Everything you need to know about a May 2027 Hawaii vacation

The month of May is our favorite month to vacation in Hawaii. It’s practically perfect. Crowds are down, rates tend to be lower, and the weather tends to be the best of the year. After the big waves of winter, the ocean conditions are calmer in May. It’s just a fabulous time to visit the Hawaiian Islands.

Let’s look into weather details, festivals and much more helpful things to know to enjoy the very best Hawaii vacation in the month of May.

How’s the weather in Hawaii in May?

Year round, Hawaii’s weather is warm with a bit of humidity. Trade winds make the humidity feel more pleasant.

Temperatures

The weather in May is not as hot as the summer and early autumn months, which is more pleasant. For the islands of Oahu, Maui and Hawaii (Big) Island, you can expect the daytime high temperatures in the mid-80s Fahrenheit (roughly 29° to 30°C). The northernmost Hawaiian island, Kauai, typically experiences slightly cooler temperatures. In Kauai, you can expect daytime highs in the lower 80s (roughly 27°C).

Nighttime lows will dip to the lower 70s Fahrenheit (21-ish °C). You may want to have a light sweater or jacket on hand in the evenings.

Rain

Historically, May is not a rainy month for Hawaii. Of course it’s a good idea to be prepared for a quick rain shower by wearing quick-drying clothing when you’re out hiking or sightseeing.

More weather information

For more information about Hawaii weather, check out our guide to Hawaii weather’s patterns and forecasts.

What should you pack for a May vacation in Hawaii?

Given Hawaii’s warm, tropical weather and laid-back vibe, casual, comfortable summer wear is ideal. Let’s look at what you should pack for daytime and evening wear.

What to pack for daytime wear for beach or sightseeing

These are the types of clothing that we wear most often during the day in Hawaii:

• • • Swimsuits (Bring at least two suits per person so that you’ll have a dry suit to wear each day.)
    • Swimsuit cover ups
    • Rash guard shirts
    • Quick-drying, moisture-wicking tops with sun protection (Hanes makes a very affordable performance shirt that we probably have a dozen of between us. It’s their Cool Dri tops. They’re quick-drying, moisture-wicking and they have built in UPF 40 sun protection. I have even used the women’s long-sleeve version as a rash guard.)
    • Rainproof, breathable jacket – for examples, for women, highly recommend this Columbia waterproof jacket, which is what I have. For men,  this jacket by 33,000ft is a good, affordable option. For kids,  this SaphiRose waterproof rain jacket has a lot of great features and is reasonably priced. If you are wondering why you should bring a rainproof, breathable jacket, see our article: Where do you need a jacket or coat in Hawaii?
    • Other shirts, like t-shirts – We recommend wearing light colors that don’t absorb the sun’s warmth as much to help keep you as cool as possible.
    • Quick-drying, moisture-wicking shorts, skorts, and/or trousers depending on your activities
    • Hat or visor
    • Sunscreen (See our recommended sunscreens for a Hawaii vacation. Note that you should use a sunscreen that’s Hawaii 104 Act Compliant, meaning that it’s made without Octinoxate and Oxybenzone. Additionally note that Maui County has banned the sale of chemical sunscreens.)
    • Lip balm with sunscreen (Our favorite mineral-based lip balm is this water-resistant Burt’s Bees SPF 30 that comes in three tropical flavors.)
    • For daytime shoes, we recommend flip flops for the beach and pool and close-toe, performance sandals for hiking and sightseeing. See our guide to the essential shoes for a Hawaii vacation.

What to pack to wear for evening/ dinner in Hawaii

For evening wear, you can leave the fancy clothes at home because Hawaii’s dress code is casual. Ladies might want to pack summer dresses or perhaps resort-wear tops with nice shorts, skorts, or trousers. For men, we suggest you pack summery shirts, like polos or short-sleeve button downs, along with nice shorts. If you have clothing with “Hawaiian prints” they’ll be perfect to wear on your Hawaii vacation.

For our expert packing tips from our many trips to Hawaii, see our Hawaii vacation packing guide. We provide many packing recommendations based on the type of adventures that you plan. You’ll probably discover some items that you need to pack that you might not have previously considered.

Where to stay in Hawaii in May

First, the good news is that since the rainy season is over, you don’t need to worry so much about where to stay to avoid rain. As the temperatures are ticking up a bit, air conditioning becomes much more desirable.

The vast majority of hotels have air conditioning, however you do need to pay more attention in your search criteria for vacation condo and villa rentals. If you are opting for a VRBO condo or other vacation rental, that’s where you have to be careful to check if your prospective vacation condo or villa has air conditioning. We’ve stayed in a couple of Hawaii vacation rentals without air conditioning and we really wished we had air conditioning. When searching for vacation rentals, look for filters that allow you to filter for rentals with air conditioning.

Hawaii ocean conditions in May

By May, the big ocean swells of winter are over. May ocean conditions tend to be relatively calm. Some seasonally-operated ocean tours begin in May. (In the tours and activities section, the next section, of this guide, see our note about tours of Kauai’s Na Pali Coast that can operate in May.)

