Explore Casco Bay’s lighthouses, islands and wildlife on a seven-hour private charter tailored to your interests.
7 hrs
Up to 6 people
Private boat, Captain, Restroom
Spend a full day cruising Casco Bay aboard a classic Maine-built powerboat. Discover lighthouses, islands and coastal wildlife at your own pace.
The charter is private for up to six guests and welcomes all ages. Alternative pickup in Portland is available for an added fee; swimming and island landings depend on season and conditions.
If the operator cancels due to weather or other circumstances you may reschedule or receive a full refund. Cancel at least 7 days before departure to reschedule or receive a full refund. Cancellations within 7 days, no-shows or late arrivals are charged the full price.
Sunset Marina, South Portland, ME
Travelers consistently praise the intimate sailing experiences led by Captain Bob and his team, particularly highlighting crew members like Lucy, Chloe, Abby, and Nolan. The warmth and professionalism stand out across every review, with guests remarking on how welcomed and comfortable they felt throughout their cruises. The captains share fascinating local knowledge about Maine's coastline, wildlife, and working lobster boats, making the trips educational without feeling like a forced tour. The boats themselves are spotless and well-maintained, equipped with everything guests need for a comfortable outing. Sunset cruises appear especially popular, though midday sails get equally enthusiastic feedback. The husband-and-wife team running many of the trips creates a genuinely hospitable atmosphere, with thoughtful touches like blankets, drinks, and snacks. People appreciate the smooth booking process and describe the overall experience as relaxing yet engaging. It's clearly a family-run operation that takes pride in sharing their home waters with visitors.
Had an absolutely amazing time on the sunset sailboat! The ride was smooth, relaxing, and such a fun way to enjoy the water. The crew was friendly, welcoming, and made the whole experience unforgettable. Beautiful boat, great atmosphere, and the perfect way to spend an evening out on the water. Highly recommend to anyone looking for an awesome sailing adventure!
Justin Melanson
September 10, 2025
Had an absolutely amazing time on the sunset sailboat! The ride was smooth, relaxing, and such a fun way to enjoy the water. The crew was friendly, welcoming, and made the whole experience unforgettable. Beautiful boat, great atmosphere, and the perfect way to spend an evening out on the water. Highly recommend to anyone looking for an awesome sailing adventure!
Justin Melanson
September 10, 2025