Waypoints Yacht Charters
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A uniquely elevated charter experience. New model yachts in premier destinations.
When you set out for the finest sailing destinations in the world, you deserve a personally crafted charter experience managed by local charter specialists with knowledge of secret anchorages, quiet spots, and not-to-miss experiences.
09/26/2026
Sail on by to see Waypoints Yacht Charters at the Annapolis Boat Shows' Fall Sailboat Show, happening this October 15-18! ⛵️
Come chat with our team, check out what’s new on the docks, and start planning your next sailing adventure. 🌊
See you soon in Annapolis! ⚓
09/23/2026
"This was my third bareboat charter with Waypoints in the BVI’s and once again they provided a top class 5-star service from start to finish!"
Looking for your own 5-star charter vacation? ⭐ Waypoints has you covered!
📸 Photos courtesy of charter guest's Tripadvisor review
Thank you Newport for a great show! See you next year. ⚓️
Meet Betty & Break of Dawn ✨
These two beauties are ready for their next adventure with Waypoints!
Charter them in Annapolis now, and keep an eye out as they make their way to our USVI fleet this fall. 🗺️
Which one would you choose? Learn more about the models: https://waypoints.com/our-fleet/
Adventure awaits. From the turquoise anchorages of the British Virgin Islands to the laid-back charm of the Bahamas, a Waypoints charter offers the best in Yacht Charters. Snorkel hidden reefs, sail between postcard-perfect islands, and let the trade winds carry you to your adventure on the water.
Book your Waypoints charter today - ask about how our Newport boat show special!
⛵ Halfway through an incredible show in Newport! If you haven’t stepped aboard yet, today’s your day — find us on Dock N-4 and let’s start planning your next Waypoints charter. Your winter sailing charter awaits!
09/18/2026
There’s still time to sail the Chesapeake 🌅
The Annapolis charter season isn’t over yet! Take advantage of the crisp fall weather, beautiful sunsets, and one more adventure on the Bay before the season wraps up.
Book your Chesapeake charter while there’s still time!
https://waypoints.com/destinations/annapolis-md/
🌊 Day 2 in Newport. Stop by Dock N-4 to explore Dufour Yachts and Fountaine Pajot Catamarans up close and chat with our yacht charter experts about bareboat, captained, and all-inclusive options.
See you on the docks!
⚓ We’ve dropped anchor in Newport! Waypoints Yacht Charters is officially at the Newport International Boat Show — come find us at Dock N and step aboard Dufour Yachts and Fountane Pajot Catamarans. Whether you’re dreaming of the Caribbean, the Chesapeake, or beyond, our team is here to help you plan your next adventure. See you on the docks!
09/16/2026
Escape to the Caribbean and spend your winter sailing the picture-perfect waters of the USVI or BVI. 🌴
Ready to escape the cold? 😎 Book your winter getaway with Waypoints now!
Click here to claim your Sponsored Listing.
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Telephone
Address
312 Third Street #102
Annapolis, MD
21403
Opening Hours
| Monday | 8:30am - 5pm |
| Tuesday | 8:30am - 5pm |
| Wednesday | 8:30am - 5pm |
| Thursday | 8:30am - 5pm |
| Friday | 8:30am - 5pm |
| Saturday | 8:30am - 5pm |
| Sunday | 8:30am - 5pm |
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