Hawaii Tips for first timer

So, my daughter and I are about to hit our 50th state in our 50 state journey in May and early June. My wife went to Hawaii but that was almost 30 years ago. I need “Must Do” for semi-active people. We aren’t huge hikers, bikers or surfers.

Islands we will be visiting: Maui, O’ahu and Lanai.

Y’all seem well traveled so I value your opinions. Food recommendations appreciated. We also love museums, history and cultural events.

While on the island of Maui you need to get up early one morning and drive to the top of Mount Haleakala and watch the sunrise. If you are really adventurous taking a mountain bike trip down inside the crater is also pretty cool.


Maui No Ka Oi - Maui is the best… or at least it was when I lived there.

Hale-Akala (House of the Sun) is a must. The locals told me how they would drive up to the 10,000+ crater when it snowed & make snowballs, then bring them down and have snowball fights.

Hale-Mahina (House of the Moon / West Maui Mountains) is smaller, less traveled, very lush because of all the rainfall. West of Wailuku, Io Needle is a nice little hike.

Depending on whether a storm is coming the north shore by Paia (NE of Kahalui on the Hana Highway) can be incredible, waves bigger than you’ve ever seen anywhere. At night it’s really humbling, the power of nature. Most of the time the surf is 10 feet or less, but I’ve seen 40 ft waves, look on Youtube for surfing competition at JAW where waves can be 90+ feet. It’s wild.

A ton of people drive to Hana on the east end - long, winding drive, places where it’s one lane, rain forest with lots of waterfalls hanging off the mountain. On the way back, I’ve just made a circumnavigation and went on the south side of Haleakala, which is windswept, a few hippies live there.

Makena beach south of Makena / aka “Big Beach” is a really big beach, visible from space.

Over in west Maui, Lahaina has a lot of historical stuff, if you keep going to west to Kapalua, a beautiful vista where Lanai and Moloka’i are visible. I would do the circumnavigation of west Maui - go past Lahaina and just keep going, all the way around back to Kahului.

Not a ton on Lanai, lots of golf, lots of beaches, an old ship wreck on the north shore.

O’ahu has a ton of stuff to do - east shore up to north shore is the opposite of Honolulu.


I’ve been to Oahu and Kauai.

Oahu is LA on an Island. It’s OK.

Kauai is where I fell in love with Hawaii. It’s small and far less touristy.

Everywhere we went was beautiful.

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North Shore Oahu is heaven on earth. Waikiki/Honolulu, meh


You’re going at perfect whale watching season. At a minimum take a whale watching boat tour on Maui. When we were there (Jan or Feb as I recall) we saw dozens of humpbacks every day just from the balcony of our room in Kaanapali. If you snorkel, there’s a good beach near the Sheraton resort. Swim out to near the end of the rock out-cropping at the beach’s north end, then float face down in the water, holding your breath as much as you can, or very quietly breathe using a snorkel. You should be able to hear the whales “talking” if you do.


Just went to Maui last fall.

  • Couldn’t get sunrise tickets for Haleakala (they only made like 30 available a couple days ahead), so went up later and I really liked it. Hiked around a little, but not into the crater. Some say sunset is just as good (or better - lower crowds, not as cold, etc.). We didn’t stay - we would have had to wait several hours and the kids wanted to go.
  • Road to Hana was a long day (pretty much on the road by 8 to sunset - timed everything out so we could get to the 7 pools (didn’t walk, but did the 4.5 mile hike to the Waimoku falls starting 1:30/2ish). Have to get reservations for a window at black sands beach (mile 32 - Wai’anapanapa state park). And the banana bread (mile 16.7 Aunty Sandy’s). Used Shaka Guide app which was worth the $15. It has over 100 commentaries (some really cheesy) but tells you were to stop or not, some background and history, some stories, music, and is guided by gps. My kids really liked the secret Lava tube at mile 23.2. Huli Huli chicken was great for lunch. Bring cash. Also, have some smaller bills and stop and get some fruit at little roadside stands (on your honor).
  • Got some snorkel gear and went to Makena Landing (good fish and turtles). Another day went to Kapalua Bay (gorgeous) and Black Rock Beach (I didn’t like it - crowded, harder to get to w/ parking, etc. - reminded me of busy Oahu beaches)
  • Went to Ioa Needle. Nice. Pretty short walk. Lush
  • Make sure to hit Leoda’s Pies
  • Went to Myths of Maui Luau. It was decent, but if you do Oahu and Polynesian Cultural Center, just do that one.
  • Everyone goes to Mother’s. My sister and parents went another time and although pricy, said it was worth the splurge. We didn’t get reservations and wouldn’t have taken our kids anyway.
  • We mostly did takeout. Da Kitchen was really good. Got 3 plates for the family of 5 (plus friend Musubi) and we were eating leftovers after that. Coconut’s Fish Cafe was good (fish tacos).


