See Big Island Volcanoes Park & Oahu Pearl Harbor

Hawaii offers an unforgettable island-hopping experience, with short flights connecting major islands. While tempting to see everything, time is precious. Planning wisely ensures you enjoy each island without feeling rushed.

Getting Around Hawaii

Island hopping in Hawaii is primarily done by air. The interisland flights are convenient and short, making it easy to move between the islands. Hawaiian Airlines, Southwest Airlines, and Mokulele Airlines are the main carriers operating these routes.

Mokulele Airlines is particularly useful as it serves smaller airports and handles routes to Lanai and Molokai, which Hawaiian Airlines has suspended. Their small propeller planes offer a unique way to see the islands from above.

For the adventurous, a ferry is an option between Maui and Lanai, offering a scenic sea voyage. Cruise lines also offer multi-island itineraries, though these can feel more regimented.

When I first started traveling between the islands, I learned quickly that the “short” flights still eat up a significant chunk of your day. Between getting to the airport, security, boarding, the flight itself, and then getting your rental car and checking into your next hotel, you can easily lose half a day. So, my best advice for families is to really assess if hopping to another island is worth sacrificing time on the one you’re already enjoying.

Major Hawaiian Islands

There are four main islands that most visitors focus on, each offering distinct experiences and connected by direct flights from the mainland. Oahu is home to the bustling city life of Waikiki and the historical Pearl Harbor. Maui boasts the stunning Haleakala Crater and the scenic Road to Hana.

The Big Island of Hawaii is famous for its active Volcanoes National Park and the Mauna Kea Observatory. Kauai, known as the Garden Isle, features the breathtaking Napali Coast.

Beyond these, Lanai and Molokai offer more secluded and tranquil getaways, accessible primarily through interisland flights. Lanai is known for its luxury resorts, while Molokai provides a glimpse into a more traditional Hawaiian way of life.

I remember one trip when we were so excited to see the Road to Hana on Maui and then head straight to Volcanoes National Park on the Big Island. We booked the flights back-to-back, thinking it would be seamless. But getting that rental car back on Maui, taking the flight, then waiting for luggage, and getting another rental car on the Big Island took so long that by the time we settled into our hotel, the kids were exhausted and we’d basically lost an entire day. It really made me rethink how much we could realistically see without making the travel itself the main event of the trip.

Planning Your Island Hop

To truly enjoy island hopping, it’s recommended to dedicate at least a week per island. For eight to nine days, you might be able to visit two islands if you have specific key attractions in mind. Anything less than that, and you risk either missing out on the best of your chosen island or spending too much time in transit.

How much time should I allow per island?

For a truly immersive experience, I suggest at least a full week on each major island. If you’re aiming for a whirlwind tour of highlights, perhaps 3-4 days per island could work, but be prepared for a very fast pace.

When Michael and I planned our first family trip, we tried to cram four islands into ten days. It was exhausting! The kids were constantly in new places, and we never felt like we could truly relax or explore one spot deeply. We learned that sometimes, less is more. Now, we often choose two islands for a two-week trip, giving us about a week for each and plenty of time to explore without feeling like we’re living at the airport.

Airlines for Interisland Travel

Hawaiian Airlines is a major player in interisland travel, offering frequent flights between the main islands. Southwest Airlines also operates routes, providing another option for travelers, especially those loyal to their rewards program.

Mokulele Airlines is invaluable for its reach to the smaller islands of Lanai and Molokai, as well as serving smaller airports on the larger islands like Hana on Maui or Kamuela-Waimea on the Big Island. These flights can offer incredible aerial views.

I always check all three when booking interisland flights. Sometimes one airline has a better schedule or price, and it’s worth comparing. Mokulele, in particular, flies into some airports that are much closer to smaller towns or specific attractions, saving you a longer drive once you land.

Boat Travel in Hawaii

While interisland flights are the norm, boat travel is possible for specific routes. A ferry connects Maui and Lanai, offering a pleasant sea crossing. For those who prefer cruising, several cruise lines offer itineraries that include multiple Hawaiian islands.

