Hawaii Island Hopping Guide :Explore Paradise Your Way

A tropical paradise with mesmerizing landscapes and vibrant culture, Hawaii has so much to offer that it can be hard to know where to start.

One of the biggest questions is which island to visit?

Oahu, Maui, the Big Island, and Kauai are the most popular, but there are lesser-known gems like Molokai and Lanai, which means the ideal solution is a Hawaii island hopping trip.

This ultimate guide provides all you need to know to organize your island hopping getaway, from an in-depth look at the diverse islands to itinerary options, tips, and more. 

Understanding Hawaii’s Diverse Islands

While there are some similarities, each island offers something unique of its own so we’ve provided a more in-depth look at the four major islands, plus Lanai and Molokai.

Oahu: The Gathering Place – Urban Adventure Meets Paradise

Oahu, the most visited island in Hawaii, offers an excellent mix of city attractions, beautiful nature, and nightlife, making it ideal for first-time visitors to the state, those who don’t want to drive, and anyone who wants to do plenty of socializing. 

The island is home to some of the state’s most famous spots, including Waikiki Beach, Pearl Harbor, and Diamond Head, while a long list of activity options awaits, from surfing, snorkeling, and sunset sailing to hiking and biking, providing a well-rounded introduction to Hawaii.

Maui: The Valley Isle – Romance, Beaches, and Road Trips

Maui is not only ideal for luxury and romance seekers, but families with children, and, in the winter, avid whale watching enthusiasts. 

If you’re island hopping between mid-December and mid-March, the whales alone make Maui a must-visit, with the majority of the 10,000 to 15,000 humpbacks migrating to Hawaii header here.

The major resort areas on the island, including Wailea, Kaanapali, and Kapula, provide everything that discriminating travelers look for, including championship golf, lavish spas, upscale shopping, world-class eateries, and high-end resorts.

Families on a budget can find some lower-priced vacation rentals and more affordable family-friendly hotels, along with free and inexpensive activities, including countless beautiful beaches to spend the day on.

There are some fantastic options for road trips on Maui, including the Road to Hana, one of the world’s most scenic drives featuring waterfalls, lush rainforests, and idyllic beaches.

A two-hour drive will bring you to the summit of Haleakala in Haleakala National Park at over 10,000 feet for one of the best panoramic views in Hawaii.

Kauai: The Garden Isle – Nature’s Wonderland

Nicknamed “The Garden Isle,” Kauai is incredibly lush, home to many botanical gardens, and often noted as the most beautiful of the Hawaiian islands.

Kauai is popular for romantic escapes and perfect for anyone who is seeking tranquility, stunning nature, and outdoor adventures.

Just a few of the must-sees are Waimea Canyon, the country’s second largest behind only the Grand Canyon, Hanaelei Bay, and the Na Pali coast with its soaring cliffs, a cascade of colors dipping to hidden sea caves and secluded beaches.

Along the South Shore, you’ll find many beaches that are ideal for families, like Poipu, where you can swim, snorkel, and watch for the endangered Hawaiian monk seal.

Big Island: Adventure, Volcanic Landscapes, & Spiritual Retreats

As its name suggests, the Big Island, officially known as Hawaii, is the largest of the state’s islands, bigger than the seven other major islands combined at over 4,000 square miles in size.

As it’s so vast, the island of Hawaii offers especially diverse landscapes with everything from emerald valleys and snow-capped summits to white sandy beaches and black volcanic sands, along with many other unique volcanic features. 

The Big Island is the best for those fascinated with volcanoes, with the chance to walk through lava tubes, witness flowing lava, and fiery eruptions at Kilauea Crater in Volcanoes National Park. 

It’s also a great choice for anyone seeking outdoor adventure, with everything from night snorkeling with manta rays that have wingspans of up to 16 feet to off-roading and hiking hundreds of miles of trails.

A big draw for yoga practitioners and spiritual seekers, you’ll find plenty of places to practice your downward dog and meditate, especially in and around Pahoa, the so-called “hippie capital.”

Molokai and Lanai: Off-the-Beaten-Path Experiences

You might want to consider Molokai and Lanai for your island hopping trip, especially if you enjoy getting off the beaten path.

Molokai is the perfect island for those who want to enjoy a slower pace, with empty beaches like Papohaku, with its wide, unspoiled white sands making it feel as if you’re on your own private island.

The island is also home to the world’s highest sea cliffs and is the birthplace of the hula dance, with a strong connection to Hawaiian culture.

