Help me plan a Hawaiian vacation

[Ucsdryder]

This is all great. Appreciate everyone taking the time.

 

[elkhunterUT]

Just returned two days ago from a family trip to Maui with all 3 of our kids (22, 19, 16). We all LOVED it.
Stayed in a privately owned condo right on Ka’anapali Beach-was perfect. We stopped at Costco on our way to the condo from the airport and stocked up on snacks, breakfast and lunch stuff. Ate most all dinners and some lunches/breakfasts out at restaurants.
Loved the Hula Grill (Hula pie is a must get while in Maui)
Island Cream Co. is also a must stop for ice cream/shaved ice.

We snorkeled a bunch at Kahekili beach, black rock beach and did a kayak/snorkel tour at Makena beach in Kihei to see the sea turtles (definitely recommend)

Boogie boarded a bunch and favorite beach by far for that was DT Fleming beach near Kapalua. Waves were perfect for boogie boarding.

Did a half day fishing trip out of Maui harbor and really enjoyed that. Kept two of the fish we caught and cooked them up at our condo. They were very good eating.

My wife and I want to do Kauai next but we LOVED Maui. Happy to answer any questions about our experiences.

 

[rookieforever33]

AI is interesting but too many people I know think its gospel. I think the answer above went off on tangents even more than long winded sliders like myself do.

 

[fmyth]

AI is interesting but too many people I know think its gospel. I think the answer above went off on tangents even more than long winded sliders like myself do.

I use it as a starting point and then dig deeper on any info provided that aligns with my vision. I'm traveling all summer in my truck/trailer and have used Grok to find dispersed camping, dump stations, community rv parks etc.

 

[Mangata]

Another vote Kaanapali beach on Maui. Mile long beach of golden sand and surf conditions for everyone from jumping off Black rock, snorkeling, and easy swimming inside the reef at the other end of the beach. Resorts have great pools & most have kid friendly pool areas.
We went every January for years on end. Maui Ocean Club three bedroom with full kitchen serves us very well, as well multiple grills downstairs to expand cooking options.
Immediately between beach and resorts is a sidewalk that spans the entire length of the beach for walking & easy access to Whaler’s Village for restaurants and tourist shopping. February is still whale season & you will see multiple of humpbacks daily. Look at VRBO and see what is available for your time frame.

 

[Mike D Texas]

My wife and I went in 2023 for our 35th anniversary. We flew into Honolulu and stayed in Waikiki for 3 days. We were ready to leave. Too crowded for us.

We island hopped on a cruise ship stopping in Maui, Hilo, Kona, Kauai and back to Honolulu.

By far our favorite island was Kauai. We took a helicopter tour and the island is absolutely stunning. As others have said, probably less for kids to do there.


Sent from my iPad using Tapatalk Pro

 

[180ls1]

You said no hunting, I'll be the bad influence. I can dig up the contact info of guys who run pigs with dogs and let you knife them - $500 last I looked.

 

[Coveyleader]

February can be a rough month for weather. Water is “colder” and expect waves/rougher water on some islands.


I never cared for Maui much, but for what you’re looking for, (Kaanapali) it may be the best option. It is pretty much Florida.

 

[Yukon Cornelius]

As a former resident of Oahu and Maui, that’s my two recommendations. February, look at south shores so you guys don’t die. South side will be calmer during the winter months. Oahu is a concrete jungle and Maui is getting there. The island with the most things to do for kids is Oahu. Resorts will have nice pools and activities for the kids typically but the ability to cook at least one meal at your place is nice.

I know families that only do resorts because the kids and wife prefer pool versus beach.

If you are doing Maui, Kihei is nice, and the west side is nice as well, but Kihei will have calmer beaches during your time frame.

Oahu is busy. Beautiful if you ignore the concrete. If you want to experience large surf, hit Oahu and spend a day on the north shore. It truly is breath taking when it’s thumping. Do not let the kids get in if it’s huge.

Regardless of where you go, pay attention to the shore breaks and the rip tides.

Kuaui is also nice and the big island, but not as much to do for families. If your kids get bored easily Maui or Oahu. If they would be perfectly fine with little crowds and more beach, any of the outer island. Don’t do lanai or Molokai with the family and Niihau isn’t even an option. You have to be invited.

Maui is my first choice. Oahu second. Kauai is third choice and big island is 4th choice.

If you do Maui, do snorkeling at molokini and pay to get there.

