Celebrate Your Group with a Very Private Sunset Cigar Experience

Celebrate Your Group with a Very Private Sunset Cigar Experience

Imagine spending an evening on the Big Island of Hawaii, high above the Pacific, with an exclusive group of just 6 to 10 people, sipping local spirits, and savoring a premium cigar as the sun dips below the horizon. For $49 per person, this roughly two-hour adventure offers a rare chance to enjoy authentic Hawaii in a setting that feels both rustic and personal. Led by Richard, a knowledgeable host, this experience is designed for those who appreciate good company, fine flavors, and breathtaking scenery.

What we love most about this experience is how intimate and relaxed it is — small groups mean plenty of space for conversation and connection. Plus, the spectacular panoramic views of Maui, Lanai, Kaho’olawe, and Hualalai from Puu Kehoni are truly unforgettable. Another highlight is the unique opportunity to taste curated cigars, including some rare “unicorn” picks, paired with local liquors. The setting’s authentic, rustic charm makes it feel like a secret escape from the busy world.

A potential consideration is that transportation is not included, so you’ll need to arrange your own way to the meeting point. Also, weather can impact the experience—Richard will cancel if storms are forecasted—but even if caught in a drizzle or wind, the raw power of Hawaii’s storms can add a dramatic touch if you’re prepared for it.

This tour suits travelers who love spectacular views, enjoy relaxing evenings with good company, and want a low-key, authentic Hawaii experience. It’s perfect for cigar aficionados, curious beginners, or anyone looking to celebrate a special occasion with a more personal touch.

Key Points

• Intimate setting: Small group sizes of 6–10 people foster personal conversations and connections.
• Stunning scenery: Breathtaking panoramic views of neighboring islands and volcanic landscapes.
• Premium cigars: Curated selection, including rare and exclusive “unicorn” cigars.
• Local spirits: Liquors available to pair with cigars, enhancing the sensory experience.
• Authentic atmosphere: Rustic, funky style that highlights Hawaii’s natural beauty.
• Weather-dependent: Cancellations possible if storms are predicted, but the raw power of Hawaii’s weather can add drama.

A Closer Look at the Sunset Cigar Experience

Location and Setting

Your journey begins at 56-3029 Akoni Pule Hwy, Waimea, a site perched above the ocean that offers what might be one of the island’s most stunning viewpoints. From Puu Kehoni, you’ll be treated to sweeping vistas of neighboring islands—including Maui, Lanai, and Kaho’olawe—and the rugged volcanic landscape of Hualalai. This spot is historically significant as the birthplace of King Kamehameha, adding a layer of cultural resonance to the scenery.

The atmosphere here is designed to feel rustic and authentic — think weathered wooden tables, breezy ocean air, and an unpretentious vibe. It’s a place that encourages relaxation and connection, far away from the tourist crowds.

The Host and Personal Touch

Richard, your guide, is described as friendly, knowledgeable, and accommodating. We get the sense he genuinely wants you to enjoy your time, whether that’s by guiding you through cigar choices or sharing insights about the landscape. He might even be joined by his Pomeranian, Buddy, which adds an adorable touch to the experience—just let him know if that’s okay with you.

The Cigars and Spirits

While you are welcome to bring your own cigars, Richard’s curated selection offers premium and rare cigars that are hard to find elsewhere—some are described as “unicorns,” meaning truly hard-to-come-by. The experience isn’t just about smoking; it’s about savoring flavors, sharing stories, and soaking in the environment.

Though Richard does not sell alcohol, he provides local liquors to pair with your cigars, giving you a chance to sample Hawaiian spirits. If you prefer, you can bring your own alcohol—making your evening more personalized.

The Experience

Imagine sitting comfortably, surrounded by the breeze and ocean scent, with a fine cigar in hand, watching as the sky transforms from brilliant oranges and pinks into a blanket of stars. The experience is designed to foster serenity and camaraderie, perfect for celebrating a special occasion, unwinding after a day of sightseeing, or simply indulging in a unique Hawaii activity.

Weather and Cancellation

Richard will cancel if storms are forecasted, but if the weather turns stormy while you’re there, you might find the raw power of Hawaii’s storms to be a memorable addition. He encourages guests to disconnect and enjoy the natural spectacle.

Practical Details

• Duration: About 2 hours, making it a perfect evening activity.
• Price: $49 per person, which provides good value considering the exclusive setting and scenery.
• Group size: Private, with only your party involved.
• Meeting point: Waimea, with no transportation included, so plan accordingly.
• Start time: 5:00 pm, aligning with sunset.

The Value for Your Buck

At $49, this experience offers a personalized, scenic, and culturally rich way to spend an evening. The combination of spectacular views, premium cigars, and local spirits makes it stand out from generic sunset outings or cigar lounges. The small group size ensures a relaxed and intimate atmosphere where everyone can partake in conversation rather than just observe.

While it’s an activity focused on relaxation and scenery rather than adventure, it provides excellent opportunities for photos, storytelling, and savoring Hawaii’s natural beauty. The fact that it is a private tour means you won’t be squeezed into a large group, and the friendly, knowledgeable host enhances the personalized feel.

Who Should Consider This Tour?

This experience is ideal for cigar enthusiasts, couples celebrating a special occasion, or anyone wanting to enjoy Hawaii’s scenery in a relaxed setting. It’s also perfect for those who value authentic local atmospheres over commercialized tourist spots. If you’re comfortable arranging your own transportation and enjoy a peaceful, scenic evening, this activity is a great way to make your trip memorable.

FAQs

Is transportation included? No, transportation to the meeting point is not included, so you’ll need to arrange your own. The meeting point is at Waimea, which is straightforward to reach by car.

Can I bring my own cigars? Absolutely—you’re welcome to bring your own cigars if you prefer, although the curated selection includes rare and premium options worth trying.

What if the weather is bad? Richard will cancel if storms are forecasted. If caught in bad weather unexpectedly, you might find the raw power of Hawaii’s storms adds a dramatic backdrop, but safety is the priority.

Are alcohols provided? No, Richard does not sell alcohol but offers local liquors to pair with your cigars. You can also bring your own if desired.

How long is the tour? The experience lasts approximately 2 hours, making it a relaxed yet memorable evening activity.

What is the group size? Small groups of 6 to 10 people, ensuring a personal and relaxed environment.

Is the experience suitable for beginners? Yes, Richard tailors the experience to your preferences, whether you’re a seasoned cigar lover or a curious rookie.

Final Thoughts

If you’re seeking a quiet, scenic activity that combines Hawaii’s natural beauty with a refined sensory experience, this private sunset cigar tour hits the mark. It’s a rare opportunity to enjoy breathtaking views while savoring premium cigars and local spirits in an authentic, laid-back setting.

The experience’s highlights—stunning panoramic vistas, personalized service, and a rustic atmosphere—make it a standout activity for those who appreciate nature, good company, and a touch of Hawaii’s unique charm. While it’s not a large group or high-energy activity, that’s part of its appeal: a chance for genuine relaxation and connection.

This tour will resonate most with travelers who want a meaningful, low-key experience that captures the spirit of Hawaii’s landscape and culture, providing a perfect backdrop for celebration, reflection, or simply unwinding after a day of adventure.

Enjoying a quiet moment high above the ocean, with a fine cigar in hand and the stars starting to twinkle — that’s what makes this experience special. For those who cherish genuine atmospheres and breathtaking views, it delivers in spades.