I've been twice to Hawaii - to Oahu, Maui, and Kauai. Kauai was my favourite but on that trip we were a honeymoon couple seeking seclusion and more privacy so its a bit of a different holiday. Great for natural surroundings but not as many hotels so you may be outside the medium-to-budget range and a lot of the beaches aren't quite as swim/snorkel friendly as on other islands. On Oahu we stayed on the Waikiki stretch and its quite bustling but the calm waters were great for swimming. You'd have quite a few dining and accommodation options for your family there and we took a day trip to hanauma bay which was amazing snorkeling and would highly recommend for your teens. you could also quite easily access pearl harbour to satisfy the historical interest, along with perhaps hiking at Diamond Head volcano which offered stunning views. If you only have about 5 days to travel, getting up to the north shore might feel a bit inconvenient unless you plan on staying there the whole time. If headed to Maui, I would imagine Kaanapali area will be best suited for a family with varied interests - Wailea is a bit more pricey, but Kaanapali has similarly reliable weather, calm waters, snorkeling just off shore near the black rock (or a half day boat to Molokini), some surfing and boating, and will have a range of chain hotels just like Waikiki so they often offer good deals (not to mention can use or collect some points). The challenge in Waikiki vs Kaanapali is the total relaxation factor - while both have high-rise hotels, Waikiki is much more dense with a busy shopping road behind the beach and Kaanapali has slightly larger resorts and is a bit less developed (but definitely still developed). Good luck in your search and have fun! I love Hawaii and its one of the only places I've been to that has something for everyone on a tropical vacation!

1. Where are you traveling from?
2. Count the number of nights you have to buy accomodation. If you have 5 or less, I'd rethink this, considering you have 3 teens to take along.
3. Take a look at flight costs before you get too far along in this planning. No great bargains going around this year.
4. You'll need a car on any island other than Oahu.
5. You should look for condo accomodations. Most hotels will not allow 5 people to stay in one room so you'd actually need two hotel rooms. Ouch.
6. A condo allows you to feed the brood breakfasts, lunches, and snacks without breaking the bank at hotel restaurants.

Maui is a great place to visit. At this late date, I hope you can find flights and accomodations that will fit in your budget. Look to condos in Kihei if Kaanapali or north is too expensive.

My vote is for Maui, the Kaanapali area or Napili. Napili being a bit less crowded but Kaanapali has nicer beaches. Kihei will be cheaper, but not as nice IMO.

Do you have cheap airfare? Will your flight be 'endless' or are you on the west coast of North America?

What's the budget for a condo (or two hotel rooms)?

Teens will probably like Waikiki on Oahu or Kaanapali on Maui. You need a rental car everywhere outside of Honolulu.

For a first visit, I'd suggest Oahu. Lots of variety, pretty well everything that you were looking for, and you can do it a bit cheaper than Maui, for most things, plus there are more flight options, usually. 5 days isn't really long enough for me (Eastern Time Zone), but you have work with what you have.
You can do Maui NEXT time!

Waikiki is vibrant and fun but also "wall to wall". I read once that the Cheesecake Factory in Waikiki is the highest-grossing one in the chain.

There's a newer development west of Pearl Harbor called Ko Olina - it's where the new Disney resort is, also a JW Marriott and a Marriott timeshare resort. It's pretty and fairly quiet. I don't personally like the location (the drive is not attractive). Other than that , there's Turtle Bay Resort on the laid back north shore, and rentals on the Kailua coast (gorgeous beaches).

Except for also having a strip of hotels, Kaanapali Beach on Maui is nothing at all like Waikiki. South of Black Rock (excellent snorkeling right off the beach) there are I think 4 hotels and 3 condo developments, as well as the Whaler's Village shopping center in the middle. North of Black Rock has some more hotels and condos , then even lower key Napili has others (less upscale) and then there's Kapalua (upscale condos and Ritz-Carlton). Kaanapali
is about 3 miles from the touristy but fun town of Lahaina.

I have't been to south Maui in years so can't comment on that.

