Highlights

• Pineapple Tour
• Sunset sailing cruise
• Surf lessons
• Wailea Beach Marriott – one of our favorite hotels
• Kilauea volcano
• Tsunami museum
• Timeshare presentation bonus points

Lowlights

• Work schedule for my wife

• Expensive food and gas

• Slow-moving middle of the vacation

• Extreme heat kept us inside more than we’d prefer

• Smelly rental car

• Losing my sunglasses and favorite hat

• Initial breakfast offering from Wailea Beach Marriott

What went well?

• No flight delays despite multiple connections
• National rental car recovery from smelly car. I was impressed with how well they handled the situation and made things right
• Wailea Beach Marriott offering us a real breakfast option
• Managed to see most everything we had on our list

Takeaways

This was a long trip at 14 nights and 15 days. We covered a lot of ground with stops on two different islands and in three different hotels. This trip was relatively easy to plan for a few reasons. First of which we had been there as a family just two years before and knew the areas on Maui well. Additionally, we had planned a very similar trip the year before what we had canceled due to a conflict so I had already done a majority of the planning. I just needed to update the dates and tweak some of the details. Finally, we were in Hawaii and it’s a naturally relaxing and “chill” place to be anyways.

Big Island

We had never been to the Big Island and didn’t really know what to expect or really what there was to do other than Volcano National Park. We didn’t expect the Big Island to be so rural and we definitely didn’t expect there to be as much traffic as there was. It wasn’t always bumper to bumper but it always felt like it took a lot longer to get from place to place than expected.

We found there also wasn’t a ton to do in the Kona Kailua area near our hotel. We expected there to be more to the town. We found one area with lots of restaurants and some nearby shops which we went to several times, though we never found a downtown that we felt compelled to explore more than once.

Maybe it was just an overall vibe that just didn’t mesh with our style. That said, we really enjoyed Volcano National Park and Kilauea Crater. It would have been even better if it was still erupting though nobody has control over that, obviously.

The town of Hilo was much more interesting than Kona to us. The downtown just seemed more interesting, even though it was a bit run down in some areas. We surprisingly really enjoyed the Tsunami Museum and were glad we ended up going.

The weather on the Kona side of the island rained every evening. I’m not sure that’s normal, but it was consistent during our stay. Since it was so warm, the rain wasn’t a huge inconvenience and it brought out some fantastic rainbows!

The Sheraton Kona Resort we stayed at was a good value for the price. The AAA rate of $170/night couldn’t be beaten, and with my wife’s elite status and access to the club lounge, we saved a bundle on breakfast each morning and dinner many of the nights we were there. The pool area was a huge hit with the boys, especially the slide. The game room was also a huge hit even though the equipment was extremely worn and well past when it should have been replaced. The kids made due. The amenities at the hotel were excellent with the complementary basketball and tennis equipment and a fair amount of open space and the fitness center had amazing views of the ocean while you worked out.

The resort did NOT have a beach and the resort itself was a few miles from the city center. There was a nearby strip mall with stores and some restaurants a couple miles away but nothing within walking distance. We had to get in the car to go do or see anything. The rooms were fairly average. The beds were both double beds and the room itself was of average size. The balcony was on the small side. Our biggest complaint about the room was that while it was sold to us as an “Ocean View” room, we only had a partial view of the bay as we looked over the parking lot and other parts of the hotel. While it’s tough to be too upset given the excellent rate we were paying, we’d rather they had been more honest with the room categorization.

While we had a good time on the Big Island, we don’t have an overwhelming desire to go back in the same we do Maui. We’d probably try a different island next time. If we were on the Big Island, we might consider staying at this resort again, though we’d likely look to stay in a different part of the island to see if that fit our style more naturally.

Lahaina

After for days on the Big Island, we were ready to get to Maui. We love Maui in general from our previous trip and had fond memories of the Lahaina area. We had done a lot on that side of the island, though much of that was stuff we weren’t interested in doing again this time.

That gave me the challenge of finding 5 days worth of “new” things to do with the kids while my wife had to work all week. The boys really enjoyed the Nakalele Blowhole and we all really enjoyed the sunset cruise. That was definitely a highlight of the trip up until that point. We had the perfect night on the water. It was so relaxing and we would 100% recommend doing it. It’s definitely on our list for our next trip.

