Waypoints Yacht Charters

Waypoints Yacht Charters

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🥰 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 in the world's best cruising destinations. Yachts available for charter are new or late model, privately owned, and professionally managed.

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

Timeline Photos 01/14/2022

Fleet Friday: We think you'll be "hoppy" when you set sail in the BVI aboard "Hoppy Choppy." This 2022 Isla 40 offers 3 cabins / 2 heads. Set sail on her in 2022 with Waypoints. https://bit.ly/3zTvD4R

Fleet Friday: We think you'll be "hoppy" when you set sail in the BVI aboard "Hoppy Choppy." This 2022 Isla 40 offers 3 cabins / 2 heads. Set sail on her in 2022 with Waypoints. https://bit.ly/3zTvD4R

Timeline Photos 01/12/2022

And now for your moment of wanderlust.

📍 Anna Maria Island, Florida

And now for your moment of wanderlust.

📍 Anna Maria Island, Florida

Timeline Photos 01/11/2022

Headed to the St. Petersburg Power and Sailboat Show? See you there!

Stop by our booth from Jan. 20 to Jan. 23 to learn more about Waypoints Yacht Charters, chat with our team members and discover more as we elevate your charter experience. https://waypoints.com/contact-us/

Headed to the St. Petersburg Power and Sailboat Show? See you there!

Stop by our booth from Jan. 20 to Jan. 23 to learn more about Waypoints Yacht Charters, chat with our team members and discover more as we elevate your charter experience. https://waypoints.com/contact-us/

Timeline Photos 01/10/2022

Sneak away and visit Fort Desoto State Park on your next charter with Waypoints Florida. Experience incredible views, secluded anchorages and amazing wildlife.

Sneak away and visit Fort Desoto State Park on your next charter with Waypoints Florida. Experience incredible views, secluded anchorages and amazing wildlife.

Timeline Photos 01/09/2022

Located on Treasure Island, Sloppy Joe's Restaurant - Treasure Island is a must-stop spot to hang out, grab a drink, and catch some live music right on the water. Visit them when you charter with Waypoints Florida. https://sloppyjoesonthebeach.com/

📷 Sloppy Joe's Treasure Island

Located on Treasure Island, Sloppy Joe's Restaurant - Treasure Island is a must-stop spot to hang out, grab a drink, and catch some live music right on the water. Visit them when you charter with Waypoints Florida. https://sloppyjoesonthebeach.com/

📷 Sloppy Joe's Treasure Island

Timeline Photos 01/07/2022

Special Savings Alert: Due to a cancellation, "Tupelo Honey" is available for charter starting Feb. 12th in the BVI. Don't miss your chance to save 15% on this 2021 Dufour 530, featuring 4 cabins / 2 heads: https://bit.ly/39GuNfH

Special Savings Alert: Due to a cancellation, "Tupelo Honey" is available for charter starting Feb. 12th in the BVI. Don't miss your chance to save 15% on this 2021 Dufour 530, featuring 4 cabins / 2 heads: https://bit.ly/39GuNfH

Timeline Photos 01/04/2022

Waypoints President Kirstie Palmer was recently interviewed by Voyage Tampa about Waypoints Florida. Check out the article: https://bit.ly/3sUEl1l

Waypoints President Kirstie Palmer was recently interviewed by Voyage Tampa about Waypoints Florida. Check out the article: https://bit.ly/3sUEl1l

Timeline Photos 01/02/2022

Serene Blue has an opening starting February 19th in the BVI! This sailing catamaran can sleep 6 passengers, Book now: https://bit.ly/3E0EuDr

Serene Blue has an opening starting February 19th in the BVI! This sailing catamaran can sleep 6 passengers, Book now: https://bit.ly/3E0EuDr

Timeline Photos 01/01/2022

Wishing you nothing but happiness and success in 2022!

Wishing you nothing but happiness and success in 2022!

Timeline Photos 12/31/2021

Start off 2022 with a trip aboard "Maho." This luxury catamaran offers 4 cabins / 2 heads as well as a dinghy, air conditioning and more. Book her today. https://bit.ly/30OrMJn

Start off 2022 with a trip aboard "Maho." This luxury catamaran offers 4 cabins / 2 heads as well as a dinghy, air conditioning and more. Book her today. https://bit.ly/30OrMJn

Timeline Photos 12/30/2021

Share if you're planning on celebrating the new year aboard one of our Waypoints yachts.

