HiP 071 – The Best Time of year to Visit Hawaii, Plus Annual Events and Festivals

Hawaii Posts
Hawaii Posts
HiP 071 - The Best Time of year to Visit Hawaii, Plus Annual Events and Festivals

(Show Notes may and in fact do contain spelling and grammatical errors. I write the script for the show and in a rough draft format, which lends itself to hasty errors)

Last monday Jan. 15 was Ben Franklin Day, as I mentioned in my world calendar last week on this day, I would take out my favorite book by Ben Franklin, which is titled Ben Franklin’s Whitten witticisms

This quote popped out. It’s one of my most often used quotes from Mr. Franklin.

“If you fail to plan, you are planning to fail!” 

Benjamin Franklin

This quote is relevant because we are going to talk about planning your trip to Hawaii, I’m going to share with you the best time to visit Hawaii. As you may know, I work in the tourist industry as a executive chauffeur. While some clients tend to be quiet in the backseat, many of them will strike up a conversation. One of the most common questions is, when is the best time to visit Hawaii.

I usually reply off the top of my head, my two favorite times are late spring in mid autumn which would be April through May, and September through October. The reasons are; the flowers are still on the trees which makes the air rich with tropical aroma. During these months there are great festivals. The temperatures are almost perfect, not too hot or humid. Additionally, most schools are in session, the tourist traffic is at a minimum which gives visitors a chance to see Hawaii in all of its beauty, relaxed less crowded. 

December 2023 was filled with cold rain and wind. Albeit, not as cold as it may be in the contiguous 48 states but if people were coming to Hawaii, expecting blue skies, sunshine and warm winds, they were sadly disappointed. It’s really hard for me to wax positive about Hawaii’s weather when tourist or faced with less than favorable conditions, especially since most people only get to visit Hawaii once in a lifetime. I can’t help but feel sorry for them because they dream trip to Hawaii an unexpected and unwelcomed rainy week

While it may be true that the four months I’ve mentioned earlier, April, May September, and October are ideal months to visit. It may not be ideal times for people to travel. In Hawaii there are two seasons, the rainy season and the sunny season. Each is about six months long in the sunny season, you’re more than likely to see sunshine in the rainy season there’s a chance you may see several days of rain in a row. Yes, there is sunshine during the rainy season, just the risk of having a windy and rain drenched week is greater during the rainy  season.

I’m a glass half full kind of guy. If you listen to the show you know when I say that there’s going be rain in the forecast to not worry you’ll be able to find sunshine somewhere around the islands and if there’s no rain, there are no rainbows. Likewise, there are no waterfalls and the longer we go without rain, the more brown and dried out the island becomes and it’s less of a green lush paradise that people imagine Hawaii to be.

If you visit Hawaii more than once, it’s probably a good idea to try to experience different times of the year. In addition, it’s a good idea to try to explore all of the islands since each island has its own unique qualities, but in this segment we’re going to talk about the weather patterns that are considered consistent year-round for these islands. I’ll also mention the activities that take place annually during different seasons.

Let’s start off with the two seasons here in the islands.  Yes i said 2, of course there are 4 seasons elsewhere The rainy season and the sunny or dry season. the rainy season is from November to March and the sunny season is from April to October. You’ll notice with these seasons that I’ve just listed my preferred months of April May, September and October are the book end of the sunny season. Since my preferred months are at the beginning and the end of the sunny season. There is a chance for rain which is nice at these times because they’re usually passing showers and followed with blue skies and in those situations you’re guaranteed to see a rainbow as opposed to cloudy, windy, rainy days. On those days the sun is blocked by the clouds so you’re less likely to see a rainbow. besides rainbows, you know what else you’ll see during these months of April May September and October you’ll see travel bargains because there are fewer people traveling to the islands during this time. So they tend to lower the prices of hotels and airline tickets. In fact, airline tickets are much more affordable than they would be during the winter vacation and the summer vacation months.

The sunny season is basically all of summer, from April to October, there are many advantages to being in hawaii in the summer time, but there may be one or two drawbacks to visiting in the summer such as the higher airfare and most expensive time of year for lodging, Also during the summer month heat and humidity us higher but not as high as it may be in most parts of the US mainland.  Hawaii temperatures in the summer tend to average in the upper 80’s, 85-88 (30C) and our lows average around 78 degrees (25C). By the way the water temperature in the summer on the south shore is about 72 degrees  Another potential drawback during the sunny season, is that it’s hurricane season, which lasts from June to November. Most of the hurricanes come up from the south south-east. All along the equator south of the islands, there are storm systems which generate waves that travel north towards the south shores of these islands. That is why we have great surf on the south shore during the summer. Precipitation during the sunny season is a little less than aone inch of rain per month.

