Island Hopping in Hawaii: A Journey Through Paradise by Jill

Hawaii, with its stunning landscapes, vibrant culture, and unique islands, offers an unparalleled
adventure for travelers. Island hopping in Hawaii allows you to experience the diverse beauty and
charm of each island, creating a truly unforgettable trip. In June 2024, my family and I experienced
an island-hopping adventure to 5 Hawaiian Islands—Maui, Oʻahu, Lāna‘i, Kauaʻi and Hawai’i Island.
Here’s a guide to help you plan your island-hopping adventure in Hawaii.

Why Island Hop in Hawaii?

Each Hawaiian Island has its own distinct personality and attractions. Island hopping lets you explore the best of what Hawaii has to offer. Whether you’re seeking adventure, relaxation, or cultural experiences, there’s something for everyone.

Must-Visit Islands and Highlights: 

Oʻahu: Known as “The Gathering Place,” Oʻahu is home to Honolulu, Waikiki Beach, and the historic Pearl Harbor. Oʻahu offers vibrant nightlife, shopping, and dining options in the city. Try a malasada or two from Leonard’s Bakery. Snorkeling at Hanauma Bay is a MUST DO!     

Maui: Famous for its stunning beaches, the Road to Hana, and Haleakalā National Park with its breathtaking sunrises and sunsets above the clouds, Maui offers a mix of adventure and relaxation. Snorkeling at Molokini Crater is a must-do activity. November-March is humpback whale season and green sea turtles are abundant year-round.  Pro tip: Try the banana cream pie at Leoda’s or shave ice at Ululani’s.

Kauaʻi: The “Garden Isle” is perfect for nature lovers. Explore the dramatic clifs of the Nāpali Coast via boat or helicopter, explore sea caves, hike through Waimea Canyon, relax in the lush tropical gardens, and soak up the sun on the pristine beaches. Our boat tour with Nāpali Expeditions along the Nāpali Coast and through the sea caves was one of my favorite vacation experiences ever. Definitely try a traditional Hawaiian plate lunch served with a scoop of rice and mac salad found all over the Hawaiian Islands.

Big Island (Hawai’i Island): Known for its diverse landscapes, the Big Island features active volcanoes, black sand beaches, and lush rainforests. Visit Hawai’i Volcanoes National Park and take a dip in the warm waters of the Kona Coast.  In Hilo enjoy the secluded swimming spot at Carlsmith Beach Park.  In Kona a night snorkel with Manta Rays (“gentle giants” of the ocean) is an extraordinary must-do adventure.  Don’t miss the poke nachos on any of the Islands!

Lāna‘i: A quieter, more secluded island, Lāna‘i offers luxury resorts such as the Four Seasons, rugged landscapes, and unique attractions like the Garden of the Gods and Shipwreck Beach. Hulopoe Beach is within walking distance of the ferry port and allows visitors to explore tidepools, snorkel, swim and relax on the white sandy beach. Lāna‘i is perfect for a day trip by ferry from Maui!

Molokaʻi: Known for its unspoiled beauty and strong Hawaiian culture, Molokaʻi is ideal for those seeking an off-the-beaten-path experience. Visit the Kalaupapa National Historical Park and enjoy the island’s serene beaches.  Check out the stunning waterfalls on Molokaʻi.

 Getting Around: How to Island Hop:

Flights: The most common and efficient way to travel between the islands is by plane. Hawaiian Airlines and Southwest Airlines offer frequent inter-island flights, making it easy to hop from one island to another. Hawaiian airlines even serves guests POG (Passion Fruit, Orange, and Guava) juice (originated in Maui) during the short flights between islands.

Ferry: There is a ferry service available between Maui and Lāna‘i. This can be a scenic and enjoyable way to travel.  During our ferry trip between Maui and Lāna‘i, we were escorted by a playful pod of spinner dolphins.  During whale season you are sure to see majestic humpback whales!

Cruises: For a more leisurely experience, consider taking a cruise that stops at multiple islands. This allows you to enjoy the journey as much as the destinations! The Norwegian Cruise Line Pride of America travels exclusively to the Hawaiian Islands.

Tips for a Smooth and Enjoyable Island-Hopping Experience:

Plan Ahead: Book your flights, accommodations, and activities in advance to ensure availability and better rates.

Pack Light: Traveling between islands is easier with less luggage. Consider packing versatile clothing and essentials. We island-hopped from Maui to 4 other islands in a week and each only brought a small carry-on.  No time wasted at baggage claim!!

Stay Flexible: Weather and other factors can affect travel plans, so be prepared to adjust your itinerary if needed.

Rent a Car: Having a car on each island gives you the freedom to explore at your own pace. Check for rental deals and book early.  On Lāna‘i a shuttle service is available to/from the port to Lāna‘i City—cash only ($10 per person each way) payable to the driver.

PRO TIP…sit next to the shuttle driver or up at the front of your tour boat near the captain.  You will be surprised at how much you learn from them about their island!    Also your MDT travel advisor can provide you with a list of restaurants for each island which highlight the island’s local specialties.

Ready to go?

Island hopping in Hawaii is a fantastic way to experience the diverse beauty and culture of the islands. Whether you’re taking a surfing lesson in Waikiki (Oʻahu), marveling at the massive cliffs of the Na’Pali Coast (Kauaʻi), embarking on a whale watching adventure in Maui, watching the tide pools which appear and disappear with the tide in Lāna‘i, hiking the lush landscapes of Halawa Valley in Molokaʻi or visiting Volcanoes National Park on Hawaii Island, each island offers something unique and memorable.

Ready to start planning your next adventure?