Take a private 2-hour cruise for up to 6 in Casco Bay
2 Hours
Up to 6 people
Private boat, Captain, Restroom
Explore Casco Bay on a private 2-hour powerboat cruise, customized to your pace and interests. Cruise past lighthouses, islands, and Portland’s working harbor with an experienced captain.
Pickup is at Sunset Marina in South Portland by default; pickup in Portland is available for an additional fee—confirm the amount with Greetwell before booking. Gratuity is not included.
Full refund if the operator cancels due to weather or other unforeseen circumstances. Cancel 7 days prior to departure for a 100% refund. Cancellations made less than 7 days, no-shows, and late arrivals after departure time are charged the full price.
Dress in layers (it can feel cooler and windier on the water), and consider bringing a windbreaker or warmer layer. Bring sun protection (sunscreen, hat, sunglasses), wear soft-soled shoes, and pack a raincoat if you want extra coverage.
Yes. You can bring your own food and drinks of any sort. If you want to keep items cool, plan to pack a cooler.
Yes. Lap blankets are available. If there’s rain, you can stay dry under the dodger and in the cabin.
Portland, Maine
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