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Hawaii advice! (Open-ended.)

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    Hawaii advice! (Open-ended.)

    Hey friends! I'm so excited … The boyfriend and I have decided to plan a trip to Hawaii later this year! I've always wanted to go, and I should really just do it before I get too old or the world collapses. XD We're looking at probably planning a week sometime in the last half of October or so; well past summer tourist season but before holiday tourist season, and before the rainier winter months.

    Topic One. The most difficult thing right now is deciding which island to go to. (Since we're only planning a week there's probably not comfortable time for island hopping.) At the moment I'm leaning towards either Maui or Kaua'i, with the Big Island as a third choice. We're more interested in relaxing, seeing the beaches and lush jungles and waterfalls moreso than fancy resorts or night life or tourist traps, which is the main reason O'ahu is at the bottom of the list. And then of course there's the question of where on a given island to stay … The rainier, lusher north side? The warmer, sunnier south side? and so on.

    There are too many questions to juggle just for this forum post -- looking at hotel or condo availability, cost (trying to keep it reasonable), local sights to see, accommodations such as restaurants and shopping, and so on. But if anyone has experience from a trip and where they stayed, I'd love to hear the cliff notes from you!

    Topic Two. I'm also thinking ahead to my packing list. I'm actually a pretty adept minimalist packer and have done plenty of long-weekend, week, and two-week trips before, but this will be my first time traveling to a tropical island, so I do have to take a few extra things into account. Based on my reading online, this is my additional shopping/packing checklist so far:
    • Sunglasses (prescription).
    • Collapsible sun hat.
    • Decent comfortable sandals. (For wet beaches and swimming holes, walking locally in hot weather, etc. Looking at maybe the Hurricane XLT2 from Teva to try on.)
    • Water bottle. (I guess they avoid plastic bottles on the island, for good reason. Boyf recently bought me a Yeti so I'm good!)
    • A couple lightweight cotton shirts, breathable and quick-drying, both short-sleeve and long-sleeve.
    • Shorts, lightweight slacks, and swimsuit.
    • A small microfiber towel. (In case we get splashed somewhere without a beach towel handy!)
    • A shop bag. (For toting stuff to the beach or grocery shopping around town.)
    • Eco- and reef-friendly sunblock and mosquito repellant. (Probably will just buy these on the island.)
    Other than this I'll be packing my usual stuff … iPhone, Watch, wallet, travel jeans & belt and walking shoes on my person; eBook and iPad Mini for the flight or if I want to type up some notes while I'm there; my little bundle of chargers and charge cables and extension cord; socks, underwear, and what ever other clothes I need not listed above; and my medications and minimalist dopp kit. Oh, and a couple small LED flashlights I usually have tucked in my bag just in case. I expect I'll be able to pack most of this into my Aeronaut 30 as usual, plus I'll bring a tiny backpack with the items I want to have access to on the plane, and to use as a daybag while exploring the island.

    I can't express how excited I am planning this trip. If anyone has any experiences they want to share, general advice on where to go, or any great packing ideas I haven't read about yet, please jump in, I'd love to hear them! ❤️
    My Bags: Burnt Orange Medium Cafe BagSide Kick Luminary 15Co-Pilot Aeronaut 30
    Aubergine Small Cafe Bag
    Everyday CubeletCanary Large Shop Bag Dawn Large Shop Bag

    Cooner ! Woot! You're guys are going to have such a fun time, Hawaii is gorgeous, I'm so excited for you!

    Overall your list sounds right on track.

    With only a week, I don't think you'll go wrong regardless of which island you go to (I love Maui (ping me if you end up going there), but they all have their unique things. Just pick a spot, plop down, relax, and wallow in how beautiful it is and what unique things you can see & do. My birthday is right at the beginning of November, so end OCT/early NOV is when I usually go.. there's no real off season, but it is a bit less crowded time of year as you note.

    I've stayed in some hotels and also AirBnBs (attached to a resident's home). None of the islands are really that big, if you're used to mainland distances (everything is relative), so you're not really that far from anywhere, though of course you don't want to spend a ton of time driving. Last thing I knew, rental car supply was an issue (may be alleviated now) so definitely get your housing and car (if needed) situated.

    Many places will have beach stuff (chairs, toys, etc) that you can borrow so you don't have to bring it all, many even including beach towels (much better than buying & tossing things like some folks do, bah humbug), so that helps keep the packing light. I usually bring a nice waffle weave linen towel that packs light, to use for whatever (including as a shawl), and use the beach towels from wherever I'm staying.

