This June will be my 20th wedding anniversary. My wife has talked about wanting to go to Hawaii for years but there has always been something that gets in the way. Looking to book something in early June for the family (me, wife + 15yo & 10yo). Ive already figured out airfare (I have SWA points that will cover it) but need to figure out which island and where to stay.

1) with SWA I have destination options of Oahu, Maui, Kauai, Kona & Hilo. Oahu & Maui are the best prices & flight times.
(A) what is the difference in locations?
(B) how much have the fires screwed up tourism on Maui?

2) may be location specific but what are the better options for lodging..... VRBO/AirBnB, Hotel, Resort, something else?

I'm sure I will have more questions but lets start with that. Thanks.

With your kids that age, I would recommend at least taking a look at Aulani, the Disney resort on Oahu.

It's not TOO Disney ... the theming is subtle but it definitely has activities and amenities geared to young people.

It's away from the hustle and traffic of Honolulu but not too far; basically situated midway between Honolulu and the North Shore. So you can take a day or two and hit both.

We went in January with no kids and really enjoyed it. There are some high-end restaurants at the resort and within walking distance to satisfy adults, and casual places for kids. Some of the rooms/suites have a kitchen, too, so you can save some money.

Disney's Aulani Resort

What do yall like to do and how long are you there?

If you're a destin sit by the beach and eat, you can't really go wrong with any of the resorts, mauis the most touristy in that fashion, but haven't been since the fire and that might effect a few of the touristy areas.

Kauais probably the prettiest, but also the smallest so if you're there long enough, it's worth island hopping to to see the napali coast, it's amazing.

North shore and resorts are nice at Oahu, Pearl Harbor stuff is a good experience if you're into history stuff.

Big island is our favorite, love the Westin. You can do the mountain, volcanoes national park, swim with manta rays. I think it gives you the best locals vibe of that's your thing.

Airbnb vs resort just depends on how you like to spend your time/effort you want to put into things. We've enjoy both pending on the trip.

As of right now, we are looking at 6/4 - 6/11 or 6/12. Soooo.... about a week.

I am perfectly content chilling on the beach with a few planned activities
Wife likes to have something planned everyday and will over plan each day if we let her.
My daughter (15) is more like me with a slight interest in a few more activities
My son (10) likes to be doing something all the time but is content to spend all his time at the beach or in a pool if we let him.

Most vacations we tend to VRBO/AirBnB so that we have a kitchen and multiple bedrooms. Though, last several we haven't used the kitchen much other than storing drinks and leftovers.

Since you have kids, I agree with the Aulani suggestion. I have extended family on Oahu and they go there a couple of times a year as a quick 3-4 day get away.

Since you mentioned Airbnb, I would also look at an Airbnb in Kailua within walking distance of Kailua Beach. That's what we did on our last trip. The beach is fantastic and you can sign-up for water activities nearby or just chill. It's a cool little town as well. We had no problem traversing the island to Diamond Head, Waikiki, North Shore, etc. so you can easily do those activities and still log plenty of beach time.

I wouldn't recommend staying in Waikiki if you want more of a getaway feel. Waikiki is fine and you should definitely check it out because it's so iconic but there's much more hustle and bustle since it's downtown.

We went on a family vacation two years ago. We tend to do pretty nice vacations and our two kids (13 and 15) say Hawaii is their favorite.

We went 10 days. We did 5 at grand Hyatt Kauai then 4 days at Westin on big island and 1 night on Oahu

Had a hard time deciding if we like Kauai or Hawaii (big island) better. Both awesome. Amazing how different they are.

Kauai is the oldest geologically and therefore the greenest. Hawaii is the youngest and very different, lots of exposed rock, etc…

We did one night in Oahu on Waikiki. Really only went because we wanted to do Pearl Harbor. If I could change one thing I would have done Waikiki first. The other 9 days were so calm, peaceful and relaxing. Waikiki is so not that. I'd have rather done it first then escaped into tranquility .