Kauai is lush and beautiful with great beaches etc. it's less developed in general. Unless the kids are really into outdoor pursuits, Kauai wouldn't be my choice with teens. I'd pick Kaanapali Beach.

Your kids will love Waikiki. Last year we stayed at a suite hotel three blocks from the beach that was quite nice: Aston Waikiki Sunset, 229 Paoakalani Avenue, Waikiki, Oahu 96815, Phone: 808-922-0511. The rooms have kitchenettes, pull-out couches, and either one or two bedrooms. We had a family group-- my husband and me, my brother and sister, my daughter and son-in-law, 17-year-old grandson, and his best friend. The boys had a great time walking up and down Kalakaua Avenue on their own (with a curfew and their cell phones).

The International Market Place has oodles of shopping kiosks and a food court the teens will like. The hike up Diamond Head is fun, and we always rent a car for a day and drive around the island stopping at different places for the views, at the Macadamia Nut Farm for purchases (and free samples), and at the little town of Haliewa to eat and to buy shave ice with ice cream in the bottom at the General Store.

For some history, go to see the Arizona Memorial at Pearl Harbor and drive up to Punchbowl Cemetery as well as to the Pali Overlook where King Kamehameha defeated his enemies by driving them over the cliffs to become the first king of the entire island chain. You can also see the Bishop Museum for more history and island lore, and the kids will like a luau.

Maybe you can tell, I love Hawaii and particularly Oahu.

Either would work for what you describe.

I think Oahu is generally less expensive and there are so many wonderful places you could stay in Waikiki. It also has the 'history' in Honolulu places like Pearl Harbor, Bishop Museum, Iolani Palace, etc. You could get a car but also it's possible to do Oahu using public transportation (and walking) onyl.

Maui is beautiful too and would make a great family vacation. You definitely need a rental car there.

I think teens would especially love Waikiki. Yes driving is easy around Oahu, maybe some traffic right in Honolulu on the freeway but no big deal. Oahu takes no advance planning imo, there's tons of information once you arrive. Just pick up free copies of Oahu Gold and 101 Things to Do (free in sidewalk dispensers) that will have maps and describe all the various activities.

Re-reading your original post and I'm thinking Waikiki might be right for you, as long as you have a car and can get out of Waikiki, too! A day visiting the North Shore, visits to Kailua/Lanikai beaches (maybe kayaking, which was a ton of fun), Hanauma Bay, Diamond Head, drive across the spectacular highway that cuts across the center of the island (really amazing scenery), Pearl Harbor, Waikiki beach itself. Waikiki is very busy, both on and off the beach, but it's a relaxed beachy kind of busy -- you don't have to get dressed to leave the beach, everyone's wearing beach or "tropical" clothes. Lots of hotel and condo choices, lots of restaurant choices, bars and restaurants on the beach, etc. etc.

We love Maui...especially Wailea- great relaxing vacation- great golf- shopping- restaurants....a bit commercial but so is Oahu.

We love Maui...especially Wailea- great relaxing vacation- great golf- shopping- restaurants....a bit commercial but so is Oahu. If these things don't appeal to you & your looking for less expensive/fancy- maybe Kihei which is near Wailea

Thanks everyone! We got our tickets to Oahu and will be staying for 7 nights. Now we're looking for somewhere to stay. Any suggestions for a family of 5?

I don't but I'd highly recommend staying I. A condo rather than a hotel - first, you can have some meals in, even if only breakfast and snacks, and second, you'll have a living room to gather, rather than hanging out in someone's bedroom.

If you don't require a beachfront location, Carolyn (above) suggested a place.

Wakiki is probably best all around for your family, and for a family - a 2 BR condo offers so much - and you can have a fridge for your food/beverages/snacks/left overs, and also keep things for your drives (buy a Styrofoam cooler and put ice in it and instant fridge for drives - and if it's squeaks - put some towels around it.

