This is a great way to see San Diego's Big Bay and have fun doing it. Don't worry that you are going to get thrashed around and seasick unless it is a super, super, SUPER windy day and there are huge white caps all over the bay. Even then this boat is so well designed and smooth I doubt even then you would get sick. But then that could be fun too ;-) With that being said you do not want to go out on a dead calm day either because you will miss the whole fun of sailing with the sails up.
The regular large boat bay cruises I have been on are fun but I think this one is the BEST.
They tack back and forth across the bay so you REALLY get to see much more of the bay then if you just past by something once which is what happens on the bay cruises.
In addition you will get a chance to steer the boat and take a turn at the cranks for bringing the sails up and tacking so you get to experience a bit of what is was like to race this boat.
The crew is super nice and the 3 hours seems to go by way too fast.
So if you are from out of town or even a local I highly recommend this trip.
And as long as you are down on Shelter Island there are several restaurants that have great views after your sail like the Bali Hai or Coastterra or if it is a nice day reserve an outside table at the Kona Kai's Vessel's restaurant and get a nice view of your boat and the Kona Kai marina while you dine. And don't forget to save time to walk beautiful Shelter Island.
Tip- Make sure to get there early to watch the video presentation that takes place 30 minutes BEFORE the sail. Even if you think you know everything about sailing and the America's Cup it is very interesting and makes the sail that much more fun.
Also the crew is 90% volunteer so if you enjoyed your sail I am sure they would appreciate a tip which you can drop in the jar after the sail which is located in the office
And no need for a cell phone or camera that you could lose overboard because they will take all the pictures and send them to your email address for no extra charge!