    Agree that buying some basic toiletries on island is easier (support the local economy) and also some may be provided if you're at a smaller hotel/AirBnB. Always good to check. Some encourage you to use/share and leave extras.
    Also good to hit a Costco or a grocery to stock up on snacks when you first arrive, save your $ for special meals.

    Reusable bottle or collapsible bottle or water bladder; definitely stay hydrated and covered up if you're not currently living in the tropics. I'm a pasty white northern snow child who goes directly to sun poisoning in any major hit of UV, so I'm the person completely covered with long sleeves, long pants, and a hat. (if you're like me, don't forget to use sunscreen on the backs of your hands, top of feet in sandals, and your ears!)

    To me Hawaii is easy in terms of easy, casual, lightweight clothes, lots of UV blocking stuff and overall pack it in/pack it out to respect how fragile the system is. Last couple times I went (pre-covid), I used my A30 (before the T30 existed) and a shop bag as my only luggage and packed a small lightweight daypack (LL Bean Stowaway because it has water bottle pockets vs a TB DLBP) and they weren't even full.

    Comfortable sandals (I have Keen's) for most walking and decent flip flops (I have Crocs) for anything really wet/sandy and lightweight hikers of some sort if you're going anywhere on a real hike, especially on lava rocks (which are wicked rough on soles). Wear the heaviest on the plane, pack the other two.
    Lightweight, light coloured clothes overall... but breezes kick up in the evenings and you may be a wee bit chilled if tired or too much sun, so a light long sleeved shirt where you can roll the sleeves up. Works well for the slightly more 'formal' dinner places too.
    Major caveat: if you go up to the top of one of the volcano/summits for sunrise or whatever - it is COLD at the crack of dawn, so seriously pack super thin/warm long underwear, merino beanie, gloves, fleece.

    Some places will have laundry available otherwise sink wash & wear items are a plus...even with only a week, between sunscreen, salt, sweat, whatever, you may want to rise & repeat.
    I bring long sleeve UV blocking shirts for when the sun gets too much and since they're collared, they work well in the evening over a t-shirt if I need a layer or it's a nicer place.

    If you plan on any snorkeling trips or surfing, think about your bathing suit and consider a rash guard and maybe inexpensive water shoes vs flips flops or whatever.

    I hope you have a fantastic time and share some cool photos
    Last edited by G42; 06-11-2023, 04:44 PM.
    “...Horace was the only cheese that would eat mice and, if you didn't nail him down, other cheeses as well"
    -Sir Terry Pratchett, I Shall Wear Midnight


      G42 … thanks for all the info! Yeah, for late October we definitely plan to make decisions and lock in all our flight/hotel/car rental stuff in the next few weeks, as that feels like 90% of what we need to worry about. And also see if we can find something with a laundry facility, and pack accordingly.

      We're in Texas for a few years now so we're not strangers to heat and sun; however the boyf does burn pretty easily in direct sunlight, and I don't usually wear sandals so I will have to be careful about my feet and shins! And yeah, definitely thinking of buying that stuff there, not only to support local businesses but also to make sure we get eco-friendly stuff compliant with their rules to preserve the coral reefs and such.

      I've read and seen some videos about how it can get cold up near the summits of the mountains and volcanoes! I think we're more interested in the beaches and some nature and walking trails in the lower regions of the island, but I'll make sure to discuss those plans with the boyf in advance to pack warmer shells if we will need them.

      Ironically … I love the beach but I'm terrified of the ocean! XD Something about being within that huge endless expanse, whether floating at the surface or swimming underwater, just gives me all kinds of phobic heeby-jeebies. So I'll be content to wade in the shallows a bit where a swimsuit and a simple sandal or flip-flop should do be good; I'll leave the surfing and snorkeling to other folks.

      Thanks again! If we can make this trip I'll certainly post a few updates and some photos here.