  • We stayed in Waikiki because of points, but tried to spend as little time there as possible.
  • First day since we woke up early (4am), we walked to Diamond head and walked in before the cars could and were the 1st up for sunrise.
  • Hanauma Bay - I love this place. Saw turtles, octopus and lots of fish. There are restrictions or fees or something and can get crowded. We went early (before 7?) so we got in before we had to watch the video. But you either have to wait for their snorkel gear place to open later (8?) or bring your own. Drives me nuts that even after the video and signs, some still stand on the coral. Idiots.
  • USS Arizona - I didn’t get to go because it was during a gov’t shutdown (Oct 2013?)
  • Polynesian Cultural Center (PCC) - my wife loves it. I think it’s pretty good. Nice to walk around to the different ‘countries’ and there are activities. Ends the day with a luau. Most of the employees are BYU-Hawaii students from around the Pacific as part of their financial aid, so nice to support their education.
  • North shore - some good beaches. Probably not get in the water. Good shrimp food trucks and shave ice up there.
  • Dole plantation - skip. tourist trap
  • East beaches were nice. Lanikai/Kailua. I think you can rent kayaks and go out to some nearby small islands (check the currents, conditions, etc.).
  • Byodo-In Temple is a nice Japanese garden to walk around.
  • Nu-uanu Pali lookout is interesting for a quick pullout if you travel 61.
  • Food: Murakame Udon (Waikiki) was both ‘cheap’ and really good. We did Duke’s for brunch. Pearl’s Korean BBQ was good. Leonard’s Bakery! (Portuguese donuts). North shore shrimp and shave ice already mentioned. Could all have changed since this was almost 10 years ago.

Have fun. Other tip - get some reef safe sunscreen before you go (Amazon) if you are going to get in. It’s required (no one checks) but is just the right thing to do to conserve the reefs.

Oh, and for covid. If you are vaccinated, easy. Load your cards into Safe Travels. They just stopped the questionnaire I think. You get a QR code and you can show that in your departure airport and get a wrist band to bypass the check on the island. I think interisland you also get to skip, but not sure on the latest. If you aren’t vaccinated, you have to get a negative test and load that (scheduling was stressful as we had an 11 year old that couldn’t be vaxxed yet). I think Maui also required regular testing now if not vaxxed. The islands take masking seriously and you will likely need to show your vaccination card at restaurants.


It’s been a long time since we went to O’ahu, and we went to Maui in 2018. If you are renting cars and driving on each island, get the GyPSy Guide for your phone/GPS. It has tours plus commentary while you drive. I used the one for Maui and for the Road to Hana (done it once, probably won’t do it again… Long day of driving). Gave you info for any stops, and the drive back included a lot of history of the island. They have one for Maui, O’ahu, Kauaii, and the Big Island - Hawaii. Maui is $15 and O’ahu is $13, and the 4 island bundle is about $40…

We’ve done O’ahu a number of times, Maui once, Big Island once and Kauaii twice. Would go back to Maui, Kauaii and the Big Island. Too busy on O’ahu, but there are many things there that are great to see (Pearl Harbor, North Shore, The PCC, Punch Bowl, etc…).

We stayed near Lahaina on Maui, and the west side has a great place for snorkeling (Kapalau Bay Beach), but get there early as the parking lot does fill up and there is no parking on the street. Lahaina has a great old town area, and there are a few good places to eat - Captain Jack’s Island Grill, Cheeseburger in Paradise… Da Kitchen is great (in Kahului). Did the tour of the Sugar Plantation on Maui as well. The highlight of our trip was being stuck there for an extra 4 days due to Hurricane Lane making landfall and closing the airport for a couple days… No major issues for us, but a lot of places shut down for a few days and store shelves were fairly bare…



They were doing work on the parking lot and it’s down to maybe a dozen - 20 spots. We got REALLY lucky and someone was just pulling out and we got one but there was an attendant there and there are some shoulder parking for now. But agree on going early. But it is an amazing little bay.

We stayed down in Wailea, so headed up earlier that day.

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So many great suggestions in this thread:

Maui is my favorite place. I enjoy biking Haleakala but not the sunrise. Wake up at 3a, long drive to crater, freezing cold and watch the sunrise. I get tons of people love it. I didn’t. We had an equally beautiful sunset in Salt Lake just a few nights ago.

Should probably do Hana once. If you have a weak stomach try to get an open top Jeep for the ride.

Luau’s are expensive. Like really expensive and not that great. Take that time and money and try Star Noodle or Moku or Mamas or a dozen other great places. Try The Gazebo for breakfast but get there for a late breakfast when the line is shorter.

Someone mentioned its a good time to go whale watching. Truth. Also you might come across a pod of spinner dolphins. Really awesome. Spinner dolphins are in Maui year round.

We’ve been there enough now that we’re trying some of the more offbeat touristy things now, like visiting a goat farm and sampling a variety of cheeses.

Not in love with Oahu, but, the North Shore can’t be beat. Beautiful beaches. North Shore also has several shrimp trucks that are worthwhile.

