Kauai is a favorite for sailors and ocean lovers because of its dramatic coastlines, clear waters, and vibrant marine life. Unlike some Hawaiian islands that focus on snorkeling or surfing, Kauai’s sailing options let you see the island’s rugged cliffs, lush valleys, and wildlife from the water—often with fewer crowds. We especially like the Kalapaki Kai Sunset Catamaran Cruise because it combines relaxed scenery with cultural insights, and the Na Pali Coast Power Catamaran for its adventurous spirit and dolphin sightings. Both tours showcase Kauai’s natural beauty in very different ways, making them top picks for any boat lover.
If you’re curious about how to narrow down your choices, keep reading. We’ll walk you through five of the best sailing experiences, pointing out what makes each one unique and who it’s best suited for. Whether you want a quick sunset, an all-day adventure, or a private charter, Kauai has a boat trip for you.
Quick Overview of Kauai Sailing Tours
Our list covers a range of sailing options including scenic sunset cruises, the iconic Na Pali Coast exploration, and private charters. You can enjoy relaxed group outings like the Kalapaki Kai Sunset Catamaran Cruise, or go for the more extensive Na Pali Coast Power Catamaran, which offers snorkeling and wildlife viewing. There’s also a sunset sail with dinner, perfect for a romantic evening, and a shorter sunset cruise for a quick but memorable experience. For those wanting exclusivity, the private Na Pali Coast charter offers a personalized adventure. Now, let’s explore each in detail.
1. Kalapaki Kai Sunset Catamaran Cruise
Starting at number 1, the Kalapaki Kai Sunset Catamaran Cruise is a favorite for its balance of scenic beauty, affordability, and laid-back atmosphere. For just $109 per person, this 2-hour cruise offers a relaxing way to enjoy Kauai’s coastlines and wildlife. The tour covers both the Hulei’a River and Kalapaki Bay, where you can see the Menehune Fish Pond, a favorite movie filming location, and the Ninini Point Lighthouse.
What makes this cruise stand out is the mix of nature and history narration from your skipper. You’ll learn about native plants, tropical birds, and the story behind local landmarks. The boat is a group catamaran, so it’s perfect for travelers looking for a social, budget-friendly experience. Snacks, soft drinks, and alcoholic beverages are included, making it ideal for a casual, sunset-watching evening.
Reviews praise the crew’s friendliness and the low-key, informative vibe. One guest said, “A memorable evening with beautiful sites and a chill atmosphere.” It’s perfect for those wanting a short, scenic, and relaxed experience with little fuss.
Bottom Line: If you want a friendly, affordable sunset cruise with great scenery and local commentary, this tour hits the mark.
2. Na Pali Coast Power Catamaran
At number 2, the Na Pali Coast Power Catamaran offers a more adventurous 4.5-hour exploration of one of Kauai’s most dramatic regions. This custom-built boat is designed for comfort but also agility, allowing it to navigate the craggy sea caves and rugged shoreline of the Na Pali Coast.
You’ll experience snorkeling or swimming depending on conditions, with chances to see dolphins, turtles, and tropical fish. The tour emphasizes wildlife encounters and scenic views, making it ideal for nature lovers who want an active day on the water. The boat’s size allows it to access secluded spots that larger ships can’t reach, giving you an intimate look at Kauai’s coast.
Guests rave about the smooth ride and knowledgeable crew, especially noting how Captain Kylie and crew members like J go out of their way to make the trip memorable. One reviewer called it “the best day of the trip,” citing the dolphins and sea caves as highlights.
Bottom Line: For those seeking a full-day adventure with snorkeling, wildlife, and dramatic scenery, this trip offers excellent value and a memorable experience.
3. Kauai: Napali Coast Sunset Sailboat Tour with Dinner
Number 3 on our list is the Napali Coast Sunset Sailboat Tour with Dinner, which offers a luxurious take on Kauai’s famous coastline. Over 4.5 hours, you’ll sail along the cliffs, valleys, waterfalls, and secluded beaches, all bathed in the glow of sunset.
