catamaran sailing school maryland

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• Sailing School The best sailing school on the Chesapeake Bay!
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We offer a full range of sailing courses with focused on-the-water instruction. Whether you’re a novice learning the basics and pursuing ASA certification, or an experienced sailor hoping to fine-tune your skills with a private sailing lesson, we have a course for you. Sail with us on the Chesapeake and Caribbean, and take your sailing to the next level!

Sail Solomons has been recognized by the American Sailing Association as an “ ASA Outstanding School ” each year from 2008 through 2012. Our instructors have been awarded “ ASA Outstanding Instructor ” from 2007 through 2012, making us the most-awarded sailing school on the Chesapeake Bay!

Our scheduled sailing courses range from novice to advanced, beginning with basic introductory courses and extending through the ASA continuum to advanced cruising. Our small class size (2-4 students) allows a hands-on focus with maximum on-the-water training. Most courses are conducted on weekends, to accommodate your busy lifestyle.

Cruising courses are taught in a live-aboard environment to fully immerse you in the cruising experience. Mid-week combination courses are also available to get you on the fast track to cruising!

ASA is the leading authority on sailing instruction in the USA. As an ASA school , Sail Solomons offers a full range of ASA certification courses that are recognized internationally, so you can begin to charter the globe!  ASA course prices include instruction, ASA texts and certification materials. All Sail Solomons instructors are ASA-certified instructors and licensed by the US Coast Guard.

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Copyright © 2024 Sail Solomons. All rights reserved. Website by Alice Ralph .

WHY SAIL WITH US?

• PERFECT LOCATION: We operate out of Herrington Harbour North, a scenic and well-kept area having been named one of the Best Overall Marinas located right on the Chesapeake Bay! Only 25 min. from the Washington D.C Beltway
• PREMIUM YACHTS: We have brand new VIKO Yachts used for our courses. Come learn to sail on new yacht
• PROFESSIONAL CAPTAINS: Our instructors have over 8+ years of sailing and offshore cruising experience, but they are award winning instructors. Learn from some of the best Captains on the Chesapeake Bay and let us help you fulfill your sailing goals.

Sailing Courses in Tracy's Landing, Maryland

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Sailing Basics

Students learn the theory and skills needed to start sailing!

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Beginner Sailing Courses

Intermediate Sailing Courses

Advanced Sailing Courses

The Sailing Academy is the closest sailing school on the Chesapeake Bay to the Washington DC Beltway. Sailing instruction focuses on teaching family and friends to cruise on sailboats. Learn to sail in a fun, friendly atmosphere!

See What Other Sailors Have To Say!

“Simply the best! Drove over 3 hours from home to take the ASA101 and 103 courses based on the reputation The Sailing Academy has built. Both Captain Angie and Captain Phin are such good coaches and teachers. So patient and made it so enjoyable to learn. I will be back!"

via Google Reviews

“Last fall we looked around Annapolis for a sailing school. We toured two nice clubs in Annapolis and then stopped at The Sailing Academy on the way home. Even though it was a rainy day, we had a great conversation with the staff and desided to take ASA 101 with them. We had a fantastic experience and learned a ton. A couple of months later we took the ASA 103 and again had an excellent experience and became more confident. Last month we went with The Sailing Academy crew for a week long flotilla in the Bahamas and we are totally hooked on sailing. The Sailing Academy also has a club with 5 boats that will let us get out on the water and explore the Chesapeake all summer long. If you want to get into sailing, this is one of the best values around and a great group of people to spend time with.."

Doug Schnelzer

“Over the top fabulous!!! I took 101, 103 & 104 traveling all the way from Long Island, NY down to Deale!!  I learned soooooo much and had soooooo much fun!  Captain Angie is the bomb!!! I fell madly in love with the Chesapeake and will be back for more very soon.  37 thumbs up!!! Not just two!! :-)" 

Ms. J Rooney

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Sailing INSTRUCTION

Learn to sail with sailtime.

• SailTime University

SailTime Annapolis invites you to discover and enjoy the finest experience in Chesapeake Bay sailing. We are an American Sailing Association (ASA) affiliate offering unparalleled excellence in sail training.

Our goal is to give you the confidence and competence to safely skipper your own vessel, whether it’s a SailTime yacht or a keelboat. Boating lessons are geared for all experience levels, from first-time sailors to seasoned salt, we can help you take your sailing abilities to the next level.

Experiential Education

We offer small class sizes (typically two to four students) to maximize helm time and accelerate your skills development. We believe that experiential education is the best way to learn, so nearly all course time is spent on the boat.

ASA 101 Course

Students learn to sail on a Beneteau First 22 , a small keelboat, in moderate winds and sea conditions in familiar waters without supervision.

ASA 103 Course

Asa 104 course, asa 105 course, asa 106 course, asa 118 course.

