2 Weeks In Hawaii Itinerary

A trip to Hawaii is an unforgettable experience, especially for travelers who manage to roll themselves beyond the beach. But with many islands to choose from, planning your Hawaiian vacation can a challenging task. In this guide, I’ll share with you an itinerary for spending up to 2 weeks in Hawaii. This itinerary is designed to gradually work up the excitement level, eventually reaching a climax in the final stop on your Hawaiian island hopping adventure.

2 Weeks in Hawaii Overview

Here’s how we’ll split our time in this sample itinerary:

  • Part I: Oahu – 2 days
  • Part II: Molokai or Maui – 4 days
  • Part III: The Big Island – 4 days
  • Part IV: Kauai – 4 days

Visiting Hawaii? Sample itineraries, guides to the best spots, and the must-see highlights in five islands await you in the Hawaii Travel Guide collection. Aloha!

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The Best Islands In Hawaii

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Part 1: Oahu (2 Days)

We’ll start this two weeks in Hawaii itinerary in Oahu, the island chain’s main international gateway. Oahu is also home to roughly 70% of the state’s population. Visitors often overlook it in transit to the more “rugged” islands (which we’ll soon head to), but once you get out of Honolulu, the scenery is mostly spectacular.

Quick Finds

Where to Stay?

Since you only have two days in Oahu, I recommend staying in the Honolulu area, either in Waikiki Beach for the action or in the Manoa neighborhood for a quieter stay. Still, if you’re looking for a place outside Honolulu, Kailua is the best option.

What to Do?

Spend the first day in the Honolulu area. In the morning, head to the Pearl Harbor National Memorial or the Bishop Museum. Alternatively, make advanced reservations and hike to the summit of Diamond Head. Spend the afternoon at Waikiki Beach and explore the busy strip.

Hiking Diamond Head - Honolulu -Oahu- Hawaii
Diamond Head
Panoramic view Waikiki Beach from Diamond Head - Honolulu - Oahu - Hawaii
Waikiki from Diamond Head
Queen’s Beach - sunset in Waikiki Beach - Honolulu - Oahu - Hawaii
Queen’s Beach, a quiet extension of Waikiki Beach

Rent a car for the next day and road trip up the windward coast from Honolulu to Waimanalo Beach (you can skip the south coast by taking the Pali Highway to Kailua). Stop at interesting sites such as Halona Blowhole, hike the Makapu‘u Point Lighthouse Trail, and work on your tan at Lanikai Beach or Waimanalo Beach, two of Oahu’s top beaches. Return to Honolulu via the famous north shore surfing beaches if there’s time.

Halona Blowhole - Oahu - Hawaii
The Halona Blowhole on Oahu’s south coast
Pali Coast from Makapu‘u Point Lighthouse Trail - Oahu - Hawaii
The Windward Coast from Makapu‘u Point Lighthouse Trail
Waimanalo Beach - Hawaii - Oahu
Waimanalo Beach
Pro Tip

Here’s an in-depth Oahu itinerary, where you can choose the days that work for you. For a quick look at the island’s best spots, check out the top things to do in Oahu.

Part 2: Molokai or Maui (4 Days)

Our two weeks in Hawaii itinerary continues with a choice between the islands of Molokai and Maui. Though the two islands are separated by just a few miles of water, they could not be any different from each other.

Option A: Molokai

If it’s cocktails by the pool, 24-hour room service, and data coverage you’re searching for – look elsewhere. Molokai is as real as Hawaii gets and finally drives home the message that you’re visiting one of the most remote island chains in the world. Life around here is beautifully stuck in the ’90s on a good day, but this is actually part of Molokai’s charm. Over 50% of Molokai’s tiny population has native Hawaiian heritage. This means you don’t have to go to touristy luau shows to meet real Hawaiians.

Quick Finds

Where to Stay?

I recommend staying in and around Kaunakakai, allowing easy access to all corners of the island. For an off-the-grid stay, the West Coast is for you! Paniolo Hale and Ke Nani Kai are perfect if you want to stay away from the island’s center in a secluded location.

What to Do?

Spend your first day road tripping on the scenic south coast drive from Kaunakakai to Halawa Valley. Stop at secluded beaches such as Murphy’s Beach and stop for lunch with the locals at Mana’e Goods & Grindz. Book a spot with Halawa Valley Falls Cultural Hike for the next day, and learn how Polynesians live off the land as you hike to Halawa Falls.

Kaunakakai Saturday Market - Molokai - Hawaii - fruits
Kaunakakai’s Saturday morning market
Mile 20 Murphy's Beach - Molokai Hawaii_2
Mile 20 (Murphy’s Beach)
View Halawa Beach Park - twin beaches of Molokai Hawaii
Halawa Valley Beach Park

On the third day, hike, hop on a mule, or take a quick flight to Kalaupapa National Historical Park. Explore the remote and stunning Kalaupapa Peninsula as your guide unveils the tragic history of this former leper colony. On your last day on the island, rent a 4WD and explore the fairy-tale-like Kamakou Preserve.