Lanai is the smallest island in Hawaii at just 13 miles wide and 18 miles long, with no traffic lights, no fast food joints, and only 30 miles of paved roads.

Visit Lanai if you truly want to get away from it all, with surprisingly diverse landscapes from red alien-like terrain to Hulopoe Bay’s brilliant turquoise water and white sands.

But how do you get between the islands on an island hopping trip, you may ask?

Transportation for Hawaii Island Hopping

Fly

The most common way to go island hopping in Hawaii is to fly. 

One-way inner-island flights are relatively inexpensive, ranging from $50 to $150, with Hawaiian Airlines widely regarded as the best, serving airports on Oahu, Maui, the Big Island, Kauai, Lanai, and Molokai.

Southwest Airlines serves airports on Oahu, Maui, Kauai, and the Big Island.

The trick to booking inter-island flights is to find a balance between the time that’s lost for travel and the chance to visit another beautiful Hawaiian island, which means always booking direct.

Ferry

Unfortunately, you can’t do much island hopping with the ferry in Hawaii, as the only inter-island ferry option travels between Maui and Lanai, operated by Expeditions.

Cruise

There are many cruises that conclude in Hawaii, but only Norwegian Cruise Line (NCL) will bring you on an island hopping adventure.

NCL visits the four most popular islands, typically round-trip from Oahu, visiting Maui and the Big Island for two days each, and Kauai for a day and a half.

Now that you know more about the islands and how to reach them, it’s time to plan that perfect island hopping itinerary!

Planning Your Perfect Island Hopping Itinerary

You’ll want at least a week for a proper island hopping adventure in Hawaii.

If you only have seven days, it’s best to split your time between two islands, as you need at least three days on each.

Those lucky enough to have two weeks can easily visit four islands on an island hopping trip, perhaps including some time on one of the less-visited islands like Lanai, which can be done as a day trip from Maui.

The Ideal 7-Day Hawaii Island Hopping Itinerary

The Ultimate 14-Day Hawaii Island Hopping Itinerary

Once you’ve determined your itinerary, you might want to think about ways to save money for a more budget-friendly island hopping vacation in Hawaii.

Budget-Friendly Hawaii Island Hopping Strategies

Best Time to Visit for Lower Prices and Fewer Crowds

While Hawaii is visited year-round, September and October are typically the quieter months, which means you’ll encounter fewer crowds. 

Early fall is also when airfare tends to be at its lowest from the U.S. mainland, and you’ll have a better chance of scoring discounted rates on accommodation.

May is worth considering as well, as a slower month in terms of tourism.

Book More Affordable Accommodation

No matter when you visit, consider booking some of the more affordable accommodation options.

With much of your time spent outside of your hotel room, it may not make sense to stay at a luxury resort.

• Oahu: FIRST CABIN INTERNATIONAL HAWAII
• Maui: Maui Coast Hotel
• Big Island: Royal Kona Resort
• Kauai: Aston Islander on the Beach

Cost Saving Tips for Car Rentals & Transport

In addition to understanding how to get between the islands on an island hopping trip, you’ll need to consider how to get around when visiting each one.

In Waikiki, there’s really no need to rent a car with so many attractions within walking distance or easily accessible by public transport, including The Bus and Waikiki Trolley, which covers all the top tourist spots and more.

If you want to explore more of Oahu, particularly the North Shore, consider renting a car just for a day or two to save.

When renting a car on any of the Hawaiian islands, book directly with the company rather than a third-party car rental site, as you can end up paying more through hidden fees and may have difficulty making changes, among other potential complications.

On Maui, the only public transport option is the Maui Bus, with 12 routes; however, it doesn’t cover the Road to Hana or Haleakala National Park, as it’s more of a local service.

The Big Island’s public transport system is called the Hele-On Bus, and it can get you around the entire island for cheap.

In Kauai, the Kauai Bus can get you between the major destinations at a low cost while being easy to navigate, as the island only has one main road, but it will take you longer to get to where you want to go due to the many stops.

Now, you have all the tools you need to book that dream island hopping vacation in Hawaii, we have just one last note…

Summary

We’ll conclude with one of our favorite aspects of a Hawaii island hopping trip: the Aloha spirit.

It isn’t just a popular way to say hello and goodbye when you’re visiting the islands.

Aloha is part of a lifestyle that brings a special magic to every island in Hawaii, something that may be the most unforgettable part of this island hopping experience.