My husband and I typically like to travel without a rigid itinerary (ie- pre-reserved lodging/activities). Has anyone had experience "winging it" in Hawaii? We will be there in October, 2003 and would like to stay in moderately priced B&B's/hotels on four different islands. Any advice would be appreciated.

Winging it is easy once you get to Hawaii. However, I would strongly suggest you book your hotel accomodations before landing. In addition, I'm not sure how long you're staying but 4 islands is a lot of ground to cover. Expect to lose a 1/2 day each time you change islands.

Years ago booking only the first one or two nights accomodations was a great way to go becuase it was cheaper to book accomodations once you were in Hawaii. But even back then few people did it, apparently because they don't like uncertainty. These days the situation has changed and it is much harder to get the accomodations that you want and get a good price on them at the last minute. Although October is not peak season, winging it on accomodations is risky if you want to stay in quality properties. You will probably end up getting properties that are not your first choice and paying more than if you booked
far in advance of your departure.

If you want to see four islands and you don't mind being on the move a lot, then go for four islands!!!

Winging it here is not as easy as it used to be..the interisland flights are often 100% filled and last minute air tickets cost way more than prebooking.

As far as lodging, why not line up several possibilities on each island, then call and see how they look for October vacancies. If many of them are booked or nearly so, you might reconsider and make room and air reservations, especially if you are on a moderate budget.
Most activities won't need pre booking.

About 7 years ago, in September, a girlfriend and I decided to do just that ... we did four islands in 10 days and had a ball. But ... we did have an itinerary for hotel stays and air. From that point on, we rented a car and winged it. It was an experience that I will never forget. The road to Hana in Maui was nothing compared to one road that we found ourselves on towards sunset .... but we lived to tell about it. And ... watch out for the blow holes!

If "winging it" means booking air and hotels and doing everything else spontaneously that is a matter of personal preference. Some people have to have an "itinerary" for every minute of every day (as per many posts on this forum). I personally prefer to plan nothing but air and hotel, and let everything else just happen.

Some "winging it" is fine, but I agree with other posters that you do need to book your accomodations in advance. At least on Maui, where I live, it is not easy to get last minute accomodations, especially at a reasonable price! As for activities, some you can book when you arrive, but others - like the Old Lahaina Luau - typically sell out at least 2 weeks in advance (as of July 22, it's booked through late August), so it can be important to plan ahead. Also, do you really want to waste precious vacation time arguing over what to do each day, then calling to reserve it only to discover it's sold out? I book activities for a living, and every day I have customers who can't do what they wanted to do because they waited too late to book it.