If you have enough sailing experience and complete a decent sailing resume, a charter company may let you take out a sailboat even if you don’t have a captain’s license. Each company is different and I’m not advocating you do this unless you have some serious experience. Even if you can sail without a captain, should you get a captain? It costs around $125-$150/day plus tips.
On our trips we have had 4 or 5 couples. My cousin took the captain role and I took the first mate/organizer/facilitator role. I found that it just wasn’t very relaxing because I was worried if people were having a good time and was worried about getting going so we got to our next spot in time and helping with the sailing. THIS TIME – we’re getting a captain. This is partly because it’s an area we’ve never been in, it’s partly because anchoring overnight has been a nervous point for us in the past, and because we want to be able to fish a bit while we’re moving and not worry about the sailing as much. The only thing I worry about is getting someone who is fun and makes for a good guide.