Chrissy4

My family of four (kids will be 14 & 12) are planning our first trip to Hawaii summer of 2018. I think we've narrowed it down to Maui and Kauai. We plan to spend 5-6 days on each island (12-14 days total including travel time). I understand we could probably spend the entire trip at just one place, but it may be our first and last time here and I'd love to see both places (and hopefully return to see more one day!). I'm wondering if there's anything to consider when choosing whether to go right when school lets out (late June/early July) or right before school gets back in (last two weeks of August). Thinking of starting with Maui and ending with Kauai but open to suggestions and still researching (does it matter??).

Also, we love staying in hotels, mostly for the pool and amenities, but also for the restaurants and convenience (I don't mind making breakfasts and lunches, but my idea of a vacation is not cooking and cleaning every dinner like when I'm home!). That being said, the kids are getting older and bigger and sleeper sofas won't cut it anymore which means we need two full beds (and ideally two bedrooms) which is surprisingly difficult to find. Even some of the sought after hotels already have these bigger rooms (2BR/suites/villas) booked for next summer. I've also heard about people advertising VRBO homes that are scams so I'm a little leery about that. So I'm wondering what people with teens do for travel and if there are options I'm not thinking of (either in general or specific properties). Do you rent two hotel rooms and hope they're next to each other? Do you book a suite/villa super early? Do you rent homes/condos and go out to eat? What sites are reputable for renting condos?

I haven't narrowed down areas within the two islands yet, so plan to do more research there (and open to suggestions), but initially started looking into Four Seasons Maui and Westin Princeville because I heard great things - and that's when I hit roadblocks on availability.

Thank you so much!!!

vincenzo32951

We've stayed in condos in Maui and Kauai. You can find some very nice places with great views. To address your concerns about scams and/or the cooking-cleaning non-vacation:

We mostly did breakfast and snacks, and ate our other meals out. Lots of restaurants nearby. One thing I like about a condo with teens: They, especially boys, are eating machines. Having snacks handy in a condo makes life simpler.

To avoid the scam problem, you can book a condo through reputable booking agents.

To make it more of a vaca, many places booked through agents offer daily cleaning services. That means no one gets stuck making beds, cleaning, etc. It will cost you a bit more, of course. But you have to decide if it's worth it to you.

jamie99

I've stayed in a condo in Maui and a hotel (Marriott) in Kauai. Both have benefits.
For a condo, as suggested, look into renting from an agency, on Kauai both Summit Pacific and Parrish have good reviews among others. If there is a problem with the unit the agency can often move you to a similarly priced unit in the same complex whereas renting directly from an owner you are unlikely to have that option.
Summer in Kauai I would look into Hanalei Bay Resort on the North Shore, terrific pools and an onsite bar with light meals.

sf7307

I would consider a condo for a week (most book by the week) on one of the islands and a hotel on the other island for 5 nights.

emalloy

As to June or August, are you and the kids more likely to need to de-stress and relax after a hectic school year or after a busy summer?

I would probably want the June dates, so I could do school shopping etc. at the sales in August.

ChiSue

Any time mainland schools are on vacation is *busy* in Hawaii. Maui has many more condo choices in both West Maui and South than Kauai has -- especially in the more desirable north. The season for north is also limited to non-winter. I'd prefer June for cooler weather; go as early as possible to avoid some of the 'rush'.

We are 'condo people'. My DH and I do not want to share a hotel room and a single bathroom with kids, nor do I want to buy them expensive meals 'out' every day. A condo kitchen beats 'room service' any day. Some condos include maid service in the rate; many can arrange it as often as you want it. A washer/dryer in the condo means you can pack lighter. I'd look for a 2BR 2Bath condo with ocean view and good air conditioning. Few condos have the same high (and *daily) resort fees that hotels charge now -- along with valet-only parking. You can still go to hotels to use facilities like restaurants, bars, spas.

Millions of people happily book on VRBO every year. Agencies have more lenient cancellation policies, but don't depend on one being willing or able to find you another condo if you don't like the one you are assigned. Places are 100% booked in a busy season. A condo -- and a rental car -- is usually cheaper by the week.

Can you fly into one island and home from another? Each transit between islands will consume 4 - 5 hours, door to door -- and run about $100 pp.

Look at what you want to see and do on each island and allocate your time accordingly.

If you are interested in Wailea, consider Wailea Beach Villas, Wailea Elua and Ekahi, Polo Beach Club, and possibly Makena Surf (may to too quiet for your teens). In West Maui, look at Montage. (Easier to tour Maui from Wailea.)

4sammy234

Hi Chrissy, I have kids that will be 9 and 13 and we are starting to look into pretty much the same vacation next summer. I have been to Hawaii so I have a little more insight, but it has been YEARS - and pre-kids - so it will be a different experience for me and I have some of the same questions!

I'm wondering what you have decided?

For us, we are leaning towards the condo route. When we stayed in condos on our last two trips (to FL and CO), we really appreciated all the extra space and the "freebies" - ie., the FL condo owners had left beach chairs, umbrellas, etc for us

I had the same concerns re: cooking and in short - we didn't ,much. We had cereal and toast and a few lunch / snack type items in the condo kitchen. Overall, we didn't do much real cooking that required cleanup so it was still a vacation. And that gave us more free time vs figuring out meal spots every few hours. Oh AND! It gave us plenty of space for storing the beer and wine that we enjoyed on the balcony at night.

I am curious what you have decided on June vs August. The weather here in TX is pretty nice in June, so we typically like to get away in August when it's not as pleasant.

Dayenu

Check out VRBO prices to compare them to hotels. You can easily find a cheaper VRBO in a complex with a restaurant and a convenience store. You don't have to use the kitchen for cooking just because it's there!

With 2 teenagers you will appreciate the convenience of the large fridge. Get snacks and drinks on the way from the airport. The washing machine is included in the price. No need to pack bulky beach towels.

We are going in August, 4 adults, 2 bdrm rented in the Wailea area. Our 3rd visit to Maui.

Shar

definitely condo. If nothing else just for having more room and a kitchen for snacks and breakfast. I find hotels can be confining after about 3 days. You can rent condos for as little as 3 days. VRBO,, FLIP KEY, Hawaiian Vacation Properties (the most reasonable I have found.) If you want maid service you have to pay for it generally when renting through these booking agents but I am on vacation and I don't care if beds are made! YOu don't have to cook if you don't want to or you can if you do. Options are always nice which you don't have in hotel room and it will cost you about the same.