, and breathtaking waterfalls. I can’t think of a better way to ring in my 30s.
Now I need to figure out what I’m going to do for Mary’s 30th…
