Follow Along our Travels!

Being located on the west coast of the US, I’ve been lucky enough to travel to Hawaii many times. Depending on where you are located on the west coast, it is a 5-6 hour direct flight to pristine white (or black or green) sand beaches and tropical weather. Each island offers its own version of paradise and can accommodate any type of traveler. If you’ve read any of my other posts or itineraries, you know we lean more towards the adventurous types of vacations. Although, even as I type that, I must acknowledge that Hawaii (Kauai specifically) is one of the only places I feel that we can completely relax. While I’ve been to Hawaii many times (and spent time on every island), this is one of my favorite itinerary and trips we’ve done in recent visits.

Maui Highlights

Maui was the island we frequented the most during special family trips. I forged core memories in Lahaina and Kāʻanapali with my mom, dad, sister, her best friend and Chuck. Every 4 years, we’d head back with the family to spend time in these perfect coastal towns. In fact, the first time I did the infamous Road to Hana was with this group and I still belly laugh at some of the memories of that trip. You see, that group is definitely less adventurous than me and Chuck so mishaps happened.

Now, obviously Lahaina has changed quite a bit in the last two years due to the devastating fires in August 2023. The entire town burned to the ground. I am not ashamed to admit that I cried when I found out because while I know Lahaina will rebuild, it is still a devastating loss for the community and economy. I can also admit that even before the fires, west Maui had been changing. Each time we visited, Kāʻanapali was more and more commercial and touristy with bigger hotels and condo complexes popping up all the time. I am part of the problem as a tourist. I saw firsthand some of the backlash from the local communities to this growth and loss of community. Due to several contributing factors (including these), the last several times we’ve been to the Hawaiian Islands, we’ve avoided Maui.

So why did we decide to go back after an almost 10 year break from this island? Mainly we wanted to do it one last time, but differently than we had in the past. We prioritized new adventures as well as truly immersing ourselves in some experiences we’ve already had.

Highlights from Maui:

• Haleakala National Park! In all the years, I had gone to Maui, I had never done this national park. We got up super early and drove up to watch sunrise. It was the most beautiful experience and I highly recommend prioritizing this if you make it to this island. We also did some hiking around the park after sunrise and it was truly worth the effort of getting a permit and waking up at 3:30am (check tips later in the post about this).
• Hana! Note: I did not say The Road To Hana (which is also awesome and should be experienced once in your life) but Hana the town is special. We stayed overnight there and got to spend some time soaking up the energy that is this small community. The town is tiny (maybe 2 restaurants open at any given time) with minimal accommodations, but it is absolutely worth it to try to stay. Not only does it allow you to not rush The Road to Hana experience, but the town itself lends itself to the mellow vibe that a Hawaiian vacation should include. A lot of people comment that it is a throwback to how all of Maui used to feel in the old days.
• Kihei: We stayed in Kihei for two nights and I loved this locals living spot for a lot of reasons but mainly because their food truck scene is legit! There is an awesome spot located in the South Maui Gardens that gathers around 10 different food trucks with picnic tables in a lush setting. All this is about 3 blocks from the beach so if you feel like taking the food to go, the sunsets in this area are gorgeous too. Food was delicious, convenient and not too expensive which equals a bunch of wins for this island!

Kauai Highlights

So unlike Maui where we hadn’t been back in close to 10 years, Kauai is my happy place and I try to get to this island every trip we make to the Hawaiian Islands. It is nicknamed the Garden Isle and this is incredibly accurate. It is the oldest of the islands and the lushness and diversity of its landscape showcases this beautifully.

Another reason I really love Kauai is the different types of experiences you can have here as a tourist. The island lends itself to all sorts of travel experiences. These include world-class hiking, ATVing, horseback riding, water sports, and of course lounging. We’ve been to Kauai around 8 times in the last 10 years and have done new things every time we’ve come. This trip was no exception. I’m going to keep the highlights on this section to just what we experienced on this trip, but if you have any questions about other things to do, let me know!

