Hawaii is a perfect vacation destination year-round. But some months are even more perfect in particular parts of the islands.
Writer John Rosenthal tells us where to spend the entire year in spectacular Hawaii weather.
Head to the capital as soon as Christmas vacations end. From Waikiki Beach to Pearl Harbor, the holiday crowds practically evaporate, and you can often find discounts on hotel rooms and rental cars. The weather is a serious bargain too: usually around 80 degrees, with infrequent rain. The hike up Diamond Head can be sweaty in June, but it’s lovely this time of year. Cool off with a day of snorkeling in Hanauma Bay Nature Preserve, a semi-circular volcanic crater where you don’t even have to swim in the knee-deep waters to see spectacular tropical fish.
The charms of Hana are inseparable from the legendary 52-mile road that connects it to the rest of Maui. You don’t want to do this curvaceous drive in the rain, and February is one of the least rainy times of the year. Take your time along the hundreds of hairpin turns and dozens of one-lane bridges. Stop frequently to enjoy waterfalls, secret swimming holes, and lonely ocean vistas. Spend a night in Hana so you can enjoy Hamoa Beach, one of Hawaii’s finest, or Oheo Gulch, where a series of stream-fed natural pools cascade into the ocean.
March: South Maui
The beach towns of Kihei, Waimea, and Makena enjoy desert-like conditions year-round, so you’re practically guaranteed sunshine. And it’s not nearly as hot this time of year as in mid-summer, when temperatures can get into the 90s. March is also one of the best times of year for watching endangered Humpback whales that migrate more than 3,000 miles from their summer homes in Alaska to mate and give birth in Hawaiian waters. From an oceanfront lanai, you may see them blowin’ out thar’, but you’ll want to hop on a cruise to see these gigantic mammals playing and breaching.
April: Kohala Coast, Big Island
The Big Island’s northwest corner has a split personality. The coastal portion is home to some of the most beautiful (and popular) beaches in all of Hawaii. It’s no surprise why luxury resorts like Hapuna Beach Prince Hotel and Mauna Kea Beach Hotel chose to set up shop here. But drive just a few miles north or east and you’re in sleepy, old school Hawaii towns like Hawi or Waimea, where you’re more likely to rub elbows with paniolo (Hawaiian cowboys) than fellow tourists. April here is warm rather than hot, with little rain.
There’s no bad time to visit Kauai’s south shore, which enjoys 80-degree days with little rain nearly year-round. Come here to relax on the calm, south-facing beaches, snorkel just a few yards offshore, play a different golf course every day, and feast at restaurants helmed by some of Hawaii’s best chefs. Roy Yamaguchi and Peter Merriman, two of the founders of Hawaii Regional Cuisine, each have restaurants on Poipu. It’s also the best launching pad for exploring the underrated Kokee State Park, located in a cloud forest above the overrated Waimea Canyon.
With 277 days of precipitation and 120 inches of rain annually, Hilo is the wettest city in America. Hey, ‘no rain, no rainbows’, as locals are fond of saying. The waterworks are at their lowest ebb in June, when a mere seven inches falls on Hilo’s east-facing beaches and ubiquitous gardens. Hawaii’s second-largest city is a shopper’s paradise. The Farmers Market, which isn’t limited to fruits and vegetables, is the best in Hawaii (here’s where to get a handmade lei). The surrounding boutiques on bayfront Kamehameha Ave., especially Sig Zane Designs, are the place for quality Aloha wear.
July: West Maui
Kaanapali, Honokowai, Napili and Kapalua are beach towns that encourage you to park yourself for a week. In July, enjoy warm but not hot weather and a sun that sets behind neighboring Lanai late in the evening. For an even closer look at Lanai, jump aboard a sailboat cruise from nearby Lahaina Harbor. Lahaina is also the place for a luau. Sample traditional Hawaiian specialties like poi (taro root pudding) or ahi poke (tuna tartare). The whole kalua pig roasted in an underground oven is almost as good a show as the authentic Hawaiian dancing.
August: Upcountry Maui
Yes, summer is when the sun rises before 6am, making a pre-dawn visit to Haleakala even more of a hardship. But unless you’re planning to bike down the mountain – coast might be a better description, since pedaling isn’t required – there’s no reason to get up super early. The National Park is beautiful all day, not just at sunrise. In fact, locals agree that sunset is the best time to visit Haleakala.
It’s a whole different world in upslope towns like Makawao and Pukalani, where small guesthouses and quaint B&Bs welcome visitors and activly encourage you to mingle with locals at unassuming shops and restaurants.
September: Volcanoes National Park, Big Island
The 2018 eruption of Kilauea closed Volcanoes National Park for about a year but the iconic Kīlauea Iki Trail reopened again in April 2019. The best time to visit is September when the air around Mauna Loa never gets much warmer than the 73°. Only time will tell what the impact will be on hiking paths like the Devastation Trail, which descends into the black-lava-floors of formerly dormant craters. But the opportunity to explore Hawaii’s newest territory should be on anyone’s bucket list now it’s safe to visit again.
Several of Hawaii’s best beaches line Kauai’s gorgeously lush north shore, including Hanalei Bay, which nabbed Dr. Beach’s top ranking in 2009. In winter, the rains responsible for this tropical jungle setting can mar a week’s vacation. October, on the other hand, is the driest time of year for hiking the Kalalau Trail, the only way into the Na Pali coast, a region of dense foliage that has stood in for Jurassic Park. The full 11 miles are for experts only, but anyone can do the first two miles, which afford a glimpse into the Kauai of centuries past.
November: Oahu’s North Shore
The last few weeks of Oahu’s dry season overlap with the first month of big wave season right before Thanksgiving. You can watch the best in the world tackle 30-foot breaks in Haleiwa Beach Park at the first leg of the Triple Crown of Surfing. Travel through south seas history at the Polynesian Cultural Center. Or spend the day sampling different preparations of shrimp at the original Kahuku food trucks. The charming town of Haleiwa itself has terrific shopping, whether you’re looking for hand-carved koa bowls or a shave ice to cool off.
At the shops and restaurants in Kailua Kona town, as well as the beaches of the luxury resorts up the coast, you’re sure to hear the sounds of Mele Kalikimaka, the song that teaches you how to say Merry Christmas in Hawaiian. And what better place to spend the holidays than the west side of the Big Island, where dry sunny 80-degree days are the norm. The only compromise you’ll have to make is opening your Christmas presents under a palm tree instead of a Douglas Fir.
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