The actual traveling part of traveling is probably the most stressful piece of vacation for me. Especially now that I am planning trips again with a baby in tow. Plans need to take into consideration nap times, snacks, leg room, things to do on the way, getting a car seat there…along with general plans for rest of the fam.
We’ve traveled with kids and babies before, but our most recent trip to Hawaii was definitely the most challenging. Mainly because it was our first trip across the country with the older girls and our first time dealing with time zone changes with them. Transportation, specifically the flights, were actually the deciding factor in why we decided to go to Hawaii when we did.
Because of the pandemic, flights to Oahu were ridiculously reasonable. Normally, one ticket from Tampa to Oahu would be around $1,400. I got all 4 of our tickets for that price. IN-FUCKING-SANE! Since visiting Hawaii was on my vision board of places I wanted to see, we jumped at the chance to go when the flights were this cheap. (By the way, I highly suggest everyone creates a vision board. They really do help you focus your life).
Since I spent some time figuring out logistics to Hawaii, I thought it might be helpful to share my thought process, timing, and the companies we chose to book with. First up, the flights to Hawaii.
Picking an Airline
Choosing an airline was something I kept flip-flopping between. Normally, we fly Southwest. But Southwest didn’t fly direct to Hawaii. I thought I wanted direct flights (see the next section for more) so I looked into other airlines like Hawaiian Airlines. But, with all the other airlines, you have to pay for your seats and your bagges. I like the no stress of Southwest’s baggage policy (2 free checked bags for each person). We were going to be traveling for a total of 12 days and my girls like outfit options. I didn’t want to worry about bages.
And, I didn’t want to pay for seats. With Southwest’s family boarding option, we get to board when the plane is super open, right after the folks that pay for early board or happen to check in early enough to get first dibs. Family boarding means you can pick pretty much any seats you want (except the first handful of rows or the emergency exits).
Picking Seats
We always go for the back.
Seems odd, right? Vince says he likes to sit there because it’s nice to be in the back and you can take your time getting off the plane. I think it’s because he has major mental issues. I think he likes sitting in the back because he doesn’t like his back facing people. Vince thinks he lives in the wild west and is going to get shot. He can’t sit with his back facing the entrance when we go to restaurants…because that’s how Wild Bill died. He really needs to stop watching the HIstory channel.
Ultimately, the back seats worked out really well with the kids. A couple of the flights weren’t full so we got rows to ourselves here and there. Most people avoid the back of the plane. Plus, I didn’t have to worry about Evie bothering more people, we got first dibs on the bathrooms, and I could stand up with the baby and move around more.
We did have to smell a heavy scent of poop occasionally since we were right by the toilets, but whatever.
The only time this was stressful was when we flew from Tampa to Houston the first day. Our layover was super short so I was nervous we would miss our connection. Having to wait to get off the plane since we were lodged in the back, wasn’t ideal. It worked out though. Which leads me to whether or not to choose direct or connecting flights.
Direct or Layovers
Originally I thought I wanted direct flights, but after thinking about it more, breaking up the 10 hours of flight time into smaller chunks would probably be better for the girls. 10 hours is a long effin time to be on a plane, unless you splurge and get first class.
I was obviously not doing that for 4 people.
At the time I was planning this trip, Southwest did not fly direct to Hawaii from Florida, Southwest also makes it super hard to book itinerary from the East Coast to Hawaii. Since the flights cannot be done in one day, you cannot just punch in your departure city and then Honolulu to your arrival city and see flight options. This wasn’t possible. I had to figure out how to get us west and then find a city that flew to Hawaii. Talk about annoying. So I looked at the route map for the airline to figure out what airports they flew direct to, check out flight times, and compared prices for the best deal/itinerary. This took me forever because I was trying to find the best flight times/cost.
Our best option ended up being flying from Tampa to Houston, then Houston to San Jose on Day 1 (about 6.5 hours total), stay the night in San Jose at a nearby hotel, then fly from San Jose to Honolulu on Day 2.
