Upcountry Sunset Tour

Upcountry Sunset Tour: A Relaxed Evening with Scenic Views in Maui

If you’re seeking a peaceful evening adventure in Maui that combines scenic drives, a taste of local flavor, and some spectacular sunset and star gazing, the Upcountry Sunset Tour might be just what you need. While we haven’t taken this tour ourselves, we’ve gone through the details to help you decide if it fits your travel style.

What we really like about this experience is how it offers a relaxed way to see parts of Maui that are often missed—like Makawao town and the upland regions—and the fact that it includes dinner and hotel pickup makes it convenient. On the flip side, it’s a fairly short tour at around 7 hours, so if you’re after a more active or extensive adventure, this might feel a bit limited.

This tour is best suited for travelers who enjoy a leisurely evening with beautiful scenery, don’t mind a group setting, and want to avoid overly busy or crowded sunset spots. It’s especially appealing if you’re looking for a low-pressure way to enjoy Maui’s highland views and starry skies without a long day of activity.

Key Points

• Comfort and convenience: Includes hotel pickup and drop-off, plus bottled water and an air-conditioned vehicle.
• Scenic routes: Goes through historic Makawao and up to Kula, providing a different perspective of Maui’s lush uplands.
• Culinary aspect: Pick-up dinner from Kula Bistro, giving you a taste of local flavors in a relaxed setting.
• Stunning views: Out to Ulupalakua lookout for sunset and star gazing—perfect for those who love natural beauty.
• Limited group size: Max of 11 travelers, making it a more intimate experience.
• Price versus value: At $189 per person, it’s a moderate price, especially with included transport and dinner, but you’re paying for a short, scenic experience rather than a full-day adventure.

An Honest Look at the Upcountry Sunset Tour

This 7-hour tour is designed as a laid-back way to enjoy Maui’s high country without the fuss of planning every detail yourself. It’s a good fit for travelers who want a taste of Maui’s quieter, more rural side, especially at sunset and during star gazing. You’ll be picked up from your hotel and driven in a comfortable, air-conditioned vehicle, which is a big plus for staying cool and relaxed in the warm Maui evening.

The highlight is the drive through Makawao town, a charming historic area known for its paniolo (cowboy) roots and artsy vibe. It’s a nice visual break from the beach scene, giving you a glimpse of local life. From there, you head up to Kula, a region famous for its cool climate and rolling pastures. The stop at Kula Bistro for dinner means you get to enjoy a good meal with a view—ideal for those wanting to combine food and scenery.

The journey continues out to Son Yet-Sen Park and then to the Ulupalakua lookout for sunset. These spots are selected mainly for their vantage points, offering wide-open views of the landscape and the ocean beyond. Watching the sunset here is generally peaceful and less crowded than more famous spots, which some reviewers seem to appreciate. Post-sunset, the night sky comes alive with stars, and you’ll get a chance to do some stargazing—an experience many travelers cherish.

What’s Included and What’s Not

The tour includes bottled water and a dinner—a thoughtful touch that makes the evening easier and more enjoyable. The vehicle is air-conditioned, which helps keep everyone comfortable, especially after a warm Maui day. However, it’s important to note that alcoholic beverages are not included, and the tour’s price does not cover them.

Since the tour operates only from Tuesday evenings in a specific window (August to September 2025 and into 2026), it’s essential to plan accordingly. The small group size (up to 11 people) encourages a more personal, relaxed atmosphere, but also means it’s a bit more exclusive, so booking in advance is wise.

In-Depth Look at the Itinerary

The drive through Makawao is more than just a quick pass-by. Known for its artistic community and cowboy heritage, it’s a place that’s worth a leisurely look if time permits. Some travelers mention that it’s a lovely scenic drive that offers a taste of local Maui life away from the beaches and resorts.

Next, heading to Kula for dinner at Kula Bistro offers a chance to enjoy a sit-down meal that’s more relaxed than grabbing fast food. The restaurant’s location in the uplands provides a cooler climate and a peaceful setting—perfect after a day of exploring or lounging. The meal itself is a nice addition, especially if you enjoy local flavors or a quieter dining environment.

