All Aboard: Big Island Sailing Tours
A comprehensive comparison of catamarans, charters, and cultural voyaging experiences
Written by a Local Expert
Kalani MillerFinding Your Perfect Voyage
The Big Island sailing fleet is diverse, with tours departing from three main hubs: Honokohau Small Boat Harbor in Kailua-Kona, the convenient Keauhou Bay just south of Kona, and the pristine Kawaihae Harbor serving the northern Kohala Coast resorts.
I've spent years on these waters, and I can tell you that the "best" tour is a personal choice. It depends entirely on your vision for the day. Are you dreaming of a quiet, romantic evening with a glass of champagne? An adrenaline-fueled adventure with the family? A deep cultural connection to Hawaiian heritage? Or perhaps the simple joy of feeling the wind in the sails?
For the Romantics & Relaxation-Seekers: Luxury Catamaran & Sunset Cruises
There is no experience that captures the romance of Hawaii quite like a sunset sail along the Kohala Coast. This is for those who want to unwind, indulge, and witness one of nature's most spectacular shows from the best seat in the house. The vibe here is upscale and tranquil. Imagine slipping off your shoes for a "barefoot cruise," often boarding from the golden sands of Anaeho'omalu Bay (A-Bay) via a small tender boat.
🌅 Hawaii Nautical - Spirit of Aloha (54' Sailing Catamaran)
This social and comfortable boat departs from Anaeho'omalu Bay and carries up to 49 passengers. The crew provides snacks, unlimited non-alcoholic drinks, and two free bar drinks per adult. A great, classic choice if you're staying in Waikoloa.
Best for: Large groups, social atmosphere, convenient for Waikoloa guests
🔋 Kohala Blue Sail Hawaii - Dolce Vita (34' Electric Sailing Catamaran)
Departing from Kawaihae Harbor, this eco-luxe and serene option is a game-changer. As Hawaii's only renewable electric charter, the sail is virtually silent. You hear the wind and the water, not an engine. The crew provides healthy snacks and beverages, and guests can bring their own drinks.
Best for: Eco-conscious travelers, peaceful experience, sustainability focus
💎 Big Island Shaka - Shaka Sail (40' Sailing Catamaran)
This private and customizable option from Kawaihae Harbor accommodates six passengers. The crew provides water, juice, and snacks. It's BYOB friendly with catering and champagne upgrades available. The perfect option for a small group, proposal, or special celebration.
Best for: Private groups, special occasions, complete customization
For the Adventurers: Performance Sailing & Snorkel Charters
If your idea of a perfect day involves feeling the salt spray as you cut through the waves and exploring a vibrant underwater world, then an adventure sail out of Kona is for you. These tours are for the active traveler who wants to do more than just sightsee. The main event is often a trip to the historic and protected waters of Kealakekua Bay, home to the Captain Cook Monument and one of the most pristine coral reefs in Hawaii.
🏊 Body Glove - Kanoa II (65' Catamaran)
This floating playground heads to the Red Hill Area rather than Kealakekua Bay. It's perfect for large groups and families who want as much fun on the boat as in the water. The high-jump platform and 20-foot waterslide make it legendary among local kids and visitors alike.
Best for: Families with kids, onboard entertainment, group fun
🚤 Body Glove - Kona Explorer (41' Super-Raft)
As a high-speed explorer, this powerful raft can reach more distant and less-crowded snorkel spots than larger catamarans. It's designed for smaller groups who want speed and access to remote sites.
Best for: Speed seekers, remote locations, smaller groups
🐠 Sea Paradise - Hoku Nui (50' Catamaran)
This classic snorkel sail to Kealakekua Bay offers comfort and views for 30-49 passengers. It's a highly-rated, comfortable, and luxurious sail to Hawaii's most famous snorkel spot.
Best for: Classic Kealakekua Bay experience, comfort, quality service
🏄 Kamanu Charters - 36' Catamaran
Known for its expansive trampoline nets, this intimate and relaxed sail to Pawai Bay carries 24 passengers. It offers a more personal feel than the bigger boats.