Rainy Season, is basically the months that include the tail end of fall, all of winter, and the beginning of spring. November to March. During the rainy season, you could see anywhere between 2 to 4 inches of rain on a monthly basis. The temperatures will hover around 80° for highs and 68° for Lows. All year round the islands benefit from the Tradewinds, which come in from a north north east direction. However, during the rainy season, there is a clash between the air masses that come up from the south west and come down from the north east. this produces thunderstorms, and sometimes several days of rain and overcast skies. At this time of year, there are immense storms, taking place in the northern Pacific just south of the Alusion Islands. these weather systems generate huge waves that travel south toward the northern facing shores of these islands. This is why the winter surf season is so epic on the north Shores.

Now, as I’ve shared with you, there are different weather patterns for different times of the year. Each one brings significant reason for different kinds of events. Most organizers would like to have optimum weather conditions for the event, such as street festivals concerts to name a few. Having worked in the surf business it’s ideal to have sunny skies and big surf but you can’t have big surf without the winter conditions up north pushing these huge waves down south. Surfing is a fickle sport you can’t always guarantee that there’s going to be waves, and to be able to get good waves on a nice weather day is really choice for organizations that set up surf contests

Considering the ethnic diversity in the islands, we have a wide variety of unique events and festivals and different ways of celebrating holiday seasons, such as Christmas. Here are some of the events that take place annually that you might want to take into consideration when you’re making your plans to visit the islands

Let’s start with spring. Spring is a great time to go whale watching, the humpback whales that have migrated south for the warm waters of hawaii during the winter, are still in the waters just off the islands you can watch the whales breaching from along the coastline or you can take a boat tours and get a close-up view of the whales. 


March 8 through the 10th in 2024 will be the 28th annual Honolulu festival. The festival celebrates the unique relationship between Hawaii and the surrounding Pacific rim communities It’s held every march. there are performance stages, educational programs, a grand parade that goes right through Waikiki and you can also take part in supporting our native forest by planting a koa tree

Also at the end of March, on the valley isle, Maui. Is the 32nd annual celebration of the arts this Takes Pl., March 29th through the 30th of this year 2024. The event is held annually at the Ritz. Carlton MAUI in Kapalua. This is Hawaii’s top arts and cultural festival, celebrating the spirit of Aloha through more than 60 of the states top artisan educators, cultural practitioners, speakers, and entertainers. 


In April of every year on the big island east side in the historic city of Hilo there is a hula celebration. It’s called the Marrie Monarch festival. This year its March 31st-April 6. It’s a celebration honoring David Kalakaua, otherwise known as the Merrie Monarch this festival offers an amazing lineup of hula from every corner of the Hawaiian islands, and all around the world. If you’d like traditional Hawaiian music and hula dancing, this is the event for you and guess what it’s in April, which is really one of the best months of the year.

Usually at the end of April there is a world famous festival that takes place in the streets of Waikiki in this year it will be on April 27 from 4 to 10 PM. It’s the Waikiki spam jam festival. Not only is spam, a favorite food in the islands. It’s a cultural tradition in Hawaii. A modern, cultural tradition. at the festival, there are arts and crafts and live music but the centerpiece is the18 participating restaurants who will be serving unique spam dishes during a signature block party following the event for two weeks 20 restaurants will be participating in “can to table” which is opportunity for you to go to restaurants and try spam in their special dishes


May has a few good festivals. May Day, May 1st-5th is Lei Day. Lei makers from all around the islands gather on Oahu at Kapiolani park to exhibit and thier leis as the public and a panel of judges walk about the grounds in search of the best lei. As with most festivals in the islands, there are local vendors for crafts, food, and also live performances from local musicians and hula dancers… but this event also boast a beauty pagent of sorts with the crowning of the Hawaii Lei Day Queen

Maui Onion Festival May 2-3 2024. Held at Whalers village in Ka’anapali Resort. the onions that are grown and MAUI are known as the MAUI sweet onion but what makes it so special? It’s the fact that it’s grown in.Kula MAUI, which is upcountry.There the soil is low in sulfur content, which is important in making an onion, so deliciously sweet. Also, the nights are cool, and that is credited with contributing to the onions, unique tast they say the Maui Jan is so sweet can almost eat it raw just like an apple. The only way you can reproduce the MAUI onion is to grow it in.Kula. 

