Waypoints Yacht Charters

Waypoints Yacht Charters


🥰 can’t beat a sunset cruise with Waypoints Yacht Charters
Waypoints Yacht Charters upgraded to #GoldenPartner and is exclusively using Booking Manager as their only System. 🇺🇸 US based fleet offers 38 vessels available for bookings from Annapolis, Nanny Cay and Vinoy Marina. ⚓ #YachtCharter
Solution Spotlight: How do you keep a cohesive look across different destination brands? Here's how Millennium worked with Waypoints Yacht Charters to create their new look. https://bit.ly/2WJLX9d
Congratulations to Tom and Laura who recently took delivery of their beautiful Dufour 430, “Opportune Moment”. This boat will be available for charter at Waypoints Annapolis!
DC Sailing Community's long weekend bareboat sailing Infinite Blue. We had a wonderful time!
Enjoying a bite to eat at Blackwall Hitch in Annapolis with #TeamACY and Cruise Annapolis team members.
Fantastic Fountaine Pajot Astrea 42 “Southern Accent” a few weeks ago. We will look for a return visit to The Chesapeake this fall. Thanks Cruise Annapolis
Agapé in Oxford
We had a great charter on the Jenneau 440 "Bella". Nice boat and a great charter company.
This is a GREAT reason to come to the Annapolis Spring Sailboat Show, April 26-28th, and get 20% off any Annapolis Charter with Cruise Annapolis! So cool!
Congratulations to Yong and Stacy on the handover of Pau Hana, a beautiful new Lucia 40 that will be placed into charter with Cruise Annapolis! The couple worked with Eric Smith during their yacht ownership journey.

#FountainePajot #Lucia40 #TeamACY #Congratulations
I have a few boats left for day sails. Call our office to inquire. You must be able to captain the boat yourself though or bring a friend who is able to captain it for you. 443-203-4107

Waypoints offer bareboat, skippered, all-inclusive, and instructional charters. 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.

Operating as usual


Fleet Friday: The name may deceive you as you experience smooth sailing aboard "Hoppy Choppy," an Isla 40 from Fountaine Pajot. This yacht offers 3 cabins and 2 heads, providing room for up to 6 guests. Book her today in the BVI. https://bit.ly/3zTvD4R


Experience the beauty of St. John's in the USVI both above and below water when you charter with Waypoints.


And now for your moment of wanderlust.

📍 Cane Garden Bay, BVI


It's 5 o'clock somewhere. 🥂

Photos from Waypoints Yacht Charters's post 04/11/2022

The Annapolis charter season has begun!

Thanks for joining us this week!


If you miss out on our emails, you might miss out on moments like this. Join our email list today. https://bit.ly/3fyfwRg


Did you know that Sage Mountain is nearly 6 times taller than the Statue of Liberty? That can lead to some impressive views!

Photos from Waypoints Yacht Charters's post 04/08/2022

Fleet Friday: Sign off, disconnect and set sail with "Knot Online," a 2022 Dufour 470, for a charter on the Chesapeake Bay with Waypoints Annapolis. This yacht offers 3 cabins / 2 heads, a dinghy, water maker, air conditioning and more. https://bit.ly/3tho8TE


We were excited that the Arabella racing team chose to sleep aboard Tupelo Honey during the BVI Spring Regatta! It was an honor to host them. To learn more about the race: https://bit.ly/35OOPpN


And now for your moment of wanderlust.

📍 Coquina Beach, Florida


Asian and Latin foods combine to excite your taste buds while you enjoy incredible sunset views and amazing cocktails at CocoMaya Virgin Gorda. You need to make this hotspot a must-visit place on your next Waypoints BVI charter. https://www.cocomayavg.com

📸 CocoMaya


Set sail on the water vapor of Neptune. Blasting off April 1, 2050! 🚀


We're here to help make your sailing dreams come true!


And now for your moment of wanderlust.

📍 Maho Bay, USVI


Last Minute Availability: Charter the BVI aboard Serene Blue and save 20%. Our guests had to unfortunately cancel their charter from April 8-16, so this vacation of a lifetime is now available to you at a significantly reduced rate! https://bit.ly/3igpIzA


Did you know that the Chesapeake Bay produces about 500 million pounds of seafood per year? We promise you'll eat a ton of it when you charter with Waypoints Annapolis.


One of our favorite places to sneak away in the BVI -- Cooper Island!


What are you waiting for? Jump in and join our newsletter today. https://bit.ly/3fyfwRg

Photos from Atlantic Cruising Yachts's post 03/24/2022

Give a warm welcome to this brand new Astréa 42 joining our Waypoints BVI fleet! 🥂


And now for your moment of wanderlust.


Photos from Waypoints Yacht Charters's post 03/22/2022

These recent guests took "Infinite Blue" on a charter in the BVI. We spy an up-and-coming captain on the water!


Experience the heart of American sailing when you set sail with Waypoints Annapolis. waypointsannapolis.com


We all have our favorite sailling spots.


Exclusive savings: If you're looking for a last-minute getaway, we're offering 30% savings on select USVI charters! Book now because this offer won't last long. https://bit.ly/3IgBKms


Yacht ownership is closer than you think. Discover Business Yacht Ownership today. https://bit.ly/38dearc


A note from Waypoints Yacht Charters President Kirstie Palmer.


"My trip to St. Thomas was a once-in-a-lifetime experience. It was a trip that opened my eyes to all of the beauty the world has to offer. I can’t wait to go back to St. Thomas and to travel to the BVI with my family.”

Maggie Simmons of Atlantic Cruising Yachts had never been outside of the continental US before. She went to the USVI and BVI, and it became a life-changing experience. Read more of her journey here. https://bit.ly/34I58UO


Did you know that Necker Island in the BVI is owned by Richard Branson?


There's nothing quite like watching the sun go down over the Gulf. Book your Waypoints Florida charter today. waypoints.com/florida


Come for the view, stay for the food. Sugarcane Restaurant in the BVI offers the best of both. We recommend you book a table there when you book with Waypoints BVI. https://www.sugarcane.vg/

📸 via Sugarcane Restaurant


Rare opportunity: Charter the BVI aboard Serene Blue and save 30%. Our guests had to unfortunately cancel their charter from March 27 to April 4, so this vacation of a lifetime is now available to you at a significantly reduced rate! https://bit.ly/3igpIzA


SPECIAL OFFER: We had a last-minute cancellation on "Serene Blue," a Fountaine Pajot Astréa 42, and now we're offering you a chance to save big. Book this yacht for March 27 to April 4 and save 20%. Don't wait. This offer will be gone soon. https://bit.ly/3E0EuDr


Some tropical colors from the USVI to brighten up your Monday!


What's the soundtrack to your sailing days?


The calm days and relaxing nights on the Chesapeake Bay are just around the corner. Book your summer charter today. waypoints.com/annapolis

Videos (show all)

Kirstie Palmer on the Future of Waypoints
2021 U.S. Sailboat Show Recap
Waypoints BVI: Opening Our New Charter Base
Serene Blue 360 Tour
360 Tour of USS Flamingo
Thank you for a great 2020 Chesapeake Bay charter season
Jeanneau 54 Chartering the Chesapeake Bay
Waypoints Annapolis
Fondest Memories of Sailing: Susan Restauri



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