Boat Cruise & Brunch Adventure in Portland, OR
Difficulty
easy
Duration
2–3 hours
Fitness Level
Minimal physical exertion required; suitable for most fitness levels
Overview
Sip rosé and enjoy brunch aboard the Calista Ann on a scenic cruise to Great Diamond Island in Portland’s Casco Bay. Intimate seating and waterfront views make this a memorable outing.
Crown Jewel Flappy Hour & Brunch
Cruise to Crown Jewel for Flappy Hour on the island or an incredible brunch!
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Adventure Photos
About This Adventure
Experience a unique brunch or happy hour aboard the classic Downeast picnic boat, Calista Ann. Enjoy a scenic cruise to Great Diamond while sipping complimentary rosé. With reservations included and space for up to 12 guests, this unforgettable outing in Portland is perfect for any occasion. Don’t miss out!
Rates
Person (All Ages): $50 Reserves your reservation for the Flappy Hour or Brunch Experience (It does not cover cost of food and beverage at the restaurant, it goes to the restaurant's cost for chartering the boat)
You do not need to make your own reservations, they are included with this booking, someone from Crown Jewel will be in touch with you once you book the trip.
Crown Jewel and Sail Portland Maine are teaming up together to bring you one of the most unique happy hour/brunch experiences in Portland. Hop aboard the classic Downeast picnic boat Calista Ann for a slow cruise out to Great Diamond. On your way out to the island, enjoy complimentary rosé. This is an experience in Portland you won't want to miss.
It takes about 30 mins to get to the restaurant by boat for the 3pm restaurant reservation. So please arrive at the marina around 2:15 and once everyone has arrived the boat will depart.
Parties of any size are welcome. The boat holds up to 12 passengers.
You can book this trip last minute, as the restaurant will set aside 12 seats every Wednesday and Thursdays till August. We are also doing Fridays in September! And brunch on Sundays the whole season!
Cancellation of this reservation must be made 7 days prior to reservation for a refund.
Adventure Tips
Reserve Early
Space is limited to 12 guests per cruise, so book your spot well in advance.
Dress in Layers
Ocean breezes can be cool; bring a light jacket even on sunny days.
Arrive On Time
Boarding starts promptly to maintain the cruise schedule—don’t miss the departure.
Bring a Camera
Waterfront views and island sights offer excellent photo opportunities.
Local Insights
Wildlife
- Harbor seals frequently spotted near the islands
- Local seabird species such as ospreys and terns
History
Great Diamond Island has roots as a military base with Victorian-era ruins scattered along hiking trails.
Conservation
The operators promote eco-friendly boating practices, minimizing impact on Casco Bay’s delicate marine ecosystems.
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Adventure Hotspots in Portland
Frequently Asked Questions
Recommended Gear
Windbreaker Jacket
Protects from cool sea breezes typical in spring outings.
spring specific
Sunglasses
Shields eyes from glare reflecting off the water during sunny cruises.
summer specific
Comfortable Footwear
Non-slip shoes help with safe boarding and moving around the boat.
Camera or Smartphone
Capture scenic views and memorable moments aboard the boat.