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How to spend two weeks in Hawaii: Kauai, Oahu, Maui and The Big Island

Are you ready to travel away from the beaten path and find adventure in Kauai, Oahu, Maui, and The Big Island?
We don’t know too many people who wouldn’t want to spend two glorious weeks in Hawaii.  If you’re on the way to the “Aloha State” and need some suggestions on how to make the most of your days in Kauai, Oahu, Maui, and The Big Island, we can help!  But, in order to really appreciate Kauai, you need a little bit of history first.

Kauai, Hawaii, has a fascinating history.

Like its fellow Hawaiian islands, Kauai is shrouded in fantastical mystery.  As the oldest of the islands, its legends run parallel to Kauai’s wonderful history.

The most popular of the legends introduces the Menehune, a mythical race of dwarfs who hid from the sight of human beings in the lush forests and hills of Kauai. They were said to be talented craftsmen, constructing Kauai’s aqueducts and fishponds in unseen swiftness. Hawaiians continue to show due deference to the Menehune, as the fishponds like Alekoko are often referred to as Menehune Fishpond.

During the era of Hawaii’s discovery by Western explorers, King Kamehameha I was exercising his influence to unite the islands under one kingdom. Initially, Kauai and the neighboring island of Niihau withstood Kamehameha’s efforts, but Kauai’s King Kaumualii eventually agreed to join the Kingdom of Hawaii in peace.

Famed British explorer Captain James Cook landed on Kauai’s Waimea Bay in 1778, thus commencing Hawaii’s introduction to the world. Waimea Town features a statue of Captain Cook to commemorate this event. In 1835, as it was discovered that the Hawaiian Islands were optimal for sugar plantations, Old Koloa Town opened its first sugar mill. Many historical registries line the island as a result, including the Waioli Mission House and sites along the Koloa Heritage Trail.

Step onto the shores of Kauai and you’ve instantly become one with history.

Hawaii, Pool
Hotel Pool

When you first arrive in Kauai…

Located about 30 minutes from the airport, we recommend checking in at Koloa Landing Resort at Poipu.  There’s only about a 10-minute walk to the beach, but after a long flight, if you want to simply lounge by the pool, this is the place to do so.  The pools are fantastic!

Some other hotel options include Sheraton Kauai, Marriott Waiohai Beach Club, Kiahuna Plantation by Outrigger, and Whalers Cove.

When you’re ready for dinner, walk up to Old Koloa town where you’ll find great dining choices such as Ko’loa PIzza, Merriman’s Seafood, and Bubba’s Burgers. Enjoy the rest of your evening as you wish and get a good night’s sleep to prepare for more Kauai exploration.

The next few days…

Over the next few days in Kauai, feel free to make up your own rules.  There are lots of eateries, bars full of entertainment, beaches to comb, and adventures just waiting for you.

When you visit Kauai, you have plenty of dining options.

Whether you are eating on a budget or looking for fine dining, Kauai mixes the best of both worlds.  People gravitate towards native cuisine, which is highly recommended, but those looking for a bit of variety should have no fear: Kauai will exceed your culinary expectations.

Cafés always have the perfect atmosphere: coffee, good food, and friendly people. The cafés in Kauai are no different and offer a variety of snacks, desserts, and delicious coffee, both local and from around the world.

Hawaii, Café and Dining
Café in Kauai

Kauai’s nightlife is a whole “vibe.”

Kauai’s nightlife is suitably more laid-back than on other Hawaiian islands. That’s not to say that you can’t find exciting places to drink and dance, but rather that the island caters more to those in search of a relaxed evening with a bit of live Hawaiian music and a good meal.

Some say that beach life is the best life.

Some of the best Kauai beaches to roam are the calm and cool Kiahuna Beach; Poipu Beach, where the sand is golden and snorkelers find their paradise; and, Baby Beach, a shallow lagoon perfect for families with young children (keiki).

Need some adrenaline-boosting adventure?

How about ziplining or tubing?  You only need to drive (or take a helicopter ride!) approximately an hour away, and you’ll be ready to zip through the air in no time!  And, a visit to Hawaii is completely incomplete without experiencing an official luau.  Smith Family Luau is highly recommended.  You’ll need to take a drive, but this garden is an absolutely gorgeous place to party the night away.  But, if you prefer a beach location, Sheraton Kauai is the way to go.

If you have at least 5 hours to spend (please note that tours will take even more time), Waimea Canyon, situated on Kauai’s west side in the town of Hanapēpē, is worth a visit as well.

Hawaii, Beach in Oahu
Beach in Oahu

On to Oahu for Days 5-7…

After you’ve had a taste of Kauai, catch a flight to Oahu, pick up a rental car, and check in at Turtle BayRoyal HawaiianMoana Surf Rider, Sheraton, or Hilton Hawaiian Village. You have a lot of great lodging choices!

Oahu is known as “The Gathering Place” and is the third-largest of all of the Hawaiian Islands. It is home to nearly one million people and also home to the state capital, Honolulu.

Spend your days learning…

Explore the beautiful Waikiki area, go on a guided Pearl Harbor private tour, which includes the USS Bowfin, and, of course, indulge in some beach time.  We suggest Turtle Bay Beach, but you’re free to choose a different beach.

Next stop: Maui Wowi…

The island of Maui is the second-largest of Hawaii’s islands and the 17th-largest in the United States.  Kahului is the island’s commercial and financial hub, while KīheiLāhainā, and Hāna, are a  few more great places to visit and stay.

But, if you’re staying in Kaanapali, we recommend the Westin Kaanapali or Royal Lahaina Resort & Bungalows.  Wailea also has great lodging such as Grand Wailea, A Waldorf Astoria Resort and the Wailea Beach Resort – Marriott.

For some “fun in the sun…”

You’ll have three days (Days 8-10) to explore this stunning island.  However, be sure to save enough time to spend an entire day at the beach.  Make it complete with Lahaina Surf Lessons — with classes for all ages and levels.

Hawaii, Luau
Luau Entertainment

You’ll want to catch a flight to Big Island around Day 11.

When you land, secure a rental car and go check in at Hapuna Beach Residences.  You’ll also want to spend a full day in Big Island at the beach.  Plan to take a fully-immersed, 12-hour tour of the island on Day 12, and choose between a Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran or a Glass-bottom Boat Reef Tour, with waterfalls and volcanoes on the sightseeing list, for your Last/Day 13 activities.

Wrap up two splendid weeks of Hawaiian magic with a spectacular dinner at Lava Lava Beach Club.

The “Aloha State” offers a wide range of activities, eateries, and sights to discover.

Whether you want to travel away from the beaten path, find some adventure, or explore a little Hawaiian city life, you can have a blast in Kauai, Oahu, Maui, and The Big Island.  Are you ready to plan a hard-to-forget Hawaiian vacation?

Get in touch and let us start planning now!