There are many businesses that offer chartered sailboat cruises in Provincetown, and Dog Gone Sailing is one of the highest-rated. Run by the knowledgeable Captain Rosie, and staffed mainly by women, the charter is perfect for smaller groups who want a more intimate sailing experience. Sunset and sunrise cruises are available, and you'll be joined onboard by Mini, the best canine first mate in Cape Cod. Prices vary by time of year.
MacMillan Pier, Provincetown, MA, United States