I can not advise you on Southwest.
I flew from Boston to Honolulu three years ago on Hawaii Airlines.
We stayed on Waikiki Beach for a few days. There are only about eight hotels that are right on the beach.
We did the Pearl Harbor tour.
One of the best things I have ever done in my life.
We only stayed on Oahu for a couple days.
If I ever go back I will stay longer.
We then flew over to the Big Island and spent a week on the Kona coast.
If you go to the Big Island you need to rent a car. It is a BIG island. We drove all over it for a week. FYI, the Big Island is not nearly as expensive as Oahu or especially Maui. A steak dinner on the Big Island is about the same as around here.
That is because they have some of the biggest cattle ranches in the country. They also grow a lot of food on the island.
I went to Maui about 25 years ago.
It is beautiful. Everywhere. Breathtaking.
It is also very expensive unless you rent a condo in Kihae. Some of the nicest resorts in the world in Wiamae.
On all of the islands there is a dry side and a wet side. It is a drastic difference.
The Kona side of the Big Island looks like the dark side of the moon.
It is one huge lava field.
Except for the coast where the resorts are.
The Hilo side is tropical jungle.
It rains all the time. Same story on Maui.
The Hana side is beautiful, when it is not raining.
I have not been to the other islands.
I can’t remember the name of the one where they filled all the Jurassic Park movies, but I know people who have gone there and they said it rained 4 out of 6 days.
That is why you need a car if you visit.
It can be raining in one area, but you drive five miles away and the sun is out.
The island you can’t remember is Kauai. It has a canyon (Waimea?) that rivals the Grand Canyon. The extinct volcano nearby is one of the wettest places on earth. Around 600” of rain per year. The northwest part of the island is accessible only by boat. That’s the area where the movie was made. My wife’s favorite island.
My favorite one there is the Four Seasons. It's nice to park at one end and just walk the sidewalk ocean front, popping into each resort. There's a golf course right above the resorts that has a Irish pub, great for getting corned beef (I know, corned beef in HI??!)