A Five-Star Fleet in the Heart of America's Sailing Capital

The Waypoints Annapolis® fleet of charter yachts is the finest fleet on the Chesapeake Bay. We have a wide array of new and newer model year catamarans and monohulls available from the world-class French boatbuilders, Jeanneau and Fountaine Pajot. Unlike many charter companies, our yachts are all privately owned and custom outfitted for optimal comfort at anchor and performance at sail. Every yacht is handpicked to provide the ultimate charter experience.

Christine NC 33 Power Boat

Christine NC 33 Power Boat

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Knot Home NC 33 Power Boat

Knot Home NC 33 Power Boat

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Soulshine Jeanneau 410

Soulshine Jeanneau 410

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Pretty Lady II Jeanneau 410

Pretty Lady II Jeanneau 410

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Weather or Knot Jeanneau 419

Weather or Knot Jeanneau 419

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Perpetual M'Ocean Jeanneau 41 DS

Perpetual M'Ocean Jeanneau 41 DS

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Summer Salt Jeanneau 440

Summer Salt Jeanneau 440

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Besame Mucho Jeanneau 490

Besame Mucho Jeanneau 490

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Recovery Room Jeanneau 51

Recovery Room Jeanneau 51

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Adeline Jeanneau 51

Adeline Jeanneau 51

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About Time Jeanneau 54

About Time Jeanneau 54

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True North Jeanneau 54

True North Jeanneau 54

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Padraigin II Jeanneau 58

Padraigin II Jeanneau 58

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Infinite Blue Lucia 40

Infinite Blue Lucia 40

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Harbour Lights Fountaine Pajot - Lucia 40

Harbour Lights Fountaine Pajot - Lucia 40

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Dandelion Dayz Saona 47

Dandelion Dayz Saona 47

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Dark Star Saona 47

Dark Star Saona 47

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OceanFront Property Saba 50

OceanFront Property Saba 50

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