      (Hmmm. I love my burnt orange color but now I'm wondering if I should get a tropical-blue colored ribbon or sash or something to tie decoratively onto my A30 for the trip …)
      My Bags: Burnt Orange Medium Cafe BagSide Kick Luminary 15Co-Pilot Aeronaut 30
      Aubergine Small Cafe Bag
      Everyday CubeletCanary Large Shop Bag Dawn Large Shop Bag


        I’ve been to all four of the main islands quite a few times, and they all have things to recommend them. So, there isn’t any question that the north shore of Kaua’i, around Hanalei, is my absolute favorite place to go. To me it’s the most quintessentially “Hawaiian”. It is lush and beautiful, with a spectacular beach and fun town to explore, and then lots of little other beaches nearby. However, it’s a little risky weather-wise…can be rainy. Fortunately, it’s only a 30-45 minute drive to the eastern and southern beaches and drier, better weather. So, if you decide to stay on Kaua’i, you can stay where it’s drier and explore up north, or stay up north, and escape to the south if the weather turns against you. Kaua’i is the oldest and most laid back of the islands, with lots to see and do (they all have lots to see and do, though). If you want a resort, Princeville is fine, but kind of isolated from the “real-Hawaii” feel, so look for something in Hanalei, or other areas nearby like Anini Beach. Or, as I said, stay south: lots of resorts and accommodations (and dry weather) near Poipu. Nothing is very far away on Kaua’i.

        Maui is also fantastic. It’s a bit bigger, with a lot more going on, but still has that Hawaiian vibe…not too much going on. Two parts of the Island where I’ve stayed are both kind of resorty: Wailea and Kapalua (Napili Bay). So many hotels/condos/resorts to choose from. Just look around and pick something in your budget near a beach that looks good. Can’t go wrong. Both areas of the island are great. Wailea is a little drier, but both are generally reliably good. I wouldn’t recommend staying in Hana (west side): very rainy…nice to visit though. Then there’s the “upcountry” to visit, when you want a break from the beaches. Some people never leave the beaches, but it’s so beautiful to head up to Haleakala, visit some of the little artists towns of Haliimaile and Makawao, and see where the locals live. Some of the best best goat cheese ever at Surfing Goat Dairy. Maui has a lot going on away from the resorts. If you decide to go to Maui, two things to book now: a car rental (true for Kaua’i too). And a dinner or lunch reservation at Mama’s Fish House, the best restaurant in Hawaii (possibly, the best in the US). Books 4-6 months in advance. Worth it…book it right after you make your plane and accommodations. I’m not kidding.

        Have fun in Hawaii! We love to visit there.


          cdgerston Thanks for all the input! I think definitely leaning towards either Maui or Kauai still, possibly Maui since there seem to be a few more "things" to do, though Kauai sounds beautiful. As a wrinkle though, I've learned that the boyf is interested in seeing some volcanic activity … We might discuss if we want to extend the trip by a couple days, start on the Big Island and tour some of the volcanic parks for a day or two as well as anything else interesting there, then hop over to a smaller island for the rest of the trip. If not we could see the volcano cone on Maui, but I think he wants to see some steam and lava.

          Yeah, I'm definitely hoping we can lock down the broad details of our trip within the next few weeks, get our plane tickets, hotel reservations, and rental car all set up before things start getting more expensive or becoming unavailable.

          If we go to Maui I'm REALLY on the fence right now with what to do about Hana. It seems like there's a few interesting-looking black sand and red sand beaches there, plus the relaxed remote town vibe, but I've read very mixed reviews on the few hotels and amenities there (very positive or very negative). Primarily our options would be (1) drive the Road to Hana, stay a night or two, and drive back; the drive sounds beautiful but stressful … (2) Sign up for one of those full-day Road to Hana minibus tours; much less stressful, but expensive, and you only get to spend about an hour on the beach in Hana before having to head back; or (3) skipping Hana entirely and just finding a few specific rainforest waterfalls and stuff to drive to instead of doing the whole Road to Hana all the way. Decisions decisions!
          My Bags: Burnt Orange Medium Cafe BagSide Kick Luminary 15Co-Pilot Aeronaut 30
          Aubergine Small Cafe Bag
          Everyday CubeletCanary Large Shop Bag Dawn Large Shop Bag


            Well, if steam and lava ends up on the itinerary, the Big Island is also worth a visit 😎. I didn’t list it because, well, I didn’t want to overwhelm your decision making, I don’t know it as well, and it’s third on my list, but it’s still pretty great. Volcano National Park will definitely give you lots of steam, and possibly some lava, and there is of course (if you’ve seen the news) lots of new and recent activity from the volcanos going on there, though not right in the park I don’t think? If you do decide to add a couple of days for a short trip to the Big Island, you won’t regret a trip to the Park there. Drives there are longer, but if you want to stay on the dry side, that’s Kona. There are some nice beaches, but not right in Kona. Things like that are kind of more spread out than on other islands. On the other hand, it’s a lot less crowded and busy. The other side of the island is much much wetter (Hilo), and I don’t know much about it, but it’s closer to Volcano Nat’l Park. We did a drive, from Kona down south around and up to Volcano, that included a great black sand beach (Punalu’u), that was one of the most beautiful drives of my life. It was a long day, but spectacular. So, you could do a couple days there and then hop over to Maui which is so close you can see it from the Big Island.

