The Hawaiian Islands.

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Related DD Posts:
Hawaii Trip Notes: Oahu (2009)
Hawaii Trip Notes: Kauai (2009)

Traveling To Hawaii…With A 5 Month Old!

Related DDF Threads:
Hawaii Master Thread: General Questions And Which Island To Visit?
Big Island Of Hawaii Master Thread
Kauai Master Thread
Maui Master Thread
Oahu Master Thread

So you booked tickets to one of my favorite places in the world with the ongoing Continental award availability glitch.  Your cell phone and money will work the same as back home and there’s Costco and Walmart on every island, so you won’t starve, but if you keep kosher you’ll probably be bringing a lot of food in your suitcases.  Not to worry though, anything that’s frozen will stay frozen in the belly of a plane, so it will still be frozen when you get to Hawaii.  You can’t bring most fruits into or out of Hawaii.

Where do you go from here?

It would be criminal to go all the way to Hawaii and stay on Oahu. I recommend spending about 5 days on an island. It’s not worth island hopping to be on an island for less than 4 days except if you want to do a 1 night trip to the Big Island to see the volcano.

The first thing you need to do is buy the “revealed” book for your island. They read like thriller novels and have great pictures and trip ideas.

Oahu Revealed
Maui Revealed
The Big Island Revealed
Kauai Revealed

The main 4 islands are:
Oahu: The center of the population base and capital city Honolulu. Most tourists go to a hotel on Waikiki Beach in Honolulu, but frankly you may as well go to a beach in Florida. There are definitely nice places to check out in Oahu, but most people just stay around Waikiki and complain afterward. Pearl Harbor is on Oahu.
Highlights: Hiking Diamond Head, watching the surfers on the North Shore’s killer waves. Kayaking on the leeward (east) coast. The only island with a Chabad House within walking distance of a resort area (Waikiki).
Lowlights: Extremely touristy and overcrowded in Honolulu.
DD stars: 3.5/5.

Maui: A beautiful island with great weather in the Windward (west coast) major resort areas (Ka’anapali in West Maui and Wailea in South Maui) and in Kihei (South Maui) where affordable condos are available for rent. A convertible is perfect for the road to Hana.
Highlights: The road to Hana (waterfalls and hiking), sunrise on Haleakala, Nakalele Blowhole/Olivine Pools, whale watching boat tours in the winter, browsing the shops in downtown Lahaina at night, beaches from Wailea and further south.
Lowlights: Still feels touristy and built-up.
DD stars: 4.5/5.

Kauai: A lush green isle with jaw-dropping scenery, most of it inaccessible without flying over it, hiking to it or having a 4WD vehicle. The weather (in the winter at least) is much better on the south side than the north side.
Highlights: Waimea Canyon, taking a helicopter your over the entire island, Na Pali Coast, Waimea Canyon, snorkeling at Poipu Beach, kayaking the Wailua River to secret falls, Polihale Beach. Grand Hyatt Kauai. Much less touristy feel than Maui and Oahu. Being the last Jew in the world to take in shabbos.
Lowlights: Traffic around Kapa’a and Lihue. Rainy and buggy on the north shore.
DD stars: 4.75/5.

Hawaii, aka The Big Island: A massive island with active volcanoes. A 4WD vehicle here is essential.
Highlights: Volcanoes erupting, hiking through past eruptions, dipping in volcanically heated hot springs, sunset on Mauna Kea, seeing Waipio Valley, Hilo Wednesday market, watching crazy people jump off South Point, diving with Manta Rays at night. Much less touristy feel than Maui and Oahu.
Lowlights: The least green/beautiful of the islands due to the black lava everywhere, Long drives to get places, Vog (Volcanic Smog) for sensitive breathers, less hotel point options (1 mediocre Starwood, no Hyatts) than the other islands.
DD stars: 4/5.

Other visitable islands include Lanai and Molokai off the Maui coast, but I have never made it to those islands (no free hotels!). Kahoolawe and Ni’ihau are generally inaccessible short of chartering your own helicopter for a couple thousand dollars.
You can book interisland tickets on Hawaiian or IslandAir for 5,000 miles per one-way with AA, Continental, or United or 10,000 miles for a round-trip with Delta or USAirways. You may be able to pull off a 3 flights for 10,000 miles on Continental by use of a stopover if you find a good agent.
Availability can be hard to find though for the times you want.