 

[Yukon Cornelius]

Must-Do ExcursionsHere are family-friendly activities tailored for snorkeling, boogie boarding, easy hikes, and other memorable experiences, keeping your kids’ ages (3-14) in mind. These focus on authentic, less touristy options to create lasting memories.Snorkeling

• Hanauma Bay (Oahu, day trip): A marine conservation area with over 400 fish species and sea turtles. It’s calm, shallow, and perfect for kids 3-14, though the 3-year-old should stick to tide pools with supervision. Book entry in advance (limited daily visitors). About an hour’s flight from Maui, so consider a day trip if the teens are keen. Cost: ~$25/adult, free for kids under 13.
  
  
• Kahalu‘u Beach Park (Big Island, day trip): Gentle waves and vibrant marine life make this ideal for beginners. It’s a bit far, but a flight to Kona is quick if you want variety. Rentals for snorkel gear are ~$15/day.
  
  
• Molokini Crater (Maui): A boat tour to this offshore crater offers crystal-clear snorkeling with fish and turtles. Choose a family-friendly operator like PacWhale Eco-Adventures (eco-focused, educational for kids). Tours start at ~$80/adult, $40/kids, with morning trips best for calm waters and whale-watching in February.
  
  
• Tip: For the 3-year-old, bring a life vest and stick to shallow areas. Older kids can use boogie boards with fins for easier snorkeling. Rent gear locally to avoid packing it.

Boogie Boarding

• Kā‘anapali Beach (Maui): Wide, sandy beach with moderate waves perfect for boogie boarding (great for the 14-year-old). Rentals are ~$10/day at beach huts. Lifeguards ensure safety for all ages.
  
  
• Poipu Beach (Kauai, day trip): If you visit Kauai, this south shore beach has gentle waves for the younger kids and enough surf for teens to boogie board. It’s less crowded than Waikiki. Rentals available on-site.
  
  
• Tip: Check beach conditions in February, as winter waves can be stronger. Stick to lifeguarded beaches and avoid rocky areas.

Easy Hikes

• ‘Iao Valley State Park (Maui): A 0.6-mile paved trail to the ‘Iao Needle, a lush, historic valley with stunning views. Easy for all ages, though the 3-year-old may need carrying on uneven steps. The teens will love the scenery for photos. Free entry for kids, ~$5/adult. Avoid after heavy rain due to slippery paths.
  
  
• Maui Coastal Trails (Kapalua Coastal Trail): A 1.7-mile trail along cliffs and beaches, flat and stroller-friendly for the 3-year-old. The 14-year-old can explore tide pools or snap Instagram-worthy shots. Free, with parking at Kapalua Bay.
  
  
• Pipiwai Trail (Maui, Road to Hana): A 4-mile round-trip trail (moderate, but manageable for the 7-14-year-olds) with bamboo forests, waterfalls, and banyan trees. Start early to avoid crowds. The 3-year-old may need a carrier. Entry to Haleakalā National Park: ~$30/vehicle.
  
  
• Tip: Bring water, snacks, and sturdy shoes. Avoid strenuous hikes like Koko Crater (too tough for young kids).

Other Must-Do Activities

• Whale-Watching (Maui): February is peak humpback whale season. Book a 2-hour eco-tour with Pacific Whale Foundation from Lahaina (~$50/adult, $25/kids). Kids will be thrilled seeing whales breach, and the educational aspect keeps it authentic, not touristy.
  
  
• Cultural Experiences: Visit the Maui Ocean Center (aquarium with Hawaiian marine life, ~$40/adult, $30/kids) for an indoor day if it rains. Free hula lessons at Lahaina Cannery Mall are fun for the 7-14-year-olds.
  
  
• Road to Hana (Maui): A scenic drive with stops at waterfalls (e.g., Twin Falls, easy 1-mile hike) and black sand beaches (Wai‘ānapanapa State Park). Pack snacks and do a half-day loop to avoid tiring the kids. The 14-year-old will love the dramatic views.
  
  
• Stargazing: Maui’s clear skies are great for stargazing. Book a family-friendly tour like Stars Above Hawaii at a resort (~$50/person) or simply stargaze from your rental’s lanai with a star map app.

