Charter a private 3-hour Casco Bay cruise for up to 6, with lighthouses and island views
3 Hours
Up to 6 people
Private cruise, Captain, Restroom
Cruise Casco Bay on a private 3-hour powerboat charter designed around your interests, from sightseeing to local maritime history. Ride past iconic lighthouses like Portland Head Light and explore Portland’s waterfront from the water.
Default pickup is Sunset Marina in South Portland; pickup in Portland is available for an additional fee—confirm the amount with Greetwell before booking. Gratuity is not included.
If the operator cancels due to weather or other unforeseen circumstances, you can reschedule or receive a 100% refund. Cancel 7+ days before departure to reschedule or receive a 100% refund. Less than 7 days, no-shows, or late arrivals are charged full price.
Dress in layers; it can feel cooler and windier on the water, and it can cool quickly after sunset (especially early in the season). Bring sun protection (sunscreen, hat, sunglasses), wear soft-soled shoes, and consider a raincoat. You can bring your own food and drinks; pack a cooler if you want to keep items cold.
Yes. You can bring your own food and drinks of any sort; pack a cooler if you want to keep items cool.
No. Pricing does not include gratuity. If you choose to tip, you can add gratuity to a credit card, Venmo, or give cash.
Portland, Maine
Bug Light Park sits on the edge of South Portland, looking out across the sparkling waters of Casco Bay toward the Portland skyline, and it offers one of the most photogenic vantage points anywhere along the Maine coast. The park is named for the diminutive Portland Breakwater Light, affectionately called Bug Light, a tiny but ornate cast-iron lighthouse modeled after a Greek monument that has guarded the harbor entrance since 1875. From the water, Bug Light Park reveals itself as a green ribbon of shoreline, dotted with picnickers, kite flyers, and history seekers exploring the World War II shipyard memorial that honors the Liberty Ships built on this very site.
On a private three-hour charter across Casco Bay, Bug Light Park becomes a natural highlight as you glide past its rocky shore and pause near the breakwater for unbeatable photos of the little lighthouse with Portland's working waterfront framed behind it. The salt air carries the cries of gulls and the distant clang of harbor bells, while the captain shares stories of the bay's lobster boats, ferry routes, and centuries of maritime heritage. After cruising past Bug Light Park, the charter weaves among the Calendar Islands, offering contrast between the manicured grassy point and the wild, spruce-clad islands further out, where seals often haul out on sunlit ledges.
This experience is ideal for couples seeking a romantic afternoon, families wanting an unhurried introduction to Casco Bay, and photographers chasing that perfect golden-hour shot of Bug Light Park from the water. History lovers will appreciate the shipyard tales, and anyone who has only seen Bug Light Park from land will discover how completely different, and how much more magical, it feels when approached by sea. With just your group aboard, the captain can linger here as long as you like, making Bug Light Park the kind of memory that defines a Portland visit.
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.
Beautiful, intimate cruise with knowledgeable and kind captain and guide.
Bryce Ferguson
October 18, 2025
Beautiful, intimate cruise with knowledgeable and kind captain and guide.
Bryce Ferguson
October 18, 2025