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Best Seller
A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast-guard certified captain, allows you to cruise through Casco Bay, enjoying views of iconic landmarks like Portland Head Light. With options to swim in secluded spots or simply relax, every charter is tailored to your group's preferences. Enjoy light refreshments and the chance to take the helm or trim the sails, making for an unforgettable day on the water.
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Private Half Day Sailing Charter in Portland Maine
4 hours
Free Cancellation
5.0
(1)
5% savings
from
$475
$451
Price varies by group size
Member Pricing
There are a lot of ways to get out on the water in Maine, but we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and comfortable from the moment you step aboard. A half-day sail is the easiest way to get out on the water and see the Maine coast from a completely different perspective. This small group Maine sailing charter is perfect if you want a relaxed few hours to cruise, take in the views, brush up and your sail trim, or just relax and maybe sneak in a swim on a warm day.
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Casco Bay Sailing Escape: Half Day Custom Boat Charter
4 hours
Free Cancellation
1
Operator reviews
5% savings
from
$199
$189
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Boston Common
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Boston North End
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Quincy Market
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Granary Burying Ground
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Boston Tea Party Ships & Museum
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Faneuil Hall Marketplace
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Boston Common
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Boston North End
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Quincy Market
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Granary Burying Ground
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Boston Tea Party Ships & Museum
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$11
Faneuil Hall Marketplace
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$10
Boston Common
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$10
Boston North End
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$10
Quincy Market
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$10
Granary Burying Ground
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$10
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