Hawaii Family Vacations Help Please

Updated on March 25, 2013
M.S. asks from Aurora, IL
11 answers

Hi Mamas,

I am looking to book a vacation for my 2 girls, husband and me. Looking to travel to Hawaii in mid November. I don't know which island to chose from since there are many. I need some help on booking this trip. If you have ever been to Hawaii on vacation, what do you recommend? What is a good price to pay? I noticed that I would be paying like $1000+ for my 3 yr old too, which does not make much sense. I would prefer to book hotel and airfair together. All inclusive resort would be nice but not necessary. Any help and ideas is highly appreciated. Thanks in advance!

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answers from Houston on

We just went to Maui about a month ago. Hawaii is very expensive. The flight there is miserable (long time on a plane). Time changes involved, the adjustment period will be tough on the 3yr old. A lot of factors to consider, how long are you staying? is money/budget an issue?
We didn't really see Hawaii as a 'kid' destination, IMO.

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answers from San Francisco on

We have vacationed on Oahu, the Big Island, and Kauai. I wouldn't recommend Oahu (super crowded) or the Big Island (volcanic wasteland - truly hideous). Kauai is beyond beautiful, relaxed, very family-friendly. We actually have a condo there, in Poipu (which is on the southern, sunny side of the island). Kauai has Hawaii's only navigable river, so you can kayak up the river and hike to the most beautiful waterfall imaginable. (Or if kayaking isn't your style, there's also a lovely river cruise.) We always take a catamaran trip around the Napali coast - which you can't get to in a car, so it's perfect and unspoiled. We try to go on a catamaran where they stop and let you snorkel. Last time out, we saw a huge pod of spinner dolphins - spectacular. If you're there in November, you can see the whales, which are migrating at that time. Kauai has many family-friendly beaches that are very easy to get to. We just love it there.

What I would recommend is that you actually try and rent a condo. The reason I suggest this is that all-inclusive places can get VERY expensive - you're paying $20+ per person for BREAKFAST! Even for your 3 year old! If you stay at a condo, you can simply head to Costco on your first day there, stock up on breakfast/lunch foods, and save yourself thousands of dollars. Plus, then you can pack a picnic lunch for your outings. Also, then you're not all crammed into a hotel room. We find that staying in a condo is just a lot more relaxed of an experience.

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answers from San Francisco on

We are taking our kids for their first ever trip to Hawaii this summer. We are spending 2 weeks on Oahu in a beach house. We are staying in Kailua...far away from hotels. My husband travels to Hawaii all the time on business so we have racked up quite a few trips alone together. This will be our first adventure to paradise with our 13,10 and 6 year old.

I know this is not what you are asking..but consider staying stateside and saving the money and also such a long flight with young children. There are all inclusive resorts in Florida you could go to and get the same tropical,beach feel.

Just an idea.

I feel so sorry for all the parents with babies and young children I see on my flights to and from Hawaii. Parents look miserable....kids look miserable.(people sitting next to them look miserable) Then everyone has to deal with the time difference once you arrive. Screws up sleep habits.

We personally have waited to take our kids til the youngest was out of diapers...no need for naps...and they can play on their own and we don't have to watch them like a hawk. Hawaii is an expensive trip to be stressed out,frazzled and exhausted.

As for Hawaii. Disney Resort on Oahu is amazing...would be super d duper fun for your kids. Expensive..but geared for young children...constant entertainment. Use a travel agent to book your airfare and resort. They can get better deals...and give you pointers.

Have fun!!!

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answers from Los Angeles on

Sounds like fun, can I join you? :)

Our favorite island is Kauai because it is quintessential Hawaii. Green, gorgeous and laid back w/ some tropical rain thrown in here and there. We like the Northern end, near Princeville/Hanalei because it is much more lush than the southern end (Poipu) and the beaches are absolutely gorgeous.

If I were you, I'd get on some alert emails for heads up on when flight costs go down. I've been seeing ticket alerts lately for anywhere from $400-$450 a ticket (that's from LAX to Lihue (Kaui) or LAX to Oahu.

At any rate, we've never stayed at a hotel in Hawaii ... wait, scratch that, we did stay at the enormous Hilton monstrosity on the Big Island once. Not quite our cup of tea taking a tram to various areas of the property. Anyway, I highly recommend renting a house while in Hawaii. We found an awesome one through VRBO the last time we went. I booked far ahead and the owner of the house knocked off $50 a night, which brought our nightly total to $150 for a 3 bedroom house with views of the ocean and a community swimming pool steps from our house. The house was fully-loaded with anything you may need for the beach and the kitchen was stocked, too, so you can cook your meals and save a lot of money that way.

I personally don't have much interest in visiting Oahu since it's so city-like. I imagine the bar/restaurant scene would have been fun in my 20s, but I'm way past that.

Oh and Hawaii has tons of kids stuff to do if you're into the outdoors!

