Planning a day on the water in Oahu? A private sailing trip on a luxurious catamaran offers a personalized way to enjoy Hawaii’s stunning coastline away from the crowds. With space for up to 12 guests, this experience is perfect for groups seeking both adventure and relaxation in a stylish setting.
From serene sailing to snorkel stops teeming with marine life, we find that this tour combines comfort, flexibility, and authentic Hawaiian scenery. Three things we really like? The freedom to tailor your day, the chance to see wildlife like turtles and whales, and the chance to create a truly exclusive experience.
A potential consideration? The cost can seem steep at $1,495 per group, but for a private, all-inclusive experience with a dedicated crew, many travelers find it well worth it. This tour suits anyone wanting a bespoke day on the water—families, couples, or friends—looking for a special, intimate adventure.
Good To Know

- Private and Flexible: Customizable itinerary with options to snorkel, swim, or relax.
- Wildlife Encounters: Opportunities to see turtles, dolphins, rays, eels, and even humpback whales (seasonal).
- Luxury Comfort: Spacious, smooth sailing on a modern catamaran with shaded lounging and nets.
- All-Inclusive Feel: Use of snorkeling gear, flotation devices, Bluetooth sound system, filtered water, and options to bring your own food or add a private chef.
- Convenient Location: Depart from Ala Wai Boat Harbor, close to Waikiki.
- Family Friendly: Suitable for most travelers and perfect for groups wanting privacy.
Why Choose a Private Sailing Catamaran in Oahu?

This experience stands out because of its personalized approach. Unlike crowded boat tours, this private charter gives your group full control over the schedule and activities. Whether you want to spend the entire time cruising, snorkeling, or simply lounging with your favorite tunes, it’s all up to you.
The two-hour duration may seem brief, but the flexibility allows you to optimize your time—snorkeling in the morning when visibility is best, or enjoying the coastline at sunset. The boat departs from a convenient location—Ala Wai Boat Harbor—making it easy to incorporate into your day without long transfers.
The luxury catamaran itself offers a comfortably smooth ride, with ample shaded space to relax, plus nets at the bow for sunbathing or just taking in the scenery. The boat can accommodate up to 12 guests, making it ideal for families, small groups, or special celebrations.
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Detailed Breakdown of the Itinerary and Experience
Departure Point and Setting
Your adventure begins at Hawaiian Parasail Inc., located at 1651 Ala Moana Blvd. From there, the crew will help you settle onboard. As you cast off, you’ll immediately notice the spacious, modern design of the catamaran, with plenty of shaded seating and cushioning for lounging.
The sail along Waikiki’s coastline is a highlight in itself. Expect to see iconic sights like Diamond Head from a unique perspective, with the gentle motion of the boat making for a relaxing start.
The Sailing Experience
The smoothness of sailing on a catamaran is a big draw. Reviewers often comment on how relaxing the ride is, with plenty of space for everyone to stretch out. The seasoned crew — who are attentive and safety-focused — will be looking out for marine life and guiding your snorkeling adventures.
Snorkeling and Wildlife Viewing
One of the biggest perks is the ability to snorkel in clear waters before 1 pm, when marine visibility tends to be best. You’ll have access to snorkeling gear, flotation devices, and a guide to help spot sea turtles, tropical fish, rays, octopus, and eels. Some reviews mention seeing big schools of tropical fish over sunken barges, adding a touch of mystery and wonder.
During whale season (December through April), there’s a good chance you’ll catch sight of humpback whales either from the boat or while snorkeling. One reviewer noted that the crew is experienced at spotting marine life, which enhances the chances of a memorable encounter.
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Customization and Flexibility
Since it’s a private tour, you can choose where to go, how long to stay at each spot, and whether to include additional activities like swimming or just relaxing. The crew is happy to play your preferred music via Bluetooth, or you can bring your own playlist.
If desired, you can add snacks and beverages at an extra cost, or even opt for a private chef to cater to your tastes. This makes the experience more indulgent and tailored to your group.
Afternoon and Sunset Options
While most tours focus on the morning snorkeling, some guests might want to extend their time or catch Friday night fireworks from the water. The flexible schedule means you can plan for a sunset cruise if you prefer, offering spectacular views and photo opportunities.
Return and Overall Comfort
After approximately two hours, you’ll head back to dock at the same location. The reusable plates, glasses, linens, and silverware add a touch of eco-consciousness, and the warm freshwater cockpit shower is perfect for rinsing off after your swim.
Price and Value

