Live Blog – Day 5 – Exploring North of Napili – Sunset Dinner Cruise – Trilogy

October 29th, 2022

Today we had plans for the evening but not much was decided for the morning and early afternoon. The day started off really clear without the morning rain we had been experiencing so we decided to head north up the Honoapiilani highway.

After a light breakfast of some cereal and fruit, we cruised through the upmarket resort district of Kapalua and headed up to our first stop.

DT Fleming Beach Park

DT Fleming Beach

We got to the park fairly early and there were still plenty of spots left in the lot, so we parked up and headed to the beach. The Condo had come equipped with two beach chairs so we headed for a quiet spot and set up camp in the sand.

The beach was pretty quiet, a few families were camping out for the day under the trees, but overall the beach copes really well with quite a few people. The surf was pretty light, at least for this DT Flemming, and we just relaxed in the sun for an hour or so along with playing a little in the surf.

I went for a little scramble on the rock to the right-hand side of the beach to get to the secret cove around the headland. As I popped my head around, a Monk seal popped his head up and then scurried off. It was nice to see but shame I had inadvertently startled him, but he was already in the ocean and not basking so not really a problem. He was unfortunately far quicker than my camera!

After enjoying the sun sea and sand for a while we headed back to the car. It was now getting on for lunch so we headed over to the burger joint behind the beach. Unfortunately, our timing was not good and there was a 30-40 min wait so we decided not to wait. Instead, we just headed further up the coast to see what we could find.

Nakalele Blowhole

We stopped at The Nakalele Blow Hole, but from the top, we could see the hole was not really firing, certainly not enough to make the arduous trek down the cliff so we just took in the view for a while before heading further up the road.

As we got to the small town of Kahakuloa, we stopped to pick u some banana bread from Julias, before heading back down the road. We had considered carrying on around, but it’s technically a no-no for the rental car insurance, and we were running late on time. We drive back up the coast through the stunning landscapes and stopped above Honolua Bay and ate our Banana bread before heading back to the condo.

I had unfortunately developed a bit of an ear infection and yesterday’s dive exacerbated it quite badly so I didn’t want to snorkel again today, so we didn’t venture down into the bay, but the waters look crystal!

Sunset Dinner Cruise – Trilogy Sailing

After a brief chill out back at the condo, we got ready for this evening’s entertainment. Namely a Sunset Dinner Cruise aboard on of Trilogy Sailing Catamarans. We got ready and summoned an uber to take us the short drive into Lahaina. These are Open-Bar cruises, so neither of us had any intention of driving!

The uber took us to the wrong address, and we pulled up outside someone’s house in Lahaina, possibly a mailing address, but a quick jig around and we were at the marina. There was a sign informing us to wait at this spot but no other recognition that a Trilogy cruise would be sailing from here. No Boat, No Crew, No Staff, just the sign and a lot of people.

Other cruise companies had their staff on hand and were sorting and boarding their guests. We were just left scratching our heads…However the sign was very clear, and sure enough, a Trilogy cat soon pulled into the harbor and the crew came over to check us in.

We were pretty much at the front of the queue and were seated right at the front of the vessel with great views right off the bow of the boat. Everyone gets their own table on these cruises so it’s great for a little privacy, but you are also seated near other people so you can chat with others too.

Trilogy Sunset Cruise

As soon as everyone was aboard we pulled out of the harbor before coming to a stop for a full safety briefing and itinerary of the night’s events. It was nice to just bob along on the water while we got the mandatory briefing rather than in the sweltering harbor.

Drinks arrived almost straight away as we started down the coast. After around 15mins of motoring, the crew pulled the sails and we got underway on wind power. It really is just so much more peaceful when the sails are up and the engine is dead. The evening was stunning and clear with some nice cloud formations over the islands and rain in the West Maui Mountains forming some cool rainbows. It looked much needed as the grass was seriously dry. Normally by now, it’s returned to a blanket of green after the summer, but the rains were late and the hills a dry orangey/brown.

Soon the first course arrived, an appetizer platter that was pretty decent, the Smoked Salmon, in particular, reminding us of a Sushi Pizza we paid an extortionate amount for at the Bellagio earlier this year! This was accompanied by some breadsticks that were really good. Next up was the salad course which was pretty awful. Just some leaves, a couple of croutons, and some shop-bought salad dressing. Oh well, we didn’t really need 4 courses.

As the sun dipped slowly behind Lanai we were treated to some stunning light. The rays beaming up from behind the clouds and the cloud buildups over Maui glowed in iridescent colors. There were no clouds in the sky so we didn’t get the pinky-purple pop that can accompany a sunset, but it was still pretty special.

Maui’s local marine fauna also largely stayed away, apart from some large needlefish and flying fish that were active on the surface once darkness fell.

The main course came just after the sunset and the lights on the boat came on to illuminate the meal. Kate had the Steak and I went for Mahi-Mahi. The steal was really good but the MahaiMahi breading was a little soggy and the fish dry, but they really have limited galley space.

Drinks had been flowing all along and we managed a good 5 drinks from the excellent cocktail menu, the highlight being the Captain’s Mule and the good old-fashioned to finish the night off. They kept the drinks coming until right before we had to pull into the harbor.

Dessert was a trio of Lilikoi Cheesecake, Fresh Island Fruit, and Dark Chocolate Truffle, all three of which were excellent.


Overall, I am very easy to please. If I am on a boat I am happy, on a sailboat at sunset with food and drinks in Maui and I really couldn’t be happier. Kate is less easily pleased but this was just a stunning experience that is hard to fault in any way really. The weather can impact these cruises, if it’s really cold or rough then they are not always the most fun, but we got an absolute cracker of an evening and the crew did everything they could to make it amazing.

Being British, tipping does not come naturally to us, we know it’s part of American culture so always do as expected but often feel a little put out (In the UK Staff are just paid properly!) But sometimes we love tipping as the recipients in question totally deserve it, and this is one of those occasions! The whole trip was just perfection from start to finish…Apart from the Salad!


Astrophotography Over Maui

We had a brief walk around Lahaina before calling up an Uber and heading back to the resort. We had a really interesting Uber Driver who just wanted to talk video games with us. Kates had never been into gaming, and it shows, and I left that world behind a few decades ago, but he was undeterred! One of the great things about Uber!

Back at the Condo, the stars were really shining. The evening had been so clear we couldn’t resist grabbing some drinks and heading out to the point, away from the lights and laying out under the stars.

Maui does not have perfectly dark skies, even from Haleakala, but there are pretty black compared to most of the mainland! and out on the point, away from resort lights the whole sky just came alive. The Milkey way streaked above us, clearly visible to the naked eye and we just lay marveling at the beauty and just reminding ourselves how lucky we really are!

Live Blog – Trip Report

<<< Day 4 – Shore Diving – Lahaina Happy Hours – Feast at Lele

Day 6 – Kapalua Coastal Trail – Snorkelling – Hotdogs >>>

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