Maui planning, tips, and trip reports

Second, Third and Fourth vote for Trilogy!

We used them for a Molokini trip in July 2014, then for Molokini and 2 whale watches in February 2020. They are fantastic!

🐠🐋
Well a friend we met at Aulani last trip also recommended them!! I guess I need to rethink taking Molokini off my list…🙄 but I know DH won’t get on that boat and I really hate leaving him alone for the day.
 
Does anyone have experience booking the Haleakala sunrise on Maui? It seems like it requires the same level of sophistication as getting a ROTR boarding group 😂
 
Can anyone recommend a private sailing company? We like to book a private boat (with captain; we don’t want to operate the boat!) to take us snorkeling etc. I see several online but am looking for a recommendation if anyone has one. I looked at Trilogy, which looks great but I think they generally take out 30+ people.
 
Does anyone have experience booking the Haleakala sunrise on Maui? It seems like it requires the same level of sophistication as getting a ROTR boarding group 😂
I didn’t have any issue booking it when we went, but it had just started and frankly I think a lot of people didn’t know about it yet.
 


Also any zip lining recommendations on Maui or scuba diving recommendations on Maui? We zip lined with Climb Works in Oahu and loved it a few years ago!
 
I have been to Maui 19 times since the 80s! Our favorite experiences include Molokini snorkeling, winter whale watching, parasailing, eating at Mama's Fish House, IOA Needle hiking, snorkeling anywhere along the coast between Lahaina and Napili, Haleakala CRater at sunrise, the Hana Highway, and that time we drove all the way around the island in our rental car! Took 12 hours.
 
Just to chime in again about our upcoming trip for 2022:
We decided to rent a condo at Kaanapali Shores Resort up in north Kaanapali rather than stay at the Wailea Beach Resort by Marriott. We really loved that resort in Wailea, but we decided to branch out a bit and stay in Kaanapali. The full kitchen in the condo will be better on our budget for some meals at the resort (and my wife does a special WFPB diet, so limited options eating out.) We pushed our dates to July 2-6 in Maui. Also, some friends may be joining us for the trip and they have never been to Hawaii - so they wouldn't know what they are missing from Wailea Beach Resort. LOL

We enjoyed the Oahu Private Tours 2-day tour of Oahu so much on our last trip - does anyone have recommendations for any island tours on Maui? Also, we will get family portraits done in Maui, so we are looking for recommendations for that also.

TIA!
 


We enjoyed the Oahu Private Tours 2-day tour of Oahu so much on our last trip - does anyone have recommendations for any island tours on Maui? Also, we will get family portraits done in Maui, so we are looking for recommendations for that also.

TIA!

I used Valley Isle Excursions for my Road to Hana and Haleakala Sunrise tours. I liked that they limited their tour groups to 12 people. You can also check Robert’s Hawaii. For snorkeling or whale watching, check out Sail Trilogy or Pacific Whale (PacWhale). Everything else on Maui you can pretty much do on your own. You can also snorkel on your own, you just have to know where to do it from.
 
Also, we will get family portraits done in Maui, so we are looking for recommendations for that also.
We’re looking too. I haven’t used any of these, and haven’t even contacted them coming out of covid—some may not even be around now. But here’s what I found online and my thoughts about them. Now I didn’t even include the ones whose style I didn’t like or who I found much too expensive (and some of these still are!). And of course these prices are it’s what was on their website when I looked; they could’ve changed by now:

-LeLuxe Hawaii in Kihei starts at $415 (1.25 hr/50 pics) looked like maybe the beat overall value to me
-Anna Kim was very nice but starts at $750, so I was out
-Maui Family Photography starts at $375 (30 min/40 pics) but very minimal post-processing
-Maui Family Photography starts at $375 (30 min/40 pics) but very minimal post-processing
-Scott Drexler is really professional looking but starts at $650 (cuz he’s a professional LOL)
-Love and Water in Wailea has this super dreamy pastel style, starts at $550
-A Place in Time in Makena is also pretty basic, starting at $349 (30 min/15 pics), but 15 pics wouldn’t be enough for me, so I’d be spending more right off the bat
-Capture Aloha had a super crisp look and starts at $395 (30 min/25 pics). I noted that they’ll travel for a fee, so they may be more west Maui area; can’t remember.

