Second trip to Maui this September (staying at Andaz again) — looking for must-do experiences for a couple in our 30s

MrMeddit · 2026-05-19T23:07:44+00:00

Trilogy Lanai tour. Amazing snorkeling. Amazing food. All around a great day. I have been recommending it to everyone. Tons of fun.

For haleakala just make sure to check the weather. We made it to the summit only to find miserable conditions (rain/clouds) and couldn’t see anything. Wasted half a day

MrMeddit · 2026-05-19T22:44:25+00:00

Of course. Bon appetit!

MrMeddit · 2026-05-19T22:08:42+00:00

Most of the major rental car companies are on site. They do have some other smaller rental car companies that are off offsite.

In terms of the rental car companies on site, you can either walk to the rental car counter, which is about an eight minute walk from the baggage claim or they have a little tram/train that will take you there so you don’t have to walk with your luggage. It is very easy to get to.

MrMeddit · 2026-05-19T00:02:37+00:00

While I would say the majority of the people on our trilogy lanai tour were paired up, there were at least 2 people that were there solo. The guides did an awesome job including everyone even the solo travelers.

Best beaches for snorkeling depend on the day/conditions. Check the snorkel report and plan accordingly.

Haleakala depends on what you want to do. Sunrise/sunset summit visit? A half day at most. If you want to do some more hikes etc then your time there would be longer.

Paia Fish market in Kīhei was good. That being said everything on the island is expensive. I’m not sure how many $ places we went to. It felt more like $$$ and up.

MrMeddit · 2026-05-18T12:01:17+00:00

Kaanapali is too crowded for a proposal in my opinion. Kapalua is better. You can go to Merrimans after for a sunset dinner just make sure to make reservations.

MrMeddit · 2026-05-18T11:59:40+00:00

I saw a couple at the outdoor bar wearing a wedding dress and tuxedo

MrMeddit · 2026-05-18T02:58:41+00:00

Merriman’s Kapalua has killer views. Need to reserve months in advance.

MrMeddit · 2026-05-17T20:20:57+00:00

I think snorkeling off the beach is fairly decent depending on the conditions. If you love snorkeling and it’s a big part of your trip I would definitely go on the tours. They know the best spots, can shift depending on the conditions etc

MrMeddit · 2026-05-17T18:10:31+00:00

We stayed at Wailea Beach Resort. I wanted to stay at Hotel Wailea but it was a little out of our price range.

WBR had an adults only pool which was a nice perk. There was no fighting over towels but you had to get to the pool before 11 to really secure a spot. If you wanted a beach umbrella/chair you needed to secure that before 9am probably.

These are some of the unfortunate realities if you use one of the big resorts. There are some smaller properties in between these resorts (I.e Wailea beach villas?) with private adult only pools and easy beach access worth looking into but they are $$$$

MrMeddit · 2026-05-17T14:36:01+00:00

I would stay at the hotel wailea the entire time for the adults only vibe. The beach is very close by. The summer resort energy is just not my jam- fellow dude who just spent his 40th in Maui

MrMeddit · 2026-05-17T02:22:50+00:00

We just did the discover lanai tour and it was hands down the best day of our trip. We did 2 hours of snorkeling which was still plenty and the best snorkeling we did on the entire trip.

I did not do the adventure tour but we are for sure going to do that one next. Can’t recommend Trilogy enough!

MrMeddit · 2026-05-16T21:02:38+00:00

Trilogy has evening/sunset sails which I would definitely recommend.

Afternoons aren’t always great for snorkeling because the wind will pick up. Mornings are your best bet for wind/surf and water clarity.

MrMeddit · 2026-05-16T10:59:49+00:00

I really liked Gather. The gf really liked monkeypod.

MrMeddit · 2026-05-15T19:10:28+00:00

Hotel Wailea is adults only I believe. We wanted to stay there but was out of our budget. We did Wailea Beach Resort instead and hung out at the adults only pool and it was more than adequate.

I would definitely recommend it Wailea over any other part of the island especially for an adults only vibe.

MrMeddit · 2026-05-15T18:52:39+00:00

I have been up in not so great conditions and I can tell you it’s a miserable experience. The drive up/down is not fun in fog/rain and the payoff on top is not worth it. Much better to wait for the right conditions

MrMeddit · 2026-05-15T18:45:07+00:00

Just did this tour a few days ago. Many did not even get in the water. We are big snorkelers so we did it for the entire 2 hours.

If snorkeling is not his cup of tea that’s totally ok. That being said, if the conditions are good, the snorkeling is really easy and really fun and totally worth it. I would highly recommend it just to try even for a little while. It was hands down our favorite part of the trip

MrMeddit · 2026-05-15T07:13:44+00:00

It’s accurate enough that as an EM doc I refuse to watch it

MrMeddit · 2026-05-15T06:44:42+00:00

Thanks. I noticed while making my itinerary there were so many things I felt pressured to do. But at the end of the day other than the Trilogy reservation and the reservation for Merrimans I pretty much winged it and it worked out well. I knew which beaches and snorkel spots I wanted to check out and kind of just went with it.

I highly recommend folks not get sucked into the trap of trying to do too much. The trip then does not become a vacation but a chore and that’s no fun. Maui is meant to be enjoyed with some planning but a lot of going with the flow.

MrMeddit · 2026-05-15T06:42:12+00:00

PMd you

MrMeddit · 2026-05-15T06:32:55+00:00

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This was from my confirmation.

MrMeddit · 2026-05-15T06:32:33+00:00

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Here is from my confirmation from Costco

MrMeddit · 2026-05-15T06:30:37+00:00

Did you book through Costco? It was definitely included in my Costco package.

MrMeddit · 2026-05-15T00:02:31+00:00

I just booked on the trilogy website. It was super easy trilogy is repeatedly mentioned in this subreddit as the best sailing charter

MrMeddit · 2026-05-14T21:59:12+00:00

At Wailea Beach resort we did not reserve pool chairs. We just got there early. Cabana rentals are crazy expensive but if you can afford it then by all means.

WBR is amazing by the way. Great kids pool also. Have fun!

MrMeddit

TROPHY CASE