What to Stay Away From?To avoid tourist traps and keep the trip memorable for the right reasons:

• Overcrowded Luaus: Skip large, commercialized luaus like those in Waikiki, which can feel inauthentic and overpriced ($100+/person). If you want a luau, choose a smaller, local one like Old Lahaina Luau (Maui, ~$150/adult, $90/kids) for cultural performances and kid-friendly food.
  
  
  
• Waikiki (Oahu): Too busy, urban, and touristy, with crowded beaches and high prices. Your kids won’t get the serene Hawaiian experience you’re aiming for.
  
  
• Unregulated Snorkel Tours: Avoid random operators at touristy docks; stick to reputable ones like PacWhale to ensure safety for kids.
  
  
• Strenuous Hikes: Skip hikes like Koko Crater or Diamond Head Summit (Oahu) with a 3-year-old and grandparents, as they’re too tough and crowded.
  
  
  
• Non-Lifeguarded Beaches: For snorkeling and boogie boarding, always choose beaches with lifeguards (e.g., Kā‘anapali, Wailea) to keep the kids safe, as winter waves can be unpredictable.
  
  
• Over-Scheduling: Don’t pack the days; kids (especially the 3-year-old) need downtime. Plan one major activity per day with beach or pool time to relax.

Sample 7-Day ItineraryHere’s a simple, flexible plan for a week on Maui, balancing adventure and relaxation:

• Day 1: Arrive, settle into Kihei condo, visit Kalepolepo Beach Park for a calm swim and turtle spotting. Cook dinner.
• Day 2: Morning snorkel tour to Molokini Crater (PacWhale). Afternoon at Kā‘anapali Beach for boogie boarding.
• Day 3: Road to Hana (half-day): stop at Twin Falls (easy hike) and Wai‘ānapanapa State Park. Picnic lunch.
• Day 4: Resort day (book 1 night at Grand Wailea or Hyatt Regency Maui for pools/slides). Evening hula lesson at Lahaina Cannery Mall.
• Day 5: Morning at ‘Iao Valley State Park (easy hike). Afternoon at Maui Ocean Center. Stargaze at night.
• Day 6: Whale-watching tour (morning). Relax at Wailea Beach (snorkeling, boogie boarding). Cook a family dinner.
• Day 7: Morning Kapalua Coastal Trail hike. Beach time at Poipu (if you day-trip to Kauai) or local beach. Depart.

Practical Tips

• Rental Car: Book a minivan or SUV early for six people (~$500-$800/week). Turo can be cheaper than major agencies, but airport drop-off is easier with rentals.
  
  
• Packing: Pack light (condo has laundry). Bring reef-safe sunscreen, water shoes, and reusable water bottles. Include swim diapers for the 3-year-old.
  
  
• Budget: Condo ($250/night x 7 = $1,750), activities ($1,000 for tours, rentals), groceries ($500), car ($600) = ~$3,850, leaving room for dining or a resort night. Shop at Costco in Kahului for bulk snacks.
  
  
• Booking: Reserve accommodations and tours 6-9 months out (May-August 2025) for February 2026, as Maui fills up fast.
  
  
• Safety: Always check ocean conditions (Hawaii Beach Safety website) and stick to lifeguarded beaches. Use life vests for the 3- and 7-year-olds.

Why This Plan WorksThis Maui-focused trip balances adventure (snorkeling, whale-watching, hikes) with kid-friendly beaches and downtime, ensuring the 14- and 12-year-olds have memorable moments (Molokini, Road to Hana) while keeping activities safe and easy for the 3- and 7-year-olds. The condo saves money and stress with cooking and space, while a resort splurge adds pool fun. Avoiding crowded spots like Waikiki and commercial luaus keeps it authentic, aligning with your goal of a meaningful family trip.If you want specific AirBnB listings, resort deals, or more details on any activity, let me know, and I can dig deeper or check current options. Enjoy your planning-free aloha adventure!

The time frame for the activities in different sides of the island are wack. Just saying. As a former Maui resident. This is not a realistic itinerary.

 

[svivian]

Big island would be my vote

Also try out some under water archery hunting while you are at it

 

[cuerro viejo]

Only on way to do Hawaii and that’s Go to lanai and stay @ 4 seasons.

Enjoy. It’s first class with essentially the only private beach. It’s money well spent

 

[Mojave]

Thanks for the input. Will it search ammo or gun stuff? CGPT and Gemini seems to be seriously woke.

Never used Gemini.

Grok will tell you how to find something firearms related, it does not default to anti-firearms. But I have had ok luck with Chat GPT a work.

