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Hawaii’s four main islands – Oahu, Kauai, Maui, and the Big Island are all worth visiting. Each island offers unique activities, cultural experiences, and landscapes, so I recommend visiting all four of them (or as many as you can). This is why I created the ultimate two-week Hawaii island-hopping itinerary to help you plan an epic trip!
The Ultimate Hawaii Travel Guide
Pro Tip: you have to fly between islands, so compare flight prices to determine the cheapest order for you to visit the islands. This itinerary is grouped by island, so it can easily be rearranged to accommodate your island order.
If you’re celebrating in Hawaii, I’ve got the best honeymoon, birthday, mother-daughter, and bachelorette party activities to make your trip extra special.
Ready to go to paradise? Here’s the ultimate Hawaii island-hopping itinerary!
Know Before You Go
Flights between islands are only around an hour, so this itinerary is based on taking early flights to arrive at the next island with almost an entire day for exploring.
A car is essential on all four of the Hawaiian Islands. Renting cars saves you money because rideshares and hired drivers are expensive. Plus, a rental car gives you flexibility over your itinerary and room to store and transport your belongings.
I drove all over the Hawaiian Islands, but I only had to fill up my tank once on each island because the islands are so small.
Four Nights on Oahu
Day 1: Arrive on Oahu, pick up your rental car, check into your hotel in the Waikiki Beach area, then see a luau in the evening.
Day 2: Hike the Diamond Head Summit Trail early in the morning. In the afternoon, tour the Pearl Harbor National Memorial and take the ferry to and from the USS Arizona Memoria. Then end your day by watching the sunset on Waikiki Beach.
Day 3: Check out of your Waikiki Beach hotel and head to the Ho’omaluhia Botanical Garden. In the afternoon, do at least one tour at Kualoa Ranch. Then check into your North Shore accommodation.
Day 4: In the morning, go surfing or take a surf lesson or go outrigger canoe surfing. Then spend the rest of the day on a scenic drive along the North Shore that includes Kahuku Point, Ehukai Beach (where the Banzai Pipeline is), Waimea Bay Beach Park, and Matsumoto’s Shave Ice.
Three Nights on Kauai
Day 5: Fly to Kauai and pick up your rental car. On your way to your hotel, hike a portion of the Maha’ulepu Heritage Trail before checking in and lounging by the pool or on a beach for the rest of the day.
Day 6: In the morning, go on a Zodiac or catamaran cruise along the Nā Pali Coast that includes snorkeling. Then in the afternoon, go on a no-doors helicopter tour to see the part of the island that’s inaccessible by land.
Day 7: Spend the first half of this day driving the scenic route through Waimea Canyon State Park and Kōkeʻe State Park. Then spend the rest of the day by your hotel’s pool or on a beach.
Three Nights on Maui
Day 8: Fly to Maui, pick up your rental car, and drive The Road To Hāna – make sure you stop at Ho’okipa Beach Park, Wailua Valley State Wayside overlook (take the stairs to the right), Hanawi Falls (bring your swimsuit), Hāna Harvest, and Wai’anapanapa State Park. Then check into your Airbnb or hotel in Hāna (I highly recommend the Hana-Maui Resort).
Day 9: Check out of your Hāna accommodation and hike the Pīpīwai Trail (moderate-difficult) in Haleakalā National Park in the morning. Then head to the Wailea area of the island to check into your next accommodation (my top choice is the Andaz Maui).
Day 10: Do a helicopter tour of Northern Maui and Molokai in the morning. Then lounge at your hotel’s pool or beach in the afternoon. End your day with a boat tour to snorkel at the Molokini Crater and watch the sunset.
Three Nights on the Big Island
Day 11: Fly to the Big Island, pick up your rental car, and head to Hawaii Volcanoes National Park. Drive the Chain of Craters Road, hike through the Pu’u Loa petroglyph field, and walk through the Nāhuku (Thurston Lava Tube). Next, check into your hotel near Hawai’i Volcanoes National Park (my top choice is the Volcano House). Then this evening, hike to where you can see lava glow at night – you’ll need to check with park rangers for where to view lava.
Day 12: Check out of your hotel and take the scenic route along the Mamalahoa Highway (Hwy. 19) to the west side of the island. On your way, make sure you visit Rainbow Falls, hike to Akaka Falls, and marvel at the views from the Waipi’o Valley Lookout. Then check into your hotel on the island’s western side (my favorite is the Westin Hapuna Beach Resort).
Day 13: Start your day by sailing and snorkeling along the coast. In the afternoon, take a surf lesson or lounge by your pool or beach, then swim with manta rays at night.
Day 14: In the morning, do a helicopter ride. Then in the afternoon, spend some time relaxing at your hotel’s beach or pool until it’s time to head to the airport to catch your evening flight.
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What would you add to this Hawaii island-hopping itinerary? Share with us in the comments!
Recommended Tours in Hawaii
For Planning The Rest Of Your Hawaii Trip
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Hawaii Island-Hopping Itinerary
Frequently Asked Questions
How many days should you spend on each island in Hawaii?
You need at least three to four days on each Hawaiian island to do the scenic drives, enjoy the beaches, and see the islands from land, air, and sea.
Is it worth island hopping in Hawaii?
Yes! I highly recommend island-hopping to visit as many of the main four islands – Maui, Oahu, Big Island, Kauai – as you can. You really need to visit all four, if possible.
What is the best way to island hop in Hawaii?
You can take short, relatively cheap flights between the Hawaiian islands. Hawaiian Airlines are other major airlines operate multiple daily flights between all the islands.
Or, if you have a large trip budget, you can take a private helicopter to enjoy the views along the way.
How much does it cost to hop from island to island in Hawaii?
There are dozens of flights every day between all the islands, so you’ll want to compare prices to find the best flight deals that correspond with your island-hopping itinerary. One-way flights usually range from $50-$150.
How many days in Hawaii is enough?
You’ll want to give yourself at least 3-4 days on each island. If you want to visit all four of the main islands – Maui, Kauai, Oahu, and Big Island – which I highly recommend, then you’ll need about two weeks.
Should I go to Maui or Oahu first?
I highly recommend going to both of these islands! If you’re visiting them both on the same trip, then it doesn’t matter which one you visit first. I would compare flights to find the best deals and then decide which one to go to first.
Which Hawaii island is the prettiest?
All four of the major Hawaiian islands – Oahu, Kauai, Big Island, and Maui – are stunning! I couldn’t choose the pretties because they all have unique and breathtaking landscapes.
Is there a ferry from Oahu to Maui?
No. You’ll need to take a flight from Oahu to Maui. Or, if you have a large trip budget, you can take a private helicopter to enjoy the views along the way.
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This Hawaii island-hopping itinerary is not a sponsored post, and the thoughts and opinions expressed in this post are entirely my own. Some of the links in this Hawaii island-hopping itinerary are affiliate links, and, at no cost to you, I may earn a small commission from this Hawaii island-hopping itinerary.