Last weekend of May is Memorial day weekend and in hawaii there is a 25 year tradition called the Shinnyo Lantern floating Ceremony. This event brings together an estimated 50,000 people annually to Ala Moana Beach, where the event is live streamed telecast. It honors loved ones, while generating a collective hope towards the future people pay to decorate a floating lamp and that sunset they release the lantern into the water, it’s quite a sight to see


If you like wine and want to attend a wine and food festival on the island of Maui, you want to visit MAUI at the beginning of June this year June 6 through the 9th is the 43rd annual Kapalua wine and food festival. This annual event attracts thousands of own files, Gorman and enthusiast of the good life to celebrate and learn and experience, the finest culinary, trends, and Viniculture 

Back on Oahu the king Kamehameha, which is celebrated all across the islands on June 11 it has one of the longest parades of any time of the year it starts in downtown Honolulu and finishes at Kapiolani Park so you can grab a chair and watch it downtown by the Palace, by Ala Moana beach park or walk outside your hotel room in Waikiki to see it go down Kalakaua Av


During the summer it gets really busy here in the islands July has the highest number of visitors but during the summer months, there are several festivals that you may be interested in attending such as

In July there is a ukulele festival. It’s the largest ukulele festival in the world. That’s because ukuleles originated here in Hawaii. This festival takes place every year in July. It’s a must see ukulele, ensembles and bands show up in the islands for a weeklong celebration and you’ll be surprised to see how far away they come from. Did you know there’s ukulele clubs in Europe and Japan if you didn’t now you know. And if you’d like to see them perform, July is the time of year to visit Hawaii, so you can attend the festival.

On Kauai in July there is the Koloa Plantation Days festival. This year is from July 18-28, 2024 the festival celebrates the sugar plantation era of the garden isle. The week long festival has a wide variety of events from cultural exhibits, ation Tours arts, crafts, music, and as silent auction, and I shouldn’t forget to mention it also both Kauai’s biggest parade of the year


At the beginning of August on the island of Kauai, they have the Heiva I Kauai it’s the international Tahitian dance competition this year. It will take place on August 3 and fourth on the island of Kauai in 2024 it will be the 22nd anniversary of a unique exciting and colorful Tahitian dance and drumming competition. This annual event provides a venue for performers of all ages, to present their talents, skills, and cultural knowledge to an audience of more than 1000 attendees each day. 

In August it’s the Dukes Ocean Festival, in the heart of Waikiki. On Waikiki’s, famous Waikiki Beach and in the ocean water just offshore there are all sorts of events for you to watch. Everything from volleyball to canoe surfing standup, paddle surfing tandem surfing little cakey surfing that’s Kids surfing all the way up to professional surfers who come back to the islands during the summer, for the historic event, which honors Duke Paoa Kahanamoku. Duke is widely considered the ambassador of ALOHA & the reason why we have lifeguards today


In the month of September usually toward the end, there is one of the most popular festivals to take place in the islands. It’s known as the ALOHA festivals this year in 2024. It will be the 76th annual ALOHA festival. It’s a weeklong celebration with a royal Court a parade and a street festival known as Ho’olaulea. 


At the beginning of the month of November, every year they celebrate Queen Emma. Which I mentioned in my feature about Queen, Emma, that I posted last year. This year it will take place on November 2, 2024 from 10 AM to 4 PM. This is the 36th annual Lani festival takes place in Waimea Kauai. There are tents with exhibits Food surrounded by performing arts music and hula it’s a colorful and floral celebration of the late great queen, Emma

on the Big island we have Kona Coffee Cultural Festival. This year its Nov. 1-10 2024. It’s Hawaii’s oldest food festival since it’s inception in 1970 the Kona coffee cultural festival organization has sought to preserve perpetuate and promote Kona unique 200 year Coffee heritage the festival and local community embrace visitors and residence by sharing, unique history and culture of Kona coffee pioneers, farmers, and artisans throughout the 10 days that celebrate Kona coffee

Then in Maui in November there is the MAUI invitational, which is a basketball tournament for American collegiate basketball.

Also, beginning in November the surf contest on the North Shore commence. So there are surf contest at Sunset Beach pipeline and Alii Beach in Haleiwa. the contest include the Triple Crown, the Eddie Aikau big wave surfing contest, the hui backdoor shootout and a bunch of WSL surf contest.


