Escape completely, as nothing compares to the great views along the island shoreline. You get a really nice onboard experience, the perfect mini-trip. We love it and so glad our travel agent turned us on to the scene.
There are a lot of good sailboat rides to choose from, and that makes it cost competitive. I think the prices are very good for what you get. You don't need much except for your camera, maybe a video camera if you want to shoot a longer scene of the beauty .
You will likely see some dolphins, and of course the waterfront area is really nice to see from the boat. You can even see the Lighthouse look out tower from the water. We were staying at the Hyatt Front Street location and could watch the sale both, and that got us even more psyched up to do this. The Western Union was a big one we did years ago and love that.
Just a comment on the best way to go sailing. You want to prep up properly and stop in at Bagatelle for one or two of the fancy island style martinis. You will love them and they you can sail away with the right island vibe.
Going on the boat rides is a definite must do item to put on your Key West itinerary. Picking out which boat you want can be kinda complex, or just go on one of the catamaran boats which are Very Entertaining. You can get discounts and coupons if you look in the little magazines that are at some of the larger hotels, or wherever the new stand is located. The free magazines are loaded with discounts for the water sports.
The water is so calm, it is easy to spot the Underwater action. Easily, this is the best spot to rent a kayak in the lower keys. We really like the area a ton and come down three or four times a year, during the summer months. Kayaking is just more pleasurable here, about two hours is what you would need. This Hurricane Hole Marina is excellent and completely satisfied us during our one week vacation.