Sunset Sail Charter

When thinking about the ideal way to soak up the stunning beauty of Oahu, a sunset sail might just be at the top of the list. We haven’t personally been on this specific tour, but based on what’s shared, it sounds like a memorable way to enjoy Hawaii’s coast. It’s a private, customizable experience that promises spectacular views of Honolulu’s skyline and Diamond Head, all from the comfort of a well-equipped sailboat.

What really draws us to this experience is the flexibility it offers—you’re able to choose your timing and scenery, which means it can suit a variety of preferences. Plus, the stunning sunset views and the chance to see marine life make it stand out. On the flip side, it’s worth noting that this is a barefoot sail, so if you’re not comfortable ditching your shoes, it might not be for you. It’s best suited to travelers who enjoy tranquil, scenic moments and want a relaxing break from more hectic tours.

If you’re looking for a laid-back, intimate way to see Oahu’s coast—whether celebrating a special occasion or simply craving a peaceful sunset—you’ll likely find this tour fits the bill. It’s not a big party boat; it’s a private group experience, making it perfect for couples, small groups of friends, or those wanting a quieter, more personalized adventure.

Key Points

• Private and customizable: You choose the hours and landscapes you want to see, making it flexible for different interests.
• Spectacular views: Landmarks like Diamond Head and Honolulu’s skyline provide stunning backdrops, especially at sunset.
• Relaxed, intimate setting: The sailing boat offers a more personal experience, ideal for quiet reflection or special moments.
• Light refreshments included: Snacks and drinks are available, and you’re welcome to bring your own.
• Ideal for photo ops: The boat’s deck and scenery create perfect opportunities for memorable photos.
• No on-board bathrooms with flushing toilets: Just be prepared for that small inconvenience, and remember to dispose of toilet paper properly.

You can check availability for your dates here:

Setting Sail: What to Expect

Starting at Pier C in Kewalo Basin, the experience kicks off with a friendly crew welcoming you aboard the Sailing Beauty of Honolulu. This vessel is described as a luxury sailboat with a brand-new deck, loaded with the latest technology to maximize your comfort and safety. The crew will check your ID and booking details, so having those ready simplifies the process.

Once aboard, you’ll quickly see why this experience is so appealing—the deck offers a prime vantage point for photos and lounging, with Diamond Head and Honolulu’s cityscape as the constant scenic companions. The boat is designed for a private group of up to 12 people, so it’s not crowded, allowing for a more personal experience.

The Flexibility of Your Itinerary

One of the main advantages here is the ability to customize your trip. You can select the hours and landscapes you’re most interested in, whether that’s a leisurely sunset cruise, a daytime sail, or a special celebration like a proposal or wedding. The crew is known for hosting special settings for proposals, weddings, and memorials, which makes it particularly appealing for romantic or meaningful occasions.

What’s Included and What to Bring

Light refreshments are provided, with snacks and drinks on offer—plus, you’re encouraged to bring your own beverages and food. If you bring glass bottles, crew will pour your drinks into shatterproof glasses and keep your bottles on ice below deck. This is a barefoot sail, so shoes are collected before boarding and stored safely; be prepared to go barefoot for the duration.

Sunscreen is a must, especially if you plan to be on deck for a while. The boat has bathroom facilities onboard, but note that the toilets cannot flush toilet paper, which must be disposed of in a small trash can. The bathroom is conveniently located across from the dock and on the boat itself.

Duration, Group Size, and Pricing

The tour lasts about 2 hours, usually in the afternoon—perfect for catching the sunset or a late afternoon sail. The cost is $699 per group (up to 6 people), which we think offers decent value considering the private setting and stunning views. For travelers seeking a more exclusive and personalized experience, this price can be justified, especially if you’re celebrating or want a quiet escape.

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The Experience from the Water

While the primary focus is on the views of Honolulu, Diamond Head, and the sunset, guests have also reported spotting marine life, which adds an exciting layer to the trip. The boat’s environment fosters a relaxed, intimate vibe, ideal for unwinding, taking photos, or just soaking in the scenery.

