Classic Motor Yacht Lighthouse Cruise: Escape the crowds and embrace adventure with a cruise aboard our classic motor yacht, the Calista Ann! Whether you’re a seasoned sailor or a first-timer, our Coast Guard certified professional captains will ensure an unforgettable experience on the water.
Flappy Hour: 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.
Private Dinner Charter: Join us aboard the Calista Ann for a custom tailored private meal aboard. Dates are not scheduled and please call us at 207-200-6650. Captain/Chef Ian of Sail Portland Maine will cook a multi-course meal onboard for you and your group. On the charter the Chef Ian will prepare fresh, local ingredients for a four course meal you won’t want to miss! These trips can be booked for any cruise time slot and leave the dock at Fore Points Marina, and cruise around the harbor seeing beautiful landmarks while enjoying these meticulously prepared dinners.
Chebeague Island Inn Dinners: Join us in the intimate Captain’s Room at Chebeague Island Inn for a private dining experience like no other. Whether you’re staying overnight or arriving by charter boat with Sail Portland Maine from Fore Points Marina, enjoy a seasonal, multi-course, family-style meal with custom wine pairings. Connect over unforgettable food as one of Maine’s top chefs shares the stories behind each locally sourced dish.
Maximum Capacity: 12