I wanted to get us to Hawaii early enough on Day 2 that we had time to get there, grab the rental car, stop and do a Walmart Grocery pickup (ordered everything online so we could just stop and have them bring it to our car), and make it to the hotel before dark. Even though we were gaining daytime with the time zone change, we had just enough time for all of that. We had unforeseen delays with the COVID check at the airport and then…the rental car.
A drama in itself.
Do You Really Need a Car?
Not everyone decides to get a car when they travel. Some people plan to spend most of their time at their hotel or rely on Ubers/shuttles to get them where they need to be.Â
We needed a car. First off, there’s 5 of us with luggage coming out our eyeballs. The 2 checked bags per person with Southwest can be a blessing and a curse. We couldn’t fit in an Uber XL. The hotel we stayed in San Jose normally had an airport shuttle (why I picked that hotel) but, because of COVID, they weren’t running it. Instead, they were calling people Ubers. It was nice, but we needed two damn Ubers because of all our stuff and Evie’s car seat. Ugh, the car seat. I had to keep installing and removing it for each Uber.Â
Very annoying.Â
So, for Hawaii, I knew we needed a car. More specifically, a minivan. We wanted to explore the island and couldn’t keep paying for Ubers. Shuttles were only an option if you did certain paid tours and were nearby the resort. My plans included activities all around the island, so I had to find a minivan.Â
If you are traveling to Hawaii and don’t have a bunch of kids or a bunch of shit, I recommend sticking to a car. The parking spaces are tight AF there. If I was driving, I know I would have side-swiped a few vehicles. Thankfully Vince was behind the wheel the whole time.Â
Tip on Booking a Rental Car
Initially, I was just going to Hertz or Budget and plugging in my dates/car needs into their sites and seeing who had the best rates. But, after advice I found in a Facebook Group for Hawaii travel, I visited the site www.autoslash.com. This site helps you find the best deal, book it, and then keeps checking out the prices daily to let you know if it becomes cheaper somewhere else.Â
I ended up saving $80 on my rental.Â
I will caveat this recommendation with a word of caution. Research the facility you are renting your car from. AutoSlash indicated that the Budget Rent-A-Car place was at the airport. This is false. When we arrived in Honolulu, we had to call a shuttle to take us to the rental car place. Hauling all our luggage around creation is not an easy task.
Not only was the rental place off-site, it was also a little…..less classy than I am used to. The bathroom is the stuff of nightmares. And, while the people were nice enough, they took FOREVER to process our car. I don’t know what took so long, but between the shuttle and them doing whatever the hell they were doing, it took us nearly two hours to finally get on the road.Â
Also, the minivan they gave us made a sound like a dying goose when you opened the sliding doors or used the remote to lock the doors. It was hilarious, concerning, and embarassing all at the same time. We had to record a video of it, just for memories.
Let’s Sum That Up
That’s a wrap on transportation for getting to and around Hawaii. Quick summary points below if you scrolled all the way here first instead of reading everything above.
- If you are traveling with kids and can’t afford first class, break up your flights in to multiple legs. The breaks are a gift for everyone.
- Choose seats in the back of the plane if you have kids, unless your connecting flights are super close. The space is nice.
- If you have to stay overnight at a hotel in between flights, be sure the hotel has a shuttle. If not, you need to rely on Ubers. And, you may need to book more than one if you have a lot of luggage.
- If you want to travel around the island (which I recommend), book a rental car.
- Book your rental car early and then use a site like AutoSlash to notify you if the price decreases. You can rebook at the lower rate without penalty.Â
- Lookup reviews for the rental car place before booking and make sure the facility is actually at the airport.Â
- Get the smallest car possible because parking spots are tight AF.
- Join Facebook Groups for traveling to your location. They are a wealth of advice and tips.
I want to go back to the islands ???