Best for: Intimate groups, trampoline sailing experience, personal attention
🌺 Kona Style - 45' Catamaran
This cultural and community-focused sail to Kealakekua Bay accommodates 32 passengers. It's Hawaiian owned and operated, offering a chance to support a local, Native Hawaiian-owned business that gives back to the community.
Best for: Supporting Native Hawaiian business, cultural connection, community impact
Ready to Battle the Pacific's Giants?
Discover private charters and traditional voyaging experiences that will transform your connection to the ocean.
Planning Guide Learn to Sail⚖️ Quick Comparison
- Romantic: Spirit of Aloha
- Eco-Friendly: Dolce Vita
- Family Fun: Kanoa II
- Adventure: Kona Explorer
- Cultural: Kona Style
🏖️ Departure Points
- Honokohau Harbor (Kona)
- Keauhou Bay (South Kona)
- Kawaihae Harbor (Kohala)
- Anaeho'omalu Bay (A-Bay)
📖 Complete Sailing Guide
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✍️ About the Author
Sailing & Cultural Expert
A lifelong sailor raised by the tides of the Kona coast, sharing the deep connection between Hawaiian culture and the sea.
For the Ultimate Celebration: A Guide to Private Charters
For a truly unforgettable milestone—a proposal, an anniversary, a landmark birthday, or a family reunion—nothing compares to the exclusivity and freedom of a private boat charter. It's your boat, your crew, and your day to design from the water up.
Booking a private charter is a straightforward process, and I always advise people to think about their perfect day first.
1. Define Your Dream Day
What do you want to do? The beauty of a private charter is the flexibility. You can create a custom itinerary that might include performance sailing, snorkeling, dolphin searching, fishing, and sunset cruising—all in one trip.
2. Choose Your Vessel
The Big Island's private fleet is diverse. You can opt for ultimate luxury on a spacious sailing yacht like the 51-foot No Wiki, which features four cabins and air conditioning for up to six guests.
3. Contact Operators
While third-party booking sites are useful for browsing, I always recommend calling the charter companies directly. Speaking with operators allows for complete customization.
For the Cultural Explorer: Sailing on a Traditional Waʻa Kaulua
Beyond the modern catamarans and sleek monohulls, there is another, more profound way to experience the waters of Hawaii. This is an experience that fills a significant gap left by other resources and connects you to the very soul of this place. I'm talking about sailing on a waʻa kaulua, a traditional Polynesian double-hull voyaging canoe.
These are the vessels that brought the first Hawaiians across the vast Pacific, guided by the stars, the wind, and the swell. The waʻa is not just a boat. It is a sacred cultural treasure. As Pwo (Master) Navigator Chadd Paishon says, "A canoe is our mother, we treat it as we would our mother, it takes care of us like our mother." To sail on a waʻa kaulua is to participate in a living tradition.
🛶 Anelakai Adventures
Departing from historic Keauhou Bay, their tours focus on the cultural significance of the waʻa and the history of the area. The experience is intimate and hands-on, emphasizing paddling and ocean awareness.
Best for: Hands-on cultural experience, paddling participation, historical education
⛵ Hawaiian Sails - Hahalualele
From the Mauna Kea Beach Hotel, you can board the Hahalualele, a beautiful 35-foot replica sailing canoe. Their focus is on sharing the history and culture of the Hawaiian people as you sail the stunning Kohala Coast.
Best for: Cultural storytelling, Kohala Coast sailing, resort convenience
🏝️ Kona Boys - Outrigger Canoe Tours
While not a sailing canoe, Kona Boys offers outrigger canoe (waʻa) paddling tours from Kamakahonu Bay in Kailua-Kona. They provide a rich historical narrative of the area that was once the seat of Hawaiian royalty.
Best for: Paddling focus, royal Hawaiian history, Kona convenience
Choosing a waʻa experience is for the traveler who seeks more than just a beautiful view. It's for the one who seeks understanding.