Choosing the Right Hawaiian Island

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A trip to Hawaii is a dream vacation for many, but choosing the islands for a vacation is only the beginning.  Although the Hawaiian Islands are made up of many islands and atolls, along with smaller islets, when it comes to vacation, you’re probably talking about visiting one of the six main islands.

Depending on what you want out of your vacation, frenetic levels of activity, rocking night life, or peaceful sandy beaches, you’ll want to choose an island that fits your personal preferences.  While sharing the basics of beautiful sun, sand, and surf, each island has its own special ambience, so be sure to make the right match up and have a perfect vacation in paradise.

Waikiki Beach shortly after sunrise ©2010, Mary Jo Manzanares

Here’s a brief rundown to help with your preliminary research.

Hawaii, the Big Island:  This is the largest of the islands, and also the youngest in development.  On the windward side of the island, you’ll find lush, tropical rain forests and quaint little inns, while on the leeward side of the island are lava rock beaches and big resorts.  There’s also an active volcano on the island, Kilauea.  The Big Island has lots of off-the-beaten-path kind of spots, and with a little luck you’ll be able to find one of the island’s hidden black sand beaches.  If you want activity, you’ll find resorts along the Kohala-Kona Coast offering golf, sport fishing, snorkeling, and tennis.  Specialty tours include Kona coffee plantation tours, swimming with manta rays, hiking across lava beds in Volcanoes National Park, or gazing at the stars at Imiloa Astronomy Center.

Oahu, the Gathering Place:  The most populated of the islands, you’ll find the best in shopping, dining, nightlife, and beautiful hotels and resorts.  The most popular area is Waikiki Beach, where you’ll find options, in all budget ranges, for hotels, dining, shopping, and things to do.  The trade off, however, is beaches that are more crowded, and a little faster, more hectic pace.  Drive or hike Diamond Head, get a little culture at the Polynesian Cultural Center or Iolani Palace, or spend a day at the beach or out on the water.  For a quieter Oahu experience, you could check out the North Shore.  With only one resort (Turtle Bay Resort), it’s a slower, more relaxed pace, and a wonderful antidote to the frenzy that can overcome Waikiki.

Maui, the Valley Isle:  Offering something for everyone, Maui is full of quiet, peaceful activities as well as home to bustling and energetic nightlife.  The windward side is fairly remote, with plenty of out-of-the-way spots to spend some quiet time.  The leeward side has plenty of resorts, and development, but you’ll also find a few secluded areas as well.  You may want the solitude of watching sunrise from the top of Mount Haleakala or the adventure of driving the road to Hana, or exploring the shopping, dining and nightlife of the former whaling village (and now main tourist town) of Lahaina.  You’ll find plenty of beautiful water for diving, swimming and snorkeling, and can choose to stay at a major resort (Kapalua, Kaanapali, or Wailea) or find a condo of small hotel.  Maui, with all it’s variety, is a popular spot with honeymooners.

Kauai, the Garden Isle:  Less commercial, less developed, and more tropical, Kauai is the oldest of the islands.  This is a wonderful island on which to relax, while still offering a few attractions and things to do.  Most activity centers around the lush tropical foliage of the island, along with Fern Grotto (a natural lava-rock grotto with hanging ferns, accessible only by the Wailua River), Waimea Canyon (the Grand Canyon of the Pacific), Na Pali Coast (cliffs, sea caves, remote beaches and waterfalls), hiking, inner tubing, and zip-lining.  Princeville and Poipu are the resort areas, and a little more upscale, and Hanalei and Koloa are older, more historic Hawaiian towns.

Lanai, the Pineapple Isle:  The smallest of the island, Lanai will appeal to people who want to escape the crowds, and be alone.  With only a couple resorts, you won’t find a lot of tourists here.  But that doesn’t mean you won’t find upscale accommodations –- two of the resorts are operated by the Four Seasons.  There’s still a variety of terrain, though, and you can go from beach to forest in very little time.  Rent a jeep and go island exploring, check out Shipwreck Beach, Kaunolu (King Kamehameha’s summer fishing village), and Garden of the Gods (which some swear looks a bit like Mars).

Molokai, the Friendly Isle:  The most secluded and laid back of the island, Molokai harkens back to what Hawaii was like years and years ago, making it one of the most historic and culturally significant islands.  There is only one resort (the Aqua Hotel Molokai with 53 rooms), although you’ll find a few small inns and private residences that rent out rooms, so the island never gets very crowded. Molokai was the residence of Father Damien, a Catholic Priest who cared for the lepers who once sought refuge on the island.  Many of the residents of the island are descendants from the original lepers who lived here.  There are, however, NO active cases on leprosy on Molokai, so it is a safe place to visit.

Which Hawaiian Island do you want to fall in love with?

Photo credit:  both from Mary Jo Manzanares


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Mary Jo Manzanares is a traveler, travel blogger, and podcaster. In addition to her blog, Traveling with MJ, she hosts the Where Else to Go podcast, and is the founder and the editor-in-chief of The Traveler’s Way, an online travel magazine. Her travel ethos is value luxury - luxury for real people - and her goal is to help travelers know when to splurge and when to save. Mary Jo has been a speaker at various industry events around the world. When she’s not traveling, Mary Jo likes lingering over a cup of coffee, wandering in a museum, sipping wine at a cafe, and sharing it all with friends and readers. Her most recent travels were to Stockholm, a Baltic cruise, and Universal Orlando Resort.


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