The Sailing Academy

The Sailing Academy ASA Sailing School providing the instruction needed to fulfill sailing dreams. Perfect Location, Premium Yachts and Professional Captains.
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See the article that tells how The Sailing Academy was started by a live-aboard cruising family. https://www.linkedin.com/pulse/from-office-ocean-jeff-bowen

As heat advisories climb we’re taking it as an opportunity to remind you that on the water, it typically feels 5°F - 15...
06/12/2026

As heat advisories climb we’re taking it as an opportunity to remind you that on the water, it typically feels 5°F - 15°F cooler than on land! Congratulations to our students this week completing their Sailing Basics & ASA 101, and ASA 103 + 104 combo courses to kick off their summer as certified sailors 😎

06/12/2026

THE most important class we teach by far is Sailing Basics. The fundamentals of sailing is what you’ll (ideally) be using for the majority of your time out on the water. There are many folks trying to rush the qualification process to bareboat chartering that simply are lacking the skill of being able to turn off the engine and sail well in any conditions. Our advice? DONT SKIP THE BASICS. Thats like building a home without a foundation!

06/10/2026

Last summer a boat exploded from the galley, WITH the owner aboard 😅. Miraculously, he survived (blown back off the boat). This happened in a marina just a dock over from one of our own boats and serves as a sober reminder of how easy it can be when gas stoves are not properly used. Propane is heavier than air, and will fill a cabin if you’re not careful to know the difference between an empty tank and blocked igniter. If your tank is full, gas is on, and flame is not lighting — DO NOT CONTINUE releasing propane.

⚓️ABOUT US⚓️

The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lifelong sailing adventure. We teach on premium yachts perfect for every skill level: whether it is at our home base on the Chesapeake Bay, on an offshore experience, or for a family sailing vacation cruising the Bahamas. Your adventure starts here! Learn how to sail a sailboat, get your ASA certifications, and join our Sailboat Club for an affordable full season of sailing

06/10/2026

Last summer a boat exploded from the galley, WITH the owner aboard 😅. Miraculously, he survived (blown back off the boat). This happened in a marina just a dock over from one of our own boats and serves as a sober reminder of how easy it can be when gas stoves are not properly used. Propane is heavier than air, and will fill a cabin if you’re not careful to know the difference between an empty tank and blocked igniter. If your tank is full, gas is on, and flame is not lighting — DO NOT CONTINUE releasing propane.

⚓️ABOUT US⚓️

The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lifelong sailing adventure. We teach on premium yachts perfect for every skill level: whether it is at our home base on the Chesapeake Bay, on an offshore experience, or for a family sailing vacation cruising the Bahamas. Your adventure starts here! Learn how to sail a sailboat, get your ASA certifications, and join our Sailboat Club for an affordable full season of sailing.

This past weekend we had 4 VIKOs from our fleet out at the same time, putting to the test each sizes performance marks w...
06/09/2026

This past weekend we had 4 VIKOs from our fleet out at the same time, putting to the test each sizes performance marks when matched beside each other. Each of the participating courses (Sailing Basics, 101, 103) got a chance to reference points of sail, right-of-way, and tacking maneuvers with direct comparison for performance differences. Days like this are the perfect example of why VIKO stood out to us as the ideal yacht for students learning the ropes (and why we are the only Sailing school on the Chesapeake Bay that uses it for training!)

⛵️VIKO strikes a perfect balance between performance and manageability. Each model is large enough to give students real-world experience with systems and handling that translate to bigger boats, but not so big that it feels intimidating.

⛵️A responsive helm and thoughtfully laid-out cockpit (it feels spacious even with a full class aboard!) means students get immediate feedback and quickly develop confidence. The boat responds well, teaches good habits, and gives a solid foundation to build on.

⛵️Because VIKO has prioritized the sailing experience, less amenities below allow for a valuable build. The factory-built to order gives us an advantage to get everything we need aboard with NOTHING we don’t. We can keep our fleet refreshed with new yachts and provide a premium experience without sinking the budget.

