Best 7-day Hawaii Vacation Itineraries & Travel Planners


We completely understand the daunting task of planning your Hawaii vacation. It’s difficult enough to select which island(s) you want to visit. Once you’ve selected an island, you have brief sense of accomplishment before you realize that you’ve got to plan your itinerary. Don’t lose heart! We’ve got some great resources to make planning much easier!

We all want to make the most of our vacation time. So, how do you get to see all the best sights and do all the best activities? How do you plan to see it all logistically? To find your ideal itinerary that suits your tastes, you’ll have to do a bit of researching. The good news is that with a great deal of thought, we’ve created some great Hawaii vacation itineraries, plus there are some useful online resources to aid you in your personal research.

First, let’s start with our Go Visit Hawaii recommendations. We may be biased, but we think our itineraries are the best. They’re logical and detailed itineraries designed to help you see and enjoy all the highlights and top island attractions.


The following itineraries may be described by their source as “perfect” but, I hesitate to describe them as being perfect. Still, they may give you some ideas to consider.

  • Go Hawaii has very general itinerary ideas. Navigate to the island of your interest from this link. Once your on the island page, look for the link for their itineraries ideas.
  • Hawaiian Airlines offers some general itinerary advice. Here are their suggestions.

If you are planning a first (or one of your first) visits to Hawaii, check out our popular planning guide for first time visitors to Hawaii. It will guide you step by step in your Hawaii vacation planning process.

  1. I hope this isn’t tacky and I understand if you don’t want to post this but…this is what I do for a living! 🙂 My main site (which needs an overhaul but I digress) shows what I provide. So far I haven’t had a disappointed customer! I started it because I think family, friends and old co-workers were going to smack me if I didn’t! LOL So I got certified through the Hawaii Visitors and Convention Bureau as a destination specialist, quit my day job and here I am. The feedback I get is lots of people don’t have the time to extensively research everything they want to do.

    If you don’t want to pay, other than the great resources you listed here word of mouth is always a great way to get some tips on places and restaurants. Of course perusing Hawaii oriented blogs almost always has some great tips or posts about places that may be off the beaten path!

  2. I had no idea you did that. Personally, I could never turn my vacation over to someone else to plan. I’m too much of a nerd for that.

    Coincidentally, I’ve been taking HVCB courses online. I literally just got started on it today and just passed the Big Island test.

  3. @Sheila – see! You’re giving this great advice away for free, when you could be charging for it! 🙂

    It’s no wonder so many people visit Go Visit Hawaii each day, they’re getting this awesome advice without having to pay a penny! 😉

  4. I am trying to cost out a trip for a group to Hawaii. Do you recommend any particular island to stay if it is a 6 day trip; arriving on Saturday – departing on Saturday? How do you visit other islands?

  5. Sheila,

    Me, my husband and 2 kids [8 and 4] anre planning a trip to Hawaii. I would like to concentrate just on Oahu and Maui.

    How many days do need? If I stay in Oahu,do i drive to Maui? would appreciate some tips here please. I don’t know where to start.

    I was planning on going the week of March break 2010. Anywhere not so expensive but good hotels we can stay at?

    thanks in advance.


    1. As Oahu and Maui are both islands, driving would be impossible. Stay outside of the Honolulu area on Oahu. Too commercial and city like. Food is VERY expensive in Hawaii. Be prepared. My 9 year old loved the jet skiing on Maui.

    2. Hi Sandy,

      I’m not sure how your comment fell through my cracks, but thankfully Jane commented and that brought it to my attention.

      As Jane mentioned, you can’t drive from Oahu to Maui. You will have to fly, which will be very short flights.

      I would suggest a minimum of 4 days on each island. That should be enough time to let you see the highlights of both.

      Since you have kids and are hoping to stay in a place that’s not so expensive, I’d recommend looking into a condo. Aston and Outrigger are two condo management companies you could look into. Also, if you have the time, you could consider We’ve found some awesome condos that way, but it can be time consuming.

      Here’s an article I wrote on the advantages of renting a condo:

      On Oahu, maybe consider the Turtle Bay area. It’s on the North Shore and it’s so beautiful there. On Maui, I’d recommend Kaanapali/Lahanina area for first timers.

