• 1 Cutter St - Embarking on a half-day sail is one of the most delightful and straightforward ways to explore the Maine coast from a fresh perspective. This private sailing charter offers a leisurely few hours—sailing through Casco Bay, admiring the scenery, pausing for a refreshing swim, and enjoying the stunning views of Maine from the deck with refreshments in hand.

Each journey is customized to suit your group and the day’s wind conditions, but a popular and frequently requested sailing route starts in downtown Portland and ventures into Casco Bay. From there, the sail passes by Portland Head Light for an up-close view from the water and navigates through the iconic rocky islands that make this coastal stretch so distinctive. When the moment feels right, the anchor is dropped so guests can swim, unwind, or simply absorb the surroundings before a serene sail back to the harbor.

• Option to take the helm or brush up on your sailing skills
• Private transportation
• Snacks
• Use of snorkeling equipment
• Alcoholic beverages
• A flexible route based on conditions and your vibe
• Time to swim or relax at anchor

• Onshore stops for exploring (like Peaks Island). For onshore stops, check out full-day options.

A half-day sailing charter provides a distinctive and personalized opportunity to discover the breathtaking Maine coastline. Setting sail from downtown Portland, this exclusive journey on Sasa, a family-operated small business charter sailboat, led by a coast-guard certified captain, lets you navigate through Casco Bay, taking in sights of famous landmarks such as Portland Head Light. With choices to swim in hidden spots or simply unwind, each charter is customized to suit your group’s desires. Delight in light refreshments and the opportunity to steer the boat or adjust the sails, ensuring a memorable day on the water.

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