If you’ve traveled to Hawaii in the past, chances are you plan to visit again. Who wouldn’t? With so much variety on what to see and do and where to go, it seems one could spend every vacation for the next few years just exploring the variety of Hawaii. Of eight islands, there are four main ones that people travel to, Oahu, Maui, Big Island and Kauai. Beyond that, two more are traversable, Lanai and Molokai, but vacationers are less likely to explore these islands because of their limited accommodations.

Despite this, even if you spend weeks on one island, you’re bound to have an array of experiences, especially since each side of the island is different. The south sides are usually drier and warmer, ideal for that winter vacation, while the north shores are usually green and lush, and see more rainfall. What I’m trying to say is, just because you’ve vacationed in Hawaii once or twice, or even five times, doesn’t mean you’ve ‘seen it all’. In fact, this post is dedicated to how you can make your repeat trip back to the islands fresh, exciting and unique.

One way to do this is to plan your trip around major festivals. If your schedule allows, pick some type of festival or event that truly interests you. A few that come to mind are the Honolulu festival, Merrie Monarch hula competition and the film festivals in Kona, on Maui and in Honolulu. There are also smaller events like the Spam Jam, county fairs and music concerts. Or, try planning your vacation around a holiday, like 4th of July or Christmas. It’ll give you a different perspective of the celebrations that take place (like seeing a surfing Santa, instead of him decked out in wool and snow) and also cultivates an open-mind.

Another way to keep things fresh is to visit an island you haven’t explored yet. If you’re a fan of Kauai, then stay in Hana or Upcountry, Maui. And if you’ve never seen Hawaii Volcanoes National Park, then it’s about time you stayed on the Big Island. If your vacation is usually all about the beach and pool time, switch it up with Honolulu and visit the historical landmarks and museums that are so abundant.

A round robin of the islands is a fun way to really get to see the breadth of Hawaii. Plus, it allows for tons of new and exciting things to explore and experience. If you visit a different side of a different island every year (just talking about the 4 main islands here) then you’ll have 16 years of different adventures in store!

Then again, if you plan to invest that much time (and money) here in Hawaii, why not just move here! But seriously, you might want to consider buying real estate on one of the islands because that way you can have a literal home-away-from-home during your vacation and then rent it out for the rest of the year. One thing we don’t recommend though is timeshares. A lot of interested buyers tend to get sucked into those and often times find out they are not everything they’re cracked up to be.

If purchasing property isn’t in your future budget or agenda, then maybe just consider extending your vacation a little longer than normal. This also helps the shake up your normal routine by really allowing for some serious unwind time. Once you hit two weeks in Hawaii, it’s like a new leaf has turned and you’re finally relaxed and in the island state of mind.

You can also try switching your vacation time frame. If you usually vacation during the summer, try booking a getaway for the wintertime. Spring and fall are also wonderful times in Hawaii as they are the ‘off seasons’ for tourism, meaning fewer people on the beaches, at the restaurants and in the hotels. While the weather might not be all that dramatically different, there are subtle changes to Hawaii’s seasons. Like whale migration, swell and wave action and snow fall on the Big Island Volcanoes of Mauna Loa and Mauna Kea.

Don’t get in a vacation rut! (Is that even possible?) Keep life exciting by shaking things up, even your down time. Hawaii is perfect for this type of vacation variety too because of everything each island has to offer. Don’t let the incredibly diverse characteristics of the islands pass you by year after year, and be sure to take advantage of the things that make Hawaii such a sought after vacation destination.


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