Honolulu Sailing Co.
Activities (4)
Waikiki Sail & Snorkel Adventure
Most South Shore days on Oahu fill up fast — beach chairs, surf lessons, shave ice lines. The Waikiki Sail & Snorkel Adventure from Honolulu Sailing Co. is a solid option when visitors want something that actually gets them out on the water without the chaos of a crowded tour boat. You board a private luxury yacht right at Waikiki Beach and you're out on the water for 3 hours — small group, guided, no shuttle nonsense. Once the captain drops anchor at the snorkel spot, you're in. Gear is all provided — mask, fins, snorkel — cleaned and sanitized before each trip. The marine life along this stretch is the real draw: spinner dolphins, green sea turtles, reef fish, and humpback whales depending on the season. Your guide handles the spotting, so you're not just floating around hoping something swims by. Intensity is low and only basic swimming ability is required, which makes the Waikiki Sail & Snorkel Adventure a natural fit alongside other South Shore plans without worrying about being wiped out. Water is included; meals and gratuity aren't, so grab something to eat beforehand. Bring a towel, hat, sunglasses, camera, and reef-safe sunscreen — leave the spray or tinted formulas at the hotel. No hotel pickup is offered; just meet at Waikiki Beach. A private charter option is available if you want the yacht to yourselves. Pricing starts from $599. The trip is weather dependent, so check conditions before you head down. Cancellation terms are as follows: 14-plus days out, no fee; 13–8 days, a 50% fee applies; within 7 days, the full amount is forfeited. For overnight charters, ASA Classes, or special requests, 60 days' notice is required for a 100% refund. A $150 cancellation fee applies to all day charters, overnight charters, ASA Classes, and Special Requests. A $100 change fee may apply to reservation changes. Gift Certificates are non-refundable. Only a NOAA Storm advisory qualifies for a full reschedule or refund. Build in enough lead time and this one earns its place on any Oahu week.
Direct with the operator. They take your booking and run your tour. We may earn a commission, never added to your price.
OFFSHORE FISHING
There's nothing quite like the rush of offshore fishing Honolulu waters aboard a sailboat – it's a whole different game. This three-hour adventure takes you well past Diamond Head's reef system into serious blue water where the real gamefish live. Your captain knows these waters and will sail efficiently to the hot spots where mahi mahi, ono, and tuna patrol. Out here in the open Pacific, you're playing by the ocean's rules – some days you'll land trophy fish that'll make your buddies back home jealous, other days you'll come back empty-handed but with stories that are just as good. That's offshore fishing Honolulu style. What sets this apart is combining the thrill of sailing with serious sport fishing. While you're making your way to the fishing grounds, keep your eyes peeled for dolphins, sea turtles, and manta rays – they're regular companions out here. The three-hour window gives you enough time to reach productive waters without turning into an endurance test. Pack smart for this one: hat, sunglasses, sunscreen, towel, gloves, and definitely a camera. Bring your own snacks and drinks to keep your energy up – complimentary water is provided, but you'll want more than that when you're battling fish under the Hawaiian sun. Fair warning though: this isn't some gentle reef fishing trip. The open ocean can be demanding, so come ready for real conditions and real fishing. If you want authentic Hawaiian sport fishing from a sailboat, this is your ticket to test your skills against Hawaii's premier gamefish species.
Direct with the operator. They take your booking and run your tour. We may earn a commission, never added to your price.