Share if you're planning on celebrating the new year aboard one of our Waypoints yachts.

Timeline Photos 12/29/2021

And now for your moment of wanderlust.

📍 Manasota Key, Florida

And now for your moment of wanderlust.

📍 Manasota Key, Florida

Timeline Photos 12/28/2021

Combining the flavors of the BVI and India, Omar's Fusion is spinning a new twist on the island's culinary scene. Be sure to check them out on your next getaway with Waypoints BVI. https://omarfusion.com/

📷 via Omar's Fusion

Combining the flavors of the BVI and India, Omar's Fusion is spinning a new twist on the island's culinary scene. Be sure to check them out on your next getaway with Waypoints BVI. https://omarfusion.com/

📷 via Omar's Fusion

Timeline Photos 12/27/2021

Caladesi Island State Park offers an unforgettable experience for anyone who charters with Waypoints Florida. Full of pristine beaches, incredible wildlife and more, it's something you just have to experience to understand.

Caladesi Island State Park offers an unforgettable experience for anyone who charters with Waypoints Florida. Full of pristine beaches, incredible wildlife and more, it's something you just have to experience to understand.

Timeline Photos 12/25/2021

Wishing you a very Merry Christmas!

Wishing you a very Merry Christmas!

Timeline Photos 12/22/2021

Christmas Palm Trees > Christmas Pine Trees

St. Pete looking very festive this time of year!

Christmas Palm Trees > Christmas Pine Trees

St. Pete looking very festive this time of year!

Timeline Photos 12/21/2021

Looking for some fun in the sun? Spring Bay off of Virgin Gorda offers incredible swimming and snorkeling, plus breathtaking views. Sail here on your next Waypoints BVI charter.

Looking for some fun in the sun? Spring Bay off of Virgin Gorda offers incredible swimming and snorkeling, plus breathtaking views. Sail here on your next Waypoints BVI charter.

Photos from Atlantic Cruising Yachts's post 12/21/2021

Congratulations and welcome to the fleet! 🎉

Timeline Photos 12/20/2021

Make magic this holiday season. Give the gift of a charter vacation. https://waypoints.com/our-fleet/

Make magic this holiday season. Give the gift of a charter vacation. https://waypoints.com/our-fleet/

Timeline Photos 12/19/2021

Did you know that Robert Louis Stevenson based Treasure Island on Norman Island in the BVI?

Did you know that Robert Louis Stevenson based Treasure Island on Norman Island in the BVI?

Timeline Photos 12/18/2021

Don't miss an email so you don't miss a moment like this.

Sign-up for our Waypoints newsletter today to get exclusive savings sent straight to your inbox. https://waypoints.com/newsletter-sign-up/

Don't miss an email so you don't miss a moment like this.

Sign-up for our Waypoints newsletter today to get exclusive savings sent straight to your inbox. https://waypoints.com/newsletter-sign-up/

Timeline Photos 12/17/2021

Whether it's the view or the food, there's a lot to love about Paradise Grille. Sit right on the beach and enjoy incredible shrimp tacos and great breakfast creations the next time you charter with Waypoints Florida. paradisegrille.com

📷 via Paradise Grille

Whether it's the view or the food, there's a lot to love about Paradise Grille. Sit right on the beach and enjoy incredible shrimp tacos and great breakfast creations the next time you charter with Waypoints Florida. paradisegrille.com

📷 via Paradise Grille

Timeline Photos 12/15/2021

And now for your moment of wanderlust.

📍 The Baths, British Virgin Islands

And now for your moment of wanderlust.

📍 The Baths, British Virgin Islands

Timeline Photos 12/13/2021

This holiday season - forget socks and toys! Gift your family a charter to remember with Waypoints. waypoints.com

This holiday season - forget socks and toys! Gift your family a charter to remember with Waypoints. waypoints.com

Timeline Photos 12/12/2021

Enjoy incredible food and an incredible view as the sun goes down over the water at Sunset Grill Restaurant, Sanibel Florida. Check out this great dinner spot when you charter with Waypoints Florida. sunsetgrillsanibel.com/

📷 via Sunset Grill

Enjoy incredible food and an incredible view as the sun goes down over the water at Sunset Grill Restaurant, Sanibel Florida. Check out this great dinner spot when you charter with Waypoints Florida. sunsetgrillsanibel.com/

📷 via Sunset Grill

Timeline Photos 12/11/2021

Norman Island is the perfect getaway to anchor when you start your charter at Waypoints BVI.

