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What things should we do in Hawaii? | Don't Ever Look Back

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RTW Destination #1: Hawaii

RTW Destination #1: Hawaii

Decisions. It seems like we’ve been making plenty of them lately for our round-the-world adventure but that’s just part of the fun, right?

Firstly we had to choose between Fiji or Hawaii as to which would be the first stop on our travels. After nearly a month of consideration, we chose Hawaii and booked one-way tickets for July 26. All seemed to be going along swimmingly until I found out that my Canadian working visa application was rejected, leaving us with some very difficult choices to make.

There were strong temptations to bring our adventure forward a month so that we could get to Europe in time for La Tomatina and Oktoberfest but we soon realized that we weren’t in a realistic position to make this happen. So instead, we booked the next leg of our North America travels – plane tickets from Maui to the US mainland (Seattle). As a result, the first destination on our trip has now been completely locked in…

16 nights in Hawaii.

Waikiki Beach

Our first night will be at Waikiki Beach - but we want YOU to tell us where to go next!

Could there be a more perfect way to kick off our adventures in style? A mixture of beaches, hiking and general relaxation seems like a perfect way to begin our long-term travel experience. But it’s not the activities that we’re most excited about – it’s the chilled, carefree nature of traveling we’re about to experience that we’re looking forward to the most.

To put our 16 nights in Hawaii into perspective, our last visit to the USA in 2009 was also for 16 nights but took in 6 different cities, 8 different hotels and absolutely destroyed our savings accounts.

For us, that’s just not the way traveling should be experienced.

We want to do this very differently.

In addition to traveling a lot slower and enjoying our time away a lot more, we’ve decided that we want Don’t Ever Look Back readers to be as involved in our travels and we want your help! So please, help us plan our Hawaiian adventures!

1. How many islands should we fit into these 16 nights?

We know we’re starting on Oahu and departing from Maui so that’s at least 2 of the Hawaiian islands we’re visiting. Is a week on each island the perfect amount of time, or should we incorporate another into our itinerary?

[polldaddy poll=4987587]

We can’t wait to see the results of the poll in a week’s time!

2. What should we do during our time in Hawaii?

As we’ve already mentioned, some things are essential to any visit to Hawaii such as relaxing on the beautiful beaches, hiking across the islands (particularly Diamond Head State Park for us) and doing a Pearl Harbor tour. We’ve also got a few unique experiences planned, including hopefully hiring a Smart Car for a day which is sure to result in some hilarious adventures. But 16 nights is a long time and we’ve got plenty of time to fill…

So the question we’re asking is this: if you had 16 nights to spend in Hawaii, what are some of the things you would do?

3. Accommodation, dining and nightlife recommendations.

If you’ve been to Hawaii before, we want your very best advice! Tell us your favorite places to eat, where we can enjoy ourselves after dark and if you have any hotel/hostel recommendations.

4. Challenge us!

One of the reasons we’re doing this trip is to try completely new things and step far outside our comfort zone. If you can think of something out of left field for us to do, we would love to hear your ideas! Although we can’t guarantee that we’ll be able to go through with it, put it out there and we’ll see what we can do!

Please leave your answers to these questions in the comments below or send them to us privately using our Contact form!

Image Credits: Koolau Mountains Image: Hawaii Tourism Authority (HTA) / Chuck Painter, Waikiki Beach Image: Hawaii Tourism Authority (HTA) / Joe Solem


  1. Posted April 29, 2011 at 5:17 pm | Permalink

    On Oahu I’d definitely recommend the Ali’i Tour at the Mac Nut Farm and hiking around the Pali Lookout area. Check out my blog for more things to do here!
    Lisa @ Oahu Mom recently posted..May Day Weekend 2011- April 30 and May 1

    • Posted April 29, 2011 at 5:34 pm | Permalink

      Thanks Lisa – that’s a great suggestion and one we had no idea about! Had a quick look at your blog and there’s a ton of awesome information on there, will definitely trawl through it all when I find the time. 🙂

  2. Posted April 29, 2011 at 5:24 pm | Permalink

    So excited for you guys! If you’re going to add a third island, I vote for the Big Island, simply because I really wish I could have gotten over there to visit Volcanoes National Park!

    I’ve never been to Maui, but Oahu has a ton of stuff to do! Definitely get up to the North Shore. And you can’t skip snorkeling at Hanauma Bay. It’s touristy, yes, but for good reason.

