Hawaii I cannot quit you. We have been on a tear for the last 3 years, we got a taste of Kauai, paused for a year, and quickly resumed visiting different Hawaiian islands 2017-2021 until we have completed the task of vacationing on them all. Do you want me to rank them? Of course you do, but it's an impossible ask. They are all unique and bring to the table different things- you can't compare. To try though, if you want a smaller island with a laid back feel, views, lots of hiking opportunities, but not all about the beaches/resorts - Kauai is your best bet. If you want beach time, resorts, tons of restaurants, nightlife, but also offers hiking and surfing- go to Oahu. The Big Island is similar to what you get from Kauai, but also offers Volcano National Park for hiking opportunities and exploring, and does have some resorts if you are looking for that option. And then there's Maui, the favorite child, which gives you all of the above. On this trip, we hit up Oahu (first time) and then revisited Maui because we couldn't get enough the first time and wanted to try staying on a different part of the island.
Friday: Landed around 3pm in Oahu from our very long trek west across the sky. We stayed in an Airbnb condo in Waikiki in the Pacific Monarch condo building. The location could not have been better. We were 2 blocks off of Waikiki beach, therefore in the heart of it all- tons of shops, restaurants and bars within walking distance. The building and condo itself- had it's pros and cons of course. 30+ floors with only 2 elevators made the trek up and down the building very slow at times. On the plus side, it did offer free garage parking which was huge. The condo we rented itself was pretty small and basic, very tiny kitchen and bathroom, no lanai, but we did not spend much time in it so it served our needs. The building also offered a rooftop pool and hot tub, which we ended up using almost every night. Great views of the city and ocean from up there (see pics below). So once we settled in, unpacked our groceries we picked up nearby, we walked the Waikiki beach path along the water as the sunset. The night does not deter people here from hanging out- everyone was on the beach to watch the sunset, and parks continued to fill up as the night stayed warm and pleasant. We had dinner at Hula Grill in Waikiki- a pretty popular classic spot, and for a reason. Not too too expensive (but everything here is basically expensive), good portions, good food, good drinks, better view during the day since it's right on the beach. We were exhausted by this point so we turned in right after dinner.
Saturday: Had to start off the trip with one of the most classic things you can do in Oahu, hike Diamondhead. From our place, it was only 3 miles away, but we decided to drive even though we probably could have biked, or even walked there. The parking lot was full at 7am when we pulled up, but we found nearby street parking only about 15mins away by foot. By the time we had walked in though, parking had become available (it's all about timing). Once in we had to wait a little bit in line for hiking tickets- which you buy from a kiosk with a cc, and then we were off. Took us under an hour up to the top and back down- slightly steep but pretty easy, tons of kids and older folks were doing it as well, its just necessary if you are going to stay in Waikiki.
After Diamondhead we drove a few minutes to our second hike trailhead Kuliolulu trail- which started on the back end of a cul-de-sac in a local neighborhood. Took us a minute to find parking in such a residential area. This trail was really tough- very steep at the end and a constant incline the entire trail, slippery, lots of tree routes, not a ton of views until the end, shaded most of the way, many stairs at the end. And of course, once we finally made it to the top- the peak- the lookout- it was too cloudy to see a damn thing. Luckily, a few clouds did separate on the hike back down and we were able to get some good views on that end, but for all that effort, I gotta say disappointment at the lookout was real. This hike took us about 3 hours/4mi.
I needed a break after our morning of hikes, so we grabbed lunch at the Barefoot Beach cafe on Waikiki. The garlic shrimp was so so good. I ate my body weight in garlic shrimp on this trip but this place was a standout. Then we headed back to our place for some pool and hot tub time. Happy hour in Waikiki was tough, most places were packed and you needed a reservation- so we found Il Lupino an italian spot in the outdoor mall, had a quick drink, then had dinner at Doraku upstairs. After we went to Kith treats for ice creams (also in the Mall), which were kind of like Diary Queen blizzards here, and were delicious.