Norman Island is the perfect getaway to anchor when you start your charter at Waypoints BVI.

Timeline Photos 12/10/2021

Fleet Friday: Sail in the waters of Tampa Bay aboard "Breaking Away," a 2018 Sun Odyssey 479. This monohull features 4 cabins / 4 heads as well as air conditioning. Book her today. https://bit.ly/2ZOmEEE

Fleet Friday: Sail in the waters of Tampa Bay aboard "Breaking Away," a 2018 Sun Odyssey 479. This monohull features 4 cabins / 4 heads as well as air conditioning. Book her today. https://bit.ly/2ZOmEEE

Timeline Photos 12/08/2021

And now for your moment of wanderlust.

📍 The British Virgin Islands

And now for your moment of wanderlust.

📍 The British Virgin Islands

Timeline Photos 12/06/2021

Create memories that will last forever.

Give the gift of a yacht charter this holiday season! waypoints.com/our-fleet/

Create memories that will last forever.

Give the gift of a yacht charter this holiday season! waypoints.com/our-fleet/

Timeline Photos 12/05/2021

Known for its abundance of natural sea sponges and historic district full of antique and art shops, Tarpon Springs is a must-stop on your next Waypoints Florida adventure.

Known for its abundance of natural sea sponges and historic district full of antique and art shops, Tarpon Springs is a must-stop on your next Waypoints Florida adventure.

Timeline Photos 12/03/2021

Peg Leg's Restaurant is one of our favorite spots and not just because it's close to the Waypoints BVI office.

It's the perfect spot to kick back and relax to enjoy a meal with family and friends. https://bit.ly/3lqqR9c

📷 via Nanny Cay

Peg Leg's Restaurant is one of our favorite spots and not just because it's close to the Waypoints BVI office.

It's the perfect spot to kick back and relax to enjoy a meal with family and friends. https://bit.ly/3lqqR9c

📷 via Nanny Cay

Timeline Photos 12/01/2021

Yacht ownership is closer than you think. Learn more about Business Yacht Ownership. https://bit.ly/38dearc

Yacht ownership is closer than you think. Learn more about Business Yacht Ownership. https://bit.ly/38dearc

Timeline Photos 11/30/2021

Dive in and join our newsletter for the latest information about charter specials, offers, news, and more sent straight to your inbox! https://bit.ly/3fyfwRg

Dive in and join our newsletter for the latest information about charter specials, offers, news, and more sent straight to your inbox! https://bit.ly/3fyfwRg

Timeline Photos 11/29/2021

It's never too early to book in Annapolis! Cruise through one of the world's top sailing destinations when you charter with Waypoints Annapolis. https://bit.ly/2V07fPc

It's never too early to book in Annapolis! Cruise through one of the world's top sailing destinations when you charter with Waypoints Annapolis. https://bit.ly/2V07fPc

Timeline Photos 11/27/2021

We're always excited to help elevate the charter experience. Check out this great review from a recent guest in the BVI!

We're always excited to help elevate the charter experience. Check out this great review from a recent guest in the BVI!

Who We Are

Cruise Annapolis offers new and nearly new Jeanneau and Fountaine Pajot yachts for bareboat and crewed charters leaving from our base in the heart of historic Annapolis, Maryland. We are a division of Atlantic Cruising Yachts. Our charter yachts are well-equipped, privately owned, professionally managed, and meticulously maintained for their owners and yacht charter guests on the Chesapeake Bay. We provide full itinerary planning and provisioning services.

To reserve a charter please visit our website, and your personal charter concierge will take care of all the details!

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
Yacht ownership is closer than you think. Join us at our Annapolis docks for a free live seminar to learn more about the...
Come see us today or tomorrow at Walk the Docks in Annapolis to take advantage of our “Boat Show” specials. Learn about ...
Waypoints Annapolis
Fondest Memories of Sailing: Susan Restauri
Leave worries in your wake— the Bay is open and ready for you! ⛵

Location

Telephone

Website

Address


312 Third Street #102
Annapolis, MD
21403

General information

Charter Specialist: Susan Restauri Direct: 443-203-4105 Email: [email protected]

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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