Cruise ship travel can be convenient for seeing several islands, but it often means limited time on each island. You’ll get a taste of each place, but it might not feel like a deep dive into local culture. I’ve found that for families seeking authentic experiences, exploring each island more independently, even if it means fewer islands visited, leads to richer memories.

Saving Money on Hawaii Island Hopping

Traveling between islands can add up, but there are ways to save. Airlines often have different baggage fees, and joining their loyalty programs can offer discounts. Southwest offers free checked bags for certain members, while Hawaiian Airlines offers discounts for its HawaiianMiles members.

Using airline-specific credit cards can also provide perks like free checked bags or bonus miles. For example, the Hawaiian Airlines® World Elite Mastercard® can offer significant savings if you fly Hawaiian frequently.

When I travel with Lily and Ethan, luggage fees are always a concern. We’ve signed up for the HawaiianMiles program because we often fly Hawaiian between islands, and that bag discount really adds up. It’s a small thing, but it saves us money that we can then spend on an extra shave ice for the kids!

Renting a car on each island is another significant expense. Booking in advance is crucial, especially post-pandemic, as car availability can be limited and prices high. Many car rental companies offer discounts through sites like DiscountHawaiiCarRental.com.

Can I use points or miles for flights?

Yes, absolutely! Most airlines serving Hawaii, especially Southwest and Hawaiian Airlines, have loyalty programs with rewards points that can be redeemed for flights and other travel. You can also earn points through co-branded credit cards.

I’ve found that leveraging credit card sign-up bonuses and everyday spending on travel-focused cards has been a game-changer for our family trips. It allows us to take more trips or upgrade our accommodations without drastically increasing our cash outlay.

Sometimes, the points you earn with HawaiianMiles can even be converted to hotel points, like Hilton Honors. This adds another layer of flexibility when planning your stay. It’s like having a secret stash of travel currency!

Accommodation and Car Rental Tips

When booking hotels, consider loyalty programs and credit cards that offer bonus points for stays with specific hotel chains. Planning which islands you’ll visit can help you strategically choose credit cards that align with your preferred accommodations.

For rental cars, reserve them as early as possible. Prices can fluctuate wildly, and last-minute bookings can be extremely expensive or even impossible. I’ve learned to book my rental cars months in advance, even on flexible rates, so I can cancel and rebook if better deals pop up.

Sometimes, renting a car for just a few days on an island is sufficient if you plan to mostly relax at your resort. This can save on rental costs and parking fees, which can be substantial, especially in tourist areas like Honolulu.

Are resort fees and parking costly?

Yes, be prepared for resort fees and parking charges, especially in popular areas. These can add a significant amount to your daily accommodation costs. Always factor these into your budget when comparing hotel rates.

We were once surprised by the combined resort and parking fees at a hotel in Waikiki. It nearly doubled the cost of our room for that night! Now, I always look for those fees upfront in the booking process and compare hotels that include them or offer better value packages.

Maximizing Your Hawaii Trip

Ultimately, the best island-hopping strategy depends on your available time and interests. If you have less than eight or nine days, focus on one island to truly savor the experience. If you have more time and are eager to explore, plan your interisland travel carefully, taking advantage of any available savings and loyalty programs.

Consider package deals from Hawaii specialists, which can sometimes bundle flights, hotels, and car rentals at a negotiated rate. Compare these deals against booking each component separately to ensure you’re getting the best value.

Remember that travel is about the journey as much as the destination. By planning smart and being realistic about time, you can create an incredible Hawaiian adventure that feels both exciting and relaxing for the whole family.

Do travel packages save money?

Sometimes. Package deals can offer convenience and a bundled discount. It’s always a good idea to price out the components individually and compare that total cost to the package price. You might find that booking flights, accommodations, and car rentals separately offers better savings or more flexibility.

I’ve used package deals before, and they’ve been great for simplifying the initial booking process, especially when I’m short on time. However, I’ve also found that by spending a little more time researching, I can often put together a more personalized and sometimes cheaper itinerary myself.