Embark on a personalized sailing adventure in Casco Bay, exploring iconic lighthouses and rocky islands. Swim, relax, and savor the coastal beauty.
Embark on a personalized sailing adventure in Casco Bay, exploring iconic lighthouses and rocky islands. Swim, relax, and savor the coastal beauty.
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1 Cutter St - Each sailing day trip in Maine is entirely customizable, designed to align with your group’s ideal day on the water. Whether it’s exploring islands, sailing by lighthouses, or anchoring in a secluded cove for a swim, the aim is to provide a day that is effortless, personal, and truly enjoyable.
Example Itinerary:
Every trip is…
- 1 Cutter St - Each sailing day trip in Maine is entirely customizable, designed to align with your group’s ideal day on the water. Whether it’s exploring islands, sailing by lighthouses, or anchoring in a secluded cove for a swim, the aim is to provide a day that is effortless, personal, and truly enjoyable.
Example Itinerary:
Every trip is customized to your group and the day’s wind conditions, but a popular and frequently requested sailing route starts in downtown Portland and heads into Casco Bay. From there, we’ll sail past Portland Head Light for a close-up view from the water and navigate through the iconic rocky islands that make this coastline so distinctive. When the moment is right, we’ll anchor so you can swim, unwind, or simply take it all in with refreshments in hand, before a serene sail back to the harbor.
- The option to take the helm, trim the sails, and brush up on your sailing skills
- Snacks
- Alcoholic beverages
- A flexible route based on conditions and your vibe
- Beautifully outfitted sailing yacht, coast guard certified captain + crew
- Time to swim or relax at anchor
- The option to take the helm, trim the sails, and brush up on your sailing skills
- Snacks
- Alcoholic beverages
- A flexible route based on conditions and your vibe
- Beautifully outfitted sailing yacht, coast guard certified captain + crew
- Time to swim or relax at anchor
- Onshore stop for lunch, shopping, or exploring. For this bonus adventure, book our full-day charter.
- Onshore stop for lunch, shopping, or exploring. For this bonus adventure, book our full-day charter.
Maine offers numerous opportunities to enjoy the water, but this charter service ensures each experience is personal, relaxed, and truly unforgettable. As a small, family-operated sailing charter, the yacht Sasa is meticulously restored and elegantly equipped to provide a warm, inviting, and comfortable atmosphere from the moment guests come aboard….
Maine offers numerous opportunities to enjoy the water, but this charter service ensures each experience is personal, relaxed, and truly unforgettable. As a small, family-operated sailing charter, the yacht Sasa is meticulously restored and elegantly equipped to provide a warm, inviting, and comfortable atmosphere from the moment guests come aboard.
Each sailing day trip in Maine is entirely customizable, tailored to the group’s ideal day on the water. Whether exploring islands, sailing by lighthouses, or anchoring in a secluded cove for a swim, the aim is straightforward: to provide a day that is effortless, personal, and genuinely enjoyable.
- Our charters are family-friendly. We’ve spent countless hours sailing with our own children, starting as young as 7 weeks old, so little ones (even infants) are always welcome.
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.