Diamond Head Sunset Cruise
There's something truly magical about watching the sun melt into the Pacific from the deck of a private yacht, and the Diamond Head Sunset Cruise Honolulu delivers exactly that experience. This exclusive 2-hour sailing adventure takes you away from the crowded tour boats and into the waters off Oahu's iconic coastline, where comfort meets spectacular natural beauty. Your journey unfolds with spectacular views of iconic Diamond Head and Waikiki stretching around you. While your experienced captain and crew handle the navigation, you're free to soak in the stunning scenery and watch for native marine life. Playful dolphins often make appearances alongside the yacht, and graceful sea turtles glide beneath the surface. During whale season, whales migrating through these tropical waters might just steal the show. As evening approaches, the real magic begins. The sky transforms into a canvas of vibrant colors that dance across the ocean's surface, and this Diamond Head sunset cruise Honolulu perfectly times your voyage to capture Hawaii's legendary sunset in all its glory. Diamond Head creates an unforgettable frame for nature's daily masterpiece. Once the sun disappears below the horizon, Honolulu's city lights begin to twinkle, creating an enchanting backdrop as you sail back toward port. It's a magical conclusion that leaves you feeling like you've experienced something truly special. The experience includes complimentary water throughout your journey. Don't forget your camera for those stunning shots, and feel free to bring your favorite snacks and beverages. Comfortable clothing works best, though a light cover-up comes in handy as temperatures cool during the evening. The private yacht setting creates the perfect atmosphere for families and friends to share this memorable evening together. From $599 per person.
Direct with the operator. They take your booking and run your tour. We may earn a commission, never added to your price.
Private Whale Watching Cruise
There's something magical about watching humpback whales breach against Diamond Head's iconic silhouette, and this private whale watching cruise from Honolulu waters near Waikiki puts you right in the heart of the action. Your 3-hour luxury yacht adventure offers the kind of intimate whale encounters that only come with having your own vessel. Every December through April, endangered humpback whales make their epic journey across the Pacific to Hawaii's warm, protected waters. They come here to give birth and nurture their calves—and honestly, there's no better place to witness this incredible cycle than from the comfort of your private yacht. While larger tour boats jostle for position, you'll have the freedom to linger where the whales are most active. The leisurely pace means you won't miss those heart-stopping moments: a mother teaching her calf to breach, the thunderous splash of tail slapping, or the graceful dance of these gentle giants just beneath the surface. Your spacious yacht provides unobstructed sightlines perfect for photography, and the crystal-clear Pacific often surprises guests with bonus sightings of dolphins, sea turtles, and manta rays. Pack your hat, sunglasses, reef-safe sunscreen (no spray or tinted types), towel, and camera—trust me, you'll want to capture these moments. Feel free to bring your favorite snacks and drinks to make the experience even more special. What sets this private whale watching cruise Honolulu experience apart is the flexibility. Want to follow a particularly active pod? Your captain can make it happen. Need a quieter spot for the kids to relax? No problem. Watching these magnificent humpbacks in their Hawaiian sanctuary is truly one of Oahu's greatest natural spectacles—an encounter that connects you to something much larger than yourself.
Direct with the operator. They take your booking and run your tour. We may earn a commission, never added to your price.
About
You'll find Honolulu Sailing Co. right here in the heart of Honolulu, where they've mastered the art of showing off our beautiful Hawaiian waters. This local outfit knows exactly what makes sailing around Oahu special - it's not just about the boat ride, it's about connecting with the ocean in a way that feels genuinely Hawaiian.
Their captains? These guys have been navigating these waters for years. They'll share stories about the reefs, point out marine life you might miss on your own, and treat you with the kind of authentic aloha spirit that makes all the difference. Whether you're watching the sun set behind Diamond Head on their sunset cruise or getting up close with our coral reefs on the Waikiki Sail & Snorkel Adventure, you're getting an insider's perspective.
What I really appreciate about them is how they keep things intimate. Small groups mean your captain actually gets to know you, and you're not fighting crowds for the best photo spots. Their private whale watching cruises are perfect when humpback season rolls around - imagine having those magnificent creatures practically to yourself. And if fishing's your thing, they know exactly where to find the big ones lurking in our deeper waters.
Here's what makes them stand out: they genuinely care about giving you a meaningful experience with Hawaii's ocean environment, not just checking activities off your list. First-time sailors feel comfortable, experienced ocean lovers get the adventure they're after, and everyone leaves understanding a little more about why we islanders are so connected to the sea. That's the kind of authentic island experience you came here for.