Grok must be 10 or 20 times more intelligent than Chat GPT. I asked Grok a question about bolt face thrust and it nailed the answer. Chat GPT gave me an excuse, and flopped around never quite getting there. This was a couple of months ago.

 

[bojangles808]

Maui is the easy button and probably you best chance of a really good vacation. They'll be whales jumping offshore all of february and the weather is best there Kihei/kaanapali. Where you stay depends on your budget ,resort or condo and if you are beach ppl/pool ppl. For resort Wailea fairmont kea lani is great for families bc it has big rooms, water slides and a great beach for boogie boarding, Mariott wailea beach resort and grand wailea also popular. Kaanapali beach also a great option with Hyatt, Westin and Sheraton all solid. Sheraton has best beach location in front of black rock (good snorkeling/cliff jumping) but Hyatt/Westin pools are better. Some resorts might have kids eat free which would help but you'd have to check. The beach is very long and whalers village restaurants are within walking distance. The F and B costs add up quick if you are only going to be on the resort property though.

South Kihei for condos would be you best value in February if you had a tighter budget. NW Maui napili/kahana condos are also an option but the weather isn't as good and surf gets rly big in winter that side. Get something within walking distance S. Kihei between keawakapu beach and kamaole sands 1. Anything with a pool in that location is great. You could buy groceries Costco/Walmart/target and eat in or there's food trucks/restaurants within walking distance as well. That would be the best bang for your buck. Some of those beaches have lifeguard stands so I think they are more restrictive on alcohol but any beach without a lifeguard stand (wailea, kaanapali) you can drink on the beach with a cooler without any issue. Iao valley , twin falls, haleakala are all day trip stops you could do. road to Hana is an all day thing if you were really feeling adventurous.

Other candidate I think of would be resort stay big island Hapuna beach or Mauna kea Beach that area. Those beaches are as nice as anywhere in Hawaii. But big island everything is more spread out and your limited on resorts/condos by these beaches. They don't have the cluster of restaurants/condos like south Kihei. but a day trip to volcanoes national park would be memorable. I think overall though it's a little cheaper than Maui or Kauai too. Grand Hyatt Kauai also another option thats really nice but the beach is not great for swimming and Kauai wintertime the weather can be more rainy. Oahu is like a LA on an island I would avoid.

 

[rookieforever33]

It just hit me. This is spot burning. We all tell people where we like to go, implying value. Others go there increasing demand. Prices go up, availability go down. Im pretty sure residents there have a certain level of disdain when non residents encroach on their areas too.

 

[Mojave]

It just hit me. This is spot burning. We all tell people where we like to go, implying value. Others go there increasing demand. Prices go up, availability go down. Im pretty sure residents there have a certain level of disdain when non residents encroach on their areas too.

Hawaii is the king of tourist hatred.

Some Asian that has been in Hawaii for 5 years, acting like she is a Native Hawaiian complaining about tourist is par for the course.

Friday nights in Waikiki are pretty wild.
Bingo Cards include:
1. Drunk active duty military doing push ups in the bar (I was one of these 30 years ago).
2. Drunk active duty telling all the girls they are a SEAL or a fighter pilot. I wasn't cool and never claimed to be, so this wasn't me.
3. Police Officers ignoring drunk tourist fighting
4. Police Officers ignoring hookers wearing see through clothing (with nothing underneath it) chatting up tourist (this was before dark)
5. Japanese 20 year olds completely wrecked on booze

 

[thinhorn_AK]

It just hit me. This is spot burning. We all tell people where we like to go, implying value. Others go there increasing demand. Prices go up, availability go down. Im pretty sure residents there have a certain level of disdain when non residents encroach on their areas too.

Hawaiins complain about EVERYTHING. I wouldn’t worry about them too much. I don’t look at til tok too much but last time I was Hawai’i I was looking at it while waiting for a flight, nearly every video was some Hawaiin person complaining about everybody else except themselves.

-don’t come to Hawaii unless a native invites you
-don’t overstay your welcome
-don’t spend money at resorts
-don’t rent jeeps
-don’t home koko head when locals are trying to use it
-don’t stand up in the plane aisle
-don’t say this
-don’t say that

Etc etc etc. they are just looking for things to complain about when in reality they likely don’t even have a job. No point in trying to appease them, just go, have a great vacation and remember: you are welcome in Hawaii, afterall it’s a US state.