What sets this tour apart is the dinner service—a locally-made Hawaiian meal paired with a glass of champagne. It’s perfect for couples or anyone wanting a romantic, scenic evening. The boat is well-equipped for comfort, and you’ll likely see dolphins, turtles, and maybe even humpback whales if it’s the season.
The combination of spectacular scenery, fine dining, and sunset views makes this a standout option, especially for special occasions or those who want a more refined experience. Travelers consistently praise the beautiful vistas and the relaxed, elegant atmosphere. One reviewer called it “a sunset to remember,” highlighting the panoramic views and dinner.
Bottom Line: If you’re after a romantic, scenic, and comfortable evening with good food, this sunset sail is a top pick.
4. Kauai: Catamaran Sunset Cruise
The Kauai: Catamaran Sunset Cruise is a shorter, 1.5-hour outing that offers a relaxed way to unwind at the end of the day. Boarding a 50-foot catamaran, you’ll cruise the waters of Nawiliwili Bay while sipping tropical cocktails and watching the Kalapaki sunset.
This tour provides a more intimate experience with traditional Hawaiian music and narration about local history. You’ll also pass by the Alekoko Menehune Fish Pond and the Hulei’a National Wildlife Refuge, giving you a taste of Kauai’s natural and cultural landscape. It’s a popular choice for travelers short on time but wanting an authentic, laid-back sunset experience.
Guests comment on the friendly crew and the beautiful, peaceful atmosphere. It’s a good option for those seeking a quick, scenic escape with drinks and mellow vibes.
Bottom Line: If you want a short, relaxing cruise with a fun, social feel, this sunset sail fits the bill.
5. Catamaran Private Charter of Na Pali Coast on Kauai
Finally, for travelers who want exclusive access and full control over their experience, the Private Na Pali Coast Charter offers a customized 5-hour adventure. Using a 40-foot Power Catamaran designed specifically for Kauai’s ocean conditions, this trip can host up to 22 people—perfect for families or groups of friends.
This private charter includes snorkeling gear, dry bags, and ample forward seating for optimal views. The crew has over 34 years of experience, ensuring a safe, relaxed, and personalized outing. You can choose your itinerary, stop for snorkeling, and explore the coast at your own pace.
While it’s the priciest option at $3,400 per group, it’s an excellent value for groups wanting privacy and customization. One recent review highlights the vessel’s stability and comfort, praising the crew’s expertise and attention to detail.
Bottom Line: If privacy, flexibility, and a tailored adventure are your priorities, this private charter is unbeatable.
$3,400.00 per group (up to 1)
How to Choose Your Perfect Kauai Sailing Experience
When selecting the right tour, consider your budget, time available, and interests. For a quick, scenic sunset with drinks, the Kauai Sunset Catamaran or the Sunset Sailboat Tour with Dinner are excellent choices. If you crave a longer, wildlife-rich outing, the Na Pali Coast Power Catamaran is hard to beat. For a special celebration or family gathering, a private charter provides the flexibility to customize your day.
Booking early is wise, especially during peak season (winter months for whale watching, summer for ideal weather). Keep an eye on weather conditions too, as Kauai’s waters can be unpredictable.
Final Thoughts
Kauai offers a diverse range of sailing experiences—from quick sunset cruises to full-day exploration of the Na Pali Coast. For relaxed, affordable outings, the Kalapaki Kai Sunset Catamaran delivers scenic views and cultural insights. For those wanting a more adventurous and wildlife-rich experience, the Na Pali Coast Power Catamaran excels. And for romance or exclusivity, the Sunset Sail with Dinner or private charters are perfect.
No matter what you choose, booking ahead ensures you won’t miss out on these unforgettable ocean adventures. Kauai’s waters are calling—set sail and enjoy the incredible views and sounds of this beautiful island from the water.