Sunday: My legs needed a rest from all of Saturday's hiking - but not that much of a rest because we started the day with a 5 mile run up along Waikiki beach, through some neighborhoods on the water, and along the coast uphill to an area where it seemed like all the surfers go on the south side of the island. Slightly uphill for the last portion but not too hard of a run. After the morning work out we downloaded the Shaka guide app (we've now used Shaka 3 times on different Hawaiian islands- the self guided tour idea really is the best if you have your own car). We did the Grand island circle tour, which took us to the Eastern and Northern parts of the island. We started out around 9am and got back to our place around 5pm- so you do get your money's worth with this app. We got to see so much of Oahu! Some highlights were: Kohala Mountains Beach Park with a view of Chinaman's Hat, Turtle Bay Beach (the name says it all) the North Shore where are the hippies and surfers hang, the Sea Arch, and the Dole Plantation (my husband was into this - I am not a pineapple lover). We stopped for lunch on the North Shore at the Beach House. Down the road, there were actually many more options (we jumped at the first) but this was a good choice regardless. Another option for food during the tour was all the food trucks before you hit the North Shore, but we weren't really hungry at that point. However, I've heard good things about the shrimp from them!
Back in Waikiki- we hit up the rooftop pool, and sauna for a little something different. Then checked out Leahi a block away for happy hour drinks (nothing special but did have a very nice bartender, and sometimes that's all you want). Then dinner at The Deck in the Queens Hotel. I would definitely recommend trying to come here during the day for lunch or drinks- looked like a really cute hotel, very nice bar and outdoor lounge area, with a view of Diamondhead. Being Sunday, most places were either closed or closing early, so we went back to Kith treats for round 2 blizzard desserts.
Monday: Started out the day with an epic fail. We tried doing a short hike to Koko arch in Koko Crater National Park. About 20mins from Waikiki, we parked in a parking lot across the 2 lane highway. Buses were stopping here to show tours the Blowhole rock formation below. We crossed the street and had to walk on the highway a little to start the hike. From there it was rock scrambling up a steep slope with the highway pretty much right below. It only took us 15 mins to get close to the arch ahead, but the weather turned, the wind really picked up and it started to rain a little. We just couldn't make it and it was so frustrating. Looking at it up ahead and not being able to reach it was so aggravating, but at this point it was pretty unsafe and extremely steep- one slip and you could really injure yourself. So we turned around defeated and got back to the car, and drove to Lanakai beach (40min drive from there). Koko Crater Park is pretty cool, I would check it out more if I ever go back. The views from the hike of the park had a very Big Sur highway feel to them.
The Lanakai Pillbox hike was good redemption hike. We had to park at a neighboring beach park and walk about 15mins to the trailhead. On the way we took a peak at Lanakai beach and were like- this water looks amazing- we got to do a beach day here (and we did the next day). The whole hike took us about an hour/4mi, and it was pretty crowded with families. We got some really amazing views though for such a quick hike.
This day was a little weather crazy, we drove through some serious rains back to Waikiki mid-island, but by the time we were back it was sunny and beautiful. We tried Paia Fish Market in Waikiki for lunch (very good and the portions were really generous), got a coffee from Kona coffee, and walked through the city to Ala Moana Beach Park and back (around 4.5 miles). Ala Moana- no real reason to go here- seems to be where people who live more downtown in Honolulu may go, the water looked calm and the beach and park were huge but no real draw here. Then pool, hot tub, the famous Duke's Canoe Club in Waikiki for dinner (basically the same as Hula Grill, so if you go just pick either no need to go to both), and drinks at the Shorefire bar across the street.
Tuesday: Run, laundry in the building and Yoga to start the day. Drove back to Lanakai beach and relaxed for a couple of hours on the beach. A tad windy to stay comfortably all day. Back to Waikiki and today's lunch spot was Royal Lobster for Lobster Rolls. As all lobster rolls go- very good but very expensive. Island vintage coffee for the mid day pick me up, followed by rooftop pool and hot tub (do you see this routine? we are creatures of habit what can I say). Dinner was at Merriman's which ended up being the longest dinner walk of the trip- about 50mins through Waikiki, then along Ala Moana Beach Park in it's entirety, to yet another mall where the Merriman's was. I absolutely love this restaurant group. We've eaten at the Merriman's on the Big Island, now Oahu, and went to a couple of their Monkeypod restaurants in Maui. It's always the priciest dinner spot, and always the best dinner spot.
