Retiring- Trip to Hawaii

Old Oct 23rd, 2005, 04:39 AM
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Retiring- Trip to Hawaii

I am retiring as an elementary teacher after 30 years. Part of the reward is a 15 day trip to Hawaii( reward to myself). We have considered a cruise, but so much time is spent at sea. What is the best way to see the islands for the first time? Thanks.
maribethp is offline  
Old Oct 23rd, 2005, 04:57 AM
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Congrats! We went to Hawaii about 5 years ago and loved it. We stayed on Oahu and Kauai. The latter was absolutely amazing.

I would suggest you choose which islands you want to see and then arrange for a car rental on each. On Kauai public transport is sparse and you absolutely have to bomb around into every nook and cranny to discover the beauty.

There are frequent smaller plane runs for most of the larger islands and they often take less than an hour - and are not overly expensive.

As for accomodations... we stayed in a condo in Poipu on was large, comfy, had pools and was in walking distance to beach - very reasonably priced (but I forget the exact name)!

As for Oahu - I would spend less time here. Honolulu is like most bigger cities (albeit with better views). The surrounding areas are fun and geared to tourists, but I think you are better off choosing to spend more time elsewhere - friends of mine loved Maui.

Have fun!
daisyblue is offline  
Old Oct 23rd, 2005, 05:45 AM
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Aloha! Post this question on the Hawaii thread and you will get a lot more replies.
pinnacle is offline  
Old Oct 23rd, 2005, 06:01 AM
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Is there an Hawaii thread?
Budman is offline  
Old Oct 23rd, 2005, 08:37 AM
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Congrats from a fellow elementary school teacher. You made it! I, however have 16 more years to go! \/

I would not do a cruise.

I would also not do a package deal, however if you blanch at spending a fair amount of time planning a trip and making on your own arrangements, then packages can be a positive thing for you.

How much do you already know about the islands? What type of a vacation are you looking for?

I have visited Oahu, Kaua'i, Maui and the Big Island. There are lots of points of contrast and comparison between these islands. Chances are that there will be some things about certain islands that will you appeal to you and things that won't. My introduction to the islands was a two week trip to Oahu when I was 16. I loved it! I spent most of the next 20 years visting Maui every two or three years. Lately ,I have been visiting Kaua'i. I want to spend some time exploring the Big Island in the years to come.

I'd pick up either a Frommers or Fodors Hawaii book that covers all the main islands and look it over. Make note of things that sound interesting. Eventually, you will start getting a feel for where you want to go, what you want to do and which islands you want to visit.

I've never been much of an island hopper, so I would suggest that you plan no more than two islands to visit for your 15 days.

You will need a rental car on which ever island(s) you choose.

There are a huge variety of places to stay on Hawaii. Resorts, condos, house rental and b & b s, so there are lots choices in that area. It can a bit ovewhelming, but I think it is the most enjoyable part of planning a trip to the islands.

Happy to answer any questions you might have.


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Old Oct 23rd, 2005, 09:42 AM
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THe state tourist board has a good website at

You can send for a free planner for each island. They will help you decide where to go. I'm like Bill, don't like the bother of island hopping but for a fifteen day trip a case could be made for, say, five days each on three islands, depends how energetic you want to be
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Old Oct 23rd, 2005, 12:01 PM
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I think you would like a land vacation better than a cruise. On a cruise, you won't stay in any one place to really enjoy it.

In 14-15 days you have time for three islands.

Oahu has much more to do and see than any other island.

Here is a thread with lots to do on Oahu. Many of the websites on the thread are good for all islands:


Big Island:

dusty56438 is offline  
Old Oct 23rd, 2005, 01:47 PM
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You've received excellent advice in all previous responses, and excellent specific resources of websites and guidebooks.
I'll add a few things for now...and please write to this board as specific questions occur in the future.
For me, cruising is a great vacation, but i agree, nix the idea for Hawaii. I've heard negatives from folks who took NCL to Hawaii. Not only did they not get enough time to see the islands-- they also had a lousy time on board. There is another cruiseline that goes there--no feedback on that one. In any case... suggest save cruise idea for another line/destination, but do try to take one sometime during your retirement .
IMHO, also agree on NOT island hopping. I'd definteiy go to Oahu for a week. So much there BESIDES Waikiki and Honolulu, which are wonderful (beautiful famous fun metropolitan and international beach at Waikiki, stunning at night; wonderful city filled with great introduction to the islands' history eg Iolani Palace, MIssion House Museum, Maritime Museum, Bishop Museum, Pearl Harbor) but only a PART of this gorgeous, fascinating island. Whatever you want is here...white soft sand beaches, gorgeous mountains, the liveliness of a big city, etc etc etc. Except for an active volcano, you can find much here of what is on the other islands. On the other hand, in Honolulu, you can walk THRU and to the top of an extinct volcano at Diamond Head.
Then, a week on one other island. I love Kauai, but Maui and Big Island have their many passionate fans!! As the expression goes, "It's all good" !! Other folks on this board have seen 3-4 islands in two weeks and been fine with it!! And depending how far you're coming, and if you think may not return any time soon, it's hard to draw limits. The more you research, the harder it will be to chose! But oh, it's so much fun!

And, while you have time to read it all, I suggest James Michener's "Hawaii" as a great way to get some history of the islands. There are disputes sbout some of the accuracies of it, and there are other historical fiction novels about Hawaii, but i think this is a most enjoyable, if loooonnnnggg, read. It starts with the geographic formation of the islands( tho i found this part a bit boring) goes through the first miraculous trips of the first settlers, over thousand of miles, the many groups from all over the world that came later, and ends with Hawaiiian the 1950s
.Happy trip-planning, congratulations on your upcoming retirement. And thanks for all those years of giving, in one of the noblest professions.
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Old Oct 23rd, 2005, 07:05 PM
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My wife and I made the same trip this past September after retiring from teaching 34 years. It was our first time to Hawaii. We stayed 14 days - 8 on Maui, 5 on Kauai and 1 on Ohau (besides wanting to visit Pearl Harbor, I wouldn't go there again). Go for the land trip - there's just too much to see and enjoy. If you go to Maui and Kauai, get the travel books Maui Revealed and The Ultimate Kauai Guidebook. These two books are RIGHT on. It was like having a native take us around the islands. Get the books now and start planning - YOU WILL LOVE IT!
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