Sunset turns smoky at Puʻu Kehoni. You sit high above the ocean as the horizon slips away, with Puʻu Kehoni’s unforgettable lookout and Richard’s cigar selection keeping the evening feeling calm, personal, and special. It’s also rooted in place, with views over Maui and beyond plus a stop at the Mo’okini Heiau area connected to Kamehameha’s story.

One thing to plan for: this is a small, off-the-road kind of outing with no transportation provided, and you’ll need to manage two steps as part of getting in and out.

Small-group sunset viewing from Puʻu Kehoni

Cigars and local spirit pairings with host Richard

Historic stops at Mo’okini Heiau and Upolu Point

Twilight sky moments, including star viewing in clearer conditions

Rustic lounge vibe, with Buddy the Pomeranian sometimes joining

Mostly outdoor time, so weather really matters

Puʻu Kehoni at golden hour: the views that do the talking

The big draw here is simple: you’re on a perch above the ocean where sunset actually feels close. Puʻu Kehoni overlooks Kokoiki, described as the birthplace of King Kamehameha, and the viewpoint is oriented so you can take in faraway islands at the same time—Maui, Lanai, Kahoʻolawe, and Hualalai. That wide, layered view is the part you remember later when you’re back home scrolling your photos.

You also get the soundscape: ocean waves, wind in the grass, and that slow shift from bright sunset colors to deep twilight. In the clearest moments, people talk about seeing the Milky Way after dark, which is exactly what you’d hope for on the Big Island when you’re far enough from city light.

And yes, you might spot the ocean “moving,” too—waves rolling in, and even whales mentioned from the deck area when conditions line up. The experience is planned for that handoff from daylight to starlight, not just a quick photo stop.

Practical note: the setting is rustic and laid-back. That’s part of the charm. It also means you should dress for outdoor air at that elevation and expect a breeze.

Richard’s cigar lounge: cigars and local spirit pairings, without the fuss

This evening is built around cigars, but it’s not a stuffy smoke-and-sit session. Richard’s role is part host, part storyteller. The tone is friendly and relaxed, with conversation that ranges from cigar enjoyment to rum and whiskey notes. If you’re a beginner, you’re not thrown to the wolves—you can take your time choosing and learn what to notice.

You have two paths: bring your own cigars, or try the host’s selection. The offering is described as premium, and people highlight a sense of discovery in what gets poured and what gets paired. One review even called out choosing your own adventure by adding flavors or mixing with local rum or whiskey, then winding down with great conversation.

On the liquids side, the rules are refreshing and straightforward. Richard does not sell alcohol, but liquor is included to enjoy with your cigar. If you want more than what’s included, you can BYOB (bring your own). That keeps the evening flexible—especially if you’ve got a favorite rum, whiskey, or something else you like to sip.

If you care about pairing, this is one of those experiences where the host doesn’t just hand you a drink. The idea is to help you make the evening taste better together: cigar, smoke rhythm, and a spirit that matches the mood.

Mo’okini Heiau and Upolu Point: a short history pause with a view

The itinerary includes two stops before the deck-and-sunset portion really settles in: Mo’okini Heiau and Upolu Point.

Heiau sites are sacred and old in a way you feel instantly, even if you don’t know every detail. The value of this part isn’t turning the evening into a lecture. It’s a brief, grounded way to connect the dramatic ocean view you’re about to enjoy with the deeper meaning of the land—especially since Puʻu Kehoni is tied to the Kamehameha connection via Kokoiki.

Upolu Point is more about the lookout feeling—getting you positioned for the “how wide is this view?” moment. You’re there for the geography: the coastline angles, the line of sight toward other islands, and the gradual change in light.

The main drawback of these stops is also why they work: you’ll spend time outside moving at a casual pace. It’s not a quick shuttle ride between spots. If you want an all-deck experience with no walking at all, this might not be your best match.

Timing and walking: a 4:30 pm start, two hours, and two steps

This is a 2-hour experience that starts at 4:30 pm, right when the sun is dropping enough to shift from late afternoon to golden hour. That timing matters. Go too early and you miss the real drama of the horizon; go too late and you’ll lose the clean transition into twilight.

The group stays small—up to 12 travelers—and the feel is described as intimate, with many evenings running closer to groups around 6 to 10 people. That smaller size is a big value, because you get more of the host attention and less of the “tour-line” energy.

Getting there is your responsibility. Transportation is not included, so plan a rental car or whatever works for you locally. People also mention the approach being a bit off the main roads, so it helps to follow directions carefully and arrive with time to park and settle.

Accessibility detail to take seriously: the experience requires ascending two steps. If you have mobility limitations, consider that part before you book. Service animals are allowed, which is good to know if you travel with one.

