🌺 14-Day Hawaii Cruise Itinerary: Island-Hopping the Aloha Way

If you’re dreaming of a tropical escape, this Hawaii cruise itinerary offers the ultimate 14-day island-hopping experience. Sail round-trip from Honolulu to four breathtaking Hawaiian islands — Oʻahu, Maui, Kauaʻi, and the Big Island — without ever changing hotels. This Hawaiian cruise blends natural wonders, cultural discovery, and onboard luxury into one seamless journey.

A 14-Day Island-Hopping Adventure in Paradise
This Hawaii cruise itinerary lets you explore four breathtaking islands without the hassle of changing hotels. Over 14 unforgettable days, you’ll cruise through Hawaii and discover volcanoes, waterfalls, beaches, and deep cultural heritage — all from the comfort of your ship.
Whether you’re planning a bucket-list honeymoon, a multi-generational family getaway, or just a tropical escape, this Hawaiian cruise blends relaxation with adventure. Departing round-trip from Honolulu, this journey includes overnight stays, scenic cruising, and immersive shore excursions on every island.

Days 1–3: Oʻahu & Kauaʻi – Culture Meets Nature
🚢 Day 1: Depart from Honolulu, Oʻahu
Arrive early and enjoy Waikīkī’s energy. Hike Diamond Head for stunning views, visit Pearl Harbor, or tour ʻIolani Palace. In the evening, join a beachfront luau before boarding your ship.
📝 Travel tip: This is a great time to meet fellow cruisers.
🌴 Day 2: Nāwiliwili, Kauaʻi
Welcome to the Garden Isle. Explore the Nā Pali Coast by boat or helicopter. Kayak the Wailua River or visit Waimea Canyon — known as the “Grand Canyon of the Pacific.” Prefer something slower? Stroll Hanalei Town or relax at Poʻipū Beach.
🌺 Day 3: Nāwiliwili (Overnight in Port)
With extra time in port, dive deeper. Hike Sleeping Giant, enjoy a plantation tour, or snorkel on the sunny south shore.
🌄 Don’t miss: Sunset views from Kalalau Lookout — unforgettable!

Days 4–6: Maui & Big Island – Volcanoes, Beaches & Upcountry Bliss
🐠 Day 4: Kahului, Maui
Maui offers something for everyone. Drive the Road to Hāna, catch sunrise at Haleakalā, or sunbathe on Kāʻanapali Beach. If you’re cruising December–April, look for humpback whales offshore.
🧘 Day 5: Kahului (Overnight)
Your second day lets you dive deeper. Visit Makawao’s art galleries, relax in Paʻia, or sip coffee at an Upcountry plantation.
🍧 Bonus: Grab shaved ice and fresh poke near the port.
🌋 Day 6: Hilo, Big Island (East Side)
Hilo is lush, tropical, and raw. Explore Hawaiʻi Volcanoes National Park, walk through lava tubes, and see Rainbow Falls. Don’t forget to sample local treats at the Hilo Farmers Market.

Days 7–9: Kona, Lahaina & Scenic Cruising
🌞 Day 7: Kona, Big Island (West Side)
Sunny Kona brings a change in scenery. Snorkel with manta rays, visit a Kona coffee farm, or tour ancient temples at Puʻuhonua o Hōnaunau National Park.
🌊 Day 8: Day at Sea
Time to relax. Attend a hula class, book a spa treatment, or simply enjoy the ocean breeze with a tropical drink in hand.
🛳️ Tip: Use this time to recharge before the final stretch.
🏖️ Day 9: Lahaina, Maui (Tender Port)
Explore Lahaina’s historic charm. Walk Front Street, snorkel at Molokini Crater, or browse the art markets beneath the iconic Banyan Tree.

Days 10–13: Scenic Cruising & Cultural Deep Dives
🌈 Day 10: Scenic Cruising – Molokaʻi Channel
Sail past remote cliffs and coastlines. Along the way, look out for dolphins, sea turtles, and flying fish.
🌊 Great for photos: Sunrise and sunset both shine here.
🌄 Day 11: Honolulu Return – Cultural Day
Back in Oʻahu, explore more. Take a surf lesson, hike to Manoa Falls, or visit the Bishop Museum.
🌆 Dinner idea: Dine at Ala Moana before heading back onboard.
🌋 Day 12: Scenic Cruising – Kīlauea Volcano
Tonight, cruise past Kīlauea. If active, lava may be visible as it flows into the ocean — a breathtaking sight you’ll never forget.
🎭 Day 13: Polynesian Culture Day at Sea
Celebrate your last day with onboard cultural events. Enjoy a traditional dance show, lei ceremony, and ukulele class.
🎶 Memory maker: Learn a song you can take home with you.

Day 14: Return to Honolulu – Farewell Aloha
🛬 Disembark in Honolulu. Enjoy one last stroll through Waikīkī, a beachside breakfast, or shopping for macadamia nuts before heading home.
🧳 Optional: Extend your Hawaii cruise itinerary with a land stay in Oʻahu or Maui.

Why Book Your Hawaii Cruise with Travel Today In Style?
When you book with Allison at Travel Today In Style, you’re getting more than a reservation — you’re getting a partner in your journey.
🌺 Tailored excursion planning
🛌 Pre- and post-cruise hotel coordination
🚢 VIP perks like cabin upgrades and onboard credit
🌴 Insider island recommendations
🤝 Real support from a trusted cruise planner
📞 Don’t just take a Hawaiian cruise — experience it effortlessly.
Let us turn your Hawaii cruise itinerary into the vacation of a lifetime.