Private Half Day Sailing Charter in Portland Maine

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast-guard certified captain, allows you to cruise through Casco Bay, enjoying views of iconic landmarks like Portland Head Light. With options to swim in secluded spots or simply relax, every charter is tailored to your group's preferences. Enjoy light refreshments and the chance to take the helm or trim the sails, making for an unforgettable day on the water.

A half-day sail is one of the easiest (and best) ways to get out on the water and 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.

• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Public transportation options are available nearby
• Specialized infant seats are available
• Suitable for all physical fitness levels

For a full refund, cancel at least 24 hours before the scheduled departure time.