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:
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! ❤️
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.)
I can't express how excited I am planning this trip.

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