The Honolulu Marathon. 26.2 miles in paradise. It’s a marathon with the Aloha Spirit. There’s no time limit and many participants walk, part of it or all of the marathon course you can enjoy the scenery and meet other marathoners from over 50 states and 40 different countries totaling more the 27,000 participats. They have options so you don’t have to run the whole marathon there’s one part of the event that’s called start to park, which is just 10 K it goes from the beginning of the marathon all the way to Kapiolani  Park, if you want to do something smaller during that weekend, they have the Kalakaua Merry mile which is on Saturday the day before the Honolulu marathon and everyone is invited to do the Kalakaua Merry mile one mile through Waikiki

And as I mentioned earlier during the winter time, it’s Christmas here in the islands but it’s not like any kind of Christmas that you’ve experienced before.  Santa Claus usually arrives in a outrigger canoe. He’s commonly seen seated on his chair at mall and shopping centers wearing an ALOHA shirt rather than his standard red and white attire. There are Christmas decorations all throughout the city and around the islands. It’s a great time of year to visit but remember it just might be a little bit wet or you could be blessed with a beautiful sun sunny week. After all it’s entirely possible because it’s been memorialized in the classic Hawaiian Christmas song. Mele Kalikimaka where the lyrics say: 

Mele Kalikimaka is the thing to say

On a bright Hawaiian Christmas day

That’s the island greeting that we send to you

From the land where palm trees sway

Here we know that Christmas will be green and bright

The sun to shine by day and all the stars at night

Mele Kalikimaka is Hawaii’s way

To say Merry Christmas to you

And then, at the end of the year of course it’s New Year’s, and if you’ve never been to Hawaii for New Year’s Eve, particularly the island of Oahu, I’m telling you it’s something you should put on your bucket list until our government clamps down on the fireworks, which I hope they never do. It is an amazing site. There are fireworks going off all throughout the island, and we’re not just talking firecrackers and pop snaps. No we’re talking giant aerial fireworks at everybody would gather at a park to watch. These are popping out of peoples backyards almost every other house. If you want to see what it looks like check out my Instagram page and look at the New Year’s Eve fireworks celebration story on Hawaii post podcast Instagram, there’s so many fireworks it’s insane and that’s what makes it such a unique experience


The Sony Open

In review my favorite months are April, May, September and October

The Rainy Season is November to March and the Sunny season is from April to October

Hawaii is beautiful year around but not every day is perfect weather. Hawaii has many festivals and events year around to give you a reason to visit all of the islands for a wide variety of festivals and events.


Whale Watching in Hawaii https://www.gohawaii.com/experiences/adventure/whale-watching


28th annual Honolulu festival – March 8 – 10 2024 https://www.honolulufestival.com/en/

 32nd Annual Celebration of the Arts – March 29 – 30 2024 https://kapaluacelebrationofthearts.com


Merrie Monarch festival – March 31st-April 6 2024 https://www.merriemonarch.com

Waikiki spam jam festival April 27 from 4 to 10 PM. https://spamjamhawaii.com


Lei Day – May 1 – 5  2024 https://en.m.wikipedia.org/wiki/Lei_Day

Maui Onion Festival May 2-3 2024 https://kaanapaliresort.com/25th-annual-maui-onion-festival/,  https://kaanapaliresort.com/25th-annual-maui-onion-festival/

Shinnyo Lantern floating Ceremony – Memorial day https://lanternfloatinghawaii.com/the-ceremony/


43rd annual  Kapalua wine and food festival – June 6 -9 2024 https://kapaluawineandfoodfestival.com

King Kamehameha Day – June 11 https://en.m.wikipedia.org/wiki/King_Kamehameha_I_Day


Ukulele Festival https://ukulelefestivalhawaii.org

Koloa Plantation Days Festival on Kauai – July 18-28, 2024 https://koloaplantationdays.com


Heiva I Kauai it’s the international Tahitian dance competition August 3 -4 2024 http://www.heivaikauai.com

Dukes ocean fest in Waikiki. https://dukekahanamokuoceanfestival.org


76th annual ALOHA festival and a street festival known as Ho’olaulea. https://www.alohafestivals.com


36th annual EmmaLani festival takes place in Waimea Kauai. https://kauaifestivals.com/festival/e-o-emalani/

Kona Coffee Cultural Festival Nov. 1-10 2024. https://konacoffeefest.com

 MAUI invitational, collegiate basketball. https://mauiinvitational.com

Surf contests on the North Shore commence. https://www.theeddieaikau.com , https://www.worldsurfleague.com, https://triplecrown.vans.com


Honolululu Marathon https://www.honolulumarathon.org


New Years Eve


Sony Open Golf Tournament https://www.sonyopeninhawaii.com

For all the events that I’ve listed, I will have a links in the show notes. Also, this segments going to be a feature segment which will be kept separate from my regular podcast so at any time of the year you’ll be able to download it and listen to all the events that are offered throughout the year and also my tips on the best time of the year for the weather.

Thank you for listening and encourage you to go to hawaiipost.com support the show by making a donation, you can donate money or you can donate your time by contributing music jingles art or anything else that you think would make the show better. Also, I encourage you to share Hawaii post with any and all your friends, especially those who are planning a trip to the islands, I bid you farewell with a fond ALOHA- AWRIGHT

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