The city is next to a port, so you definitely want to go sailing in the sea. We had booked our sail with Maine Sailing Adventures. It was a wonderful experience. The crew was very friendly and I would definitely recommend them for anyone who is looking to go sailing in Portland or even the rest of Maine. The weather in Portland is generally on the colder end. So remember to carry your jackets when you go sailing. It WILL get colder out on the waters. But the cold is totally worth the view.