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Maui and Kauai Activities - When to Book

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Hello All!

My fiancé and I are traveling to Hawaii on our honeymoon in the second half of October. We decided on 6 days/6 nights on Maui at the Sheraton Black Rock in Kaanapali and 6 days/5 nights on Kauai at the Grand Hyatt in Poipu. We have a list of potential activities/restaurants we would like to enjoy while we are in Hawaii and I was hoping to get some input on how far in advance we should book these activities as well as which activities are must-dos/what can be skipped. I don't want our honeymoon to feel too planned out or jam-packed with activities, so we will not be doing all of these. I am worried about making sure activities don't sell out on us, so it would be great to know a timeline for bookings and any recommendations on companies to use for some of the these would be greatly appreciated. I was thinking it would be reasonable to have one full day adventure/road trip, one half day activity, one nicer dinner out, and one dinner/activity on each island, leaving the rest of the time for exploring and relaxing at our leisure. Thanks in advance for your advice!

Maui:
-Road to Hana
-Haleakala sunrise/bike down the mountain (probably on the first day since we will be up early from the jet lag)
-1/2 day (morning) snorkeling at Molokini
-Iao Valley
-Old Lahaina Luau (I've heard to book 2 months in advance)
-Dinner at Mama's Fish House or Merrimans (how far in advance to book dinner at sunset?)

Kauai:
-Day trip to the North Shore
-Helicopter Tour
-Waimea Canyon
-Captain Andy's sunset dinner cruise on the Na Pali Coast
-Dinner at the Beach House (again, how far in advance to book dinner at sunset?)

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