I took my family on a 2 week trip to Hawaii during the 2019 to 2020 holiday season.

Itinerary Summary

• Started the journey on December 17th with a long but well priced flight on AA from Boston(BOS) to Maui(OGG) with an overnight in Philly(PHL) (staying at the Renaissance Philadelphia Airport at a great rate and a nice Titanium upgraded) and stop in Dallas(DFW) for only 30k points per person. Arrived in Maui in the early evening.
• Reserved a mid-sized car from Avis, but maybe through being nice to the agent or my preferred status, was able to get an upgrade to a Jeep Wrangler, the perfect rental car for Hawaii in my opinion.
• Stayed at the Aloha Surf Hostel (see review) in Paia from Wed to Sat morning. Paid $185 per night for the “Ohana” shed.
• Moved to the Hyatt Regency (see review) on Saturday (12/21/20) and stayed through the following Saturday for 20,000 hyatt (transferred from chase) points per room per night. This was a great use of Hyatt points as rooms were going for over $600.
• On Saturday flew from Maui (OGG) to Kauai (LIH) in the mid afternoon on Hawaiian Airlines using 7,500 AAdvantage points per ticket
• Checked into the Grand Hyatt (see review) and stayed through Jan 2nd
• Mid-day on Jan 2nd flew from LIH to LAX on United for $404 per person
• Reserved a midsized car from National and got a Minivan from the executive aisle so canceled my parent’s reservation for a 2nd car and put 6 of us and our luggage into the Minivan.
• Stayed at a well priced Marriott in the Valley and got upgraded (Titanium status) to a suite so the 6 of us piled in shortly after midnight to get a bit of sleep
• Moved to an aunt’s house in the Valley for the next night and got to spend some quality family time
• Took a direct flight from LAX to BOS midday on Jan 4th using 12,500 Avios points per ticket.

Maui

Haleakala Volcano

On Dec 19th, we left the kids with a babysitter (hostel employee) and drove to the Haleakala Volcano. There is an 11 mile hike starting at the top of the volcano and ending part way down the road though requires a ride from the lot to the top to start the hike. I had done this hike years earlier with my sister-in-law so I knew the ropes. We drove up to a hiker’s parking lot then hitch hiked to the top. After about 10 cars passing by, we got picked up by a women who was looking to hike the Volcano herself. We decided to hike together with a plan to drive her back to her car at the end of the hike. It was a beautiful hike through what looked like Mars to us. Looking down at the clouds we even saw a rainbow. 5 hours later we were back at our car and drove our new friend back to hers. Then headed back to the hostel.

Paia

Paia is a very nice surf town on the North side of Maui. It is not near any large resorts as it can be rainy, but it is near the big waves and the airport and is very centrally located to get around the island. Paia has a very convinient supermarket about a 5 minute walk to the hostel and plenty of cafes and restaurants, but do note that it is hard to get breakfast before around 8:30am.

On Dec 20th, we explorer Paia and some areas close by. We went to Twin Falls, a small waterfall that is at the very beginning on the road to Hana. Has a fruit stand out front and a very short and pretty easy walk to the water, though not quite easy enough to get a stroller all the way down.

There wasn’t any Verizon internet by the waterfall and I needed to send an email so backtracked 15 min or so to a store/cafe called “Jaws”. It was a nice place but their internet wasn’t working. Luckily, I was saved by a very nice real estate agent that had a working hot spot. If you are looking for real estate in Maui, let me know and I will introduce you.

There are various small shops where you can buy stuff you forgot though at full retail. E.g., $60 bathing suit for a kid. Also not so far from the airport area where there is a Walmart and Target.

Paia Bay Coffee Bar - decent cafe with good coffee, though very limited cooking facilities meaning limited hot options. It was also open the earliest in the morning for those transitioning time zones. On our second visit there an order for an ice americano came out hot and they thought that then pouring it over ice was a appropriate fix (ends up too watery). No big deal, but at their prices, I wasn’t expecting that.

Charley’s Restaurant & Saloon - fairly traditional american diner breakfast options. Pretty good. Though I think they only have drip coffee if you are looking for something more advanced.

Kaanapali

On Dec 21st, we left the hostel and drove to the Hyatt Regency on Kaanapali Beach on the northwest of the island to meet up with my extended family. This area is shielded by a mountain range from the rains so stays pretty dry even in the wet season. We stayed at the Hyatt Regency (see review) for a very enjoyable week. The beach was very nice and we enjoyed the resort and some surf lessons nearby.

Starbucks - there is a Starbucks in the Marriott on Kaanapli beach which was a 5 minute walk on the boardwalk so we ended up there most mornings. Note that the line could be 20 minutes long during the holidays.

Whaler’s Village - Whaler’s Village is an open air mall on Kaanapali beach accessible via the boardwalk from the major hotels, though a bit of a walk. It has a few large restaurants. We at lunch one day at Leilanli’s and it was very nice. They also have a low end food court (Subway, etc.) and a few other food options including Acai kiosk. There is also a cookie store where if you walk in and say “Airport” they will give you a cookie for free (you can also sample mini cookies). There are various retailers there as well. We checked into the boxing day sale at LuLuLemon for forgotten sportswear.

Road to Hana

Went with part of the family for a round trip to Hana. We got lucky with great whether. This is the second time I have done this road (years earlier I did it as a full loop) and the big lesson learned is that there just isn’t enough time to enjoy it in one day. If I ever did it again, I would certainly either bring camping equipment or book a room in Hana for the night. The drive along from Kaapapali to Hana if you didn’t stop is over 3 hours each way and the whole point is to stop a lot. With 6 hours dedicated to just driving, there isn’t really that much daylight left to enjoy.

We used the Shaka Guide audio tour app (something like $30 to buy all of the Maui tours). While the speaker could be a bit annoying with bad jokes, it was very nice to be guided. He had some wonderful ideas.

We first stopped back in Paia at the Hana Picnic Lunch Company. They seemed to be set up to sell picnic lunches for people doing the road. There selection is limited, there is some food on the road to Hana and by the time you get to lunch, the food may already be bad unless you have a cooler (which, of course, they will sell you). Instead, I would pack a lot of dry trail mix that you can eat if you don’t happen by a nice lunch on the road at the right time.

We stopped at a waterfall that I forgot its name. Went the wrong way in the woods for a while with my 7 year old daughter and 70 year old father so not the most fun, but eventually found the first waterfall. Though by then we weren’t in the mood to get above it.

We stopped at a “Secret” Lava Tube Cave, kind of cool to walk through. Would be nice to have a flashlight, but the phone’s worked well enough for this very short walk.

We stopped at various state park waypoints for quick views from the car.

We made it to the black sand beach shortly before dark. It was really cool for the kids to play in the black sand and see the roaring waves (certainly not a swimming beach). There were a lot of people camping nearby which made me jealous as I still had a 3 hour drive back to the hotel in the dark.

Finally making it to Hana, we looked for the red sand beach before dark, but didn’t make it. We then grabbed some dinner at a local restaurant.