The Best Island Hopping Itineraries in Hawaii

Hawaii Tourism Authority (HTA) / Tor Johnson

So you’ve decided to go to Hawaii, but now how do you choose which island—or islands—to visit? If you have less than a week for your Hawaiian vacation, it’s best to stick to just one. After all, you’ve traveled all this way, so you shouldn’t spend your precious vacation time at car-rental counters, hotel check-in, or airports. But, with seven nights or more, a little island hopping is definitely in order. Here are six of our favorite island-pairing itineraries to help you plan your Hawaiian escape. By Trina Kudlacek

Hawaii Tourism Authority (HTA) / Tor Johnson

Romantic Escapes: Maui and Kauai

Why Maui: You’ll find waterfalls, salt-and-pepper sand beaches and incredible views as you follow the twisting turning Road to Hana. The luxury resorts in Wailea or Ka’anapali will provide lots of excellent dining and spa treatment options. And for those who want to start their day off early, there’s the drive up to Haleakala to see the sun rise—or for couples who prefer to sleep in there’s the arguably even more spectacular sunset from the summit. Timing Tip: Spend 4 nights.

Why Kauai: The north shore communities of Hanalei and Princeville provide the opportunity to get away from crowds and indulge in some spectacular beaches, hiking, and helicopter rides. At Princeville you can experience views straight out of South Pacific as well as romantic dining and spa options at the St. Regis Hotel while a drive to Ke’e Beach at the end of the road provides innumerable options for pulling over and grabbing a beach just for the two of you. Timing Tip: Plan to spend at least 3 nights.

Hawaii Tourism Authority (HTA) / Tor Johnson

Family-Friendly Attractions: Oahu and Maui

Why Oahu: By far the most kid-friendly island is Oahu. For sea life, visit the Wakiki Aquarium and Sea Life Park or let the little ones get up close and personal with fish at Hanauma Bay. At Pearl Harbor you can visit an aircraft carrier or, if the kids are at least 4, a World War II submarine. Then there’s the Honolulu Zoo and a slippery slide filled water park, not to mention some very kid friendly and safe beaches (Lanikai, Kailua and the lagoons of the Ko’Olina Resort). Timing Tip: Plan to spend 4 nights on Oahu.

Why Maui: Whales! Though you can see whales from any island between November and April, there is no better place than Maui. If your visit doesn’t fall during peak whale watching season, visit the Whaling Museum, the Hawaii Humpback Sanctuary or the Maui Ocean center (to get an up close look at some of Hawaii’s smaller sea creatures). Away from the water, there’s the Sugar Cane Train. Timing Tip: Plan to spend a minimum of 3 nights.

Hawaii Tourism Authority (HTA) / Tor Johnson

Pristine Beaches and Beauty: Big Island and Kauai

Why Big Island: The Island of Hawaii is big enough to contain all the other Hawaiian Islands inside it and there's no end to the options for those who want to get off the beaten track and get their hands (and feet) dirty—or sandy. See lava flowing or steam rising from Kilauea. Visit beaches in your choice of gold, white, green or black sand. Snorkel or dive just off shore from an ancient Hawaiian settlement. Or, hike through rain forests to hidden waterfalls. The choices are endless on this island. Timing Tip: Plan to spend at least 4 nights. The big island is BIG – you’ll need the time to explore.

Why Kauai: The Napali Coast is the main draw for those seeking secluded beaches and incredible scenery. If you are interested in hiking to otherwise inaccessible beaches along sheer sea cliffs, this is as good as it gets. Along the way to the famed Kalalau trail head you’ll pass by beaches, wet and dry sea caves, over streams, and past taro patches. Or, head up to Waimea Canyon to see the Grand Canyon of the Pacific. Want waterfalls? Opaeka’a Falls outside Lihu’e is one of the state’s most breathtaking. And there’s no better place for bird watching than Kilauea Point National Wild Life Refuge. Timing Tip: Plan to spend at least 3 nights.

Hawaii Tourism Authority (HTA) / Tor Johnson

Adventure Travel: Kauai and Big Island

Why Kauai: Kayaking, helicopter tours, hiking an ancient trail along steep sea cliffs more your speed? Then Kauai is the island for you. Book a kayaking or helicopter tour to one of the most remote and inaccessible spots in the islands, the Napali coast. To hike the entirety of the Kalalau Trail, you’d really need to spend about a week on this island alone. On the west side you can hike into the immense Waimea Canyon. Timing Tip: Plan to spend at least 4 nights (or as many as possible).

Why Big Island: The Big Island has plenty to offer for those interested in more adventurous travel. Snorkel or dive with manta rays, soak in volcanically heated pools, hike through lava tubes and fern filled forests or, if your timing is right, hike out to see the lava oozing down the side of Kilauea. At night, head up to the summit of Mauna Kea for some of the best star gazing in the world. Timing Tip: Plan to spend at least 3 nights.

Hawaii Tourism Authority (HTA) / Kirk Lee Aede

Volcanic Views: Big Island and Maui

Why Big Island: Start by flying into Hilo and head straight to Volcanoes National Park and Kilauea Volcano. Plan to spend at least two days at Kilauea. You’ll need time to really explore the caldera, drive to the end of Chain of Craters Road, and have some time for hiking in and around this active volcano. While eruptions are unpredictable, helicopter companies can get you views of otherwise inaccessible lava flows. You can also make a visit up to the summit of Mauna Kea with a tour company. From the top of the tallest mountain in the world, you’ll see views not only of the observatories (Mauna Kea is one of the best places in the world for astronomy), but also Kilauea and Haleakala looming in the distance. Timing Tip: Plan to spend at least 4 nights.

Why Maui: Though all of the islands in Hawaii were built from the same hot spot in the earth’s crust, the only other island to have had volcanic activity in recorded history was Haleakala on the island of Maui. The House of the Sun (as Haleakala is known) has great hiking and camping opportunities within this confluence of two valleys—what seems to be a caldera is really the merging of two valleys over millennia). Timing Tip: Plan to spend 3 nights.

Hawaii Tourism Authority (HTA) / Sri Maiava Rusden

Golf and Spa: Maui and the Big Island

Why Maui: For upscale resorts with great spas and top-tier golf you can’t beat Maui. Wailea's and Ka’anapali's resorts in Maui have endless options for spa treatments. And, the Maui golf can’t be beat with Kapalua, the Dunes at Manu Lani, and Makena Resort topping the list of spectacular courses. Timing Tip: Plan to spend 4 nights.

Why Big Island: In addition to having incredible natural scenery, the Big Island offers world-class resorts and golfing along the Kohala Coast. The Mauna Kea and Hapuna Golf courses rank among the top in state while the courses at Mauna Lani Resort and Waikoloa Village allow the unusual experience of playing in and around lava flows. Relaxing spa treatments are readily available at the top resorts.Timing Tip: Plan to spend at least 3 nights.

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