May is one of the best times to visit Hawaii since it falls into the shoulder season where you’ll often find great travel deals. It’s the perfect time to experience Hawaii in Summer without the summertime crowds!
The first south swells of the season have usually hit, so you’ll see lots of action at the beaches in and around Waikiki. Waters on the northern sides of the islands are generally calmer in the summer, perfect for snorkeling, diving, and stand up paddle boarding!
One of the greatest parts of traveling to Hawaii is that weather will rarely be much of a factor when deciding when to go. In general, Hawaii is warm and sunny almost year round, with two major seasons—Winter and Summer. May kicks off summer season in Hawaii.
Starting with summer, from May through mid-October, daytime temperatures are in the 80s and night times from the low 70s to the low 80s. Consistent trade winds keep summer temperatures tolerable. Konas can blow in from the south or west and bring humid, sticky, or sweltering weather and thunderstorms. Showers are short. Days are longer.
Because May has brought about less winds and warmer temperatures, May can be a great time to save a few bucks and go camping in beach camping in Hawaii. For a list of the best campgrounds on Kauai, check out Where to Camp in Kauai: A Guide to the Garden Isles’ Best Spots for Pitching a Tent.
Because the winter rainy weather has subsided by May, this time of year can be an ideal time to check out the Na Pali coast. With lots of sun, you can choose to Hike the Kalalau Trail, or if you’re not up for the 18-mile hike, you can take a Na Pali Catamaran Tour.
With calmer seas, May is the perfect time to go snorkeling or diving at Tunnels Beach in Kauai.
Calmer oceans make for some ideal snorkeling and diving conditions, and snorkeling in Maui is some of the best in the entire archipelago.
Lots of May Sunshine also makes for perfect conditions to get outdoors. Visitors to Maui in May can opt to go mountain biking on Kaupo Road or go camping at Haleakala National Park.
May is a great time to get out and enjoy the blue skies with a drive to the Dole Pineapple plantation.
Still want to know more about what to do during your vacation to Hawaii? Check out these posts:
Things to do in Kauai
Popular things to do in Maui
Free things to do in Hawaii
5/1 – Lei Day - While the rest of the world celebrates “May Day”, in Hawaii, May 1st is Lei Day. You’ll often see people sporting fresh flower lei and there will be many opportunities to learn how to make one yourself. If you are on Oahu, the city sponsors a beautiful Lei Day festival at Kapiolani Park with demonstrations, a royal court, and more. Details here. For other islands, check out this article. (all islands)
5/1 – Heart & Soul in Concert – This free concert at Ala Moana Center Stage is to raise awareness for Big Brothers Big Sisters of Hawaii. One of the members was Hawaii’s Big Brother of the Year and the group has been nominated for Na Hoku Hanohano awards for Most Promising Artists and Island Contemporary Album of the Year. 4pm to 6pm. Details here. (Oahu)
5/5 – Cinco de Mayo Block Party – Nuuanu Avenue will be full of food, music, and other entertainment for the annual Cinco de Mayo block party again this year. Free and open to the public, with live music from 6pm to 10pm. Details here. (Oahu)
5/6 – First Friday – The monthly First Friday block parties take place in Downtown/Chinatown on Oahu and in Wailuku, Maui. You’ll find a variety of activities, performances, live music, food, and entertainment to enjoy. (Oahu, Maui)
5/7 – Maui Onion Festival - This free event takes place annually at Whaler’s Village and is dedicated to all things celebrating the sweet Maui onion. Enjoy the festivities, maui onion eating contest, recipe contests, chef demonstrations, beer garden, and live entertainment. Details here. (Maui)
5/8 – Mother’s Day - Open Table has a listing of restaurants where you can take your mom out for Mother’s Day brunch or dinner, which is always a nice treat. (Big Island, Maui, Oahu, Kauai)
5/14 – Maunalua Bay Heritage Festival – This festival provides an opportunity for the community to learn and explore the cultural and biological heritage of the Maunalua Bay region through kupuna talk story events, cultural and historical booths and demonstrations, and a learning expo showcasing current science and management of the Bay’s natural resources. Details here. (Oahu)
5/14 – Visitor Industry Charity Walk – The Visitor Industry Charily Walk is a statewide event sponsored by the Hawaii Hotel and Lodging Association and takes place on O‘ahu, Maui, the Big Island and Kaua‘i, being described as one of the largest single-day fundraising events by a nonprofit organization in the state, benefitting numerous nonprofit organizations on four major Hawaiian islands. Read more details for Kauai, Maui, Oahu, and the Big Island. (all islands)
5/14 & 5/15 – Hawaii Book & Music Festival -The 6th Annual Hawaii Book and Music Festival is held on the Honolulu Municipal Grounds and features local authors, entertainment, publishers, and booksellers. Guest authors, including NPR’s Sarah Vowell, will be featured this year as well. Details here. (Oahu)
5/22 – 5/28 – Restaurant Week Wailea – Prix fixe menus for only $29, $39, or $49 at some of the best restaurants on Maui will be available for this week. Check the website for menus for your favorites and book reservations as far in advance as possible if you want to score a table! Details here. (Maui)
5/26 – 5/29 – Na Honku Hanohano Music Festival – This music festival celebrates local music and culture and includes workshops, entertainment, and more. The most anticipated festival event is the Na Hoku Hanohano Awards on Sunday evening, known as the “Grammy’s” of Hawaii. Details here. (Oahu)
5/27 – Divas Night Out – This monthly “girls’ night out” at the Grand Wailea on Maui is a two-part evening featuring delicious food, fashion shows, spa treatments, and more. Held on the last Friday of every month, it’s been popular with both visitors and locals alike. Details here. (Maui)
5/27 – Art After Dark – This monthly event is held at the Honolulu Academy of Arts from 6-9pm on the last Friday of every month. It draws a young professional crowd and themes rotate monthly – this month’s theme is Marrakech Express. Events throughout the evening usually include gallery tours, hands-on projects, entertainment, cocktails and food. Details here. (Oahu)
5/30 – Memorial Day Lantern Floating - If you’ll be on Oahu for Memorial Day, a popular ceremony is held yearly at Magic Island featuring thousands of floating lanterns launched at the shore at sunset. It’s a gorgeous evening, and a great way to remember your loved ones. Details here. (Oahu)
The great part about traveling to Hawaii during May is that you’ll be able to enjoy the beginning of the summer season weather, without having to deal with high-season airfares. May falls into the shoulder season in Hawaii, when fewer tourists make for cheaper rates on flights to Hawaii, less expensive hotel rooms and plenty of great deals to Hawaii.
It can be more affordable to find a hotel in Hawaii during May than at other times of the year, as peak travel season to the islands has not yet arrived. Whether you are looking for a high-end resort, mid-range hotel in Hawaii or even a hostel in Hawaii (though beach camping in Hawaii is always another option), than you should have no problem finding empty rooms and maybe even discounted prices during May.
Photo from R.J. Malfalfa flickr