We were excited about staying in the Sheraton Maui, and ironically and unintentionally it would be the 5th Sheraton hotel we had stayed at in a row. It just worked out that way. While the initial check-in experience wasn’t the best, we ended up liking our hotel. It didn’t have the best view and was a bit far away from the ocean, it was at least properly described as a partial ocean view.

The resort had a huge amount of green space which we took advantage of quite often. The beach at the resort is fantastic. It’s nice and wide with safe but fun waves for the boys. The evening cliff dive was a favorite of the kids and we got an excellent view of the luau without having to actually pay for it.

The resort’s pool also kept the kids occupied despite not having a real slide or a lot of open space for them to throw a ball back and forth. It also had some shady areas which is important given the intensity of the summer sun. The pool and beach got busy, but we never felt like it was so crowded we couldn’t find a spot despite the hotel being near capacity.

We also have to highlight the breakfast buffet. Not only did it come as a benefit of my wife’s status, but it was free for all four of us. Often we only get free breakfast for two, which is what is officially specified by the loyalty program. We appreciate the hotels that go above and beyond and extend the benefits for the kids as well. It was great having the benefit and the buffet was fantastic on top of that. We filled up every day and for us that makes a huge difference.

We did the timeshare presentation just for the points. While we had no intention of buying, it was still worthwhile to go. The points we got were well worth the time, though we also learned about some of the other properties and destinations that we would be interested in visiting in the future. We’re always looking for ideas of other places to visit! It was clearly not a good value for how we travel, though.

In the end, this part of the trip felt slow. We just didn’t have as much to do and fill the time. Some people love Lahaina but after a few visits, we had reached our fill. We would have enjoyed it more if we had spent 3 days there instead of 5, though since we used points for that part of the stay, we got the 5th night free so from a value point of view it made sense. It also didn’t help that we were there Sunday until Friday and my wife had to work those days.

Wailea Beach

This area continues to be our favorite place on Maui. The final five days of the vacation went by almost instantly. Not only were there more things in that area of the island that we wanted to do, or do again, the hotel itself had so much to do as well. The boys really enjoyed both the beach and pool areas. They loved the game room and their ability to play video games, something they don’t get to do at home. They enjoyed the routine and independence of the movie night.

The breakfast situation was a disappointment. What was offered at check-in may have met the most minimum of fine print requirements, but paled in comparison to its peers? Going from a fantastic full buffet to a pastry and a coffee and an even more expensive hotel was, to be honest, a bit insulting. In the end, after we complained the resort did offer something equivalent to their peers, though even that was frustrating that we had to complain to get that.

Despite that frustration, we still love this hotel. The room had queen size beds to limit the fighting between the boys. The resort grounds are picturesque and interesting. There’s lots to see, do, and eat within walking distance and even more within a short drive. It’s on the side of the island with more things that we are interested in doing are located. It just hits all the buttons and was a fantastic value on points, even before the 5th night free.

If we had planned this again, we may have been better off booking 10 days here and making day trips to Lahaina instead of splitting between Lahaina and Wailea Beach. That said, we still had a ton of fun.

Overall

This trip was like three different trips one after the other. Each portion was quite different and had it’s own hits and misses. Of the three our favorite was Wailea Beach portion that closed it out. By the end, we were very sad to leave, though we were excited to go home.

I was extremely happy with the car rental on Maui. While the first rental car with the smell was disappointing, National recovered better than I could have hoped. We got a bigger, better, newer car and a free tank of gas for the inconvenience. I’ll definitely be willing to pay as (slight) premium next time to rent from National next time I rent a car.

Our flights were all on time and went smoothly despite having two connections on the way to the Big Island. Our luggage didn’t get lost and even came out on the belt quickly in all the destinations. Seemingly every time we go to a tropical destination it seems our luggage is delayed so this wears a treat.

The weather was super hot as we expected. It took a lot of us so we had to schedule our outside activities around that and pace ourselves. These are not new things for us though.

The kids got to experience new things such as the pineapple tour, glass blowing, surfing, and sailing. Anyone of those could have been the highlight of a vacation and we got to do all of them so I’ll call that a successful trip.

Hawaii will definitely be on our destination list again. We’d probably try to check out Kauai as well as Maui again. Maui is the island that fits our vibe best of the ones we’ve seen so we’ll definitely be excited to return.