06/08/2026

The stakes could not be higher. (Jerry is a FAA Certified Drone Pilot, do not attempt this at home🫡)

We had Baywatch Aerial Imagery come shoot some footage of our sailing courses in action and we saw firsthand just how much coordination it takes to be a drone pilot— ESPECIALLY overtop of water 😅. We had 6 of our boats out at the same time, chasing them around by both air & sea. He did a great job communicating with our Captain to coordinate boat maneuvering that considered footage angles, battery life and movement to optimize our session. Thanks Jerry!

You know what they say: A family who sails together, stays together. Actually, we don’t know if thats what they say— but...
06/04/2026

You know what they say: A family who sails together, stays together. Actually, we don’t know if thats what they say— but based our experience it might be true. This week we’re welcoming back a family crew to start their ASA 101 Certifications after they completed Sailing Basics with us a couple weekends prior. These non-consecutive combo courses can really help space out practice time, weather conditions, and muscle memory to build the kind of confidence we’re shooting for.
⚓️ABOUT US⚓️

The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lifelong sailing adventure. We teach on premium yachts perfect for every skill level: whether it is at our home base on the Chesapeake Bay, on an offshore experience, or for a family sailing vacation cruising the Bahamas. Your adventure starts here! Learn how to sail a sailboat, get your ASA certifications, and join our Sailboat Club for an affordable full season of sailingj

06/04/2026

After our Electric Shock Drowning tip went viral, we chatted with a lot of folks that simply were never trained on basic shore power safety around water and boats. If this isn’t common practice for you already, here’s a quick one you should do each time you plug back in to shore power. Avoid carrying a live wire from the dock-to-boat, and instead make it a habit to transport power cables from the boat (plugged in), to a dead box, only turning on the breaker after the fact.

⚓️ABOUT US⚓️

The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lifelong sailing adventure. We teach on premium yachts perfect for every skill level: whether it is at our home base on the Chesapeake Bay, on an offshore experience, or for a family sailing vacation cruising the Bahamas. Your adventure starts here! Learn how to sail a sailboat, get your ASA certifications, and join our Sailboat Club for an affordable full season of sailing.

06/02/2026

Nautical flags are NOT decorative, but instead used as a universal visual language to communicate critical information between vessels and shore stations. Using these helps overcome language and cultural barriers through specific, standardized meanings. Flown individually, flags often represent a specific, sometimes urgent message. So here is another test for you— nautical flag edition.

⚓️ABOUT US⚓️

The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lifelong sailing adventure. We teach on premium yachts perfect for every skill level: whether it is at our home base on the Chesapeake Bay, on an offshore experience, or for a family sailing vacation cruising the Bahamas. Your adventure starts here! Learn how to sail a sailboat, get your ASA certifications, and join our Sailboat Club for an affordable full season of sailing

It’s time for your practice exam. Knock the dust off to see if you can answer these 5 questions from the Basic Keelboat ...
05/30/2026

It’s time for your practice exam. Knock the dust off to see if you can answer these 5 questions from the Basic Keelboat Sailing exam. Never been certified, but still got them right? It MIGHT just be time for you to come see us… Let us know how you did in the comments below!

⚓️ABOUT US⚓️

The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lifelong sailing adventure. We teach on premium yachts perfect for every skill level: whether it is at our home base on the Chesapeake Bay, on an offshore experience, or for a family sailing vacation cruising the Bahamas. Your adventure starts here! Learn how to sail a sailboat, get your ASA certifications, and join our Sailboat Club for an affordable full season of sailing

Address

411 Deale Road
Deale, MD
20779

Opening Hours

Monday 10am - 4pm
Tuesday 10am - 4pm
Wednesday 10am - 4pm
Thursday 10am - 4pm
Friday 10am - 4pm
Saturday 9am - 1pm

Telephone

+14108677177

Website

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