Hope this helps some. I was focusing on south Maui mostly, but this gives you an idea what kind of pricing to expect anyway.
 
This has great info! We went to Oahu in 2015 for our third anniversary I believe (obviously been too long) and now I want to surprise my husband for our next anniversary. He always says that was his favorite trip so far.

With regards to the tours on Maui which are really worth it or would it be better for us to just do the stuff on our own in our rental. We don’t mind driving but I’m just not sure.

I would definitely like to do the Road to Hana and Mt. Haleakala at sunrise. Are these tours worth it or could it be done on our own? Pros/cons?

What about the IOA Needle hike I saw someone mention? Any tips for that?

We are looking at 4 nights in Maui and then 4-5 on Oahu.
 
I would definitely like to do the Road to Hana and Mt. Haleakala at sunrise. Are these tours worth it or could it be done on our own? Pros/cons?

What about the IOA Needle hike I saw someone mention? Any tips for that?

We are looking at 4 nights in Maui and then 4-5 on Oahu.

IMO both tours are worth it, but can also be done on your own. Unfortunately, the person driving can’t appreciate the scenery on the Road to Hana until they stop. There are audio tours and apps you can download for the tour. This website lists the stops. If you go all the way around, it will take about 10-12 hours depending on traffic. Think two lane country roads and dirt roads in places.

My Haleakala Sunrise tour picked me up at 3am from the hotel. After we met up with the other people on the tour, we went up to Haleakala. We arrived around 30-45 minutes early so we could get a good spot and see the small museum. It is cold at the top, so bring a winter coat or layer really well.

I wouldn’t classify the path to the viewing platform for the Iao Needle as a hike. It is only 0.6 mile long and is paved. It’s been a couple of years since I went there, but the parking fee had to be paid in cash. You may want to double check to see if that is still true. Here’s the website for the park.

Only you can decide what works best for your family. Most sites in Maui can be done on your own, it just depends on whether that’s what you want to do.
 
It is cold at the top, so bring a winter coat or layer really well.
He’s serious here. Do NOT haul 4 hoodies all the way to Hawaii and leave them in your room. Because the tiny gift shop may only have two hoodies left that are 2Xl and $65 each. Because then you may wind up with exactly ONE selfie of your whole family before they literally run back to the car. Hypothetically speaking, of course 🙄

The drive to Hana is tiring because it’s so tedious—you have to pay attention the whole time. No cruising and checking out scenery. I’d say it might be worth doing if you don’t have your heart set on spending more time at any particular stop; with a tour, you won’t get to choose that. We enjoyed going at our own pace, but I can definitely see the appeal of not having to watch for turnoffs, navigating the bridges, and finding parking spots.
 
we split time at Waikiki/embassy suites (used for home base for touring most of island Via a rental car).

last few days on the island, drove over to Aulani and didn’t leave until time to board cruise ship

on Maui for 2 days, we used valley Isle tours & did the full loop/road to Hana.

Next am they picked us up for sunrise at Haleakala. Seriously, an awesome experience!
 
Black rock at Ka’anapali beach was my daughters favorite snorkel spot.. she’s a beginner and it was perfect for her to go out and explore. There are turtles there and super close.. it seemed like there were more later in the day (around 4-5pm) but they would literally swim by you when you were standing in knee high water.
 
