Hi! My boyfriend and I are planning our first trip to Hawaii for end of September – beginning of October 2008. We’re not yet sure about specific dates or how long we'll stay (most likely a week to 10 - 12 days). We have a timeshare with Fairfield/Wyndham, and they have properties in either Honolulu or in Kailua-Kona (Big Island.)
A little bit about us: We are in our early 30s, live busy, hectic New York City lives, and while we love the citylife, we would favor a relaxing, quieter getaway rather than shopping, big cities, etc. We love nature, hiking, kayaking. We want to swim, snorkel, see national parks, rainbows, waterfalls, lovely paradise views , volcanoes (though I worry about my allergies). My boyfriend is a kitesurfer. I love learning about foods, culture, history. We're definitely not partiers (and want to avoid the party scene). And we are on a bit of a budget.

We would very much appreciate your help with the following:
1. Is Sept-Oct a good time to visit? Is it less crowded than the summer months?
2. For first time visitors, do you recommend one island over the other (BI vs Oahu)? I know that Fodorites have recommended a week per island. Should we see both islands? Is BI quieter than Oahu? Is there more history/culture in Oahu? If we stick with BI for this trip or go to Oahu for 3 nights and stay in BI for 7 nights, are we still getting a ‘full’ Hawaiian experience (I know this has more to do with what we make of it..but I’m asking in terms of things to do and “must-sees”)?
3. I am concerned about vog (I have bad allergies). Is there a way to avoid this?
4. Any experience with Fairfiled resorts? We are considering the following properties:
Waikiki Beach Lewers Street, Honolulu
Kona Hawaiian Resort Ali’I Drive, BI
Royal Sea Cliff Ali’I Drive, BI
Mauna Loa Village Kaleioppa Rd, BI
Are certain areas quieter than others, certain resorts nicer, or less likely to be exposed to vog?
We’re planning to rent a car/scooter, and we like romantic dinners we cook together rather than eating out too much (it is a luxury to have a real kitchen compared to our tiny shoebox city kitchens).
Thank you for your help! And apologies for the naïve questions.

I think staying on Lewers Street in Waikiki might feel too busy and crowded for what you are seeking.

The Ironman Triathalon is scheduled for Oct 11th. If you are interested in seeing it...getting caught up in the excitement...watching the athletes practice then Kona will be the place to be.

We were on the BI about a week before the event years ago and were amazed at cyclists & marathon runners out there in the heat.

There is more to see & do on Oahu than any other island.

Seven nights or less, stick with one island.

Eight - twelve nights, split the time with Oahu & Big Island.

Lots of info:

http://fodors.com/forums/threadselec...1&tid=34812564

Thank you all! Any tips on which resort to select? Thanks. And what to do about vog..