No matter what time of the year you visit the Hawaiian Islands, you must respect the power of the ocean. It’s very, very important to know ocean safety.

Experts advise swimming at Hawaii beaches that are monitored by lifeguards. For snorkeling, I recommend you choose an organized-tour company as they are more informed of the safer spots and tend to keep an eye out for their snorkelers’ safety.

What tours and activities are special in Hawaii in the month of May?

First, check out our Hawaii vacation itineraries which ensure you get to experience all the “must see and do” sights and activities. For a condensed version, see our top Hawaii activities and tours by island.

For the most part, top island activities can be enjoyed throughout the year, but some experiences are seasonal. For the month of May, with calmer ocean conditions, you are more likely to be able to take ocean tours, like snorkeling, without cancellations.

For visitors headed to Kauai, taking a boat tour of the Na Pali Coast is one of the top activities. Taking a tour that leaves from the North Shore, gets you to the scenery sooner as compared to tours that leave from the South Shore. While tours that run out of the South Shore can generally run all year, the tours from the North Shore can only run from about April to October. Even then, ocean conditions in April and October can be iffy, but by May, the conditions are more consistently conducive for tours to depart from the North Shore. For a well-rated Na Pali Coast tour that leaves from the North Shore, check out this snorkel tour.

From Maui, you’re more likely to be able to take a snorkel tour to Honolua Bay.

Natural occurrences in Hawaii in May

Some special seasonal occurrences in May to note are:

• Lahaina Noon is a fascinating phenomenon that happens twice a year, in May and July. Lahaina Noon happens when the Sun passes directly overhead for locations on Earth in the tropics. The angle is such that an upright object, like a flagpole, will not have a shadow. See this link for the list of locations, dates and times that you can observe a Lahaina Noon in Hawaii.
• Jacaranda trees are adorned with stunning lavender-hued blooms. Jacaranda trees are typically found in the upcountry areas of the islands, such as the Kula area on the slopes of Haleakala.
• Though the humpback whale season is over, if you’re really lucky, in early May, you might see a whale lingering before their journey back to Alaska. It’s not very likely that you’ll see one, but keep a look out when you are on ocean tours. We have seen humpbacks as “late” as the first week in May.

Hawaii night sky viewing in May 2027

Hawaii is an outstanding place to stargaze! That is due to the limited light pollution. So, do take advantage of the opportunity to see the stars.

Here are some of the top things you’ll need to know for stargazing this May:

• See this link to find moonrise and set times. That link is set for Honolulu, but other islands won’t be too far off the times. Ideally, you’ll want to minimize moonlight as the light washes out the visibility of fainter stars and planets.
  • The new  moon(i.e. moonless) will be on May 6. That would make early May the ideal time for stargazing.
  • In May 2027, there will be a full  moon on May 20.
• The Eta Aquarids Meteor Shower peaks overnight May 5-6. See this link for more information. 

May 2027 festivals and special events in the Hawaiian Islands

Cultural festivals offer a fantastic way to learn more about Hawaii. No matter what the focus is at a festival, you’ll find a wonderful blend of food, music, and crafts. Here are the major cultural festivals happening May 2027. Please note that some event dates haven’t been announced yet for 2027. Click on the links to the event websites to learn more.

Hawaii, the Big Island

May 1 – Lei Day is a statewide celebration of the Hawaiian Lei. The official Lei Day is May 1, however, celebrations might be held on other days. Here’s what we know for 2027 Lei Day:

• • • Waikoloa Beach Resort is hosting several Lei Day celebrations on May TBD for 2027.
    • Check with the concierge at your accommodation for other potential celebrations.

May TBD for 2027 – Hilo Chocolate Festival

May TBD for 2027 – Honoka’a Western Week

May TBD for 2027 – Hilo Hawaiian Music Festival

Maui

May 1 – Lei Day is a statewide celebration of the Hawaiian Lei. The official Lei Day is May 1, however, celebrations might be held on other days. Check with the concierge at your accommodation for potential celebrations. Here’s what we know for Lei Day 2027 on Maui:

• • • May TBD for 2027 – Lei Day Heritage Festival
    • Check with the concierge at your accommodation for other potential celebrations.

May TBD for 2027 – The Annual Maui Matsuri Festival 

Oahu

May 1 – Lei Day is a statewide celebration of the Hawaiian Lei. The official Lei Day is May 1, however, celebrations might be held on other days. Here’s what we know for  Lei Day 2027:

• • • May 1 – 99th Lei Day Celebration In Kapiolani Park (in Waikiki area)
    • May TBD for 2027 – May Day at the Bishop Museum

May TBD for 2027 – Wahiawa Pineapple Festival

May 31 -Memorial Day Events – A ceremony at Punchbowl and Lantern Floating Festival are two of Hawaii’s top Memorial Day events. Check our Oahu Memorial Day Events page for more details about those and other events.

Kauai

May 1 – Lei Day is a statewide celebration of the Hawaiian Lei. The official Lei Day is May 1, however, celebrations might be held on other days. Here’s what we know for  Lei Day 2027:

TBD

May TBD – Waipa Aina Festival

May TBD – Kauai Steel Guitar Festival