Kailua Kona is a foodie’s paradise, offering a mix of authentic Hawaiian flavors, spectacular ocean views, and lively cultural shows. What makes dining here special isn’t just the food—it’s the setting and the stories behind every dish. One experience we especially like is the From Hawaii: Historical Dinner Cruise Tour to Kealakekua Bay; it combines an island-style dinner with sunset views and storytelling from a historian, making it a memorable way to spend an evening. Plus, you might spot dolphins or humpback whales if you’re lucky. Kailua Kona’s dining options range from elegant sunset cruises to lively luaus, each offering a taste of local culture and cuisine.
If you’re trying to decide which experience suits you best, you’ve come to the right place. Below, we outline the top three dining experiences in Kailua Kona, highlighting what makes each one stand out—whether it’s the setting, the cultural entertainment, or the food. Read on to find the perfect match for your Hawaiian adventure.
1. From Hawaii: Historical Dinner Cruise Tour to Kealakekua Bay
At number 1 on our list is the From Hawaii: Historical Dinner Cruise Tour to Kealakekua Bay. For $200 per person, this 3-hour cruise offers a unique blend of Hawaiian history, wildlife spotting, and sunset views. The tour departs from Kailua Kona and takes you to Kealakekua Bay, known for its crystal-clear waters and vibrant marine life. The highlight is the onboard storytelling by a historian guide, who shares tales about the powerful kings who once ruled these lands, adding depth to your experience.
What sets this cruise apart is the combination of cultural storytelling and a scenic sunset. As you relax with a well-prepared island-style dinner, keep your camera ready for dolphins, turtles, manta rays, and even seasonal humpback whales. Live traditional music keeps the atmosphere lively, and a complimentary cocktail helps you unwind as the sun dips below the horizon. This experience is perfect for history buffs, nature lovers, and those wanting a more intimate, relaxed evening on the water.
Bottom Line: This cruise offers a rich mix of Hawaiian culture, wildlife, and stunning vistas, all wrapped into a 3-hour package that feels both educational and leisurely.
2. Kailua-Kona: Voyagers of the Pacific Luau with Buffet Dinner
Coming in at number 2 is the lively Kailua-Kona: Voyagers of the Pacific Luau with Buffet Dinner. For $178 per person, this 2.5-hour event combines Hawaiian culture, delicious food, and entertainment in an oceanfront setting overlooking Kailua Bay. The all-you-can-eat buffet features a range of Polynesian classics, from kalua pork to tropical fruits, satisfying any appetite.
The highlight here is the entertaining show, which includes traditional Hawaiian music, hula dancing, and the dramatic Samoan fire-knife dance. A special Imu ceremony, where a roasted pig is ceremoniously unveiled from an underground oven, adds an authentic touch. Drinks like Mai Tais and other cocktails are included, making it a festive evening. The setting—right on the water—adds to the sense of being immersed in Hawaiian culture.
This luau is ideal for travelers looking for a family-friendly, all-in-one cultural experience that combines good food with lively entertainment. The reviews note the show is “very engaging,” making it a memorable night out.
Bottom Line: Perfect for those wanting a fun, upbeat evening full of Hawaiian traditions, great food, and spectacular ocean views.
3. Big Island: Private Island Circle Tour with Lunch and Dinner
At number 3, the Big Island: Private Island Circle Tour with Lunch and Dinner offers a full-day exploration with a focus on scenic beauty and local flavors. Although it’s primarily a land tour, it includes thoughtfully curated lunch and dinner options that highlight the island’s diverse cuisine. Priced at $1,660 per group (up to 2 people), it’s a significant investment but suits travelers seeking a personalized experience.
This tour covers iconic sites such as Punalu’u Black Sand Beach, Hawaii Volcanoes National Park, and lush waterfalls near Hilo. It also includes a visit to an authentic Kona coffee farm, where you’ll taste fresh, locally grown coffee. The tour’s strength lies in its flexible, private nature—your guide shares insights tailored to your interests and takes you to less-touristy spots you wouldn’t find on a larger group tour.
While this is the most expensive option, it offers an all-encompassing Hawaiian experience—combining sightseeing, culture, and food—perfect for travelers wanting a deep dive into the Big Island’s unique offerings. Reviewers note the trip is “a feast for the eyes and the palate,” especially for those who enjoy a full-day adventure.
Bottom Line: Best suited for travelers who want a private, comprehensive tour with meals included, and who don’t mind the higher price tag for a personalized experience.
$1,660 per group up to 2
How to Choose the Best Dining Experience in Kailua Kona
When deciding between these options, consider your budget, schedule, and interests. If you love storytelling combined with a scenic cruise, the dinner cruise to Kealakekua Bay offers a laid-back, educational evening. For a lively cultural show with plenty of food, the luau provides a vibrant night out. And if you’re after an in-depth, private exploration with delicious local cuisine, the Big Island private tour might be your best choice—albeit at a higher price.
Think about what kind of experience best matches your trip style. Want a romantic sunset with a touch of history? The cruise is unbeatable. Looking for a lively, family-friendly show? The luau hits the spot. Craving a personalized, full-day adventure? The private tour is your ticket.
Booking early is always wise, especially during peak travel seasons, to secure your preferred date and experience.
Final Thoughts
Kailua Kona offers a range of exceptional dining experiences that go beyond just eating—these are opportunities to soak in Hawaiian culture, enjoy stunning vistas, and share memorable moments. The dinner cruise is perfect for a relaxed, scenic evening, while the luau packs lively entertainment and local flavor into a shorter outing. For those seeking a comprehensive, personalized adventure, the private island tour offers unmatched flexibility and depth.
No matter which you choose, booking in advance will help ensure you get the best experience. These options cater to different preferences—whether it’s a romantic sunset, cultural celebration, or a private day of discovery—and each promises a taste of true Hawaiian hospitality. Enjoy your culinary journey in Kailua Kona!