Custom Sailing Adventures in South Portland, Maine
Difficulty
easy
Duration
2–6 hours
Fitness Level
Suitable for most fitness levels; minimal physical exertion required but able to move safely on deck.
Overview
Set sail on a private, custom adventure in South Portland, Maine. Perfect for birthdays, corporate events, or romantic evenings with stunning coastal views.
Custom Sail
2, 4 or 6 Hours • Up to 6 People • Ages 18+ to Book
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About This Adventure
Embark on a unique sailing voyage aboard Endurance, perfect for any occasion—be it a birthday, corporate event, or romantic evening. With options for 2, 4, or 6 hours, this unforgettable experience promises stunning views and cherished memories on the water, making every moment truly special.
Duration
2, 4 or 6 Hours
About
Whether it's a birthday party, corporate event, family gathering, bachelor or bachelorette party, or a romantic evening, a sailing voyage aboard Endurance is a memorable experience!
Adventure Tips
Dress in layers for changing weather
Maine's coastal weather can shift quickly; bring a windbreaker or warm layers even in summer.
Arrive early for boarding
Arriving at least 15 minutes before your scheduled sail helps ensure a smooth departure.
Bring seasickness remedies if prone
If you tend to get seasick, pack medication or natural remedies for comfort onboard.
Wear non-slip shoes
Choose footwear with good grip to move safely on the wet deck.
Local Insights
Wildlife
- Harbor seals frequently spotted near shore
- Ospreys nesting along coastal trees
History
South Portland’s maritime heritage dates back centuries, with historic shipbuilding and fishing industries shaping the community.
Conservation
Efforts to protect Casco Bay’s marine ecosystem include monitoring water quality and supporting sustainable boating practices.
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Adventure Hotspots in Portland
Frequently Asked Questions
Recommended Gear
Windbreaker or waterproof jacket
Protects against wind and spray to keep you comfortable throughout the sail.
all specific
Non-slip deck shoes
Ensures safe footing on the wet boat surfaces.
all specific
Sunscreen
Protects your skin from the reflected sun off the water.
summer specific
Seasickness medication
A helpful precaution if you are prone to motion sickness on the water.