Waypoints Annapolis

Charter the historic Chesapeake Bay with the help of our knowledgeable concierge. Bareboat and crewed charters on pristine European yachts.

[Waypoints Annapolis @WpAnnapolis]

Reduce the costs of a new yacht with Business Yacht Ownership®. Learn more from the leaders today. https://t.co/qQUvrZvdXu

[Waypoints Annapolis @WpAnnapolis]

Welcome to the fleet, “Celtic Star”! This MY 44 from Fountaine Pajot offers 3 cabins / 3 heads and plenty of fun. Book her today. #FleetFriday https://t.co/4Oot82oL6t

[Waypoints Annapolis @WpAnnapolis]

Chartering the Chesapeake is for everyone. Learn why Millennials are falling in love with chartering Maryland’s waters. https://t.co/x34HUVmMfi

[Waypoints Annapolis @WpAnnapolis]

“Rise” is a proud member of our Chesapeake Bay fleet. This 2021 Fountaine Pajot Astréa 42 offers 3 cabins / 2 heads and offers unparalleled comfort and sheer pleasure. Book her today! #FleetFriday https://t.co/htPaGEvHKU

[Waypoints Annapolis @WpAnnapolis]

Learn how it is possible to offset new yacht costs with income, special financing, and potential tax advantages. https://t.co/qQUvrZvdXu

[Waypoints Annapolis @WpAnnapolis]

The world is rich with extraordinary destinations. The Jeanneau 51 was created to take you there. Learn more about chartering this 3 cabins / 2 heads yacht today. #FleetFriday https://t.co/XE2sAxl74p

[Waypoints Annapolis @WpAnnapolis]

A girls’ weekend in Annapolis is just what you and your friends need! Learn how you can save on the perfect weekend getaway in Annapolis today. https://t.co/MRmxXEq3IO

[Waypoints Annapolis @WpAnnapolis]

Enjoy sunset on the Chesapeake Bay with a cocktail in hand during our Sunset Open House tomorrow! Step aboard award-winning yachts from Fountaine Pajot and Dufour and learn about our exclusive charter specials: https://t.co/OJm8vovls0

[Waypoints Annapolis @WpAnnapolis]

Create an incredible memory this Father’s Day. Book a charter for a Father’s Day celebration and save 15%. Learn more and don’t miss this offer. https://t.co/MRmxXEq3IO

[Waypoints Annapolis @WpAnnapolis]

Yacht ownership is closer than you think. Learn more about Business Yacht Ownership®. https://t.co/qQUvrZvdXu

[Waypoints Annapolis @WpAnnapolis]

You won’t want to miss our Sunset Open House on Wednesday, June 9th! Meet and greet with our team, enjoy cocktails on the Chesapeake Bay, and step aboard award-winning yachts from Fountaine Pajot and Dufour available for charter. Register today. https://t.co/OJm8vovls0

[Waypoints Annapolis @WpAnnapolis]

Set sail from Eastport and explore all the Chesapeake Bay has to offer! Book by June 3rd to save 15% on your next charter adventure. https://t.co/dgfMKyl05e

[Waypoints Annapolis @WpAnnapolis]

Discover the smartest way to own the yacht you’ve always wanted with Business Yacht Ownership®. Learn more today. https://t.co/FSh3KWcHGm

[Waypoints Annapolis @WpAnnapolis]

This just in: "Infinite Blue", a 4 cabin Lucia 40, is available for charter this weekend! Save 10% by booking now. https://t.co/eP4jJj0FsF

Exterior shot via Christa Rae Photography

[Waypoints Annapolis @WpAnnapolis]

The Anderson family just got off of a 5-day charter aboard "Adeline", a Jeanneau 51. These repeat clients are already planning their next charter vacation with us!

[Waypoints Annapolis @WpAnnapolis]

It's National Maritime Day! Get out on the water and celebrate.

[Waypoints Annapolis @WpAnnapolis]

Make this the year you explore the hidden gems of the Chesapeake Bay.

[Waypoints Annapolis @WpAnnapolis]

Check out some of our long-time charter clients recently heading out on the water for an overnight sail on the Chesapeake! Who else is ready for calm waters in 2021?

[Waypoints Annapolis @WpAnnapolis]

"39 North" is here to take you in any direction you want to go! This Jeanneau 389 returns to our fleet and is a 3 cabin / 1 head monohull that's sure to bring you lots of fun on the water. Book her today. #FleetFriday https://t.co/4owxVYG2Cq

[Waypoints Annapolis @WpAnnapolis]

You’ve always dreamed of yacht ownership but it’s closer than you think with Business Yacht Ownership®. Learn more today. https://t.co/qQUvrZvdXu