            As to Hana, I don’t know how to advise you. I went once a long time ago for a day trip. The road is spectacular, and daunting. It rained a lot. It was lovely, but I wouldn’t want to stay there for more than a couple of days because it’s so isolated and the weather is so dicey. But you might get great weather, IDK. We actually tried again once with our kids in the car, and had to turn back because they got too car sick: VERY curvy road. Maybe, if you plan to go back more than once to Hawaii, you can save it for a future trip. Or keep it for a day trip this time. There’s so much to see and do on Maui.
            Last edited by cdgerston; 06-15-2023, 05:13 PM.


              My two cents on the Road to Hana/Piilani Hwy -

              It's a beautiful drive with great views, but you definitely have to be patient since it's a very slow road. As cdgerston says, it is a very curvy road, lots of hairpins, narrow lanes, little to no shoulder, etc. You need to watch for folks who are enjoying the scenery more than the road, people randomly crossing, bikes (!), and some folks who go faster than is safe. You will also get tail-gated by faster/impatient drivers (some are locals who really know the road) and it may be quite some time before there's a spot for you to pull off for them to pass (and I highly suggest you do let them pass).
              I get motion sickness, so taking a tour wasn't an option.

              The Road to Hana section gets crowded and many view/activity spots don't have much pull off area for parking, so that slows things down and contributes to a lot of other issues.

              For the Piilani Hwy section on the other side of Hana, I think it's over-hyped as scary/dangerous, but it depends on what your driving experience and comfort level are and whether heights & edges bother you or not. I found most of it to be a laugh-out-loud joyful experience for the views and the sheer fun of the drive. That road and Ho'okipa Beach on the north shore are my favorite parts of Maui.

              You can check at the ranger station in the Kīpahulu District section of Haleakalā National Park (which is ten or so miles past Hana) for any current road issues. The road is well maintained up through the Nat'l Park section and they'll know if the less maintained section past that over to Kula has any issues that day.

              For reference, the first time I drove it I started in Makawao and did the whole circular drive with stops, in one reasonably long day. I brought snacks and lots of water, snagged lunch in Hana, and made it to Maui Wine in Kula for a nice tasting at the end of the gorgeous drive. From Kula back to Makawao was just time, but a nice road. (Maui Wine is about the fun ambiance)

              If I were staying out in West Maui or wanted to spend more time in that section of Haleakalā, I'd arrange for one night Hana so that I wouldn't feel rushed or drive any of it at night.
              Overall, it's just not that big an island so it's all about the time vs the distance.

              I've also done the loop around west Maui, which is very cool in a different way.
              Last edited by G42; 06-15-2023, 06:26 PM.
              “...Horace was the only cheese that would eat mice and, if you didn't nail him down, other cheeses as well"
              -Sir Terry Pratchett, I Shall Wear Midnight


                Update: WE PULLED THE TRIGGER!

                After talking about it for weeks, Sunday afternoon the boyf and I said f*** it and sat down at the computer and booked all our flights, car rentals, and accommodations. We might plan a few more things over the next couple months (i.e. dinner reservations, pre-purchase admission tickets, etc.) but right now all the basic stuff is locked in for eight nights in late October. Two nights on the Big Island, six nights on Maui.