The scenic drive to Son Yet-Sen Park and Ulupalakua lookout is brief but impactful. Expect panoramic views, especially around sunset, and the chance to snap some memorable photos. The star gazing at night is often a highlight for many, with dark skies free of city lights, making for impressive celestial views.

What Travelers Say

Even though there are no official reviews yet, the general idea is that this tour is appreciated for its serenity and scenic value. The quiet spots, away from the busier west Maui areas, offer a more intimate and peaceful experience. Some travelers may find the schedule a bit tight or wish for more time at each stop, but overall, the tour seems to deliver on its promise of a relaxing, scenic evening.

Transportation, Timing, and Practicalities

The air-conditioned vehicle comfortably seats up to 11 people, making it a small-group experience that feels cozy but not crowded. Timing is from 3:00 PM to 10:00 PM, which means you’ll be experiencing Maui’s evening in full swing—perfect for sunset and star gazing.

The meeting point at Safeway in Kahului is easy to find, and since the tour ends back there, it simplifies logistics if you’re staying nearby or plan to return to your hotel afterward.

Price and Value

At $189 per person, this tour is priced reasonably for what it offers: scenic drives, dinner, hotel pickup, and star gazing in a small group. It’s a shorter experience, so if you’re looking for a full day of adventure, it might not be enough. But if your goal is a relaxed, scenic evening that combines good views and cultural sights, it’s a worthwhile choice.

Who Should Consider This Tour?

This experience is ideal for travelers who prefer a slow-paced, scenic outing over an action-packed day. If you enjoy being outdoors at sunset, taking in views, and sharing a peaceful evening with a small group, you’ll probably find this tour quite pleasant. It’s suitable for those with moderate physical fitness, as it involves some walking and standing at viewpoints.

If you’re after a budget-friendly, hassle-free evening that combines food, views, and star gazing, this tour hits the right notes. However, if you’re seeking extensive sightseeing or a more active adventure, you might want to explore other options.

Final Thoughts

The Upcountry Sunset Tour offers a gentle way to see Maui’s high country and enjoy its spectacular sunset and night sky. It’s not a tour for adrenaline junkies or those craving a lengthy expedition, but it compensates with peaceful scenery, comfortable transport, and a relaxing vibe. The inclusion of dinner and hotel pickup adds value and convenience, making it a good choice for travelers who want a simple, yet memorable Maui experience.

For those wanting to escape the busy beaches and explore Maui’s uplands in a small group, this sunset and star gazing experience could be a highlight of your trip—especially if you’re visiting during the tour’s operational months.

FAQ

Is hotel pickup included?
Yes, the tour offers pickup from your hotel in Maui, making it easier to enjoy the experience without worrying about transportation.

What’s included in the price?
You’ll get bottled water, an air-conditioned vehicle, and dinner from Kula Bistro. Alcoholic beverages are not included.

How long is the tour?
The tour lasts approximately 7 hours, starting around 3:00 PM and ending back at your hotel by 10:00 PM.

Can I cancel if my plans change?
Yes, cancellations are free up to 24 hours before the tour. Within 24 hours, the full amount is non-refundable.

Is this tour suitable for children?
While not explicitly stated, the moderate physical activity and small size suggest it’s suitable for travelers who are comfortable with walking and standing. Service animals are allowed.

What are the best times to go?
The tour runs Tuesday evenings from late August 2025 through September 2026, aligning with sunset and star gazing opportunities.

Are there any alcohol options?
No, alcoholic beverages are not included, so plan accordingly if you want to bring drinks along or purchase them separately.

If you’re looking for a low-key way to enjoy Maui’s highlands, beautiful sunset views, and starry nights—all with the convenience of a small group and dinner—this Upcountry Sunset Tour could be a good fit. Just keep in mind it’s a short evening experience meant to relax and unwind, rather than an all-day adventure.