    My “challenge” to you is to go shark cage diving on the North Shore!! Hawaii Shark Encounters in Haleiwa is the way to go.
    Amanda recently posted..Love to Laugh Don’t Miss Chicago Improv

    • Posted April 29, 2011 at 5:37 pm | Permalink

      Thanks Amanda, we can’t wait! At the moment the Big Island is the next on our list, but we’re interested to see if anyone has compelling reasons to visit any of the others.

      I’ve saved a lot of your Hawaii posts for reference and have added snorkeling at Hanauma Bay to our list. Believe me, we’ve got nothing against touristy things and we seem to enjoy most of them haha.

      And that’s a brilliant challenge! If we do it, we can only hope that there will be sharks this time around! 🙂

  3. Posted April 29, 2011 at 7:53 pm | Permalink

    Ok so in Oahu, there’s a really nice drive up along the east coast of the island, and if you go to around.. to the NW of the island there’s an awesome place called Sunset Beach, where I spent a few days staying… Which is beautiful! Other than that I spent most of my time in Oahu in Honolulu. (I also did a one day film tour of the island, where they drive you round in a 4×4 and show you where Jurassic Park and other films were shot.. That was pretty cool!)

    I voted to go to the Big Island too, I stayed there for a week, but in reality you could do most of it in 3 or 4 days. It has black sand beaches which I really dislike so I wasn’t a huge fan. Other than that, there are loads of places to go snorkelling (with sea turtles!). Also worth a trip to the volcano. You can walk right up to where the lava flows into the sea which is pretty cool. Also visited rainbow falls which is a HUGE waterfall (with loads of rainbows!). Oooh, and I went whale watching but got soooooo seasick! My non-seasicky boyfriend enjoyed that though!

    Maui is probably the best place to choose to go to last. It’s the most chilled and laid back, and I spent most of my time relaxing and sunbathing. But you MUST drive the Hana Highway. It one of the best roads in the world, has amazing scenery – waterfalls and such.

    i have loads of photo albums of hawaii on Facebook so you can check those out too! 🙂
    Lauren recently posted..I Bought My Backpack!

    • Posted April 30, 2011 at 3:20 pm | Permalink

      Thanks for so much great advice Lauren!

      We do plan on exploring some of Oahu by car so will try and check out Sunset Beach. It’s a shame that it’s not surfing season (same goes for whale-watching season too!) but I guess we’ll have to make do with the warm, sunny weather haha.

      We’re starting to get sold on the Big Island and squeeze it in between Oahu and Maui. Swimming with sea turtles, the volcano and rainbow falls all sound amazing!

  4. Posted April 30, 2011 at 1:57 am | Permalink

    Hawaii seems like a great first stop on a trip. It’s still the US, so you’re not completely jumping into an uncomfortable, unfamiliar environment. But you’re also experiencing plenty of culture that you wouldn’t get in the lower 48.

    I have one goal when I eventually visit Hawaii: To see snow! Most likely on Mauna Kea, during winter. But it’s probably too late for that this year.

    Also, Kalalau Trail is consistently rated one of the most dangerous hikes in the world. So for me, I’d want to give it a shot!
    Scott – QuirkyTravel recently posted..See rock &amp roll history at Sun Studio in Memphis

    • Posted April 30, 2011 at 3:33 pm | Permalink

      Definitely agree Scott – it’s gonna be a great way to ease into long-term travel.

      Snow in Hawaii would be very cool, we would love to see that as well!

  5. Posted April 30, 2011 at 2:46 am | Permalink

    I’ve only been there for a couple of days, all on Oahu, but my picks are Sunset Beach (you can drive or catch the bus – over to the other side of Oahu), hiking Diamond Head where you can get some pretty incredible views, and snorkelling in Hanauma Bay. Enjoy!
    Claire recently posted..Postcard- From Boston with love…

  6. Posted April 30, 2011 at 3:14 am | Permalink

    Dunno about Hawaii, but when you hit Seattle, I’d be happy to take you out to show you the ropes of geocaching (the headquarters of this world-wide game of hide ‘n seek.) Tons of incredibly creative cache hides here, and a great way to see some of the best hidden corners of the Emerald City.
    Dyanne@TravelnLass recently posted..Apostille- Ashmostille – Who Knew

