Private Half Day Sailing Charter in Portland Maine

d experience the Maine coast from a completely different perspective. This private sailing charter is designed for a relaxed few hours—cruising through Casco Bay, taking in the views, stopping for a refreshing swim, and enjoying the best view of Maine from the deck with refreshments in hand. Each trip is tailored to your group and the wind conditions that day, but a frequently requested, guest favorite sailing route begins in downtown Portland before heading out into Casco Bay. From there, we'll pass Portland Head Light for a close-up view from the water and weave through the classic rocky islands that make this stretch of coast so unique. When the timing feels right, we’ll drop anchor so you can swim, relax, or just soak it all in before a peaceful sail back toward the harbor.