Hawaii 2014 Postscript – Hawaii Trip Planning – Part 1

Let me add a final episode about Hawaii in answer to a query from my cousin Robin who lives near Boston.  She asks “how to plan such a beautiful trip.”  For us, it’s not too difficult.  We own a timeshare week on Oahu, plus some extra vacation points.  We can stay anywhere we like, but we gravitate to Oahu, with side trips to other islands.  So, our planning consists of picking a week and a location.  We rent a car, read a bit of literature and travel guides, and go see what we can see.  After going to Oahu for several years, we have developed a small backlog of things we’d like to do – maybe we’ll get to them next year.  Maybe we won’t.  One thing is clear – we are getting better at hanging out beside the pool or ocean rather than driving places every day (I even left my camera at home several days! – fortunately, I had my iPhone 🙂 ).

To help with your planning, I’ll share some basic planning tips, perspective of the three islands we have visited, and some hotel and flying tips…


Shangri-La seen from Diamondhead

Shangri-La, as seen from Diamond Head

We do a small amount of preparation so that our trips aren’t totally haphazard.  If it’s a new island, we read up on it ahead of time and talk to fellow visitors.  For example, a friend at work told me that the Road to Hana and a visit to Haleakala were key activities on Maui, so we put those activities on our mental list of things to do.   Aside from that, we knew that we could just hop in the car and do some exploring.  The random car drives are often the most interesting (as in our last day of Maui).  For a few things, though, spontaneity won’t work.  For example, we wanted to visit Doris Duke’s Shangri-La near Diamond Head on Oahu, with its notable collection of Islamic art.  We didn’t make advance reservations, and it was booked, so we’ve had to postpone until next year.

Then there is the question of which island or islands to visit.  Most of our time has been spent on Oahu, so I’ll focus there and then follow with some comments on Hawaii (the “Big Island”) and Maui, which we visited for four or five days each.  I can’t comment on Kauai because we haven’t been there, although I am told that it is the most beautiful.  Maybe next year…

Hawaii map from lonely planet.

Your Objectives

Perhaps you caught the drift of “maybe next year” in my comments above.  The concept of an island can be misleading if you think of islands as being small.  Oahu is maybe 40 or 45 miles long at its longest dimension, but is nearly 600 square miles of city, mountains, military bases, beaches, gardens, trails, parks, and more.  That’s a lot to explore.  Maui is another 100+ square miles larger, and Hawaii is 4000 square miles!  There is always more to explore on every island, which is why we keep going back.

So, don’t build an itinerary around doing everything in just a week, or even two, especially if you want to take advantage of the perpetually wonderful weather to relax a bit.  Whatever time you have, just go with a prioritized list based upon your interests and don’t fret when you can’t do it all – you’ll just have a reason to go back again.  With that in mind, ask yourself what you’d like to be doing on your vacation.  Sight seeing?  Hiking?  At least one Luau?  When you travel, do you like to stay in one place and get to know it well, or do you prefer to live out of your suitcase and move every 3 or 4 days?  Do you like scenery?  Shopping?  Wildlife? …

I’ll try to relate our experiences from each of the islands so that you get a feel of what we saw as the options for activity.  You can review your objectives against our experience.  I hope that proves helpful.


Don’t let this get to you, but at first, Oahu seems dominated by the capital city of Honolulu and Waikiki.  That’s no surprise, because nearly 1,000.000 people live on Oahu, and the bulk of that number are concentrated near the city.  27-mile-long Interstate H-1 traverses the southern side of the island and reaches 12 lanes in the heart of the city, with all the rush-hour congestion you’d experience in similar-sized cities.  If you stay in Waikiki, you won’t experience the highway right away.  But, until you get to the beach you’ll feel like you are in any upscale, mid-rise, downtown area, albeit with a wonderful tropical climate.  But, if you are staying at one of the K0’olina resorts to the west, you’ll hit this highway for 30 or more minutes and say, “We traveled for 14 hours for this!”