    • Posted April 30, 2011 at 3:38 pm | Permalink

      Geocaching looks very interesting and sounds like a great way to explore a city! Thanks for the offer Dyanne, we might just take you up on that! 🙂

  7. Posted April 30, 2011 at 8:11 am | Permalink

    We only went to Maui, which was good but quite expensive and there isn’t heaps to do there that you can’t do anywhere else from what I’ve heard. We’ve heard awesome things about Kauai and the Big Island…Kauai is a must-see place. If you do go to Maui, though, there’s an amazing sushi place there (can’t remember the name but everyone will know it) – definitely worth a splurge if you like that.
    Andrea recently posted..Five Course Tasting Menu at Bodega Ruca Malen Mendoza

    • Posted April 30, 2011 at 3:41 pm | Permalink

      We haven’t looked at our budget yet but if we can keep accommodation expenses low then hopefully we won’t spend too much!

      I think having a bit of relaxation on Maui before we get started on the mainland will be a really good thing and Amy is very keen to check out the sushi place (though personally I can’t eat the stuff!).

  8. Posted April 30, 2011 at 9:34 am | Permalink

    I could easily spend a week just on Oahu, there is so much to see and do (or not also)!

    I voted for just 2 islands even though I have never been to Maui, but people love it. I have only done Oahu and love it every time I go, but I am finally going to The Big Island this summer! Can’t wait!

    For Oahu, North Shore and Windward sides are a must. I could spend days just sitting around Windward (love the area around Ka’a’awa), it’s so beautiful!

    Can’t wait to read about your time there!!
    Rebecca recently posted..New Zealand- Mt Cook and around

    • Posted April 30, 2011 at 3:44 pm | Permalink

      Awesome Bec – I think we’ll be spending a week on Oahu and then working the rest out from there. The North Shore is high on our list and I’m sure we’ll find some time to check out around Windward as well.

      When will you be at The Big Island? If it’s early August, let us know!

  9. Posted April 30, 2011 at 12:09 pm | Permalink

    Great first choice! I’ve never been, so I don’t have any suggestions.. but I’m sure you’ll pick the perfect places and have a great time!
    Seattle Dredge recently posted..The Royal Wedding Destinations

  10. Posted April 30, 2011 at 4:06 pm | Permalink

    If you only can, visit four or more islands for more stories and photos. Enjoy. Happy weekend! 🙂
    Rizalenio recently posted..Malate Church

  11. Posted April 30, 2011 at 11:28 pm | Permalink

    Hope you have lots of fun on your trip. don’t know about hawaii but will love to hear more about your travel experiences.

  12. Posted May 2, 2011 at 2:50 am | Permalink

    I’ve been to Maui twice and both times spent about two weeks there. We never ran out of things to do.
    On our first trip we went up to the top of Haleakala to watch the sunrise and I would recommend you do that. The peak is about 10,000 feet I was hit with a bit of altitude sickness, but I still managed to crawl out of the car to see the sunrise. It was amazing. There are a bunch of tours that can take you up if you don’t want to drive on your own, and most of then combine it with a bike ride back down. It looked like that would have been a fun option.
    We drove the road to Hana, and while most people rave about it, we found it a bit lacking. I think we were there at the wrong time of year though. It was winter and a lot of the water falls that people rave about were barely just trickles. Not sure what they are like in the summer. If you do the Hana drive, that could take up two days of your time. It really does take a good day to drive to Hana, and turning around to go back would have made it a really long day of driving.
    There are a ton of different beaches to experience. Big Beach in Makena was great, but if you are adventurous, climb over the out-cropping of rock at the north end and try out Little Beach. It’s the unofficial nude beach. If you haven’t ever done it, that is the place to try it out. Totally diverse group of people. Hippies, gays, families, retired couples. Everyone was very welcoming and the water is great for body surfing.
    We found the best deal on a rental car at http://www.aloharentacar.com/ . We wound up getting a Jeep convertible, which was awesome to drive around the island.
    Have a great time!
    david recently posted..Help Me Plan My Road Trip

  13. Posted May 5, 2011 at 12:47 pm | Permalink

    Just by looking at that photo, I can imagine how much fun and great time you guys will have. Especially like you said, beach and hiking. How wonderful does that sound.

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