1 mom found this helpful


answers from Santa Barbara on

I never use a travel agent but did use one in September for a last minute trip to Oahu (six days ahead). I booked my flight because I had United miles to use...I love first class. I have a friend that is a travel writer and she has written about Hawaii-Aloha.com. They were great (you can book online or speak to an agent). Long flights are not bad, your destination is Hawaii! Who cares about the time change, you're on vacation! Everything is really expensive, just allow for that and have fun!

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answers from Honolulu on

Use a Travel Agent.
They know of travel packages/hotels/flights/airfare etc.
And www.seatguru.com allows you to PICK what seats you want in an airplane. We used this, and the Travel Agents and Airlines use this too.

Each island is different. Yes, it takes research.
It really depends on what you want to do or see. Each Island has different sights to see etc. And each island has different environments/ambience etc.

Oahu is the main island. It is a city. Not some country like back in the old days type environments. It is very populated. The other islands are more "country" like. Not as fast paced etc.
But each island, is, unique.
There is no way I can tell you which Island to go to.
It is a personal preference.

And yes, Hawaii is expensive.

And you'd also need to rent a car once you get here.

If on Oahu, the Hilton Hawaiian Village hotel, is very nice/family friendly and they have everything. Just as an example. But I have no idea what their rates are.

Again, I would recommend you use a Travel Agent.
They often have special prices.
But, it is also seasonal too.
Rates are never static.

1 mom found this helpful


answers from Eugene on

I love Kona on the dry side of the Big Island. Get a car, you can drive and see plenty. Nice weather. There is lots to do there, snorkeling, shopping, kayaking, submarine, see the volcano. We rented a vacation house up in the hills where it was 10 degrees cooler and we had a view of the ocean. If you want an all inclusive resort, there are a couple in the area. People have recommended using Costco Travel. Airport close by, too.

My siblings rave about Maui and Kauai but it's been years since I've been so I can't recommend myself. But I'd avoid Waikiki/Honolulu like the plague. It's crowded like being in Los Angeles with more humidity.


answers from Dover on

I've never been but would love to go to Hawaii. If I were you, I would see which island would provide the best chance of bumping into Alex O'Loughlin in person...that would make the whole trip worth whatever the cost!

Have fun and enjoy.



answers from Pittsburgh on

Don't let people discourage you if you want to go! I travelled on a family vacation to Hawaii from the east coast when my son was 2, and we are doing it again this fall with my kids now age 3 and 6. My then-2 year old did fine on the flight, and I'm sure my kids will do fine this time too. It is long, you just need to be prepared with electronic games and lots of snacks.

If you haven't been to Hawaii before, I suggest you stay on Oahu. There is the most to do on Oahu - the Polynesian Cultural Center and the Arizona Memorial. Plus rent a car one day and drive the entire way around the island, stopping at the Dole Pineapple plantation.

The flights are also best in and out of Oahu, they are pretty limited to the other islands.

Don't get me wrong - I love the other islands - Maui is very restful, with mostly beaches and not a lot of other things to do. Kau'i is pretty undeveloped and very pretty. But if you've never been to Hawaii before, Oahu is the place to start, IMO.

Airfare is expensive right now. We didn't find a way around that. We are staying at a Marriott resort outside of the main city on Oahu this time, because we'd rather have a small suite for the price of a single room on Waikiki beach. More space for us to spread out with the kids. But it does mean that we'll need a rental car for the week, whereas if you stayed in Waikiki, you probably wouldn't need a car except for the one day if you do the island drive. So that's a trade-off you'll want to think about.

This is where we are staying, and I can't WAIT! http://www.marriott.com/hotels/travel/hnlko-marriotts-ko-...



answers from New York on

Check out the weather. I think November to January is the rainy season. I have to agree with Diane. Oahu to start. Plenty to do there. You might want to consider flying to one or two of the islands too. Have been there twice. Second time for six weeks!


answers from San Francisco on

First of all, Hawaii IS expensive, but it is oh so beautiful and awesome with kids of all ages!
Maui seems to be the most "popular" island, and it is awesome. It's a little more built up so there are more restaurants, shopping areas, etc. We stayed at a little condo on Napili Point (just north of Kaanapali) which was very child friendly. We also honeymooned there at the Kaanapali Westin, HEAVENLY!
Went to the big island once and stayed at a place called Kona Village, but sadly it was ruined and never rebuilt after the last tsunami :-(
My favorite is Kauai. Very relaxed, rural, "old Hawaii" feeling. Not heavily built up but still enough restaurants and big resorts to be entertaining. We stayed at Poipu Beach, again, in a condo. Lots of kids in the area.
Last year we went to Oahu and stayed at the Royal Hawaiin, right on Waikiki Beach. SO fun, classic hotel built in the 1920's (one of the originals.) Very different though, because it's a big city and very crowded and urban. But it was a fun scene, and my teenagers really enjoyed it. We also went to Pearl Harbor which was really cool.

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