At $1,495 for up to 12 guests, this tour offers a cost-effective way for a group to enjoy a private boat experience. When split among friends or family, the per-person cost becomes quite reasonable, considering the exclusivity, flexibility, and luxury provided.
In comparison to larger, less personalized tours, this private charter ensures you’re not competing with other guests for space or time—adding a layer of comfort and intimacy that many find priceless.
What’s Included and What’s Extra?
Included are snorkeling equipment, flotation devices, a snorkel guide, filtered water, Bluetooth sound system, and the use of eco-friendly linens and silverware. You can bring your own food and drinks, or choose to upgrade with catering.
Extras include parking (a dollar an hour in the marina), and snacks or beverages—not included in the base price—allowing you to tailor your onboard culinary experience.
Who Would Love This Tour?

This private sailing adventure is perfect for small groups wanting a customized, luxury experience on the water. Families looking for a relaxed day with the kids, couples celebrating a special occasion, or friends wanting to explore Hawaii’s marine life in style will find it ideal.
It’s especially valuable for those who wish to avoid crowded tours and prefer flexibility in their itinerary. The opportunity to see whales and turtles, combined with the comfort of a private vessel, makes this a memorable slice of Hawaii’s natural beauty.
Final Thoughts

Choosing this private 2-hour sailing trip means gaining a personalized, comfortable, and scenic experience of Oahu’s coastline. The ability to snorkel in calm, clear waters, see marine life, and relax on a luxury catamaran sets it apart from more generic group tours.
While the price tag is on the higher end, the exclusive nature, flexible schedule, and added amenities provide a level of value that many travelers find worthwhile. Whether celebrating, exploring, or just unwinding, this tour offers an authentic, hassle-free way to experience Hawaii from the water.
If you’re after a bespoke adventure that combines nature, comfort, and flexibility, this tour ticks all those boxes—making it a great choice for your Hawaiian getaway.
FAQ

How long is the tour?
The experience lasts approximately 2 hours, giving plenty of time to relax, snorkel, and enjoy the scenery without feeling rushed.
What is included in the price?
Your booking includes snorkeling equipment, flotation devices, a snorkel guide, filtered water, Bluetooth sound system, and eco-friendly linens and silverware. Food and drinks are additional, but you’re welcome to bring your own or upgrade with catering.
Where does the tour depart from?
The tour starts at Hawaiian Parasail 1651 Ala Moana Blvd, which is conveniently located near Waikiki and accessible for most travelers staying in the area.
Can I bring my own food and drinks?
Yes, you can bring your own food and beverages, or opt for the private chef service at an extra cost to enhance your experience.
Is this suitable for children?
Most travelers can participate, making it a good choice for families, provided children are comfortable with boat outings and snorkeling.
What about whale watching?
Whale sightings are possible during December through April, and the crew is experienced at spotting marine life, increasing your chances of seeing humpbacks during their season.
What about parking?
Parking is available at $1 per hour in the marina, making logistics straightforward for most travelers.
Is the tour weather-dependent?
Yes, the experience requires good weather. If canceled due to poor conditions, you’ll be offered a different date or a full refund.
To sum it up, this private sailing tour balances luxury, flexibility, and authentic encounters with Hawaiian marine life. It’s a perfect choice for small groups seeking a memorable, customizable day on the water in Oahu.
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