Perhaps this is the first question people ask themselves and number one thing they start thinking about before they start planning a trip to Hawaii. To answer this question, you must first ask yourself what are the trip priorities for yourself and your trip companions? What kinds of experiences are you looking to have? What are your must-haves? Every island offers a slightly different experience. The Hawaiian island chain stretches some 1,500 miles and comprises of 137 islands. There are 8 main islands - 6 of which tourists can visit. Let's take a quick look at each island to see which would be the best fit for your trip!
Oahu - Known as "The Gathering Place" this island is the hub of Hawaii, home to the city of Honolulu, and around 70% of Hawaii's entire population lives on the island of Oahu. Oahu also sees more tourists and visitors than any other Hawaiian island. If you are looking to have all the creature comforts of a city during your trip - this would be it. There's lots of shopping, chain restaurants, and night life in the city. There's also public transit. Oahu is a city where East meets West and offers the best of both worlds. Of course, there's the famous Waikiki and Waikiki Beach, Diamond Head, and Pearl Harbor. Oahu is not all city - if you take a drive to the north shore it is quite scenic there and has a more rural feel to it. Beaches on Oahu are plentiful and there are some that are fantastic - but they can get crowded. Oahu is a safe bet for those wanting a classic tourist experience, a cultural immersion, a mix of city and country, great beaches, and the most possible amenities.
Big Island - Actually called Hawaii Island and "Big Island" is its' nickname - but everyone just calls it Big Island, this island is the youngest and biggest of all the Hawaiian islands, comprising 63% of Hawaii's landmass. It's actually big enough that all the other Hawaiian islands could fit inside of it nearly twice over. There are two big towns on the Big Island: Kona on the sunny and dry west coast (pretty much all the resorts are on the sunny west coast of the island due to the fact that it is sunny and dry), and Hilo that's on the wet and lush east coast, the laidback town that still gives off "old Hawaii" vibes. While Big Island is the second most populated island in the state of Hawaii due to its' large size, it doesn't give off a crowded feel. Big Island can be described as diverse - it contains 10 of the world's 14 climate zone classifications which is largely owed to the two towering mountains of Mauna Loa and Mauna Kea. Mauna Kea is also considered to be the tallest mountain in the world - taller than Mt. Everest if you measure the mountain from its' base at the sea floor. Big Island is home to Volcanoes National Park which has an active volcano that you can visit. There's a lot of nature to be explored on the island as well as a lot of agritourism operations. There are some good beaches on the west coast of the island, and some excellent snorkeling! However, being a young island, many of the beaches are black sand and/or rocky. There's also a green sand beach! There's not much nightlife or chain restaurants on this island. Big Island is a good choice for those who want variety and something more nature-focused but not excessively rural or uninhabited. Be prepared to rent a car and drive. One strategy for Big Island is spending half your trip based out of a West coast town and half your trip based out of an East coast town, if possible, to get the best of both worlds.
Maui - Known as "The Valley Isle" this island is more of a middle ground between the hustle and bustle of Oahu and the more laid-back, rural feel of the Big Island. Maui has tons of great beaches and great snorkeling too. Due to the number of great beaches, they don't usually feel too crowded. There's not too many chain restaurants but there's still a lot of great dining and shopping. Aside from amazing beaches, Maui's big attractions are Mt. Haleakala - which you can drive to the top of, Road to Hana - an incredibly scenic all-day drive, and Molokini Crater - a popular snorkeling spot at a partially submerged volcanic crater accessible by boat. There's a pineapple plantation that offers tours as well as an amazing Lavender farm up at 3000 feet on the side of Mt. Haleakala. In the Winter and Spring months, Humpback whales can be seen as mother's come to the warm Hawaiian waters to give birth to their young. There's plenty of other fun activities and nature-related things to keep you busy in Maui as well. There's not too much nightlife to be had here. Maui seems to have a little of everything yet still maintains its' own character and unique identity.
Kauai - Known as "The Garden Isle" this is the oldest of the main Hawaiian islands and one of the smaller of the islands. When you think of a "tropical locale" this is what you imagined. Kauai, especially its' North shore, is incredibly lush, scenic, and absolutely gorgeous. If you want to see a lot of waterfalls this is your place. Kauai is home to the Na Pali coast, a series of breathtaking tall coastal cliffs that can be seen from a drive to the top or from by boat tour. Kauai is a nature lover's dream. It certainly has a more rural feel and the local building code dictates that buildings can't exceed the height of a coconut palm - so no tall resort buildings here. While the north shore is lush and tropical, the southern shore is sunnier and dryer. Kauai does have some decent beaches but not nearly as many or to the quality of Maui or Oahu. Some of the best and most scenic beaches are on the North shore (there's still good ones on the South shore!) and are not swimmable in the winter due to winter swells. Kauai used to be off the radar but more and more people seem to have been discovering it over the last decade or so, as a result, you now have to have reservations for these beaches due to limited parking since it is so rural. There's no chain restaurants spare a couple fast food places, and definitely no nightlife. If you come here expecting a ton of big city offerings you will be disappointed. Kauai has everything you'd need - just not a lot of upscale options. Most people come here for nature, for relaxation, and for peace.
Molokai and Lanai - Molokai is known as "The Friendly Isle" and Lanai is known as "The Pineapple Isle" - these are the two smallest of the main islands and the two least visited.
Molokai has the tallest seacliffs in the world and is home to a lot of native Hawaiians. The island has a very small population. As a result, there are very few places to stay and there is not a huge tourism industry on Molokai - this is likely by design. There are still people that visit the island (you can fly-in). It is beautiful in many ways. This wouldn't be an ideal island to visit for your first visit to Hawaii. More research would be needed before visiting.
Lanai is a privately island owned by Larry Ellison the founder of Oracle. Aside from flying into Lanai here is a ferry from Maui that runs to Lanai for daytrips. There are a few attractions and couple of hotels here including the Four Seasons Lanai but overall there's not a whole lot. This island would be ideal for a side trip / day trip or perhaps a luxe secluded getaway if you are staying at the Four Seasons.
Conclusion
Oahu - Mostly urban, great beaches, can be crowded, lots of attractions, lots of amenities, great food and shopping, has nightlife easy for tourists.
Big Island - Large & spread-out but less crowded, a few good beaches (but some great snorkeling), most diverse geography and landscape, a lot of nature, will need to drive, only island with active volcano, no chains (but good food options), not a lot of shopping little to no nightlife.
Maui - Middle ground between Oahu and Big Island. Lots of great beaches and snorkeling. Good dining (not many chains) and shopping. Little nightlife. Good balance between nature and 'city'.
Kauai - Lush and tropical, fairly rural, smaller island. Some decent beaches and decent snorkeling - scenic north shore beaches often inaccessible in winter and require reservation. No chains and limited shopping. Nature lovers dream.
Molokai - Rural, sparsely populated, not a lot of tourism, not recommended for first-timers to Hawaii
Lanai - Privately owned but tourists welcomed, a few resorts including Four Seasons, only good for a daytrip from Maui or a luxe getaway.
Choosing an island can be a daunting endeavor but no matter which island you choose you can't go wrong! You can also watch some Youtube videos to help you decide.
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