What islands did you have in mind?
I’d swim.
No US based airline is worth the price of a ticket.
Drive to Florida instead, or somewhere on the Gulf, take a Caribbean cruise.
One piece of advice: You are, of course, travelling FIRST CLASS, right? So try to figure out IN ADVANCE where the First Class lounges are located in the airports you'll be going through. You'll want to make a bee-line straight to them as soon as you land!
I highly recommend the one at the Honolulu Airport (if your lay-over is long enough, you might want to try getting a massage) - but don't bother about the "First Class" lounge in Hilo (Big Island): It's a remote, cramped room with a water fountain and a vending machine (stocked with stale candy).
Regards,
About an 8 hour flight. Try to fly on a Mon/Tues/Wed during late Sept, Oct, early Nov, late April, early May, when plane loads are light, then it’s possible to have a row all to yourself. Do not go late in May else you’ll get caught in things like UH graduation, Ironman events, WalkAThins. Load up your phone or tablet with Kindle books or movies.
Does Southwest serve Hawaii? Don’t they only fly 737s?
Haven’t done it, but Southwest only flies 737s, and that seems like a very long flight in such a tiny aircraft.
If it’s a single aisle plane just be prepared for a long,uncomfortable,flight!
First of all, congrats on your upcoming anniversary.
That being said, in my opinion, travelling to Hawaii is currently not worth it.
From the Southwest page about Hawaii flights...
Hawaii Travel Advisory
*Travelers must provide a U.S. vaccination card or valid negative COVID-19 PCR test from a State-of-Hawaii-approved Trusted Testing Partner in order to be exempt from a 10-day quarantine.
*Travelers must create a Safe Travels account, upload test results, and receive a QR code prior to landing in your destination.
*After completing Hawaii travel requirements, Travelers may be eligible for Hawaii Pre-Clear to have the opportunity to be pre-cleared at their final departure gate or other centralized location and bypass airport screening upon arrival in Hawaii.
Until all this CoupFlu bullsqueeze is no longer active, there’s no reason to go to Hawaii. I’ve always wanted to go there, but as long as this crap is being done, it’ll never happen.
Most important when flying Southwest: Book EARLY and pay the extra $25 so you get to board and pick your seat first.
Airlines might serve meals by then. In any case, carry food on board with you.
Fly non-stop - you do not want to have to deal with the LA airport.
Track the pandemic rules. Hawaii has been very restrictive, but is easing up.
Since you are former military, look into the Hale Koa hotel right on Waikiki beach. However, Maui is much nicer than Oahu!
The Everglades are a sight to behold! Truly amazing!
Is Southwest getting some larger aircraft? I think their fleet only has 737s. Some of them are the stretch models, but they’re still only 6 seats per row.
We learned to break up the return trip by spending a day or so in either Phoenix or Las Vegas, which are both nice places to spend a couple of days. If it's summertime, then Vegas is your best option unless you like 120 degree weather. That routine also allowed us to get get somewhat back into our normal time zone for the final leg back.
You mentioned you were going to Oahu. That is actually my least favorite island to visit. Honolulu is basically New York City with palm trees. Now as a first time visitor, there will be plenty to do and certainly check out Pearl Harbor and all the memorials as well as Waikiki Beach. You can also get away from the city and get a more Hawaiian experience.
My favorite island is the Big Island and we stay at Kailua-Kona which is the dry side of the island. Rent a car and see the whole island, from tropical rain forests to active volcanoes to ranches that would make you think you are in Oklahoma or Texas. Pretty much every climate (except arctic) can be experienced on the Big Island. But if you really want to see snow in Hawaii, the Big Island is the place to see it if you visit at the right time. Mauna Loa and Mauna Kea sees at least some snow every year. Then you can be back at the 80 degree beaches in an hour or so. Check with your rental car agency though, some of them don't allow you to take their rentals on Saddle Road (which is the way to the interior mountains).
Maui is our second favorite island. The best restaurants and beaches. You can still find your own "private beach" for the day if you know where to look and you can surprise your spouse by going into the ocean naked.
If you want a really quiet experience, try the island of Kauai which has (relatively) minimal commercial development and a lot of open spaces, including a rival to the Grand Canyon.
Anyway, after your Oahu trip, you will definitely want to go back and explore some of those other islands.
We made the trip several times, with young children, in the 90's, on United and AA. The difference between a wide body jet and a Southwest 737-800 is that you have two aisles instead of one. The seats all have the same basic distance and pitch. To me, the only issue was the lack of meal service, but I plan ahead for that.
I prefer the Southwest experience to AA, Delta or United, but I was a (mostly) business traveler flying two or three times each week.
All flights to Hawaii for Southwest route thru Las Vegas, Phoenix, Oakland, San Jose, San Fran or San Diego. (Yes LAX also, but why?!). Phoenix, Vegas or San Jose would be my choices.
From DSM you will stop in Las Vegas to fly the leg into Oahu. Getting back you will need to schedule a layover before you catch the morning flight back to the Midwest. KCI and STL have better options for the return flight schedules.
So what you have is a 2 1/2 to 3 hour flight, a bio break at a real airport, then another 5 to 6 hour flight to the Islands. About the same as BOS to LAX or East Coast to Seattle.
Coming back, you will face the overnight challenge, so pick a city that you don't mind a layover before the final flight to DSM.
You can certainly build a trip that gets you to Hawaii in one day, and a flight back home in one day, but the Southwest flight scheduler will not allow for a planned double connect. You can have more than one stop but only one change of planes in their system, per flight record. So if using DSM, you can book two round trips and manage it that way.
I used to post here, and it is a wealth of information from folks that practically live on Southwest:
We spent some time on Oahu and some time on the Big Island. Big Island is more interesting IMO. Highlight of Oahu was visiting Pearl Harbor.
I did it last fall from HOU. I’m an employee so I flew standby & picked flights based on how empty they were. Took 2 days each way - wanted to give myself plenty of breaks - concerned about blood clots due to vax.
First day non-stop HOU to SJC, spent the night in an airport hotel. Next day SJC-OGG-HNL. Spent 4 nights in Waikiki. Then flew HNL-KOA. Stayed 10 days. Flew home KOA-OAK, spent the night at an airport hotel then OAK-HOU.
I prefer the aisle seat & got it for all flights even though I was last to board. On all legs except OAK-HOU the window & middle seats were empty, & on that one the middle seat was empty. I expect that won’t be the case now that covid restrictions are easing.
The airports from which SWA flies non-stop to Hawaii are SAN, LGB, LAX, SMF, OAK, SJC, PHX & LAS. I believe the plan is to add more. Hawaiian airports we fly to are HNL, OGG, LIH, ITO, KOA.