                Here's our plan, if anyone's interested:
                • Fly into Kona on the west side of the Big Island, spend the night in a resort on the beach. (Decent discount as they'll be doing renovations on the exterior of the building during the day, but we'll only be there one night so no big deal.)
                • Next day, drive across the island, see one of the volcanos (depending on what activity is going on then), and then spend the night at an inn next to Kulaniapia Falls where we can go swimming and hiking.
                • Hop a short flight from Hilo on the east side of the Big Island up to Maui. Check into a little condo rental in Kihei on the west coast, kitchen and washing machine, ocean-view lanai, and a short walk past the pool and across the lawn to the beach.
                • Six days later, fly home directly from Maui.
                Whereas the two days on Big Island will be pretty hectic, the six days on Maui will be more relaxed and see-how-we-feel. Among some possibilities:
                • Visit various beaches other than the one outside our condo.
                • See the Maui Ocean Center Aquarium.
                • Visit Twin Falls or some other rainforest waterfall type area.
                • Spend a day up in Lahaina, the old capital with what looks like a pleasant old downtown area and a park under one of the world's oldest banyan trees.
                • Visit Haleakalā National Park, if we're not already volcano'd out after the Big Island.
                • Find lots of local restaurants and food trucks and fresh fruit and produce. :9
                We thought long and hard about the Road to Hana, but ultimately the drive sounds stressful and the guided tours are expensive and take up a lot of hours. While Hana sounds very charming with some nice beaches, we'll be sitting on an island chock full of charming areas and nice beaches. XD Maybe we'll save Hana for a future trip, if we ever pull this off again. Also for the future: Maybe visit Kauai or Oahu.

                For now … I'm very excited, and I've got three and a half months to pay off this credit card debt. XD Thanks for the input, everyone!
                My Bags: Burnt Orange Medium Cafe BagSide Kick Luminary 15Co-Pilot Aeronaut 30
                Aubergine Small Cafe Bag
                Everyday CubeletCanary Large Shop Bag Dawn Large Shop Bag


                  Another update!

                  Man, it was heart-wrenching and tragic watching news about the wildfires on West Maui last month. So much loss and pain and uncertainty all those people have to endure now, so many having lost everything … I hope they'll be able to rebuild and be made whole again somehow, even though it will take years at best.

                  Of course, not to take away from all that real suffering, it also potentially affected our plans as well … I've always been very sensitive about making our visit as respectful as possible, to avoid being the stereotyped horrible American (mainland) tourists, and suddenly everyone was saying to keep away from Maui and leave them alone. We didn't want to cancel the trip we'd waited so long to plan, but of course we would if that were the right thing to do … but I also wondered, can they really just shut the entire island down indefinitely …?

                  Fast forward a few more weeks, and it looks like our travel plans should generally be okay and intact as-is. The islands need tourism dollars to sustain their economy, and while on one level lefty-me sees that as another indictment against rampant capitalism, I'm also glad if our visit will help inject a few more dollars (above the ones I donated after the fire) and help the locals out a bit. Our plan, even moreso than before, is to visit respectfully and honorably, enjoy the local scenery and customs, and tip as generously as possible.

                  We're staying in a condo in Kihei and have already heard from them that our reservation is still good. Sadly, the one thing on our list I was really looking forward to, spending a day (maybe two) in Lahaina to see the old capital, walk the waterfront and visit the banyan tree park, is now completely off the table. Not that I expect we'll have a shortage of other activities to fill the time there, but I am sad over the loss and that we missed visiting there. (While I've never been I had watched several walk-through videos on YouTube, so I feel like I've been there on some level and somehow makes the loss a bit more real to me.)

                  So yeah, a bit of solemnity involved, but our visit is still on.

                  (Also unfortunate: Unrelatedly, American cancelled our return flight home leaving Saturday evening, from Maui to Denver to Austin. The only flight I was able to rebook leaves Saturday lunchtime, from Maui to San Francisco to Chicago to Austin. So we lose one "day" of bumming around Maui, have three flights instead of two, and get home around the same time anyway. Extremely annoying, but oh well, what can you do.)

                  Anyway, as fits the interests of this message board, my plan is still to travel with my A30, with a few shirts and shorts (we'll have a laundry at the condo) and a Shop Bag and sun hat and Yeti water bottle in the main compartment, my dopp kit and charge pouch in one end pocket, and my sandals and swimsuit in the other end pocket. I'll also have my teeny tiny backpack/crossbody convertible with my iPad Mini, Nook, sunglasses, and a few other odds and ends to have handy for the flight AND to use as a little daypack when we get there.

                  Aloha and be well everyone If I think of it I'll try to post some packing photos when we get ready for the trip in late October.
                  My Bags: Burnt Orange Medium Cafe BagSide Kick Luminary 15Co-Pilot Aeronaut 30
                  Aubergine Small Cafe Bag
                  Everyday CubeletCanary Large Shop Bag Dawn Large Shop Bag