In this article, I’m going to cover just about everything one would need to know in regards to a Hawaii vacation. I’ll cover when is the best time to book a vacation, the best time of year is to go regarding weather and what to pack for Hawaii to take the guessing work out of what to bring, or what not to bring. The goal here is for you to have a perfect vacation getaway.
When considering what to pack for a trip to the Hawaiian Islands, there are two major things to think about; the activities you will be doing and what sort of climate you will be doing them in. Hawaii is not all flowered shirts and flip-flops. Far from it. Each of the islands has its own unique vibe, and what you do will dictate how you should pack.
If you plan on visiting one of Hawaii’s stunning dormant volcanoes, at 10,000 feet you are going to need to dress in layers! We went on an epic sunrise bike tour to Haleakala National Park in Maui, and at the crack of dawn at the summit, the temperatures were pretty chilly.
The Big Island has the widest array of climates with its desert stretches of road, temperate rainforests and the cool dry wonder of Mauna Kea. Maui has Haleakala Crater and Oahu has Diamond Head. In fact, the Hawaiian Islands put together encompass the vast majority of the planet’s climates. So, you should be prepared with a variety of clothing and gear options.
But before we dive into what to pack for Hawaii, let’s cover some other commonly asked questions.
When Is The Best Time To Go To Hawaii?
Naturally, most vacation travelers come to Hawaii when the weather is lousy elsewhere. Making the mid-December to April time of year the more popular “busy season.”
Of course in the busy season, the prices for resorts go up, and the capacity is generally higher. In particular, the last two weeks of December and the first week of January are prime time for travel dates to Hawaii. Spring break is also jam-packed with families taking advantage of the school holiday.
Some people have limited choices to when they can book a trip to Hawaii, so they prefer to focus more on the weather as a guide. The following is a quick breakdown of what to expect throughout certain months of the year. For a more exact look at Hawaii’s climate throughout the year from island to island, check out this excellent climate of Hawaii website.
Hawaii Climate Overview
- SEP-NOV Autumn, Great waves, Decent rainfall mostly at night
- DEC-FEB Winter, Highest rain for the year, Huge waves
- MAR-MAY Spring, Mostly Pleasant, Smaller waves, Good for swimming
- JUN-AUG Summer, Highest temperatures for the year, Minimal amount of rain
When Is The Best Time to Book A Trip To Hawaii?
Naturally, more time give you more options. If you can be flexible with your travel dates, you can get a better deal. However, my advice would be to watch rates like a hawk. They can fluctuate quickly often, so you’ll need to be ready to pounce if you see a great deal.

Image Credit: CheapAir.com
A study by CheapAir.com found that the average prime booking time is about 70 days before you want to leave. They have looked at the seasonality of booking to give you more detailed booking window recommendations.
What to Pack for Hawaii
Alright, time to get focused on what to pack for Hawaii… or more accurately, what is it that are you forgetting that you should bring on your trip. The list below is broken up into helpful sections followed by recommended highly reviewed items at Amazon with free shipping to make life easier for you.
Clothing For Her
- A sundress and maxi dress for walking around town and going to dinner.
- Two tank tops/t-shirts and two pairs of shorts. You can mix and match these!
- A pair of moisture wicking/quick drying trousers and/or a pair of jeans.
- At least two Swimsuits and a cover-up – but that entirely depends on how much time in the water you plan to spend. Some people bring a swimsuit for each day they will be in Hawaii, and that’s fine! You can even wear a swimsuit underneath your street clothes for a quick change to the water later. Just know that most hotel lobbies require you to have at least a cover-up over your swimsuit.
- A light sweater and a windbreaker/rain jacket. Unless you plan on spending ALL of your time at the beach and/or pool, you will (I hope!) be doing some exploring in the rainforest and mountains. It will get chilly and wet!
If you are going out to a fancy dinner, don’t bother bringing formal attire (unless you are attending an event that specifically calls for it, of course!) You are on island time now and even the most upscale restaurants have a casual dress code. A nice maxi-dress or collared shirt/capris for the gal and a button-down shirt/casual slacks/shorts for the guy will suffice.
Clothing for Him
- Two Casual shirts for running around town and a couple of dressier button-down casual shirts for evening or going to a nice dinner or show. And, I have to say this: if you don’t want to look like a tourist, don’t wear a Hawaiian shirt!
- A pair of moisture wicking/quick drying trousers and/or jeans.
- Two pairs of casual shorts.
