island cruise portland maine | casco bay cruisesCome celebrate Flappy Hour aboard the beautiful Calista Ann, our motored picnic boat! Enjoy one of the best Casco Bay cruises with a glass of rose in hand as we glide through the tranquil waters of the Casco Bay to Crown Jewel on Great Diamond Island. This is the most unique, exclusive island cruise Portland, Maine has to offer, and an experience you won’t soon forget!

Our round trip fare is $50 per person. This includes a guaranteed reservation at the restaurant, a 30 minute trip out to Great Diamond Island, an hour of dining ( with1.5 hours for brunch excursions) and approximately 30 minutes back to mainland Portland. Charters depart from Fore Points Marina, conveniently located in downtown Portland. Both individual and group reservations of up to 12 guests are available!

Crown Jewel Flappy Hour 2023 Dates

Memorial Day Weekend

Friday, 5/26: 2:30pm (Portland departure) – 4:30pm (Portland arrival)

Sat, 5/27: 10:30am (Portland departure) – 1:00pm (Portland arrival)

Sun, 5/28: 10:30am (Portland departure) – 1:00pm (Portland arrival)

Mon, 5/29: 10:30am (Portland departure) – 1:00pm (Portland arrival)

Wednesday and Thursday Flappy Hour

Every Wednesday & Thursday from 6/21 – 8/30

 2:30pm (Portland departure) – 4:30pm (Portland arrival)

Friday Happy Hour

Shoulder season only

Friday, June 2nd: 2:30pm (Portland departure) – 4:30pm (Portland arrival)

Friday, June 9th: 2:30pm (Portland departure) – 4:30pm (Portland arrival)

Friday, June 16th: 2:30pm (Portland departure) – 4:30pm (Portland arrival)

Friday, September 8th: 2:30pm (Portland departure) – 4:30pm (Portland arrival)

Friday, September 15th: 2:30pm (Portland departure) – 4:30pm (Portland arrival)

Sunday Brunch

Every Sunday from May 28th – September 17th

10:30am (Portland departure) – 1:00pm (Portland arrival)