Where to start planning a Hawaii vacation?

My wife and I have wanted to travel to Hawaii ever since we got married. We were considering taking our honeymoon in Hawaii, but we ended up in Rome. The problem with planning a Hawaiian vacation is that there’s too much to do. Which islands do you visit? Which attractions do you skip?

I think you start with things you really want to see. For me, it’s the Polynesian Cultural Center, a luau, and a nice beach.

The Polynesian Cultural Center is said to be worth at least one full day. It’s on Oahu. Also on Oahu: the Pali Lookout, with its spectacular views of the windward side; Iolani Palace, Punchbowl, Waikiki, Pearl Harbor, the pineapple fields; the north shore (I don’t surf but may want to watch), Waimea Bay, Pipeline, Sunset Beach. Oahu vacation rentals are one possible alternative to hotels.

That will keep a vacationer busy! However, I think I’d like to visit at least one other Hawaiian island and Molokai seems like an interesting choice. A condo in Molokai might run around 800/week. This is considered the “most Hawaiian” island, and features the 2774-acre Kamakou Forest Preserve. Kamakou is home to 5 species of endangered birds and over 200 Hawaiian plants that don’t grow anywhere else. It’s very laid back (not much night life).

I suppose I now have some direction for my Hawaii vacation plan, but there’s a lot more left to think about so expect more in the future. My goal is to have a Hawaii vacation more or less planned and scripted in a month or two.

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  1. fairycatz says:

    Don’t leave out the “Big Island” as you plan your trip. Volcano National Park is astounding; and the Northeast coastline has beautiful spots. Kailua-Kona is pretty amazing too! Check out some of the B&B’s! If you like resorts the Hilton Waikoloa is 5star fab! Good luck in your planning! And remember, you can always go back! Mahola!

  2. Linda says:

    My suggestion would be to plan a CRUISE of the islands….for the same price you can see ALL the islands PLUS enjoy all the activities a cruise ship has to offer…consider it your “loating” hotel for your week long vacation.


  3. steve says:

    If you do the polynesian cultural center, plan a whole day due to the exorbitant admission price. Secondly many of the actors are part-timers and don’t show up until after work on weekdays. The Arizona memorial is a must if you are on Oahu. On Maui, do the bike trip down the volcano and in Lahaina there is a fabulous dinner and magic show (sorry, I can’t remember the name).

  4. ann says:

    I would suggest getting as many travel books as possible to check the package rates, and the pictures will help you to decide which island to choose.I have been to all but the “forbidden” one. Molokai is beautiful but there are no “night spots”. It can be reached by ferry from Maui. Also, if you are considering spending some time there you may need to fly over. The big island of Hawaii has lots to offer. Also, find out when the Aloha Festivals are scheduled; they are at different times for each island.Don’t get a rental car in Oahu, the traffic is horrendous.Kauai has wonderful areas in the Poipu area of that island which is more sunny than the other areas. Have a great trip.

  5. Nancy says:

    The best way to start planning a highly anticipated vacation to Hawaii is to consult a travel professional. It sounds like you have some specific ideas already. Every island has its own different character and personality. Every one you talk to will have a different opinion as to which is “the best”. The best is, in fact, different for every individual. Meeting with a travel professional who will listen to your likes, dislikes and expectations will help define YOUR vacation – and you won’t need to take a month or more to plan. A professional can help you plan the vacation of your dreams in very little time. They will be able to provide you with the tools and information you need. If you talk to a Hawaii professional, it will be the vacation that is right for you. In addition, a travel professional will be able to save you money. They are skilled at finding the best deals, bargains, and package prices that can save you hundreds of dollars. In addition, if there are any problems, you have recourse of someone you trust to talk to, and who has “clout” with the hotels, resorts and various agencies involved. A good travel professional also has contact with a sales representative of each resort, hotel, etc. and will VIP their guests because of the special relationship. This means you may receive a room upgrade, an extra amenity, etc. This will not happen when you book packages on the internet since there is no personal involvement. Keep in mind that all this service generally comes at no extra cost to you, in fact you will end up saving money. By the way, the best books on Hawaii are “The Revealed” series – Oahu Revealed, Maui Revealed, etc. They are available at any book store.