In general, we moved too many times. I don't regret doing it that way because I don't know if we'll make it back there and I really am glad we saw PH. Aside from that, one island hop or none would be my preference

Considering how much everyone loves the trip we may go back. If so, was thinking only doing Maui

There's a lot of good info on YouTube. Seems like Maui is fine right now and the locals need some visitors so they'd appreciate it

A quick breakdown:

Kauai we kayaked up the only river in the state one day. Went to Waimea canyon (which is awesome and could be a national park). Catamaran the Nepali coast. Beach and pool at grand Hyatt were awesome.

Hawaii we went to volcano natl park. Did a zip line (not great but ok), played some golf and enjoyed the Westin . We also did a dolphin thing on Hawaii, snorkeled a coral reef and swam with the rays


We probably over booked things. Again, I was thinking we would only be there once (which may be true, at least before kids graduate)

My summary: a trip to Hawaii is going to be amazing. Any island will be awesome. You probably can't really muck it up unless maybe you stay in Honolulu which I think most would agree, would be a huge mistake

Family did Kauai only this past June. Loved every minute of it. Did hiking, Napoli coast tour, horseback riding and a Luau. When we go back will skip the Luau. The best thing we did and would recommend was a helicopter tour. Saw the whole island from a different angle. Stayed at the Sheraton resort in poipu. I can recommend and would stay again, as it was cheaper than Grand Hyatt.

Frankly, if I wasn't going to do a bunch of outdoor activities like hiking and snorkeling, I'm not sure I would recommend Hawaii. I loved Hawaii, personally, but we did something outdoorsy/adventury every day.

The time change messes you up and it's not easy to get to. If you just want to chill at a beach and stay on a resort there are a lot of options in the Caribbean and Mexico that would be cheaper and less of a pain for travel and time change.

E said:

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If y'all are adventurous check out Kauai. It's the greenest of the islands and has a ton of activities.

The Grand Hyatt is a great resort for families.

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Kauai is by far my favorite. It's beautiful!

The Big Island (fly into Kona) is my favorite island and I've been to all of them. Kaui is my 2nd favorite.

The Big Island is great because you can do a lot of sightseeing activities or just sit on the beach. You could take a volcano tour, spend several days snorkeling at different spots around the island from the shore or take a snorkeling boat trip, tour the coffee plantations, go swimming at the black sand beach, hiking, etc.

I think the Mauna Lani/Fairmont Orchid have the best hotel beach area. The resorts are beside each other.

If you are a high roller, the Four Seasons Resort there is a really good one.

Mauna Kea Resort area has a good beach and there are also condos if you don't want to stay at the Mauna Kea Resort Hotel.

There is a resort up on Hapuna Beach, but the water there can get dangerous for kids sometimes. It depends on the ages of your kids. We've never stayed there.

When we have the kids with us we often stay in a condo as it's just easier having a kitchen and laundry available with them around. When we do this we usually stay in the Waikoloa Resort area. There are nice shopping areas, restaurants, good golf courses, etc. here. There are 2 hotels there and a ton of different condo communities to choose from. The beach at A Bay isn't a favorite, but we usually do day trips to different beaches when we stay in this area. We have different areas of the island that we like to snorkel at from the beach. So, the lackluster beach in this area isn't a deal breaker for us.

The Mauna Kea Resort area has a better beach and condos or hotel.

If you want a resort hotel with a nice beach right by your hotel then choose the Mauna Lani or Fairmont Orchid.

I only been to Hilo and loved the island. Are you going to orginize trip by yourself or do you prefer to use travel agency services? Recently i checked some TravelUP reviews and it seems that those guys really know their business. But of course, there are a lot of people who are planning trips by themselves and it works just fine.

Still considering some alternatives (Caribbean, Costa Rica, Mexico) but purely looking at Hawaii (since that is what I asked about) in early June, Maui is currently the best flight option. Via SW it is roughly 10-15k pts cheaper per ticket round trip (x4 people). So if we end up booking this trip I am inclined to atleast fly into Maui. So some questions based on that.....

1. What are the best areas to stay?
2. What are the must see/do/eat attractions on Maui?
3. What are the options for island hopping if we were to decide to visit another during our stay?
4. Can you feasibly island hop for a day trip or should that be a relocation?
5. Outside of Pearl Harbor, what are the top see/do/eat attractions worth taking the time for a side trip?

The best resource I've found on Hawaii. Their YouTube videos are great.

https://thehawaiivacationguide.com/