Airports are as follows:
Oahu: Honolulu (HNL)
Maui: Kahului (OGG). IslandAir also flies to Kapalua (JHM) in West Maui.
Kauai: Lihue (LIH)
Big Island: Windward (Resort westside coast): Kona (KOA)
Big Island: Leeward (Volcano eastside coast): Hilo (ITO)

The best airline is Hawaiian. They are the traditional Hawaiian airline and fly a modern Boeing 717 fleet with a 2-3 seat configuration. The route map is interesting. For example you can fly nonstop from Kauai to Maui, but not from Maui to Kauai. Most flights go through Honolulu, though there are nonstop flights from Maui to Kona and Hilo.
You will earn miles on any mainland carrier you want for the Hawaiian flight.
Baggage fees are $17 per bag for the first 2 bags and $25 thereafter.

IslandAir flies to the smaller islands and secondary airports and they also connect Maui and Kauai better than Hawaiian.
They fly rickety propeller planes though, so you’ll have to decide if the nonstop flight is worth it.
Baggage fees are $15 for the first bag, $30 for the 2nd bag, and $35 thereafter.

Go Airlines flies smaller jets primarily on routes competing with Hawaiian. Don’t tell the locals you flew Go though as they hate them for killing off beloved Aloha Airlines. A better reason to dislike them is their spotty on-time and cancellation record and that they don’t interline baggage or take/earn miles from the mainland airlines.
Baggage fees are $15 for the first bag, $17 for the 2nd bag, and $25 thereafter.

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24 Comments On "The Hawaiian Islands."

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Was there a link to the CO glitch? I’m sure it’s dead now but I’m still curious what it was!


FYI, for kosher food there is a great store located near the airport in Maui.

It’s called Down to Earth

They have many frozen chuf k products as well as non perishable such as potato chips and other products which are either “ok”, “ou” or “chuf k” .

Somewhat like a whole foods. A bit pricey though. If you keep kosher as we do.


Never been there but good to know. I tell my concierge clients to also check out Mana Foods in Paia (things are affordable here too!), Whole Foods in Kahului (very expensive), and Lahaina Farms (very expensive) in West Maui. Plus you can get hot kosher meals off the kosher menu at the Hyatt.


Fair warning: Island Air very well may be the worst airline in the world when it comes to comfort and/or service.

The planes are exceptionally cramped (i.e. someone you don’t know very well may end up sitting in your lap), lavatory is basically a cramped drawer which you must be under 5”6 to barely fit into, and huge delays are a given (always blamed on the unpredictable weather – If it looks crystal clear to you they will blame it on the other Island’s weather).


Lol…the plane was rickety as I said, but I’ve had worse service in Thailand 😉

Don’t really need to use the loo on such short flights, but it is quite cramped.

Like I said, Hawaiian is the best, but they don’t always fly nonstop when you need to fly nonstop with a baby…which is why we took IslandAir from Maui to Kauai.

In retrospect I should’ve gone to Kauai first and taken the nonstop Hawaiian flight to Maui, but I like having the flavor of Kauai linger last…


@Dan: Dan, we stumbled upon it and were amazed at how many kosher products we found.


how about kosher in kauai?


The usual suspects, Costco, Walmart, Star Market, Safeway.
And there’s always Starbucks and Jamba Juice.



Completely agree. Hawaiian is definitely much better.

Who was worse in Thailand? gotta know who to avoid 🙂

If using continental miles and cannot find availability on for Hawaiian you may want to check out Hawaiian’s website and book thru them (you can transfer Amex points instantly to an Hawaiian account), though it will cost 10,000 miles each way rather than 5,000 but totally worth it in my opinion if its between Island Air or Hawaiian.


Can you book inter-island flights with Hawaiian airlines using BA/Avios miles thru AA?


Does your Kauai highlights imply that Grand Hyatt is the favorite?


@ kenny it should cost 7500 each way on hawaiin


Virgin Atlantic (of BofA & 1K per Hertz /Avis rental fame) only charges 6K RT for inter-island flights on Hawaiian. Have heard CO may be 5K. Still, interislands can be had for $70 up ow advance purchase on HA anyway.


Some people love ’em, but we had terrible experiences with Air Asia.



The real problem with using miles for interisland flights is that they don’t make the flights that connect to/from mainland flights available for use with miles.

Plus with miles I would need to pay for baggage, which is free with my corp account.


You keep mentioning your concierge services but there is no link or information about it on your website?

Please inform us 🙂


I am going to kauai soon and have hyatt points and starpoints! I’m basing my decision where to stay on your showdown report!!!
I gotta book the rooms, so can u please let me know which one is the winner???
Thanks 🙂


Dan – Have you been to the Big Island?


It’s for special people 😉

Just look at the highlights.



So gh Kauai then? I didn’t see your st Regis trip report


Just curious- how do you have Platinum status with Continental? did you fly 75,000 last year?


hey dan planing a trip to miami beach end of jan first time going there where do u recommend to stay nice decent clean hotel on the beach.


This is not correct…..

You will earn miles on any mainland carrier you want for the Hawaiian flight


How do we become special?

dr ron

NYC to Hawaii business class what is best mileage to use?