What to do when it rains for the entirety of your Hawaiian vacation

Share on FacebookTweet about this on TwitterShare on Google+Share on TumblrShare on StumbleUponPin on Pinterest

01. Introduction: Hawaiian island hopping!
02. Alaska Airlines 737-800 economy class San Diego to Kona
03. Island Air ATR 72 Kona to Honolulu
04. Vive Hotel, Waikiki
05. Mokulele Airlines Cessna 208 Grand Caravan Honolulu to Ho’olehua
06. Mokulele Airlines Cessna 208 Grand Caravan Ho’olehua to Kahului
07. Mokulele Airlines Cessna 208 Grand Caravan Kahului to Kona
08. What to do when it rains for the entirety of your Hawaiian vacation
09. Grand Naniloa Hotel, Hilo
10. Hawaiian Airlines 717-200 economy class Hilo to Honolulu
11. Hawaiian Airlines A330-200 Extra Comfort (premium economy) Honolulu to San Diego

I’ve always been a big fan of expecting the worst but hoping for the best, and that line of thinking has served me well over the years. Travel is a very complicated thing with many moving parts working in unison to create unforgettable memories, and oftentimes one little hiccup can send the entire expirence spirailing out of control. For many, the possibility of something going wrong makes travel a lot more stressful than a day at the office.

raindrops in hawaii

Rain, rain, rain!

Unfortunately, except for the very beginning and end of this Island-hopping trip, it rained. And rained. And then it rained some more. It was sunny in beautiful when I first arrived in Kona, and it was sunny and beautiful when I was back at the airport ready to fly home two days later. But every moment of the time in between was rainy. Some of it very heavy with incredible wind. Perfect timing, right?

Even though I always plan for the worst, I wasn’t really expecting it to rain that much and it was starting to bring me down halfway through the second day. What are the odds that it would rain this much on the exact days that I would be here? I was really looking forward to bright sunshine and gentle warm trade winds, but what I got was something just short of a typhoon.

hawaii scenery in the rain

I can only imagine what this would look like under bright sunshine. Still beautiful though, right?

Oh well. Life can’t always be perfect. Despite this minor setback, I still found myself having a very good time and feeling the wanderlust flowing through me like it always does when I travel. I felt energized and curious, anxious to explore and see new-to-me landscapes.

Here is how I managed to have fun in Hawaii despite all the rain:

1). I didn’t have an overly detailed itinerary

Everyone knows at least one person who just can’t relax during vacations. You know exactly who I’m talking about: the person who plans nearly every minute of every day, and is always 10 minutes away from complete meltdown if something strays off track. It’s stressful to be around people like this, and I don’t like to travel with anyone who is more obsessed with hitting all the sights than just taking it hour by hour and going with the flow.

driving in Hawaii rain

Enjoy the experience and get out there no matter what the weather!

It’s ok to have a plan though. I always have a general plan of things I want to do when I travel, but it’s not set in stone and I’m ok if I miss something. My sister takes things one step further by actually writing everything down and compiling maps, but she’s still smart enough to throw it all in the trash on a whim if things just don’t work out that way. That’s exactly how she planned our southwest adventure and Lake Tahoe trips – structured, but still highly flexible. They were both awesome trips by the way…

2). I was enjoying the moment

Every time I started feeling depressed thinking about all the rain during this trip, it didn’t take long for me to come to my senses and realize that this was still a lot more fun than a normal weekend at home. It’s not often I get the chance to jet off to Hawaii and leave the stresses of normal adult life behind, so just enjoying the fact that I was seeing things I’ve never seen before in the most beautiful part of the world was enough to keep me happy and pushing forward. We take too much for granted in this life, bouncing from one thing to the next without thinking, so taking a moment to stop and look around is a refreshing feeling.

rainy Hawaiian day

Rainy Hawaii is better than no Hawaii.

3). I learned to embrace the beauty of Hawaiian rain

Have you ever experienced a heavy Hawaiian rain storm? I don’t mean looking out at the pouring rain from the comfort of your 5 star hotel room – I’m talking about being out in the rain without an umbrella, barefoot, and grinning from ear to ear as you feel every rain drop pelt you with a slight cold sting. No? Well I’m here to tell you that you’re missing out on one of life’s amazing little pleasures.

driving through hawaiian jungle

The jungle comes alive in the rain!

The rain in Hawaii just feels different. It sounds different as well – the mix of rain falling on large palm fronds and exotic birds singing is something special, a soundtrack you aren’t going to find many other places on earth. Enjoy theses moments. They don’t come often.

4. I turned it into a scouting trip

One of my dream jobs has always been to be a location scout for the Hollywood movie studios. They essentially pay you to fly around the world searching for just the right location to shoot movie scenes, and for a traveler who needs a day job, it doesn’t get much better than that. That’s why I always morph into “scout mode” whenever I’m on a trip that isn’t going as planned. I’m essentially giving up on the current trip, throwing in the towel on trying to make it the epic adventure I had planned. Instead, I start planning my return trip (the redemption trip, as I like to call it) because hey – I’m always looking for an excuse to travel and trying again always sounds like so much fun.

rainy hawaii airport

I’ll be back. You can count on that.

So – for the remainder of this trip, I’m mentally taking notes about the things I want to see next time. There will always be a next time.

Making the best of unfortunate situations is a completely mental process, and it does take practice. I remember all too well the feeling of being an impatient 8 year old boy who never got to eat what he wanted for dinner (I’m so sorry mom!), and it wasn’t until I was in my mid 20s that I started feeling like I had learned that expecting amazing things to happen every moment of every day was a sure fire way to live a miserable life.

Focus on today, enjoy the moment, and if at first you don’t succeed, you can always try again.

How the heck am I able to fly in business class all the time?

Subscribe to my mailing list and and I'll share with you a detailed list of the top 5 tools that I use that allows me to fly in international business for free on a regular basis!

Thank you for subscribing! Please check your email - a confirmation link has just been sent to you and your subscription will not be active (and the free report not available) until you click that link.

Something went wrong.