View of Pali Cliffs from Kalaupapa - Molokai Hawaii
The Pali Cliffs from Kalaupapa
Kalaupapa Peninsula - Molokai - Hawaii
The Kalaupapa Peninsula
Pepeopae bog hike - Kamakou Preserve - Molokai Hawaii
Pepeopae Bog Trail
Pro Tip

Here’s a complete Molokai itinerary, where you can pick and choose the most appealing days for you. For a quick look at the best spots, check out the top things to do in Molokai.

Option B: Maui

Maui is one of the world’s most famous islands, riding its reputation as a paradise island like a pro surfer. The island has transformed its agriculture-based economy into a multi-billion dollar tourism factory. Though “paradise” is not the perfect way to describe one of the more overdeveloped and busier Hawaiian Islands, Maui certainly rewards its active visitors. It strikes a good balance between beach and nature.

Quick Finds

Where to Stay?

If you want to stay close to the best swimming beaches, base yourself either on Maui’s south shore around Kihei, Makena, and Wailea or in the Kalapana resort area of West Maui. For a quieter stay, look for Northshore accommodations around Kahului, Wailuku, or vibrant Paia. If you’re seriously looking to avoid the crowds, search for a suitable place in Upcountry Maui, an area overlooking the Pacific on the foothills of the Haleakala Volcano.

What to Do?

Spend your four days in Maui in a delicate balancing act between spending time on Maui’s best beaches and active sightseeing. I recommend embarking on the road to Hana on your first day. It’s one of the best scenic drives in Hawaii, where you’ll cross 54 one-lane bridges and nearly as many waterfalls. Along the way, hike the Pipiwai Trail in Haleakala National Park, make landfall on black and red sand beaches, and go for a dip in natural swimming pools fed by waterfalls.

Pipiwai Trail Hike Bamboo Forest - Road to Hana - Maui Hawaii
The Pipiwai Trail
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Kaihalulu Red Sand Beach - road to Hana - Maui Hawaii
The Red Sand Beach
Three Bears Falls - road to Hana - Maui Hawaii
Three Bears Falls

Relax on the second day on one of West Maui’s beaches. In the afternoon, explore historic Lahaina, a town devastated by the 2023 wildfires, and in the evening, attend a luau if you haven’t done so already. It’s back to Haleakala National Park on day three, but this time to the summit area. Enjoy the beautiful drive, witness Mars-like vistas, and hike part of the challenging Sliding Sands Trail. On the final day, join a snorkeling tour to Molokini Crater and relax on south shore beaches, or drive the scenic Kahekili Highway.

Rainbow in West Maui Hawaii
West Maui Rainbow
Haleakala Volcano summit - Maui Hawaii
Haleakala Summit
Big Beach Maui Hawaii 2
Big Beach
Pro Tip

Here’s a complete Maui itinerary for spending up to 5 days on the island. For a quick look at the island’s best spots, check out the top things to do in Maui.

Part 3: Big Island (4 Days)

Our two weeks in Hawaii itinerary continues with four days on the Big Island. It’s larger than the rest of the Hawaiian Islands, put together, and by far the most diverse destination in the archipelago. You could theoretically ski, get soaked by torrential rain, and work on your tan at the beach – all on the same day.

Quick Finds

Where to Stay?

Although it’s not a must, consider splitting your time evenly between the sunny Kona Coast in the west and the tropical (and obviously wetter) Hilo Coast in the east. This will reduce driving times and might make sense if you intend to explore the Big Island fully. The Big Island’s top beach resorts are around Waikoloa, about 45 minutes north of Kailua-Kona. For quieter stays on the Kona Coast, villages such as Holualoa, Captain Cook, and Kealakekua could suit your taste.

What to Do?

Spend your first day on the island hiking or driving to one or more of the Big Island’s best beaches on the Kona Coast. Here, you ride waves, meet sea turtles, and snorkel. For sunset, I recommend heading to Kaloko-Honokōhau National Historic Park for guaranteed sea turtle sightings. On your second day, hit the road and head north to the Kohala Region. Visit historic small towns that seem to be stuck in the 1950s, like Waimea and Hawi, and hike the valley floors of quieter Pololu Valley or the busier and grander Waipio Valley.

green sea turtle beach - Kaloko-Honokohau - Big Island Hawaii
Kaloko-Honokōhau National Historic Park
Waipio Valley Overlook - Big Island Hawaii
Waipio Valley Lookout

On the third day, slice through the middle of the island on Saddle Road and explore the lush east coast. Start at Akaka Falls and drive to Hilo via the Hawaii Tropical Botanical Garden. In Hilo, check out the authentic farmers market and grab lunch at Suisan Fish Market. In the afternoon, take to the skies on a scenic helicopter flight over Kilauea or explore the remote and beautiful Puna Peninsula. If you’re driving back to Kona, consider watching the sunset in Mauna Kea. You can also stick around for some stargazing.

