So glad we did this trip! My husband and I have lived in CT our entire lives and somehow had missed this little gem. Another couple we know raved about it, so we decided to give it a try. When researching it beforehand, I checked out the website www.thimbleislands.com which gave some basics about location, times, cost, etc. The website is a bit disorganized and haphazard, I got enough info to head out. Since it was a beautiful Saturday afternoon in August when we went, there were plenty of people on the dock waiting to go on the cruise too. Yes, parking is a bit of a challenge, so I recommend just paying the $5 and parking across the street at the church. Or just "stalk" some people and hope for the best, but no one seemed to be leaving when we were looking for a parking spot! Head towards the dock at the far left of the area. There are 3 boats that do the cruise, ranging in size from like 20 people to 50 people. It appeared that they left approximately quarter of the hour, on the hour, and quarter after the hour. However, since there were dozens of people waiting on the dock, it appeared that people just filed onto the next available boat until it filled up, while the rest of the people waited for the next boat to show up. That being said, we only had to wait about 15 min to get on a boat. We happened to get the larger, two-decker boat. I originally thought I wanted to be on the top deck so I could take better pics (I take a LOT of pics!), but the top was filled so we had to sit on the lower deck. It turned out that this was better anyway. On the bottom deck I could move about and take pics off either side of the boat, while on the top deck you must remain seated at all times. It was a lovely and informative ride, going around each of the dozens of islands and admiring the amazing homes. Fun to learn about the pirates too! The entire cruise is about 45 minutes long, then allow a few minutes before and after for boarding. Afterwards, we walked around the dock and village and had an ice cream. Overall, a lovely few hours on the CT shore! If you haven't done this, don't miss out!