Check out the condos in/by the Iolani - on the south end of Waikiki beach. There are others there as well. see http://www.highrises.com/honolulu/iolani-court-plaza-condos/

And definitely go snorkeling at Hanauma Bay ( http://www1.honolulu.gov/parks/facility/hanaumabay/information.htm 20 minutes or so from Waikiki) - maybe more than once. Check out renting snorkel gear for the week from the likes of Snorkel Bob's (also adds in the various travel mags you will find at the airport).

Go early to beat the crowds, get a good parking space, and don't leave any thing valuable in the rental cars. Certainly not in plain sight.

From there - continue on the drive around the south side of the Island - to Kailua - and either come back to Waikiki through the Koolau's (tunnels through the mountains) or continue on up to the north shore - Turtle Bay - past the fabled surfing beaches (Sunset, Pipeline, Waimea) which will be flat in the summer, and have the obligatory shave ice in Haliewa, or do the north shore drive another day. Doesn't take that long really.

<<<Doesn't take that long really>>>

In fact, we went kayaking in Kailua one morning, and drove up to the north shore (Haleiwa) for lunch. Back to Waikiki in time for dinner.

I would like to second the very good suggestions to at least a car for one day and drive around the island,, you can stop at various places and be back for dinner if you choose. Can't get too lost,, its an island, lol We stopped once just at some random North Shore beach and saw a sea turtle on the beach( they had a person "guarding " him so no one could bug him, but there was just our family and about 4-5 other people there!
Parking in Waikiki is a rip off, most hotels charge, and often more then 20-25 dollars a day,, so as you don't really need a car for most of Oauha I would suggest just a one or two day rental.

Definately check out Hanauma Bay, great safe snorkling, but get there early!

Thanks! We finally got a place at Waikiki for the first 3 nights then we're off to a beach in the north ko olina.. Marriott.. I think that's it (hubby doing planning). Anyway, I'm a huge LOST fan. When we rent a car I imagine we should use it to check out their spots? Anyone have any info on this? Also, what's diamond head?

Just to clarify - Ko Olina is not north - it's southwest.

Diamond Head is an extinct volcano just to the southeast of Waikiki. You can walk up to the top (about a 45-minute hike, of which the last part is 99 steps up) for a great view.

Ko Olina is half an hour west of Honolulu. The very Disney Aulani is there. Can you get north shore instead? Turtle Bay or Haleiwa

Turtle Bay is a resort, Haleiwa is a town -- I don't think there are any hotels on the North Shore other than Turtle Bay.

Definitely try to get to the North Shore for a few days if you can - but out west - at the Marriot's Ko-Olima (sp?) is probably fine for some beach time.

Nothing like however the great ambiance of the North Shore - and if Turtle Bay resort is full - also check VRBO. A friend of mine and his wife rent their guest house out - and it's just on the north side of Waimea Bay, where the HUGE surf comes in during the winter.

There are vacation rentals at both Turtle Bay and Haleiwa. Look on VRBO.

OAHU....Hannauma Bay (sp?) for snorkeling but get there early. You can rent equipment in Waikiki. Drive to North Shore is awesome and beautiful but remember you will have to drive back into WAIKIKI so plan trip accordingly to avoid traffic. Def. pearl Harbor with the Missouri and the memorial to the Arizona...There is a swap meet outside of honolulu and if you can break away from the kids, I highly recommend Doris Duke Shangri La. You have to go thru the Honolulu Academy of art for tix as they re the only touring company and tix are limited Also a good walking book on Honolulu takes you thru Chinatown, and the Iolani palace and other historical landmarks. We enjoyed using ours. Fireworks at the Hilton Hawaiian Village on Friday nights is fun to watch, I have walked up Diamond Head and it is very doable (bring water. There are crowds of people so you are not alone and the views are awesome. You can take a bus to the base. Buses are very good in Honolulu. Most ABC stores have schedules or you can go on line to find out which bus to take to Diamond Head....HEADS UP. Waikiki Beach is rocky so be sure to have some kind of water shoes. Reasonable dinners if you go to the early bird specials....many restaurants have them and there is a California Pizza Kitchen right on Kalakaua. $4.00 martini's at the the "Top of Waikiki" restaurant are decent.

