Visit Us at the Annapolis Boat Show to Learn More About Our Boutique Charters. Set Sail with Us!

Chartering a yacht offers a lifestyle that is the perfect blend of luxury, adventure, and seclusion. It allows you to escape the mundane and embark on a voyage where the horizon is your only limit. Imagine waking up to the gentle lull of waves, sipping fresh squeezed juice on the deck with the morning sun, and exploring secluded coves and hidden beaches. Chartering offers the freedom to create your own itinerary, whether it’s diving into crystal-clear waters, enjoying water sports, or indulging in gourmet meals prepared by a private chef. It’s a lifestyle that promises the thrill of exploration and the tranquility of seclusion, providing the ultimate escape from the everyday and a chance to create unforgettable memories with friends and family.

April 26 – 28, 2024

New Booth Location! 

Dock B,
City Dock, Annapolis, MD


Step Aboard the Latest Fountaine Pajot & Dufour Models

While you’re at the Annapolis Sailboat Show, picture yourself on your luxury vacation by experiencing the latest monohulls and catamarans from Fountaine Pajot and Dufour available for charter. Allow us to help you plan your next charter experience from one of our many bases…with even more base locations coming in 2024! 

Elba 45
dufour-41
Dufour 41
Dufour 470
Dufour 530
Dufour 530

Stop by Our Booth and Meet the Team!

We invite you to join us at the Annapolis Boat Show, where stepping into our booth will be like entering a mini Boat Show paradise. You can expect no shortage of delicious cocktails and good times as we discuss how to make your next boutique charter adventure absolutely unforgettable. Swing by and meet the team.

Sip on the Waypoints Signature Cocktail!

Our team is buzzing with excitement! Join us at our booth where we’ll be serving up our Waypoints Signature Cocktail and ready for some awesome charter chatter. We promise you won’t leave without a smile!

We Love Our Anthony!

You know him from the BVI base, and we love him! Sadly, Anthony won’t be able to make it to the Annapolis Boat Show this year, but you can catch him at our BVI location doing what he does best! Anthony’s unmatched expertise and passion for sailing are at the heart of our charter experiences, and we can’t wait for you to sail with him in the beautiful British Virgin Islands. So if you’re planning a trip there or just want to say hello, drop by our BVI base and let Anthony show you the ropes (quite literally!) for an unforgettable adventure!


Ready For Yacht Ownership? 

Join Our Growing Waypoints Fleet!

Waypoints partners with  Atlantic Cruising Yachts  to make your dreams of yacht ownership come true. By purchasing through Atlantic Cruising Yachts and entering your boat into our fleet, you can save on the costs of yacht ownership. Learn more by visiting us at the Boat Show!

RSVP & Meet Us at the Annapolis Boat Show!

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We Can’t Wait to See You!