Set sail on a private, custom adventure in South Portland, Maine. Perfect for birthdays, corporate events, or romantic evenings with stunning coastal views.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–6 hours
Fitness Level
Suitable for most fitness levels; minimal physical exertion required but able to move safely on deck.
Wildlife
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.
Portland Maine Sailboat Adventures
Set sail on a private, custom adventure in South Portland, Maine. Perfect for birthdays, corporate events, or romantic evenings with stunning coastal views.
Portland Maine Sailboat Adventures offers guided sailing excursions based in Portland, OR. The company operates the 36' sailboat Endurance and presents a range of public and private sails on Casco Bay and surrounding waters. Trips include a two-hour Sunset Sail, a two-hour Day Sail aboard Endurance, and customizable Custom Sail options available in two-, four-, or six-hour durations for events such as birthdays, corporate outings, or romantic evenings. Each outing focuses on scenic island views, historic lighthouses, and local wildlife observation, with attention to passenger comfort and safety.
Crews are experienced in coastal navigation and vessel handling, and safety briefings and life jackets are provided for all guests. Reservations are recommended because group sizes are managed to ensure a quality experience on board. Ticketing options cover public sails and private charters; custom sails can be tailored to timing and route preferences.
The business emphasizes straightforward booking, clear trip descriptions, and reliable departure times from Portland, OR. Photographs and trip summaries help set guest expectations before arrival. Portland Maine Sailboat Adventures has built local recognition for operating Endurance and delivering memorable nautical experiences suitable for families, couples, and small groups. Guests seeking a short coastal outing or a longer, private celebration will find flexible options and a professionally maintained vessel. For questions about accessibility, group rates, or specific itinerary requests, contact details and booking procedures are available through the business listing.
Experienced skippers adjust routes daily for weather and wildlife viewing, ensuring safe, scenic sails and consistent guest satisfaction and comfort.
Tours Offered
3
Sunset, Day, Custom sails
Trip Lengths
2–6 hours
Two-hour public sails, longer privates
Group Type
Small groups
Managed group sizes for comfort
Departure
Portland, OR
Boarding point for Casco Bay sails
Book a Sunset Sail, Day Sail, or Custom Charter aboard Endurance — limited group sizes for a better experience.
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.
Windbreaker or waterproof jacket
Protects against wind and spray to keep you comfortable throughout the sail.
all
Non-slip deck shoes
Ensures safe footing on the wet boat surfaces.
all
Sunscreen
Protects your skin from the reflected sun off the water.
summer
Seasickness medication
A helpful precaution if you are prone to motion sickness on the water.