Highlights from Kauai:

• Cabins at Kokee State Park: We arrived during the evening and the minute we stepped out of the car, we looked up and you could see the Milky Way clearly — with our naked eye. Now, I do a lot of camping and hiking so I’m no stranger to a good starry night, but this was incredible. The Hawaiian islands are (obviously) completely isolated in the middle of the ocean the cabins location at the edge of Waimea Canyon make it the perfect spot for stargazing. The cabins themselves are basic but the night sky experience was worth booking these.
• Waipo’o Falls via Pu’u Hinahina and Canyon Trail Hike: This is in Waimea Canyon. Now, if you haven’t even peaked at Waimea Canyon from an overlook, it is a must do while in Kauai. It looks just like the Grand Canyon but it is in the middle of an island in the middle of an ocean. Pretty mind blowing. However, on this trip we actually made it into the canyon to hike which was (for me) an exceptional hiking experience (and a little sketch if you are scared of heights). This trail is mostly through the trees/bamboo but there are some exposed ridges and even a swing that goes near the edge (not for the faint of heart)! The views and the uniqueness of the trail make it a highlight.
• Napali Coast via Ke’e Beach: On the itinerary, you’ll notice we did not hike the Kalalau trail on this trip. However, we have done both a 4 mile and 8 mile version of this hike and it is hard but incredibly worth it. I recommend it to anyone in decent hiking shape. But that’s not what this highlight is about! On this trip, we got to experience one of the more epic sunsets I’ve ever seen on the Kauai coast. Now that was just lucky, but the reason this is a highlight is because I highly recommend getting out to this beach area in the afternoon/evening. This area is permitted now, so you have to plan in advance when you want to be there at this time (also note, that if you are going to do the Kalalau trail you need to start way earlier than sunset). At Ke’e Beach, you can walk along the beach (away from the Napali coast) for a long ways and see some pretty epic surf breaks. It is a relaxed way to view Hanalei area from a different perspective.
• Hanalei Bay Resort: This is our go-to spot when we are in this area of Kauai. It is a combo hotel/condo resort. It has all the amenities you could need including two beautiful pools, BBQs, tennis courts (and they were repainting for pickleball when we were there!) and even a restaurant on site. More than that, most units have full kitchens so you can save some money by cooking in. Also, the location is perfect for exploring the Princeville/Hanalei Bay areas of Kauai. It isn’t the cheapest place, but honestly the cost is very expensive everywhere on this side of the island.

Tips about This Itinerary/Trip:

• The Road to Hana. Now, tips for this could be an entire blog post; however here are a couple based on our most recent experience:
  • On the itinerary there are a lot of stops/options listed. And honestly, we did 4 of them. We also added one or two that weren’t on there that we found in the Maui Revealed book. The reason there are so many options listed but only a few hikes done is because we were making decisions on the fly. I highly recommend being flexible on the Road to Hana as you may have to pivot based on weather, parking or the fact that hikes that were open a few months ago may be closed now. Be wary of any hikes that take you through private property as well.
  • It must be said but the hikes/experiences on this road are usually unpaved, slippery and sketchy based on the weather. Make sure you know your limits and only stop and hike if you feel safe doing so.
  • Get on the road as early as possible to give yourself the best opportunity to visit as many spots as possible.
  • Don’t be a tourist a*hole by blocking the road waiting for parking or even worse blocking the road by parking in it. It may sound crazy to recommend that but it happened multiple time to us (where we were dead stopped because of parking issues).
  • Water shoes with a hard toe area or old hiking/tennis shoes are a must if you plan on doing any of the waterfall hikes. These are mostly along the river rocks and stubbed toes are super common.
  • The road itself is narrow and winding. Like a lot more winding than I even remembered from years ago. If you get carsick easily, be wary of this road or take loads of Dramamine with you.
• For Haleakala, allow a lot more time that you think to get up there in order to make it for sunrise. The road is winding and it will be dark so you have to go slow. Not to mention, it is permitted so you are stopped at the NP gate prior to entrance. You could be there for 5 minutes or 15. If you want to actually view sunrise, it is worth getting up the extra 30 minutes early so you don’t miss it!
• For Haleakala, if you are coming from the mainland, do this on day 1 for the itinerary for an easier wake up call! Hawaii is 3 hours ahead of the west coast of the US, so waking up at 3:30am for sunrise at the peak is like waking up at 6:30am at home. If you do it early in your trip, it makes it a lot easier on the body.
• For Haleakala, bring layers of clothes! I was freezing before sunrise (the peak is at around 10K feet), but then when we hiked we went down to the valley floor where it was very hot. It also rained on us during this hike so bring lots of layers!
• For Kokee State Park, I wish we had gotten there before sunset. We landed and had to drive straight over which means we didn’t actually spend much time in this park (besides the epic evening views), I would have liked to explore it.
• Hanalei town closes fairly early (around 8pm for most restaurants). We cut it very close to missing dinner time by waiting until sunset was done before driving back into town. Plan accordingly by either having leftovers ready at your lodging or make reservations somewhere that accommodates a later dinner.