Not available at this time.

ASA 103/104 Combo Course

Boating education.

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Sailing Charters, Lessons & Captain Services in Annapolis, MD & Abroad

We Have a Chronic Sailing Condition

sail with us and you will too!

Annapolis Sailing Charters

Sail the Chesapeake Bay on your own private yacht. Select a trip from our popular itineraries below, see more sailing trips in the Chesapeake Bay or contact us to customize an itinerary just for you.

Annapolis Sunset Cruise

Catch the gorgeous Chesapeake Bay sunset aboard a luxury catamaran. Perfect for a romantic evening, cocktails with friends or a way to end a day exploring Annapolis.

Mid-Week “3 Hour Tour”

“Just sit right back and…” feel the wind in your hair, go for a swim or just enjoy the views. Great for office outings and happy hour hangs.

Celebrate Your Special Event

Birthdays, anniversaries, bachelorette parties and other occasions are more fun on your own private yacht! We’ll tailor a cruise for your special day.

Chesapeake Overnight Sail

Get away for a night (or 2) and enjoy adventures on the water, excursions into nearby towns, sunset cocktails and sleeping under the stars.

Annapolis Sailing Lessons

ASA certified instructor, Captain Shawn Owen helps students of all skill levels become confident and safe sailors. With decades of experience teaching snowboarding and music, Shawn has a laid back, positive attitude and a passion for sailing and seamanship that will be contagious when you sail with us.

If you’ve never sailed before and are interested in trying it out to see what all the fuss is about, this class may be the perfect way to give it a shot.

Intro to Sailing

Interested in one on one training? Or maybe you want to get you and your crew up to speed before an upcoming charter? We can customize private instruction for up to 4 people for an extremely competitive rate.

Private Sailing Instruction

New boat owner needing insurance checkout or just looking to brush up skills on your own boat? We offer instruction and certifications aboard your boat to maximize benefit and personal knowledge of your vessel.

Learn on your Boat

The American Sailing Association is a national and global leader in sailing education and bareboat chartering certifications. We offer ASA Courses 101-106, as well as the 114 catamaran certification. If bareboat chartering is something you see in your future, then this could be your best avenue to achieve the necessary skills and qualifications required to handle your own charter vessel.

ASA Courses

Learn To Sail

Browse our charter fleet.

This catamaran features expansive deck spaces and an innovative open-concept design, creating a seamless flow between the interior and exterior.

Dos Milagros

Experience the ultimate luxury sailing adventure on the stunning Chesapeake Bay aboard the exquisite 2017 Beneteau Oceanis 45, a true gem in the world of yacht chartering.

Let us plan your customized “escape” on this well appointed catamaran sailing the Chesapeake Bay out of Annapolis, MD

A magnificent vessel that seamlessly blends luxury, performance, and comfort on the open seas.

This sleek and modern vessel feature 3 cabins, each equipped with its own private en-suite bathroom. Expansive deck with plenty of seating and lounging areas.

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Life is Just Better on a Boat

sail with us!

Sailing changed my life for the better in nearly every way. It makes me more present, more thoughtful, more focused, healthier, happier, just better as a person in most every way. I would be honored to help share it with you and then watch it become a part of your life.

Keep it chronic.

- Captain Shawn

• ASA 114 – Catamaran Cruising

ASA 114 Catamaran Cruising

This course is unavailable (2023)

Person (Ages 16+): $1045

Two Day Course 9am – 4pm Daytime – no overnight

Catamarans are very common among cruising charter fleets, popular for their stability and comfort. This class takes students through the significant differences between operating a cruising mono-hull and a cruising catamaran.

Students will learn how to maneuver the vessel under sail and power. How to dock and anchor the vessel. As well as gain an understanding of the systems and safety functions of catamarans. Students will demonstrate the taught skills and knowledge through practical skills and a written test to achieve the ASA 114 Cruising Catamaran Certification.

This course requires 2 students to run. If minimum capacity is not met 14 days prior to the course the school will cancel for a full refund to the student.

Prerequisites

• ASA101 Basic Keelboat
• ASA103 Basic Coastal Cruising
• ASA104 Bareboat Cruising

Please Call to Inquire

Please call or email us if you have questions.

410.267.7205

[email protected]

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ASA Sailing School for Catamaran Cruisers & Liveaboards

Build sailing techniques & prepare for the sailing lifestyle, asa sailing school & live-aboard instructors.

A catamaran sailing school was unheard of years ago. In the early days of Catamaran Guru, catamaran experts, Stephen & Estelle Cockcroft kept their cruising kitty going by teaching American Sailing Association courses and offered liveaboard orientation experiences aboard their monohull and later their catamarans. They know by experience that a liveaboard seaschool is the best way to learn to sail.

