This post contains affiliate links.
The Hawaiian Islands were supposedly discovered by a Polynesian man named Hawai’i-loa. His descendants populated the surrounding islands, which he named after his children. While it temporarily when by other names, King Kamehameha took the throne in 1819 and christened it Hawai’i. The Aloha State is named for its friendly people. I have been lucky to visit Hawaii multiple times and have been to most of the islands. Going to Hawaii from California is equivalent to going to the Caribbean from the East Coast so my first trip was as a child with my parents.
Maui
My first time visiting Maui, we saw a gorgeous waterfall, something I have never forgotten and haven’t found again on multiple trips.
My husband and I received a timeshare offer to go to Maui. My daughter was only a year old, so we didn’t pay for her flight. We ended up buying at the Westin Kaanapali North because it was amazing for families, couples or even single travelers looking for serenity. (I do not recommend a timeshare unless your are organized and able to plan in advance. I highly recommend a timeshare if you can. It has afforded my family the opportunity to travel without paying for hotels 80% of the time.) There are also easy catamaran trips you can take to either Molokai or Lanai.
My last trip to Hawaii was back in Maui at our timeshare. After a visit to Haleakala, we drove the Road to Hana again…and my son got sick again. I wish I could say lesson learned, but we had forgotten the dramamine. The good news: I think we found the waterfall I remembered from my childhood!
Lanai
From Maui we visited Lanai, the Pineapple Island, and my son had his first snorkeling experience. One of the guides put a snorkel on him and draped him over a surfboard. The thing I was most amused by on the island was the historical jail. I think it is safe to assume there isn’t much crime on the island.
Driving the Hana Highway in search of those waterfalls from my childhood ended up being vomit inducing for my son so we didn’t have success. We tried to remember to travel with dramamine after that experience.
The final time we took the Hana Highway, we drove the entire road. Some websites indicated car rental places wouldn’t allow it, but we didn’t find that to be true. We had also been told part of the road was unpaved. The part that was unpaved didn’t amount to more than a mile, if my memory serves me correctly and really wasn’t that bad.
Finishing the drive this way, you go past the one winery in Maui. While most of it wasn’t my style, I did find the pineapple wine enjoyable and refreshing. There is also the Ulupalakua Ranch Store & Grill across the street if you need more substantial food. One of my favorite finds in Maui is the Surfing Goat Dairy. It was our last stop on our day, returning from the road to Hana. They even package the cheese so you can take it home. Cheese tasting anyone? Very fun!
Visiting a Luau while in Hawaii is such a treat. It can be pricey and a little cliche, but it is definitely something you should try once in your life.
Oahu
My second trip to Hawaii was with my parents to Oahu. One of the highlights and musts of Oahu is Pearl Harbor. I was quite young the first time I visited, but it was a highlight at that age and again as an adult.
After a visit to Kauai, I was lucky to get a 3 day stopover on Oahu where I took my family to Pearl Harbor. While there, we met Herb Weatherwax, a survivor of the USS Arizona. He had been on leave that day, probably the only reason he survived, considering so many of the crew on the Arizona did not make it. Sergeant Weatherwax passed away a year after we met him.
Hawaii, aka The Big Island
My husband accepted a timeshare offer for a free stay on the Big Island (you need good credit to get these offers and have to be willing to give up 90 minutes of your vacation time to listen to their pitch). Since my son was under two, we didn’t have to pay for his flight which made the trip much more affordable. We didn’t buy that timeshare but had a wonderful time seeing the island. The lava wasn’t flowing at the time, but we could see smoke from the caldera. We also went to a gorgeous black sand beach.
Kauai
My husband and I agreed to another timeshare offer to go to Kauai without using our ownership. While we didn’t love the hotel, we did love the island. The Napali Coast is beautiful and worth a boat trip. The weather had been rainy all day, but it miraculously cleared up and we had pictures of whales in an incredible setting.
My daughter was still quite young at the time and I bought her sunglasses for this trip. She is a sunglasses addict now!
Each island has a different vibe and something special to offer. One thing that is consistent are the sunsets.
We love Hawaii!