  6. Kelsey says:

    I find Honolulu to be too much of a city. When I think Hawaii, I think paradise. My paradise isn’t a city. Oahu is Honolulu and Honolulu is one of the 50 largest cities in the USA. Besides all of this, Dog, The Bounty Hunter, operates on Oahu and that dude scares me.

    Go to Kauai. There’s no Dog, not many people, and it is one of the most unbelievable places I have ever been.

    I wish I was planning a trip to Hawaii!

  7. MOPARDAN says:

    You seem to be falling into the typical Hawaii travel dilemma, what to do? First remember the biggest mistake people make when going to Hawaii is trying to see and do too much. A good rule of thumb from an experienced Hawaii visitor is. Five days, one island. Seven days, two islands. Ten days, two or three islands. Fourteen or more, visit three or all islands. First time visitors should consider Oahu and Maui or Big Island. If you are beyond the “touristy” stage consider Kauai the Garden isle. If activity is your goal, Maui. If discovery and history, Oahu, Kauai, Big Island. If your looking for adventure and activities consider a ten day Maui (5 day), Oahu or Big Island (5 day) trip. Now the MOST IMPORTANT part of Hawaii travel. We do things in Hawaiian time here. To truly absorb the Hawaiian experience, ONE day activity or exploration, ONE day rest and veg on beach or waking tour of a town and beach. If you do an activity each day you will get home needing a vacation from your vacation.

  8. mike says:

    We,my family and I went to Oahu this last december,first time for us.Honalulu is a cluster,but everything else is heaven.Diamondhead is a to do,the top has a view made by the Gods.Northshore is beautiful also,but I come home and a month later I see this magazine called Adventure,this months issue,and it showes all the top spots of each island.Nothing I dont think one could do in a week, but possibly so.

  9. James Trotta says:

    Thank you for the comments. I will try to incorporate some of them into my next ‘draft’. I would liek to comment directly on Nancy’s idea that a professionsl can save me time, because I want to take the time to plan my vacation. That’s the whole point of my website; I started it so I could keep a journal of all the vacations I plan/go on. Planning vacations is kind of a hobby!

  10. brian sheriff says:

    Doing Hawaii for the first time? Be prepared for two trips at the very least.

    You’ll have thousands of those “we should have…” moments. Hey, but isn’t that what fun travel is all about?

    The one thing nobody can dispute about doing Hawaii is that the first time you see the locals and wanna be locals in Aloha shirts you’ll swear to yourself that you’ll never tell the folks back home about how goofy everybody looks. Whoa!!! Hold on to your leis there a minute… talk about touchy. Okay back to the shirts. But on your second visit I guarantee y’all (excuse the Texan, I’m a Texas educated Zimbabwean) be fixen’ to buy yourselves the loudest shirts in carnation the minute you step off the plane! Ladies, and you folks’ll be wrappin’ your pretty selves in them loveable – at second visit, muu muu dresses. Ahaa… Hawaii. There’s no place like Hawaii for bringing the best out of people, especially tolerance. I’ve never met a person in Hawaii that I didn’t like.

    Now, before your first trip, remember to pack lots of “honey we’ll do it better the next time” ointment. Because if you write-off Hawaii after one visit you’ll be doing yourself one heck of an injustice. Bon vo-ya-gee as Bugs Bunny would say.

  11. kaui says:

    I recommend staying at least 5-7 nights at each location. There is just too much to do on every island. If you move more than that you will be spending too much of your time packing, traveling, and unpacking again.

    I’d also recommend going to Kauai first. It has tons of beaches but no night life. Oahu has night life shopping etc. but too many people for me.

    On my first trip, I stayed on Oahu first, then the Big Island, and finally Kauai. It was exactly wrong. I spent the first 5 days trying to find a secluded beach on Oahu and couldn’t. By the second week I was finally ready for some night life but found none on Kauai.

  12. Diana Hyneman says:

    I went on a cruise this summer in Hawaii. I loved it. If I went to stay at an island I would go to Molokai. This is the least developed island. There are also ferries to take you to Maui and I think Lani. You can get discount tickets on the internet. I loved the other side of Oahu, but the side by Honolulu and Waikiki are VERY crowded. You might as well go to Miami.If you would like more info you can email me.

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