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.
- 1 Cutter St - There are numerous opportunities to enjoy the water in Maine, but this charter ensures each experience is personal, relaxed, and truly unforgettable. As a small, family-operated sailing charter, Sasa is a meticulously restored and elegantly equipped yacht, designed to be inviting, cozy, and comfortable from the moment guests come…
- 1 Cutter St - There are numerous opportunities to enjoy the water in Maine, but this charter ensures each experience is personal, relaxed, and truly unforgettable. As a small, family-operated sailing charter, Sasa is a meticulously restored and elegantly equipped yacht, designed to be inviting, cozy, and comfortable from the moment guests come aboard.
Each sailing day trip in Maine is entirely customizable, tailored to your group’s idea of a perfect 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.
A half-day sail offers the simplest way to experience the Maine coast from a fresh perspective. This private Maine sailing charter is ideal for those seeking a few hours of relaxation, enjoying the scenery, and perhaps taking a swim on a warm day.
- 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.
Every journey is customized to suit the group and the day’s wind conditions. A popular and often requested sailing route starts in downtown Portland and ventures into Casco Bay. The trip includes a close-up view of Portland Head Light from the water and navigates through the iconic rocky islands that define this coastal area. At the perfect moment, the…
Every journey is customized to suit the group and the day’s wind conditions. A popular and often requested sailing route starts in downtown Portland and ventures into Casco Bay. The trip includes a close-up view of Portland Head Light from the water and navigates through the iconic rocky islands that define this coastal area. At the perfect moment, the anchor will be dropped, allowing guests to swim, unwind, or simply enjoy the surroundings with refreshments in hand, before a serene sail back to the harbor.
- 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.
