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.
10/03/2026
We can’t wait to see you at the show! 🌴
Meet us on the docks at this year's Annapolis Sail Boat Show from Oct. 15–18 and experiences the sailing capital of the world through destination inspiration, industry conversations, special activations, and a true taste of the BVI.
With 75,000 attendees annually, and welcoming visitors from all 50 U.S. states, four Canadian provinces and more than 25 countries, we are excited to showcase the destination alongside our wonderful partners: Peter Island Resort, Scrub Island Resort, Spa & Marina, Island Time BVI, Virgin Gorda Yacht Harbour, Elite Culinaire, Hendo's Hideout, Leverick Bay Resort and Marina, Cane Garden Bay Beach Hotel, and Virgin Islands Shipping & Maritime Authority.
From free seminars, a boat show block party, Spinlock demos, and so much more, this opportunity is one you will want to participate in.
Learn more and grab your tickets: https://bit.ly/4xU7xn2
Ready to wander? We made it easier. 🌴🗺️
Meet the new Waypoints website!
A fresh new look, an easier way to explore our destinations and yachts, and plenty of inspiration for wherever you’re dreaming of sailing next.
The seas are calling. Are you answering? 🌊
Explore → Waypoints.com
09/29/2026
Sail San Diego & earn your ASA certifications! 🌊⛵️
Through our partnership with Seaforth Boat Rentals, you can charter along Southern California’s stunning coastline and take your ASA courses on the water.
Adventure, sunshine, and sailing skills — what more could you ask for?
Ready to set sail? Book your San Diego adventure! Link in comments to get started.
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/
Click here to claim your Sponsored Listing.
Category
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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