Akaka Falls - Big Island Hawaii
Akaka Falls
Hilo Farmers Market - Big Island
Hilo Farmers Market
The Kalapana lava flow area - Big Island
Lava flow from the Kilauea Volcano

Spend your final day on the Big Island in Hawaii Volcanoes National Park to get acquainted with the Kilauea Volcano. Start your visit on the Kilauea Iki Trail and explore the Thurston Lava Tube’s dark interior before returning to the car. Then, drive the length of Chain of Craters Drive and enjoy the views from the Holei Sea Arch. Before returning to Hilo or Kona, ask park rangers if any worthwhile post-sunset lava viewing areas are open.

Hawaii Volcanoes National Park Big Island - Kilauea Iki Crater
The Kilauea Iki Trail
Hawaiian Pu’u Loa Petroglyphs - Volcanoes National Park Big Island
Petroglyphs on the Chain of Craters Road
Holei Sea Arch - Hawaii Volcanoes National Park Big Island
Holei Sea Arch
Pro Tip

Here’s a complete Big Island itinerary for spending up to 5 days on the island. For a look at top spots, check out the top things to do on the Big Island.

Part 4: Kauai (4 Days)

Our two weeks in Hawaii itinerary is about to reach a climax in the final leg. The “Garden Isle” is blessed with such immense natural beauty that even a quick trip to the gas station is a scenic drive. It is the oldest of the major Hawaiian islands, so Mother Nature has had millennia to erode its volcanic peaks and carve the island’s lush interior into absolute works of art.

Quick Finds

Where to Stay?

Once again, if you want to reduce driving times, split your time on the island between the north and south shores. These are Kauai’s most interesting sections, putting you close to its major attractions. In the sunny and dry south shore, anywhere between Poipu and Hanapepe is great. Up north, the area from Princeville to Hanalei is stunning. Alternatively, stay on the central coast between Lihue and Kapa’a.

What to Do?

Spend the first day driving from Lihue to Hanapepe. First, check if it’s market day in towns along the route and work it into your itinerary. At Koloa, explore this historic sugarcane-era town. Then, head to Poipu Beach if you’re traveling with children or Shipwreck Beach to escape the crowds. Pick up the Maha’ulepu Heritage Trail, and for sunset, head to Salt Pond Park or Menehune Fishpond Overlook.

Eroded sharp limestone sea cliffs - Maha'ulepu Heritage Trail - Kauai, Hawaii
The Maha’ulepu Heritage Trail

On day two, start early and drive the scenic Waimea Canyon Drive. Admire the “Grand Canyon of the Pacific” from many lookouts and continue to Koke’e State Park for spectacular views of the Na Pali Coast and several trails. Serious hikers can start the day on the breathtaking Awa’awapuhi Trail. In the evening, head to Luau Kalamaku for Kauai’s best traditional Polynesian show.

The Awaawapuhi Trail
Pu’u Hinahina Lookout - Waimea Canyon - Kauai
Pu’u Hinahina Lookout in Waimea Canyon
Pu’u o Kila Lookout - Na Pali Cliffs - Kauai Hawaii
Pu’u o Kila Lookout in Koke’e State Park

On day three, head up the coast to Hanalei Bay. Slightly north of Lihue, gaze at Wailua Falls and continue to the bird sanctuary at Kilauea Point (reservations required). After lunch at Kilauea Fish Market, rest at Secrets Beach (Kauapea Beach) or spend the afternoon at pretty Hanalei Bay.

Wailua Falls
Hanalei Bay Beach - Kauai - Hawaii
Hanalei Bay

On the final day of your two weeks in Hawaii adventure, head to Ke’e Beach and hike part of the Kalalau Trail. Both are part of Ha’ena State Park, so you’ll need to make advanced reservations. The Kalalau Trail, stretching along the Na Pali Coast, is one of the best hikes in Hawaii. Hike from Ke’e Beach to Hanakapiai Beach and continue to Hanakapiai Falls if you’re a serious day hiker. After the strenuous effort, relax at Ke’e Beach or head to Tunnels Beach. Alternatively, join a morning Na Pali boat tour or a thrilling scenic helicopter flight.

Na Pali Cliffs from Kalalau Trail - Hiking in Kauai - Hawaii
The Kalalau Trail
Tunnels Beach Kauai - mountain and lagoon
Tunnels Beach
Pro Tip

Here’s an in-depth Kauai itinerary for spending up to 5 days on the island. For a quick look at the island’s highlights, check out the top things to do in Kauai.

More from Hawaii

I hope you’ve found this two weeks in Hawaii sample itinerary helpful for crafting your Hawaiian adventure. Want to see more of Hawaii? Guides to the best beaches, scenic drives, and plenty more await you in the Hawaii Travel Guide collection. Aloha!

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