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Casco Bay Area Guide

Great Diamond Island is one of 200+ islands located within Casco Bay, which surrounds the city of Portland

Sometimes referred to as The Calendar Islands, mythically suggesting that it's possible to explore a new Island each day of year

Aquatic activities are plentiful during the warmer months. Our Guest Services Team is happy to assist with planning your day on the water


Portland Paddle – Spend a day on the water with Portland Paddle. Experienced guides offer stand-up paddle board and kayaking lessons, group excursions, and guided tours seven days per week May through September

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Maine Sailing Adventure – For a relaxed few hours on Casco Bay, consider booking a trip with Maine Sailing Adventures. These two-hour sails aboard The Frances, a replica of working coastal pilot cutters that sailed the waters of Maine in the early 1800's, will surely give you taste of summer in Maine.

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The Lucky Catch – Lobsterman for a day! Aboard Lucky Catch cruisers you'll have the chance to dress like a lobsterman and pull your own traps. Tours are offered May-October and reservations are highly recommended.

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Charter Tours – Please contact us at 207-805-9836 so we may curate a private tour of Casco Bay to best fit the interests of your group. Capacity is limited to 6 passengers.