What your $49 covers: liquor included, BYOB for extras, no transport

At $49 per person for about two hours, the best way to think about value is this: you’re paying for the host, the setting, and the pairing component—not for a big, scripted attraction.

Here’s what you can count on from the experience info:

• Liquor to enjoy with your cigar is included
• You can bring your own cigars
• You can BYOB for any additional alcohol you want
• Transportation is not included
• The experience is English-speaking

So the “value” isn’t only the price tag. It’s that you get a full-evening vibe: guided cigar enjoyment plus a setting built for sunset and stars. And because it’s small-group, you’re not paying for a crowd experience.

If you’re the type who wants to see Hawaii from an ocean-high vantage point and you also like cigars or want to try one in a relaxed way, this price can feel like a steal. If you’re not interested in cigars at all, the experience may feel narrower than you want—it’s designed around tobacco enjoyment.

Bringing your own cigar, or picking from the host’s selection

You’re explicitly welcome to bring your own cigars. That’s smart if you have a favorite brand or strength profile and you don’t want to gamble on what’s on offer.

At the same time, the host encourages you to sample the selection. People describe it as excellent, including premium and rare options—so even if you brought one, you might still want to try a choice from what Richard offers. The best part here is that you’re not doing the whole cigar tasting alone. You’re with a host who talks through the experience and sets a calm pace.

A practical tip for your comfort: plan to take your time. This isn’t the kind of event where you rush, light, and leave. The timing is built around the light change outside.

Also, if you’re sensitive to smoke, be honest with yourself before booking. This is a cigar-focused setting, so it’s not the place for smoke-free preferences.

The vibe: rustic lounge, ocean air, and Buddy the Pomeranian

The mood is described as authentic, funky, and rustic. That’s a real selling point for me. You’re not walking into a polished showroom. You’re arriving at a home-style, personal property feel—people even mention being met at the gate, which helps you get oriented fast.

A friendly detail: Buddy, Richard’s Pomeranian, may join you. That’s adorable for many guests and worth flagging to the host if you’d rather not have a dog in the mix. (The key is that you can communicate preferences in advance.)

The evening also has a private-feeling rhythm. With small groups and a laid-back deck setup, you can actually hear conversation without competing with constant tour chatter. And if a storm catches you? The host’s approach is to appreciate the raw power from the lounge when possible rather than turning it into a letdown. That’s the kind of attitude that makes experiences feel human.

Who should book this sunset cigar session on the Big Island?

This works best for:

• Cigar lovers who want a sunset setting that feels special, not generic
• Couples and small groups who want a calm, conversational evening
• People who like pairing a drink with a slow activity
• First-timers who want guidance in a relaxed, friendly tone

It may not be ideal if:

• You want transportation included
• You’re not comfortable with two steps
• You dislike being outdoors for part of the experience
• You prefer smoke-free settings

One of the most encouraging parts is that beginners are welcome. The host doesn’t treat cigar enjoyment like a secret club. You can participate at whatever comfort level you bring, from casual sipping to full-on cigar attention.

Should you book Enjoy Sunset with a Fine Cigar in Hawi?

If your dream Big Island evening includes a high viewpoint, real sunset color, and a cigar experience with local spirits, I’d book it—especially if you’re traveling with someone who also likes atmosphere and conversation.

Choose it when:

• You want a small-group sunset with a strong sense of place
• You’re curious about cigars and open to sampling what the host offers
• You’re comfortable handling your own transportation

Skip it when:

• You don’t want cigar smoke in your evening plan
• You need rides and door-to-door transport
• Your mobility needs make two steps a problem

If you do book, do two things that make the evening smoother: plan your drive to the meeting point early, and let the host know in advance if Buddy joining isn’t for you. Then show up with a relaxed mindset. This is the kind of trip where the view does the talking—and your cigar simply keeps the pace.

FAQ

How much does Enjoy Sunset with a Fine Cigar cost?

It costs $49.00 per person.

How long is the experience?

It lasts about 2 hours.

What time does it start?

It starts at 4:30 pm.

Where is the meeting point?

The meeting point is 56-3029 Akoni Pule Hwy, Waimea, HI 96743, USA.

Is transportation included?

No. Transportation is not included.

What is included with the cigar?

You’ll get liquor to enjoy with your cigar.

Can I bring my own cigars or alcohol?

Yes. You can bring your own cigars. You can also BYOB for alcohol that is not included, since additional alcohol is not included.

How many people are in the group?

The experience has a maximum of 12 travelers.

What happens if storms or poor weather are expected?

The host will cancel if storms are expected. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Is the experience accessible if I have limited mobility?

It requires ascending two steps. Service animals are allowed, and most travelers can participate, but you should plan around those two steps.

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