Crown Jewel Flappy Hour & Brunch

Portland, Oregon, offers a fresh way to enjoy the city’s waterfront with Crown Jewel Flappy Hour & Brunch aboard the Calista Ann, a classic Downeast picnic boat. This intimate cruise, accommodating just 12 guests, sets sail from the heart of Portland, carving a path toward the captivating Great Diamond Island in Casco Bay. Guests sip complimentary rosé while soaking in panoramic water views that unfold around the bay.

The Calista Ann’s timeless design enhances a maritime experience that feels both nostalgic and uniquely Portland. Great Diamond Island is a gem of coastal charm where lobstering heritage meets modern leisure. Its rugged shoreline and tranquil coves form an inviting backdrop for the cruise, offering a refreshing escape from the cityscape.

Throughout your journey, the cool ocean breeze and gentle sway of the boat meld with the warmth of socializing around thoughtfully curated brunch or happy hour fare. What sets Crown Jewel Flappy Hour & Brunch apart is the blend of exclusivity and simplicity. With reservations required, the experience ensures a relaxed pace and personal atmosphere rarely found in larger tours.

The onboard crew’s friendly service complements the local vibe, connecting visitors to Portland's maritime culture in an authentic way. Ideal for celebrations, casual outings, or a pause from the everyday, this cruise introduces travelers and locals alike to the understated beauty of Casco Bay’s islands. It’s a standout offering for those seeking waterfront immersion paired with convivial dining—the kind of trip that feels like a cherished local secret once shared.