We just returned home from 2 weeks in Hawaii. Spent 7 nights at Maui Ka'anapali Villas before 3 nights at Alunai/4 nights in Waikiki. It was me and my 15 yr old son and we had a great vacation! On Maui we loved hiking Sliding Sands Trail at Haleakala, Road to Hana and Pipiwai Trail, snorkel trip with Trilogy, beach at MKV, shave ice and more shave ice at Uluani's.
Bought the Gypsy Guide for both islands are really enjoyed getting some history of the islands as we drove. Highly recommend Trilogy and the photographer we had took great shots in and out of water and photo package for the 2 of us was $69.
 
Just wanted to chime in with my own Maui experience! My full trip report is in my signature. We stayed at the Westin Maui in the Kaanapaali beach region and it was probably my favorite resort out of the 4 we stayed at during our trip, including Aulani! Its on the small side, amazing pool, next door to Whaler's Village for easy shopping and dining, and at the time they also offered a free shuttle to Front Street Lahaina. I'd recommend it to anyone.

We were there in late September and one thing we noticed that for almost our entire stay there, it was incredibly windy. From the first moment we stepped outside the airport, we were smacked in the face by the wind. We found it difficult to lay on the beach because of sand blowing in our faces. The wind did keep humidity at bay and temperatures were mild, which was great for touring. We also found the waves to be large and rough and that kept me out of the ocean, as someone who is not a strong swimmer. It didn't rain at all during our stay so I'm not sure if this weather is par for the course this time of year, or if we had a bout with inclement weather. Just something we noted.

During my research, I found that the two of the highest rated luaus were in Maui - Old Lahaina Luau and Feast at Lele. OLL is a traditional Hawaiian luau. Pre-covid, they sat you at communal tables and it was buffet style; however, I believe they are now serving you. There's also lawn seating on a cushion if you prefer. There's no fire dancing, since that's native to other South Pacific cultures. Feast was a little different as it incorporated around 5 or 6 different South Pacific cultures (and had fire dancing), and they coordinated the meal course with the country being presented during the show. They had servers and seating was at your own table, assigned in the order in which you booked. Both included alcohol. We chose Feast because we were on our honeymoon and wanted our own table. Loved the show and even though some of the food was not to my taste, I was impressed with the amount of food - we did not leave hungry even though we left a lot of food on our plates at each course!
 
shave ice and more shave ice at Uluani's.
That’s on my list! Here’s my dirty little secret….in 14 days on our last trip, I didn’t try shave ice once! In my defense, I have sensitive teeth so frozen stuff is not my favorite thing….but I did go to Matsumoto’s to try it, but refused to stand in a 100-deep line for sometime didn’t really want. Kids had it several times and enjoyed it.
 
During my research, I found that the two of the highest rated luaus were in Maui - Old Lahaina Luau and Feast at Lele.
The menu for Feast at Lele sounds amazing!! And definitely a fantastic choice for a honeymoon for sure. But we compared menus for several, and DD really likes the Te au Moana menu best and it’s much closer to where we’ll be staying, so I guess we’ll do it. Anyone here been to that one? It’s the one at the Marriott Wailea Beach.
 
That’s on my list! Here’s my dirty little secret….in 14 days on our last trip, I didn’t try shave ice once! In my defense, I have sensitive teeth so frozen stuff is not my favorite thing….but I did go to Matsumoto’s to try it, but refused to stand in a 100-deep line for sometime didn’t really want. Kids had it several times and enjoyed it.
The longest line we waited in was in Waikiki at Vintage Island Shave Ice. At one point my son said mom this is like waiting for 7 dwarfs without a FP🤣
 
I haven’t decided on which Luau yet but trying to decide between doing one on Oahu or Maui. We haven’t been to Maui so I don’t know if I would rather venture more there and do a luau on Oahu?

I also saw some people mention photographers on Maui. Pros/ cons for photos on Maui versus Oahu? Like I said previously we have never been to Maui and have Oahu so unless there’s a specific reason for Maui I think I rather explore the island rather than worry about pictures there.

I appreciate all the feedback!
 

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