What To Pack: Hawaii In The Winter

Hey There!

I’ve got some exciting news: I will be spending 5 days in Hawaii for work, leaving this Friday. I am super stoked about this trip, but it came as a total surprise and it’s very last minute. First things first, what do I pack?!

90% of my travels are work related and the other 10% are for pleasure. This trip is scheduled as a work trip and I will be working EVERY single day that I’m there, but that doesn’t mean that I don’t get to explore after hours. Packing light can get tricky when you are trying to fit in a dual purpose trip aka work & pleasure.

Checked bags are not for me

I avoid checking a bag AT ALL costs!! Waiting in line, paying the extra fee (only with some airlines), wasting 30 minutes or more waiting for my bag at baggage claim… that does not sound fun to me! Instead I bring a carry-on and a computer bag (or in some cases a purse). I have managed to fit 15 days worth of clothes in a carry-on bag. Yesssss this is no joke!

Though this can get tricky when you need to bring several different styles of clothing and/or shoes. Work often requires specific attire and then beach days and/or exploration days are the totally opposite. So what do you do in these situations?! PLAN AHEAD.

Do as much research on your activities while there so you don’t over pack. Write out a mock itinerary of your day to day activities: starting with the morning and working your way all the way until you are under the covers and about to knock out.

  • Outfits that can be dressed up or down with one simple change.
    • Ladies, you all know what I’m talking about here. We all own that dress that is extremely professional with the right blazer and them BAM remove the blazer and you have the perfect cocktail hour dress. OR throw a jean jacket with it and you have yourself a casual sun dress. Outfits like these are so practical for packing minimally.
  • Wear your chunkiest shoe to the airport.
    • This might seem like a pain to go through the TSA security check, but it will open up so much space by not adding them to your luggage. Pack the sandals and heels, wear the sneakers.
  • Travel Compression Bags ARE GREAT!!
    • These bad boys do wonders for fitting as much as you can in a tight space. They are also good to have if you are going to a beachy destination. Throw your moist clothes and water shoes in one and seal it up tight, no worries about getting your other items sandy or wet!
  • Check The Weather.
    • Seems obvious right? Well there has been countless times I have arrived at my destination and one of the girls I’m working with did not research the weather. They were so unprepared and thankfully everytime we were all able to share excess sweaters and/or shorts, but doing something as simple as checking the weather prior to packing can make or break a good vacay. I check in often: two weeks prior, one week prior, 3 days, and then 2 days before. Weather can change so quickly so checking in on what the weather is going to be like during the days of your trip, are not only super simple and not time consuming AT ALL, but they will also get you pumped for your trip. Who doesn’t like a little reminder that they will be spending a few days somewhere tropical?!
  • Hawaii Summer vs. Winter
    • It is a tropical destination and the weather stays pretty warm even in the Winter months, but be prepared it is NOT Summer. I can expect much wetter weather than normal, chilly nights, and possible temps below 80 degrees.
    • Pack at least one cardigan, one heavier coat or jacket, and a pair of jeans. You can expect 1 out of 5 days to be rainy and chilly. A wind breaker might be nice for those random rain storms.
    • If you plan on spending some time hiking one of their many beautiful trails, expect muddy conditions. During the Summer months you can hike just about any trail in Shorts, a tank top, and sneakers. Well that is not the case in December. It might be a little over-cast and muddy, but I still highly recommend checking out a trail or two!
    • It’s location makes for close to perfect weather year round so definitely don’t skip the sun dresses and ‘kinis ladies!

I have decided to save a few of my tips for my Instagram story! Go check it out as today is the day, that I am packing for my trip!

Make sure you follow me on Instagram, Twitter, and Facebook to see content from this trip! As always, I hope you enjoyed reading this article. I love to receive feedback so if you have any, comment below. Have a wonderful week friends!




7 thoughts on “What To Pack: Hawaii In The Winter

    1. What’s the link, I’d love to read it! It can be tricky when it comes to not over-packing, but yet being prepared for weather changes. I’m glad you enjoyed it! Have a wonderful rest of your week!! Xx

  1. This couldn’t have come at a more perfect time!! I leave for Hawaii this week. Thanks for sharing, love following your blog.

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