Nothing beats Hawaii. Good luck, and enjoy.


Be very careful of rips at Paia ( and basically anywhere there is wave action)
Read up on rip tides and stay safe.
We did one of the snorkeling trimaran sailboat cruises which was reasonably priced/ decent food and brought us to some excellent coral reefs (which were disturbingly desecrated in some areas).

Have a wonderful time. Check up on covid apps. I think you might need to have specific QR codes on your phone - at least it will make things a lot easier…

We loved Maui so much we’re going to go back to Kauai in March. Hoping the pandemic is settled down by then.
Have fun! Post some pics.

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everyone’s a little different but if you’re there for 7 days, spend 6 of them snorkeling.

10 days - 8 snorkeling


We went in August, Haunama Bay was difficult to get in and restricted so we booked a Sea Turtle snorkle trip on a catamaran for 1/2 day. Awesome experieince.


On Maui, you have to do Haleakala and Road to Hana at least once. If you ever come back, they can be skipped. We actually stayed 3 days in Hana last November and it was my favorite. So laid back and beautiful and no crowds, like much of Hawaii was probably 70 years ago. If you do Road to Hana, try to get reservations for Wai’anapanapa state park. It is pure beauty, and you can hike all around to get different views and perspectives (I would chose this over the 7 sacred pools).

I cold spend a full day wandering around the shops of Paia, and relaxing on Ho’okipa beach.watching the surfers, windsurfers, and kite surfers. You will also always see turtles on Ho’okipa beach.

My favorite place to eat on Maui is Paia Fish Market. They have locations in Kihei, Lahaina, and Paia. I dream of their Mahi Mahi sandwich and coleslaw.

The north east end of Maui, past Kapalua is fun to explore. The Nakalele blowhole if fun to hike around, and watching the blue-green waves crash one the rocks is mesmerizing.

You can’t really go wrong on beaches. We like Keawakupu beach on the south end, Napili or Fleming beach on the North for smaller crowds. But don’t skip Kaanapali beach, from the Whaler Village up to Black Rock, even though it’s crowded, it’s a lot of fun with lots to do.


My big adventure when on Maui many years ago for business, was to stay on for a Saturday at the end of the trip, rent a good road bicycle and ride UP, Haleakala. As I recall, the ride, starting at the PaiaFish Market, at sea level, is about 40 miles, and ascends 10000 feet. I started early, completed the ride up in a little over 4 hours, discovered a nice Italian restaurant in a town part way up the mountain, in which I had dinner that evening (I looked but could not recognize the name of the restaurant among those currently operating).

Its a beautiful ride, spectacular vistas from the summit, and there are a lot of local bike shops used to providing rentals. There is an organized ride/race to the top for which a few locals were training the day I rode up. Most tourists, do the opposite: rent a bicycle and a lift package to the top, and then cruise down the hill. I’m sure that’s fun also. (I cannot tell you how many people rode down in the four house I was ascending, most of whom felt compelled to yell, “You’re going the wrong wayyyyyyyyyy”.)

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I second this, the sunrise bike ride is outstanding. Also, if you do the road to Hana, get the narrative cd, or it’s probably downloadable now, for the drive. It is set up to narrate the trip with the speed limit and it’s like having your own personal guide along with you. It’s unbelievable what you miss without it.


2nd this. We at at Paia Fish Market in Paia and it was super tasty. Saw turtles at the beach above. My general observation was that the east side had bigger waves and stronger currents so was good for more experienced folks inc. surfers, etc. The west side is more calm and seemed better for snorkling. My mom almost got swept out at Black Sands and my Marine recon bro-in-law had to go get her.

You crazy

We were going to do this but my 2 boys are short and they were just shorter than what the bike shops could accommodate. It seems the self-guided pace is nicer than a tour because they push you along. The streets are narrow in places. It’s nice gravity takes you, but some have said it got old. I would have liked it, but I think some of my family would have been meh afterwards.


With respect to the Road to Hana, we did it on a small tour bus and I’m glad I did. Had I been driving all I would have seen is the road. Your eyes most definitely cannot wander to the scenery on that drive. You’ll either be hit by another vehicle, including some larger trucks delivering things, or drive off the road. Being a passenger meant I got to take the scenery in better.


They prolly have ebikes now making the climb much more accessible.


For a first time trip to Hawaii I would not recommend Lani. There’s really nothing to do there compared to the other islands. Better to add the time to Maui (not Oahu) because Maui No Ka Oi.

You know Hawaii is a mess right now, right? I would wait.


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Only one person mentions Pearl Harbor? I cant think of anything more significant or more rewarding to do.

I love Maui too, but Hanauma Bay below Diamod Head is spectacular, as someone said above. And you can hike to the top of Diamond Head. Its easy with a great view.

The other thing about the North Shore of Oahu-in January, the breakers are so big it can be dangerous to get in the water. By late April early May there are no waves at all. Its like glass.