Though no longer offering instruction or liveaboard orientation experiences themselves, their passion to help others follow their nautical dreams of yacht ownership has kept them involved in sail training and hands-on cruising lifestyle experiences.

Why catamaran sailing school is important

The ASA sail training courses provide a good grounding for all new sailors and advanced courses increase competency and confidence. While learning to sail monohulls will provide many useful basics of sailing knowledge, instruction aboard a catamaran, and even better aboard your catamaran or a similar model is the best possible scenario.

Getting yacht insurance , especially a policy you can afford, requires proven related boating experience. The only way to get that experience safely is with a catamaran sailing school that offers liveaboard hands-on experiences.

Another vital role sea school plays for cruisers is getting the enthusiasm and confidence of the first mate up. While not always the case, often one partner in a sailing duo is the driving force of the cruising life dream while the other is often reluctant. Here are our tips on overcoming the reluctance of a catamaran cruising partner .

The top tip is to participate in a liveaboard experience with a seaschool even before you buy a boat. 

Weeklong liveaboard sailing school is invaluable for anyone who plans to own their own boat, but especially those who plan to be full-time cruisers. During these hands-on sailing experiences, your seaschool instructor combines our real-life practical methods with the most up-to-date sailing theory courses. These experiences set you up to enjoy a stress-free cruising lifestyle. Especially when you can train aboard your own boat, you can become comfortable with your equipment and configurations for operation and safety.

You not only learn how to be a team as you sail, anchor, trim sails, and navigate safely from point A to point B, you also get your questions answered by experienced liveaboard sailors about how to downsize, provision for long cruises, and mostly, how to enjoy watching the sunset in a gorgeous anchorage with your favorite beverage in hand.

CATAMARAN SAILING SCHOOLS & LIVEABOARD EXPERIENCES

Sail with us to learn.

Week-Long Liveaboard Courses Rare RYA Classes & Certifications

Catamaran Guru’s real-life practical methods combined with up-to-date sailing theory in lessons aboard recent model catamarans…or your own boat! 

Prepare for certifications or take the first step aboard to embark on your dream life of boat ownership or cruising

Classes in S Florida and the Bahamas.

Our Seaschool Students Excel As Sailors & Cruisers

We are very proud of our former seaschool students. Most of them have embraced yachting, sailing, and cruising in some way or another. Many of our graduates have successfully own their own boats. Some are long-term cruisers or charter boat owners and some have even done successful circumnavigations. Others have done long-term sabbaticals and several liveaboard school graduates have even moved on to successful careers in the marine industry as yacht brokers, charter yacht operators, and charter management.

got questions? contact us!

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For more than 30 years, we have been a part of the catamaran community and created Catamaran Guru™ to encourage and educate all the aspiring sailing out there. We understand the dream of traveling the world by catamaran and created a one-stop-shop to make that dream a reality for you.

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Our Frequently Asked Questions page has the answers to questions such as: how many students are on a boat, what are the deposit requirements, sample itineraries, cancelation policy, what is included in the price and more.

Courses, rates, and schedules are at a Courses, Rates & Schedules , click on the blue box labeled "Check Prices and Availability".

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Our business office will be closed December 18 to January 3. During this time frame it will be easier and quicker to contact us by email. We will return calls but will have limited telephone access so it may be a few days. We apologize for any inconvenience.

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• Phone: (954) 763-8464
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We actually went somewhere (Key Largo), rather than returning to the dock each evening. The course was made to be an adventure, as well as simply instructional. The weather was “made to order” — sun and gentle breeze Saturday through Wednesday, then Force 8 for our ‘foul weather instruction’ on Thursday.

I thought it was an excellent, challenging course. It definitely wasn’t a “cruise.” The instructor expected a lot from the students. I like that.

I have nothing but the utmost praise for your entire operation and the quality of the instruction that I received. Al Hatch is a consummate instructor and brings to this activity a love and a passion that is genuine and expansive. I hope to be able to return to Blue Water to experience some of the higher-level courses of instruction, and I certainly would have no trouble at all recommending your company to anyone.

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Starboard Sailing is for those of you who would like that little bit extra in sailing lessons. Our extended, in-depth courses are designed to that higher level of learning. That gives you more time at the helm and a better experience of sailing. This extra time and attention insures you are a capable and confident sailor at the end of your voyage.

Starboard Sailing only uses cruising sailboats similar to what is chartered all over the world. Our boats have large, stable, comfortable cockpits and cabins. Clean and well maintained, these boats are fully equipped with wheel steering, inboard diesel engines, and electronics.

Starboard Sailing is just north of Baltimore, Maryland on the Middle River. The quiet, well protected waters of Middle River are perfect for beginning sailors while just a short sail from the greater Chesapeake Bay for practicing your advanced sailing skills.

Come sail with us on the beautiful Chesapeake Bay Western Shore. At Starboard Sailing, we will put you on the right course!

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