Hawaii is one of those wonderful vacation destinations that has something to offer during any time of the year. Deciding what to pack is always easy when you’re heading to Hawaii: flip flops, sunglasses, a couple of swimsuits, and your most casual clothing. When you book a waterfront vacation rental in Hawaii, you can effortlessly spend your days relaxing at the beach, or partake in attractions like whale-watching cruises and luaus. If you’re deciding when to plan your trip, take a look at the range of activities and events that occur during each season.

Source: Flickr/Bernard Spragg. NZ

1. Summer

While there’s really no bad time to visit Hawaii, summer brings a combination of heat and crowds, as families on summer vacation head to the islands. Summer is the dry season, so if you’re not a fan of rain, you’ll appreciate the general lack of rain. While summer is not peak season in Hawaii, it does get crowded, so you may experience a bump in the cost of your airfare or rental car.

Summer also brings calmer seas to the Hawaiian Islands, which is good news if you’re hoping to splash in the surf with your kids, but less than great news if your surfboard was on your “what to pack” list. All other oceangoing activities, including kayaking, swimming, and paddle boarding are all just as good in summer as in any other season, and possibly even a tad better thanks to those calm, warm seas. In particular, summer is a great time for snorkeling; if you didn’t cram your own gear into your suitcase, check out Snorkel Bob’s on Maui, Kauai, Oahu and the Big Island for rentals.

If you have flexibility in scheduling your vacation, try to come at the very beginning or very end of summer, when it’s not so hot and while kids are still in school (or starting up again). You’ll also have an easier time finding the perfect vacation rental during these tiny shoulder season periods.

2. Fall

If you can tear yourself away from the daily grind in the fall, you’ve found a wonderful time to visit the Hawaiian Islands. Fall weather is absolutely perfect, with highs in the 70s and the rainy season not yet in full swing. Airfare prices also drop during the fall; you can expect to find some of your best airline deals between September and early December.

Because of the drop in tourist numbers, locals come out to celebrate their state in the fall with the Aloha Festivals, a six-week series of festivals that takes place across six islands. Enjoy parades, block parties, and special cultural events throughout the islands, and take advantage of special Aloha Week discounts at restaurants like Cinnamon’s on Oahu. Also, head to the Big Island in the fall for the Ironman Triathlon. Cheer on these world-class athletes as they break records in running, cycling, and ocean swimming, and head to popular athlete hangout spots like Island Lava Java or Da Poke Shack to bump elbows with the Ironman stars.

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3. Winter

There’s a reason Hawaii gets crowded in the winter — it’s just too wonderful to be believed. While other states are shivering in the snow, visitors to Waikiki Beach are enjoying an average daily high temperature of 80 degrees and strolling through Lahaina in the evenings wearing flip-flops and shorts — when it’s not raining, of course, since winter is Hawaii’s rainy season. If you’re a surfer or a surfing fan, winter is likely to be your favorite time of year here, because it’s also when the giant waves are visiting. Head to the Vans Triple Crown of Surfing on Oahu’s North Shore to watch the pros at their best, or check out the 20-foot waves at Maui’s Peahi surf break or Kauai’s North Shore.

Humpback whales also head through Hawaii’s protected waters during the winter, so a whale-watching cruise is a must-do attraction when you visit, especially between January and March. Check out Pride of Maui for amazing whale- and dolphin-watching cruises on Maui. If you’re on Lanai, head to Ultimate Whale Watch, and on the Big Island, Captain Dan McSweeney’s Whale-Watching Adventures and Tom’s Barefoot Tours both get you out on the ocean to watch these gentle giants breaching and splashing.

4. Spring

As winter turns to spring, rain clouds disappear from Hawaii and the dry season begins. Beginning in April (after spring break), airfare prices start to drop. However, you’ll see an uptick in crowds around the first week of May as Japanese tourists show up for Golden Week, a cluster of Japanese holidays. Spring is a particularly beautiful time to visit Hawaii as flowers explode around all the islands. A particularly great week to visit, if you’re headed for the Big Island, is the week immediately following Easter. Book a vacation rental in Hilo during this week to enjoy the Merrie Monarch Festival, which is named for the last king of Hawaii and celebrates Hawaiian culture. Buy tickets early to see some of the top hula dancers in the world in competition at the Edith Kanakaʻole Multipurpose Stadium.

5. The Best Time to Visit Hawaii

The best time to visit Hawaii varies depending on your priorities. If you’re traveling on a shoestring, booking a vacation rental will definitely help you stay within your budget as opposed to staying at pricey hotels, and traveling during the fall makes a big difference in costs as well. If the weather is an issue for you, consider May and June or September and October for a combination of warm water temperatures and less rain. If you want to avoid crowds, again take a look at September, October, and May, and try to avoid summertime and especially the winter holiday weeks.

Of course, if you have special activities you want to participate in, they’ll help determine your vacation planning. You’ll find the best snorkeling in the summer, which is also the best time of year for nature photography. However, book your trip between October and April if you’re a surfer or want to watch great surfers in action, and plan on a winter or spring vacation if whale-watching is on your list.

 
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