Reviews and Feedback

From what’s shared, guests have appreciated the stunning scenery and the professional crew, describing the experience as “beautiful,” “relaxing,” and “a sunset to remember.” Some mention the boat’s new deck and up-to-date technology as enhancing the trip, making it more comfortable and photogenic. The ability to customize the experience by choosing different scenic routes has also been highlighted as a plus.

That said, some reviews note that it can be hot in the sun, so packing sunscreen and a hat is wise. Others mention that the experience is quite peaceful—so if you’re after lots of entertainment or lively music, this might not be the right fit.

The Itinerary in Practice

Imagine arriving at Pier C, greeted by friendly crew members, then stepping onto the sleek Sailing Beauty. Once under way, you’ll be treated to panoramic views of Honolulu and Diamond Head, with plenty of opportunities to snap photos. As the sun begins to dip, the sky turns into a canvas of oranges, pinks, and purples—views that are truly postcard-worthy.

You might choose to sail past iconic landmarks like Diamond Head and enjoy the cityscape’s glow as the evening sets in. Marine life sightings are a bonus, and the crew’s professionalism helps make this a smooth, hassle-free experience. If you’ve booked a special occasion, the crew is known for hosting memorable proposals and weddings, making your celebration even more meaningful.

Throughout the trip, light refreshments keep everyone comfortable. The relaxed pace and quiet environment allow for genuine moments of connection—whether that’s with your partner, friends, or yourself.

Who Would Love This Experience

This tour is perfect for travelers who value serenity and scenic beauty over high-energy activities. It’s especially suited to couples, small groups, or anyone wanting a private escape with a view. If you enjoy taking your time to enjoy landscapes and want to avoid large crowds, this sail offers a peaceful alternative to bus tours or crowded boat trips.

It’s also ideal for celebrating special moments—whether a proposal, anniversary, or small wedding—thanks to its customizable nature and romantic setting. Keep in mind, it’s not designed for those with mobility issues due to the nature of the sailing vessel and the “barefoot” policy, and it’s not suitable for wheelchair users.

Final Thoughts: Is It Worth It?

For around $700 per group, this private sail offers a more personal, scenic, and relaxed way to experience Oahu’s coast. When you consider the stunning views, the chance to see marine life, and the flexibility to tailor your itinerary, many will find it offers solid value—especially if you’re after an intimate celebration or a peaceful sunset.

It’s not the cheapest activity on the island, but the exclusivity and the quality of the environment make it stand out. If you love the idea of drifting along the water with Honolulu’s skyline as your backdrop, this trip is likely to leave you with lasting memories. Just remember to pack sunscreen, go barefoot, and enjoy the ride.

FAQ

Can I customize the hours and landscapes I want to see?
Yes, you can choose your preferred hours and the landscapes you want to see, making it a flexible experience tailored to your interests.

Where do I meet the boat?
The meeting point is Pier C at Kewalo Basin, 1125 Ala Moana Blvd, Honolulu. The gate is locked, so wait outside for the crew to come and welcome you aboard.

What’s included in the price?
The price covers a sailing charter, a skilled crew, a customizable adventure, views of Diamond Head and Honolulu, and lite refreshments.

Are refreshments provided?
Yes, snacks and drinks are available on each charter, and you’re welcome to bring your own beverages and food.

Is there a bathroom onboard?
Yes, there are bathroom facilities onboard, but keep in mind that toilets cannot flush toilet paper, which must be disposed of in the small trash can.

What should I wear?
Dress comfortably for a boat trip—bring sunscreen, a hat, and perhaps sunglasses. Remember, it’s a barefoot sail, so shoes will be collected before boarding.

Can I bring glass bottles?
If you bring glass, crew will pour your beverage into shatterproof glasses, and your bottles will be kept on ice below deck.

Is this experience suitable for children?
The data doesn’t specify, but given the relaxed, intimate setting and the vessel type, it might be best suited for older children who are comfortable on boats.

Is it good for special occasions?
Absolutely. The crew can host special settings for proposals, weddings, and memorials, making it a versatile choice for memorable moments.

This Sunset Sail offers a quiet, beautiful way to experience Oahu’s coast, especially if you appreciate spectacular scenery and a relaxed vibe. It’s best for those wanting a private, customizable experience with stunning views and a peaceful atmosphere.

You can check availability for your dates here: