Step aboard the Calista Ann for a private cruise along Maine’s dramatic coastline. Discover historic forts, lighthouses, and marine wildlife on this personalized motor yacht adventure.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2 hours (standard), customizable longer charters available
Fitness Level
No special fitness level required; suitable for most adults and families
Wildlife
History
Portland’s harbors have been critical maritime hubs since the 17th century, with forts guarding the coastline through multiple conflicts.
Conservation
Sail Portland emphasizes environmentally mindful practices, supporting local efforts to protect marine habitats and minimize pollution.
Sail Portland
Step aboard the Calista Ann for a private cruise along Maine’s dramatic coastline. Discover historic forts, lighthouses, and marine wildlife on this personalized motor yacht adventure.
Sail Portland is a Portland, OR-based operator offering curated coastal cruises and private charters designed for small groups and special occasions. The company presents three distinct experiences: an Adoptable Dog Cruise that partners with the Animal Refuge League, a Crown Jewel Flappy Hour & Brunch aboard the classic Downeast picnic boat Calista Ann, and a Classic Motoryacht Chartered Cruise showcasing coastal sights, historic forts, and lighthouses.
Each offering is structured to combine scenic sailing with specific guest experiences. The Adoptable Dog Cruise pairs sunset views over Casco Bay with opportunities to meet adoptable dogs supported by the Animal Refuge League. The Crown Jewel Flappy Hour & Brunch includes complimentary rosé, reservations for parties, and space for up to 12 guests on Calista Ann. The Classic Motoryacht Chartered Cruise provides private-yacht amenities, a dedicated crew, and narrated insights into local maritime history while watching for seals and porpoises.
Sail Portland emphasizes small-group experiences, private bookings, and community engagement through partnerships. The presence of a dedicated crew on motoryacht charters and the partnership with a local animal-rescue organization add practical and community-trust elements to the offerings. All descriptions, vessel names, guest capacities, and partner relationships reflect the provided trip information and available public details about the company and its sailings.
Location
Portland, OR
Launch point for all cruises
Max Guests
12
Private group bookings available
Trips Offered
3
Diverse coastal experiences
Community Partner
Animal Refuge League
Supports adoptable dog sailings
Check availability for private charters, brunch sails, and adoptable dog cruises departing from Portland, OR — book the experience that fits the occasion.
Bring Your Own Snacks and Drinks
Food and beverages, including water, are not provided, so pack accordingly for your cruise.
Dress for Changing Weather
Layers and a windbreaker are recommended as coastal conditions can shift quickly on the water.
Use Sun Protection
Wear sunscreen, hats, and sunglasses to guard against strong coastal sun exposure during the cruise.
Arrive Early to the Marina
Give yourself extra time to find parking and check in at the departure point located at 1 Marina Way, Portland.
Sunscreen
To protect skin from strong sun reflections on the water during the cruise.
summer
Layered Clothing
Warm layers keep you comfortable as temperatures can vary on the coast.
spring
Polarized Sunglasses
Enhances visibility on the water and reduces glare while spotting wildlife.
summer
Windbreaker
Provides protection against coastal breezes during cooler months.
fall