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The Hawaiian Islands.

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.

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