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Build Your Sailing Skills.

Hands-on sailing instruction, expert guidance and a clear path to your next adventure - right here in Tampa Bay.

ASA Training Classes

Build real skills with professional, hands-on instruction. From beginner to advanced, earn internationally recognized ASA certification.
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Long Trips & Adventures

Put your training into practice on unforgettable multi-day sailing cruises to the Florida Keys and beyond.
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Private Charters

Relax, and let us handle the details. Perfect for families, friends, and special occasions.
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ASA Certified Training
ASA Certified Training
Multi-Day Sailing Adventures
Multi-Day Sailing Adventures
Private Charters
Private Charters
Experienced, USCG Licensed Captains
Experienced, USCG Licensed Captains

What Our Customers Are Saying

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Markus H profile picture
Markus H
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We had a great time despite some rough weather. Captain Nordie is great and even makes a full day of classroom a fun experience. Did ASA 101 challenge and ASA 103 with him and will come back!
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Allie M profile picture
Allie M
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Thank you, Captain Nordy and Skipper Adrian at Flagship Sailing, for an unforgettable morning learning how to sail! This is something I’ve wanted to do for 20 years, and I’m so glad I got to experience my introductory course with you. Your patience and guidance made me feel safe, comfortable, and well taken care of throughout the lesson. The beautiful views and dolphins made an already special experience even more amazing! Thank you for helping me fulfill a longtime dream and creating a memory I’ll cherish for a lifetime. I highly recommend Flagship Sailing to anyone wanting to learn to sail!
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Brad K profile picture
Brad K
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This is a great place to improve your knowledge, skill, and appreciation of sailing. Nordie, Adriane, and their team are outstanding teachers, highly professional, committed to the success of their students, and wonderful people!
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Shane B profile picture
Shane B
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Captain Nordie was awesome and I learned a lot on our four hour charter. Great experience!!
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Viktor T profile picture
Viktor T
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I started sailing in August of 2025 and initially completed ASA 101 and 103 at a different sailing school. While that program gave me a basic introduction, I did not find it comprehensive enough to build real confidence and competency on the water. That changed when I discovered Flagship Sailing. Their program was significantly more thorough, practical, and focused on developing real-world sailing skills. Since joining, I completed ASA 104, 105, 106, and 118, and the difference in both the quality of instruction and hands-on experience was night and day. A huge part of that experience was learning from Capt. Nordie and Capt. Adriane. Their teaching style strikes the perfect balance between professionalism, patience, safety, and making the learning process enjoyable. They create an environment where students are challenged appropriately while still feeling supported and encouraged. One of the things that really sets Flagship apart is the sailing community they build. Being local to the area, I was invited to many sailing opportunities between classes, which helped accelerate my learning far beyond the formal coursework. That experience ultimately culminated in participating in a regatta race from St. Pete to Isla Mujeres, Mexico — something I never would have imagined doing less than a year after starting sailing. Another underrated aspect of the program: they take great care of their students while underway. The crew feeds everyone extremely well and genuinely makes sure nobody goes hungry during longer sailing days or passages. If you are serious about learning how to sail — not just passing certifications — I highly recommend Flagship Sailing.
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Scott S profile picture
Scott S
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Captain "Nordie" and instructor Adriane were awesome giving us a grand overview of what sailing involves and we got to actually tac back and forth across the open ocean having never sailed before. A great first time introduction. Thanks Guys!
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Sarah M profile picture
Sarah M
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We love sailing here! I've taken a few ASA courses with Nordie and participated in the Mexico trip as well-- all of my experiences have been amazing. Nordie is an amazing and patient teacher who is always incredibly prepared. My husband and I recently took a full-day charter and had so much fun getting right back into it. I cannot say enough good things about Flagship and the people who work there! Will absolutely be back anytime I am in Florida.
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Peter L profile picture
Peter L
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Highly engrossing and competent ASA 103 course. I had taken the ASA 101 course last year, and this year's 103 course was a worthy continuation of the previous course I had taken. Thank you, Captain Nordie!
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Max B profile picture
Max B
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Very friendly environment, and Captain Nordic is an excellent instructor—learning to sail while having fun!

Flagship Sailing Offers

Year round sailing instruction that is personal, enjoyable and affordable, utilizing a vacation oriented environment, which includes private beaches, swimming pools, tennis courts, ashore restrooms and showers. Our classes take place aboard sailboats that are responsive, easy to control and matched to your skill level. At Flagship Sailing you will learn to sail safely and enjoyably without being intimidated in the process.