A hike up Dimondhead is a great family walk. Just plan to go early in the morning (like before 8 am), when there is still some shade. Otherwise you will be in the full sun for the whole hike which is much less pleasant. Also, if you ahven't already done so, go online immediately and reserve tickets for Pearl Harbor.

layanluvs... we may be at Ko Olina at the same time (???). I'm coming in to the J W Marriott on the 27th for 2 nights (or are you back home by that time).

The teens won't be very impressed with the Doris Duke Shangri-La tour. Don't bother bringing them. But do bring water. It is hot and humid there.

Where are the rocks on Waikiki?

The rocks?

I've never used water shoes on Waikiki Beach myself. Maybe some parts are different but where I hang out (usually either in front of Kapiolani park or in front of Fort de Russy) aren't rocky.

I just wanted to come back and say a big thank you to everyone who helped me plan this last minute trip! This was one of the most relaxing trips my husband, kids and I have taken in a long time. Oahu was the perfect island for us and perhaps we'll go to Mauii sometime in the future. I'm not big on writing detailed trip reports, so I apologize, but here's my summary (I hope others will benefit from our experience):

As you all suggested-- we stayed on Waikiki Beach and loved it! It wasn't crowded at all (the hotel was fully packed but who cares!). We had an ocean view room at the Marriott which was clean and spacious. Our rate included buffet breakfast for two adults (of course, the breakfast does get old but isn't that usually the case with these hotel breakfasts?). I'd recommend our hotel. We loved the swimming pools, the fitness room, the location, and the service was great. Hey, it's Marriott and usually our experience with Marriott is A+.

I was nervous it was going to be a huge party (like in Miami) but it wasn't (maybe b/c we went toward the end of August?). Waikiki beach was perfect in every way. We loved the beach. We loved the free cookie samples at the Honolulu cookie shops (and bought a few boxes for family). We loved the restaurants (eat at a burger place called Mahalo at the shopping center where the Sheraton is located. They have delicious burgers!). We actually enjoyed looking around the many ABC stores too (those only sell alcohol in DC, lol).

We used a combination of taxis, the bus and car rental to get around the island. We hiked Diamond Head for a beautiful view! I highly recommend doing that. We also hiked in Manoa Falls through a rainforest to find an ok waterfall (I've seen better but it's still worth it! Go!). One word of caution: some people were "swimming" and drinking from the waterfall's water. Please don't do that! It has a bacteria that can be deadly. We tried warning them but they just wouldn't listen (my kids were so upset and afraid for them). We visited the Bishop Museum. I'm not sure I would recommend doing that. If you have time and want some history, then go ahead. However, it didn't "impress" us. I really wanted to learn more about the native Hawaiians and their history. I actually learned more online than in the museum. The museum was pretty empty when we visited. It was just o.k. We hung out at the beach most of the time and just tried to relax (we've got pretty stressful jobs). We skipped Pearl Harbor (we originally wanted to go but the beaches kept calling us and with only 7 days we kept asking ourselves if we really wanted to see a memorial? We live in DC so...we skipped it).

We did go to Hanauma Bay and loved it. However, it didn't have as much coral as I thought it would have. Then again, we've been to Sharm Elsheikh and that's like the capitol of coral reefs. It was gorgeous though and I'd say go early and go! We rode the public bus one day and kind of accidentally did a tour of the east side (so we drove by Sandy Beach, the blowhole? which looked beautiful and that area surrounding it).

When we finally rented our car, we went to Ko Olina where we stayed at the Marriott Vacation Club. The Ko Olina lagoons are beautiful and great for kids. We loved the vacation club. We could barbecue, swim and relax without leaving the resort. Of course, we did leave nonetheless! We drove through beautiful mountains (I think we were on Pali highway? We just followed a scenic route on the east side). We stopped at Kailua beach (I apologize for my spelling. It was a beach town on the east side that, at some point, was rated the number 1 beach in America). After seeing a few gorgeous beaches, we couldn't understand why it was rated #1 but ok it was beautiful.

