A World-Class Full-Service Charter Experience

Chartering with Waypoints Annapolis® is more than a vacation, it’s a chance to make your dreams of sailing a reality. The Waypoints Annapolis® charter experience is designed to make your journey as relaxing, rewarding, and memorable as possible.

The experience begins with your personal charter concierge, who will walk you through the entire process, helping you choose your yacht, your destinations, and everything you need for an amazing charter vacation. We’ll help plan out a customized route for your sailing adventure, starting in the sailing capital of the U.S., Annapolis, and visiting the best waypoints on the Chesapeake. St. Michaels, Tilghman Island, Baltimore, and anywhere you wish to travel. Bareboat, skippered, or ASA instructional charters are all available.

Beyond the Chesapeake, we provide the same world-class charter experience from a host of destinations (link to main destination page), up and down the Atlantic Coast and Caribbean, including the Bahamas, Newport, Rhode Island, Ft. Lauderdale, Florida, St. Petersburg, Florida, Key West, Florida, and the Virgin Islands.

For more information on the charter experience, contact your personal charter concierge.

RatesASA InstructionImportant Information For Charter Guests

Reserve Your Charter