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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.


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.

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