We visited byodnu temple (again sorry if i'm spelling it incorrectly). I'm a huge LOST fan and I just had to see a few spots where LOST was filmed. The temple was in a beautiful location, the drive to it was beautiful and I do recommend visiting it. It's a quick trip but the scenery is beautiful. Of course, we drove to the North Shore too! Again, we took a scenic route through the middle of the island stopping at the Dole Plantation. We knew that it was a tourist trap but it was a quick stop nonetheless (we didn't do any tours, my hubby just bought chocolate covered pineapple which we later discovered was sold in all of the ABC stores for a few dollars less! haha live and learn). My girls bought the pineapple soft serve ice cream which was ok but a bit too sugary for me.

At the North Shore, we stopped for shaved ice at Matsumoto and yummmmoooo! I got the tropical flavors and again yummmoooo! I highly recommend this place so go! We also stopped for shrimp at a shrimp truck (Mackys) and it was good too. I liked the coconut shrimp the best, then the lemon pepper and then the garlic flavored shrimp. After we were well fed, we stopped at a couple of beaches. Of course, we also visited the beach where LOST was first filmed.

We drove by China Town (not my thing), the royal palace we saw from the outside and downtown Honolulu. We didn't do everything but it was just so relaxing to hang out at the beach! My kids tried to surf and realized how it looked easier than it really was.

Of course, the native Hawaiians are really nice and it was interesting to learn that more than 90% of them opposed annexation to the U.S. That's not what I learned in school!

Mahalo for reporting back on your visit to Oahu. Although you did a lot, it sounds as though you got on Island Time enough to soak up enough Aloha to bring home with you! (I keep some Hawaiian music CD's in the car to calm me in expressway traffic.)

Yes, commercial interests are why the US annexed Hawaii. Maybe we should revisit ALL the 'history' we learned in school? LOL This stuff continues, with Matson Line the uncontested giant shipping agent in Hawaii.

Great summary! Brings me back to our trip in June. Kailua beach is nice but not as nice as some others I have seen outside of Hawaii. But just south of that is Lanikai which I think is just beautiful, but a little narrow. Thanks for the memories, and i too, love the H3 highway, it's so pretty!

Great trip summary!

I'm on Oahu right now. I started out at Ko Olina at the J W Marriott, using points. FABULOUS place!! I'm currently at the Courtyard Waikiki (not so hot) and will be moving to the Marriott Resort on Waikiki this afternoon. I've booked a really nice room there, and since I'm platinum w/Marriott, I should get an upgrade to a really nice room with beach view. I don't usually move from hotel to hotel like that, but I wanted to save a bit of $$$ by using points, staying off the beach, and then moving to the beach and paying for that view for the last 2 nights here. I have had a car for the full trip, and have been driving everyday.

I'm doing the island drive today. I'll stop for shrimp, of course. I've yet to do the shave ice, but just might make that stop today. We'll see.

My 6-might trip has been for shopping (which has been super) and visiting with friends from the internet. Two days ago I had dim sum at Empress of China at the Chinese Cultural Center with a FB friend. What a great meal! Yummy!!!

Last night was a visit with 3 fodorite friends at a place called Ryan's Grill, at Ward Center shops. We laughed and talked travel for nearly 4 hours! The burger and cold beer I had was tasty. It was a really enjoyable evening. It's always nice to visit with my fodors friends face-to-face. I come to Oahu once a year to do this!

I'm not a beach person (I don't swim) but I love being ON the beach, listening to the surf. Sooooo relaxing for me. I love spending time on a balcony overlooking the water (and/or Diamondhead) sipping my coffee, reading a good book, posting on fodors, etc. That's what Oahu is all about for me.

Thanks everyone! Simpson... U sound like you're having a lot of fun! Enjoy

Thanks, layan. I AM having a great time. Two more days and then back to Illinois but I'll be back again next year.

Thanks, layan, for sharing your trip with everyone... I always appreciate knowing how a trip actually turned out after giving feedback on the initial plans. Sounds like a great trip!