Waikiki Private Sunset Sail Romantic and Private: An Authentic Hawaiian Experience

Imagine gliding across Waikiki’s sparkling waters aboard a luxurious 48-foot yacht, with only your closest friends or family onboard. Priced at $799 per group (up to 6 people), this private sunset sailing offers a personalized way to experience Hawaii’s natural beauty, away from crowded tourist spots. Starting at 5:00 pm, the tour lasts about two hours, providing ample time to enjoy the scenery, wildlife, and the peaceful rhythm of the ocean.
What we love most about this adventure are two key details. First, the intimate setting means no crowded decks or noisy groups—just your party and the gentle sounds of the sea. Second, the chance to see marine wildlife such as dolphins, sea turtles, and during whale season, even humpback whales, makes it a true highlight. The stunning views of Diamond Head and Waikiki Beach from the water are simply breathtaking, especially as the sun dips toward the horizon, painting the sky in vibrant oranges, pinks, and purples.
One potential consideration is the weather dependency. Since this activity requires good weather, poor conditions can lead to cancellations or rescheduling, but you’re offered full refunds or alternate dates if needed. This tour suits travelers seeking a romantic, personalized experience that combines scenic beauty with the chance to connect with Hawaii’s marine life and nature in an authentic way.
Key Points
- Private and intimate experience for up to 6 guests
- Stunning sunset views over Waikiki and Diamond Head
- Opportunities to spot whales, dolphins, and sea turtles
- Flexible cancellation policy with full refunds if canceled 24 hours in advance
- Perfect for couples, families, or small groups looking for a peaceful escape
- Weather-dependent activity, with options for rescheduling or refunds
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A Deep Dive into the Waikiki Private Sunset Sail

An introduction to the experience
This private sunset sailing adventure in Waikiki is a fantastic way to see Hawaii from a different vantage point. For $799, you and up to five others can enjoy the luxury and comfort of a spacious 48-foot yacht. The journey begins at Honolulu Sailing Company‘s dock on Ala Moana Boulevard, a quick, easy-to-access location in Honolulu. We recommend arriving a little early to settle in and take in the views before setting sail at 5:00 pm.
What makes this tour stand out
The private nature of the trip is its biggest draw. Unlike crowded boat tours, you get exclusive access to the water with your loved ones, which amplifies the sense of relaxation and connection. The yacht’s comfortable deck offers plenty of room to lounge, chat, or simply enjoy the scenery.
We’re particularly impressed by how personalized the experience feels. During the sail, you can expect an unobstructed view of Diamond Head, Waikiki Beach, and the Hawaiian coastline, all of which come alive in the golden light of sunset.
The scenery and wildlife
As the yacht begins to glide across the water, you’ll love the crystal-clear waves and the gentle sea breeze. The captain might point out notable landmarks along the coast, but the real magic happens as the sun dips below the horizon, casting a warm glow that rivals any postcard.
And if you’re lucky, you might catch sight of dolphins playing nearby, or during whale season, humpback whales breaching and spouting just offshore. Many travelers describe this part of the trip as serene and almost meditative, with the stars coming out as the sky darkens.
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Tips for the best experience
- Wear light, comfortable clothing and bring a light jacket for the evening breeze.
- Use sunscreen even in the late afternoon; the sun can still be strong.
- Bring a camera or smartphone to capture the stunning vistas and wildlife sightings.
- Be prepared for possible weather cancellations—check the forecast and confirm details with the operator if conditions look uncertain.
What travelers say
While this experience currently has no formal reviews, the description and features indicate that it’s highly valued for its scenic beauty and personalized approach. The fact that most bookings are made 14 days in advance suggests it’s quite popular among travelers seeking an exclusive, peaceful activity.
Practical details
Meeting at 1025 Ala Moana Blvd Pier A, the tour begins promptly at 5:00 pm. It’s a mobile ticket experience, making it convenient to access. The 2-hour duration makes it a manageable addition to a day full of sightseeing or relaxation.
Cost and value
At $799 for up to 6 people, this activity averages out to about $133 per person, which is a fair price considering the intimacy, luxury, and exclusive nature of the sail. Compared with larger group tours or sunset cruises, this private experience ensures you get undivided attention and a tailored environment. For couples or small groups wanting a special memory, it’s an excellent investment.
Cancellation and weather considerations
The tour offers a full refund if canceled 24 hours in advance, which provides peace of mind given Hawaii’s unpredictable weather. If canceled due to poor weather, you’ll be offered a different date or a full refund, ensuring no financial risk.
Who Should Consider This Tour?

This private sunset sail is ideal for romantic couples celebrating an anniversary, families wanting a peaceful day on the water, or small groups seeking an intimate adventure. It’s perfect if you value personalized service and want to avoid the crowds. It also suits travelers who appreciate stunning scenery combined with wildlife sightings in a relaxed setting.
Final Thoughts

A private sunset sail in Waikiki offers more than just sightseeing; it’s an authentic way to connect with Hawaii’s natural beauty. The combination of luxury, intimate surroundings, and breathtaking views makes it a worthwhile experience, especially if you’re looking to celebrate a special occasion or simply enjoy a peaceful evening on the water.
While it is weather-dependent, the high-quality experience, personalized nature, and stellar scenery make this tour stand out in a city filled with busy beaches and crowded attractions. If you’re after a relaxed, scenic, and romantic adventure that leaves you with memories as vibrant as the Hawaiian sunset, this sail is a solid choice.
FAQ

How many people can participate?
Up to 6 guests can join per booking, making it ideal for small groups or intimate occasions.
What is the price and what does it include?
The cost is $799 per group, which covers private use of the yacht for about two hours. It’s a completely private experience only for your group.
Where do we meet?
You meet at Honolulu Sailing Company, located at 1025 Ala Moana Blvd Pier A. The tour begins at 5:00 pm.
What should I bring?
Bring light clothing, a jacket for the evening breeze, sunscreen, and a camera to capture the views.
Is this activity suitable for children?
Yes, most travelers can participate, but consider the age and comfort of children with open water and boat movement.
Can I cancel if the weather is bad?
Yes, there is a full refund if canceled 24 hours in advance. If canceled due to poor weather, you’ll be offered an alternative date or a full refund.
How long is the experience?
The sailing lasts approximately two hours, giving you plenty of time to relax and enjoy different angles of the sunset.
Is the activity flexible?
Yes, since it’s private, you can sometimes request minor adjustments, but the schedule and route are generally fixed.
What makes this tour different from other sunset cruises?
The private setting, luxury yacht, and small group size ensure an exclusive, tranquil experience with unobstructed views.
Can I see marine wildlife?
During whale season, you might see humpback whales, and dolphins and sea turtles are often spotted around the yacht, adding a special touch to your evening.
This private sunset sail offers an authentic, peaceful way to see and feel Hawaii’s magic. It’s perfect for those who value personalized service, stunning scenery, and a relaxed, intimate atmosphere. Whether celebrating a special moment or seeking a quiet retreat, it’s a memorable way to end your day in paradise.
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