Wednesday: Waking up at the crack of dawn every morning really paid off on days like today. I feel like we lived 2 separate lives in one day. We started out the morning in Waikiki with our last run - and finally swam and relaxed on the actual beach for an hour, before we checked out of our Airbnb and headed to the airport to continue our trip and fly to Maui. The flight was quick- maybe 25mins in the air- and we landed back on our favorite island. First stop was Maui brewing company- about 25mins from the airport for some pizza and beer. Then off to our place - the North Shore lookout B&B in Upcountry Maui - Makawao. It was about 4:30 when we checked in- enough time for a swim in their amazing slightly heated pool, then hot tub (I was not about to stop this tradition), then sunset in the hot tub!!! Our room was huge and the place itself was really nice. Tons of places to sit, a couple fire pits and hammocks, amazing views of the ocean far far away. Very hard to find though, barely marked on a gravel road way in the Upcountry. Being so far from the beaches was a little annoying. If we had gone back to Haleakula National Park, or done the road to Hana again, this would have been a better location. We stopped at the Rodeo General Store in Makawao for some wine and beer and snacks (pretty good selection for a small general store). For dinner we drove to the Halimaile General Store right outside of Makawao town (about 15 min drive). Very big restaurant with tons of indoor and outdoor seating, pretty good for a local upcountry spot. After we took advantage of our amazing B&B's location with some drinks by the firepit and stargazing. The B&B's cat Mimi joined us.
Thursday: What's a B&B experience without the free breakfast?! This is where they lost me a little. Great coffee, but only one option per day for breakfast, and the portions were pretty small. Today was a meat board - which had nothing for me. I would have loved some toast, fresh OJ, pastries, anything additional to the main. But it was kind of a bummer breakfast. For being such a nice place, they need to up their breakfast game. We drove about 40mins to the Waihee ridge trail on the northwest part of the island that I had never really been too. This was another pretty steep hike of incline the entire way, took us about 2 hrs up and back to do/4mi. My favorite type of hike though, views of the ocean and the mountains on both sides almost the entire time. Pretty exposed most of the hike so it got hot, but there were sections of shade and breeze that helped balance it out. Heading back to the place we got lunch in Paia town at Cafe Mambo (another great garlic shrimp experience) and about 5mins from our place went and hiked the Kakapao loop trail. This trail, although it had a slight incline the one way, was more like a wooded walk, very well marked and took us a little over 2 hrs to do 6.5 miles. Then it was pool, hot tub and dinner! We drove, in the dark, 1 hr and 15mins to the west side of the island just to eat at another Merriman's (totally worth it). Similar menu to Oahu, however they were doing a pricey pre-fix menu. Having to drive saved us from drinking a ton and kept the bill down (slightly). This place looks like it has amazing views during the day- right on the water with a good amount of outdoor seating. I think we saw 2 proposals- this is where Maui goes to get married.
Friday: Last day! Turns out, we were really lucky it was and we got out when we did. The next day all of Hawaii was hit with some crazy storms. We only experienced some bad weather on this day- and were able to escape the rain and even get in some beach time in Wailea- but eventually the storms were everywhere and we just had to deal with the rain. For breakfast at North Shore - a slightly better offering of Biscuits and Gravy. But again, no accompaniments. It started to rain upcountry- so we packed the car for a day of running and beach opportunities. We drove 45mins to Keawakapu beach park- where we parked the car and caught the Wailea beach path that goes through all the ocean resorts (we ran this often a few years ago when we stayed at an airbnb in this area). After the run we did a quick change into our bathing suits and caught a few hours of sun, even got to swim a few times in the ocean, before the real rain caught us around 2 and we quickly headed to lunch at Coconuts fish house down the street. Not the best spot, but good in a pinch. We were also a mess and did not want to go anywhere fancy, which in Maui is sort of tough to find in this area! We slowly headed back to the upcountry, but stopped once again in Paia town, this time for some shopping. I love the surf and souvenir shops here, super cute. Makawao also looked like they had some cute boutiques, but everything in that town closed pretty early (5 or 6pm). Back to North Shore- we packed up and stopped for one last dinner on our way to the airport. Cassanova Italian in Makawao ended up being packed and for good reason- really solid italian food and wine, and I loaded up on my carbs before the long journey home. We may need to take a break from Hawaii next year, but I'm sure we'll be back soon!