    3. Sheila
      I am wanting to take my wife to Hawaii to celebrate her 70th birthday (I am 72). We are both in good health however we want to avoid activities that would involve extensive walking. We hope to go in September for 7 days. Could you offer advice as to the most appropriate Island (we were thinking Maui or The Big Island?). Also is there a specific hotel or resort that is strategically located as a good home base for day trips, shopping and sightseeing. Much appreciated.


  6. Hi I am looking for some top tips please help I would like to come over Xmas new year as it my big birthday this will be my dream holiday I will be coming with 4 boys ages 5 1113 is this a good time was thinking condo as my mum in law wants to come with myself and husband. Is this a good time ? Which island would love to sim with dolphins and I am a big elvis and 50 first dates fan ! Please recommend thanks look forward to hearing from u

  7. Hello Sheila,

    Need your suggestions, Me and my wife planning to visit Hawaii for the first time can stay for about 5 nights, can you recommend which Island is better, little cost savings and to do activities,
    we are planning at the end of Sep or what time do you suggest for any best prices on airfare and hotels, we are coming from D.C.

    Appreciate your help.


  8. Hello Sheila,

    Your website is really impresive for finding info to Hawaii,
    I have zero knowledge until yesterday and after reading through your website, now I am able to plan a trip to OAHU and Maui

    we decided to trip for 7 nhts staying in mid Oct 12, 4 nhts in OAHU and 3 Nhts in Maui, planned to tour first day in Oahu with tours covering all the locations and later pick best and visit personally,
    can u recommend location’s to live and also tours.
    Most imp suggest must see places in Oahu and Maui for 4 and 3 days trip and time they may take,

    our interests would be some thing different like snorkelling, whale watch, beaches,litle hikking, river cruises, One helicopter tour…


    1. Hi John

      Glad you’re finding Go Visit Hawaii useful for your Hawaii vacation planning. Thanks for that kind feedback.

      These are the best things to see and do on Oahu:

      For Maui:

      In my opinion, Maui is the better island for a helicopter tour.

      Mid-October is too early for humpback whale watching. Though there may be an early arriver, whale season doesn’t start until mid/late December.

  9. My husband and I are newlyweds and we are going to hawaii for 7 days at the beginning of December. Figured this would be one of our last trips before we start working on a family so we want it to be fun and romantic 🙂

    We are flying into Honolulu but we really want to experience two islands while we are out there. I have been doing a little research but cannot find itineraries for two island trips (general ones like how to get to one island to another, rent a car? Take the ferry? Etc…). We really want to see Oahu and Maui.

    We are thinking to stay at Turtle Bay Resort for the first part of the trip and do more “tourist” types of things like the Dole farms, Pearl Harbour and just relaxing at the resort. Then we really want to go to Maui for the second part of the trip to do more adventurous activities. Lastly, back to Oahu for the last night (since we already booked our flights arriving and departing from Oahu).

    Any helpful tips on getting to and from the islands would be great! Other tourist type things during December? Is December a good month to explore these two islands? Is it worth trying to visit both islands within 7 days? Actually, any tips would be greatly appreciated!!!

    Thanks for the help!!

    1. The only way to get to Maui from Oahu is flying. See my article on inter-island travel in Hawaii –

      With 7 days, I’d encourage you to stick with either Maui or Oahu. When you consider the amount of time you spend packing, checking out of the hotel, returning rental car, waiting for flight, flying, getting rental car, checking into next hotel, etc….you’ve used a lot of valuable vacation time with not-so-fun travel logistics. There’s really so much to do on each island.

      Before about December 21st, the rates are normally pretty good as the tourist demand is low.

  10. Hi,
    I’ve tried to access the “trip details” for the Hawaiian Airlines Kauai itinerary “Seven Perfect Days in Paradise” but it takes me to the airline’s homepage. I searched there but no luck. I’ve googled and came back to the general itinerary. I’d love those details for estimated time, etc… per activity. Any help or suggestions?

    PS – leaving Saturday!

    1. Brian – our only suggestion would be to contact Hawaiian Airlines. We don’t have any control over their website.

      1. Thanks for the quick reply. Our flights are booked with them, so hopefully they can direct us to the page. Thanks for the help! Love your suggestions and site. Been very helpful in our planning. Looking forward to a great 30th anniversary trip!

  11. Trying to plan a trip for June. Thinking of staying in Maui but really want to see Pearl Harbor. Will only be there for a week, this is an anniversary trip. Any help would be appreciated.

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