- At least two pairs of swim trunks. Especially if you will be spending a lot of time in the water.
- A light sweater, a light jacket and/or rain jacket.
When you’re looking to save space on you what to pack for Hawaii to-do list, the guy’s portion of clothes usually takes of the least amount of luggage space. This is usually where the women can add that extra thing. Truthfully, guys don’t need to worry about as much, there are lots of opportunities to buy what you need in Hawaii. Besides, if you wanted a Hawaiian shirt, get one in Hawaii.
Shoes
Your feet are important no matter where you are traveling too. While a vacation might be the perfect time to upgrade your footwear, make sure you break them in beforehand. A new pair of shoes of sandals needs time to get used to your feet. Don’t make the first time you ever wear them on your vacation, especially if you plan to do a lot of walking or if your traveling in them. Comfort is key.
- Waterproof Shoes/Sandals – Closed-toed sandals are perfect for hiking and being in the water.
- Hiking Shoes – good sturdy hiking shoes or boots to support your ankles are needed for any hiking.
- Flip Flops or Sandals. Bring at least two pairs of shoes for whichever activity you plan on doing the most.
Travel Gear & Accessories
It goes without saying you shouldn’t buy something for the sake of buying it, but you also don’t want to have a boring vacation. If you’re a more of a beach bum and just want to hang out, that’s cool, but try expanding your horizon’s with something new like snorkeling, surfing or planning a Day Trip.
As I’ve gotten older, I have found that I’ve spent less at the swim-up bar and more time exploring all the things to do while on vacation. If you’re going for more than a week, check out some of these travel gear recommendations and accessories.
- Underwater Camera. Especially if you’re going to snorkel. Taking an underwater photo of a sea turtle just a few inches from you is fantastic.
- Waterproof Beach Bag
- Waterproof Phone Case – everyone has a smartphone. And chances are you will want to take a quick photo somewhere very near the water. We’ve all dropped our phone at the most inopportune time, so this item is essential.
- Lightweight Waterproof Backpack – great for hiking, biking, or just walking around. So much better than a purse and hands-free.
- Mosquito Repellant. You will need this if you will be spending any time in the rainforest or tropical areas.
- Sunscreen with a high SPF. Hawaii is close to the equator, making the sun’s rays stronger than back home. Of course, there is plenty of sunscreen to buy in Hawaii, but expect to pay more.
- Fast-drying travel towel – no need to bring regular or beach towels. They are bulky in your suitcase, and most hotels will provide them for you.
- Refillable Water bottle.
- Hat
- Polarized Sunglasses
- Binoculars if you will be doing any whale/bird/lava watching. Check out our article on the Best Compact Binoculars available.
- A small first aid kit is a very good idea, and pretty much essential if you will be doing any hiking.
What NOT to bring
- No need for high heels, ladies! That is unless you just can’t do without them. But even then, you will look out of place unless you are going to a nice restaurant or show.
- If you already own snorkeling/diving gear and plan on doing any of that, of course, bring it. I highly recommend snorkeling, it’s so much fun! But many people will buy snorkeling gear just for their one trip. Don’t. There are so many places on the islands to rent gear, and it’s not that expensive.
- Don’t bring unnecessary gadgets or valuables. This is true when traveling anywhere. Unless you absolutely need them during your vacation, give yourself peace of mind and leave them at home.
- Do NOT bring any plants or fruits. If you do, you will be subject to quarantine, and bringing such items into Hawaii will disrupt the fragile ecosystem.
Don’t Overpack! It’s easy to get carried away and bring all of your fair-weather clothing. But be choosy and only pack a maximum of 4-5 outfits, even on a two-week trip. You can do laundry while you’re there and it will save valuable suitcase space.
Leave some extra space when packing. You will surely leave Hawaii with at least one or two souvenirs, and you want to save room for those! If you forget to pack anything, don’t worry. Anything you could possibly need that you forgot can be bought once you get to paradise. Just know that it will likely be more expensive than if bought at home.
Hawaii in 2018 – Is it Safe to Travel to Hawaii Right Now?
As you may have heard, there has been two weeks of volcanic activity that has sent lava flows into neighborhoods and destroyed at least 26 homes. Due to this, the Foreign Office has issued an update to its travel advice for those planning on visiting Hawaii, following a volcanic eruption of Mount Kilauea on Big Island on May 4. Click Here for an up to date link to Hawaii travel and news information. From there you will see there is nothing to worry about.
Thanks for reading and enjoy your trip!