Private charters

Private Sailboat Charters in Key West

For Your Destination Wedding or an Unforgettable Celebration

From an intimate sail for two to a celebration of up to 49 guests, our private sailing charters are designed to fit your vision. Each charter aboard our majestic wooden schooners is fully customized, with curated food and beverages, a full liquor bar, and optional live music—whether that’s a DJ, folk singer, or steel drum percussionist. Private charters are also perfect for birthdays, family gatherings, camps, and corporate events. Team-building outings, client entertainment, holiday parties, or conference sunset sails all feel more meaningful at sea—and we handle the details to make it effortless.

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wedding charters

Say “I do” on the deck of a classic two-masted schooner. Whether you’re planning an intimate ceremony, rehearsal dinner, or sunset reception, our private sailing charters in Key West or summer voyages in Camden, Maine offer a timeless and unforgettable setting for your special day.

Private Events

From birthdays and family gatherings to corporate celebrations and team outings, our private schooner charters turn any event into something truly memorable. With customizable food, drinks, music, and sailing routes, we’ll help you create a relaxed, one-of-a-kind experience on the water.

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get in touch

Have a question or need a hand planning your sail? Our friendly team is here to help—just get in touch and we’ll take care of the rest.