Have I turned you off on Oahu, yet.  I hope not.  I just wanted to tell you this up front, because on Oahu you are likely to hit H-1 frequently and be frustrated by it.  But, and this is the good part, 99% of the time the destination you choose will be worth it:

  • You may be passing through Honolulu on your way to swim with the Dolphins at Sea Life Park or to walk to the top of Makapuu Point above the lighthouse to look for whales, or to drive to the Pali lookout to experience the stiff cliff-side winds as you look toward the US Marine Corp Air Base at Kanehoe Bay.

View fr. Makapuu Point toward Rabbit Island and KanehoeView from Makapuu Point to Rabbit Island (large island near top center) and Sea Life Park opposite Rabbit Island to the left, with Kailua in the far distance.

  • Maybe your destination is in Honolulu – visit the Iolani Palace, the only royal residence in the US; or the Honolulu art museum; or the Aloha Tower where we recently saw the new Queen Elizabeth docked; or the Cemetery of the Pacific in the “Punchbowl”, an extinct volcanic crater; or Chinatown.
  • The east side of Honolulu is Waikiki.  My wife and daughter shop on Kalakaua Avenue, the best of big-city shopping, while I go somewhere with my camera.  Afterwards, we meet up at the Royal Hawaiian Hotel for a Mai Tai or Pina Diamond Head from Royal Hawaiian HotelColada at the beach-side bar.  Yes, the Waikiki  beaches are the ones that Elvis made famous – people really do surf there (and anywhere in Hawaii with a sand beach – and some not so sandy!).  From the bar patio, you have a great view of Diamond Head, Oahu’s iconic, dormant volcanic crater, pictured right.  When you have a few hours, drive up and into the crater, then climb the trails and steps to get a wonderful view of Honolulu and it’s suburbs (yes, I know that thinking of suburbs on a tropical island is really bizarre – but…).
  • Going up Diamond Head is must-do for me because it is an easy way to see a little bit about how volcanoes built the islands.  Plus, it is an easy way to get a high vista of Honolulu.
  • The main must-do on Oahu, west of Honolulu, is to visit the Arizona Memorial in Pearl Harbor.  When the Japanese bombed Pearl Harbor on 7 December 1941, the Arizona sank with 1177 sailors on board.  They are still buried in the USS Arizona Memorialship.  The memorial was built in 1962 and hosts over a million visitors annually.  Be sure to arrive early, because it is first-come, first-served on the boat that takes you across the harbor to the memorial.  While you are waiting, there are ample historical exhibits and movies to keep you busy.  The memorial, pictured right, is built like a bridge spanning the sunk wreckage.  At the far end of the memorial is a room with the names of the sailors who perished on board.  From either side of the memorial, you can easily see  the wreckage just below the water’s surface, as well as a few of the ships structures which break the surface.
  • The kitschy Oahu must-do is at the Aloha Stadium in Alea, not far from the Arizona Memorial: the Aloha Stadium Swap Meet is open Wednesdays, Saturdays, and Sundays.  Only $1 entry fee gains you access to 400 “vendors, crafters, and artists”.  Good to do once for about 15 minutes (that’s just my perspective!).

Well, that scrapes the surface of things to do around Honolulu. In my next post, let me give you a feel for the less urban activities – things you might really expect on a tropical island.

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  1. rfis9 March 18, 2014 at 8:26 am #

    You have hooked us! We are gravitating toward your Hawaiin adventure because of your exceptional photographic and writing skills. Looking forward to Part II . . . Both the glamor and the kitch. Thanks so much, Lloyd!

    • lloydbloom March 18, 2014 at 6:32 pm #

      Hi Robin. Glad I’ve helped you decide. More to come on Oahu, other islands, and a few thoughts in lodging.

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  1. […] for the brief hotel and flying tips that I promised at the introduction to Part 1 of this postscript.  I’ll reserve observations on Maui and Hawaii (the Big Island), for the […]

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