Florida Sailing Schools

Florida Sailing Schools and Powerboat Schools

Cape Coral, Captiva Island, Fort Myers Beach, the Keys, St. Petersburg
Sailing Lessons & Powerboat Lessons on Gulf of Mexico & Tampa Bay

Offshore Sailing School’s Florida Sailing Schools and Florida Powerboat Schools provide all levels of US Sailing certification courses and US Powerboat certification courses in beautiful locations on the Gulf of Mexico, Tampa Bay and the Atlantic Coast.

Westin Cape Coral in Marina Village – Ft. Myers, FL Powerboat School

Cape Coral in Ft. Myers, Florida, is home to the Westin Cape Coral in Marina Village, on the broad banks of the Coloosahatchee River. With glorious sunsets and views of shores you can explore by kayak, this location is perfect for the Offshore Fast Track® to Power Cruising Course. The Westin has a lot to offer, so we suggest spending a day or two extra enjoying its many amenities before or after you take your course. Your first day underway, you navigate through the channels leading to Pine Island Sound and the Gulf of Mexico, learning to handle a 37′ power cat in close quarters with other vessels. Underway you are surrounded by avian and sea life. A pod of dolphins may play in your wake. Ospreys fly overhead. Pelicans dive. Egrets and herons stand stoically along the shore. During your week aboard, you’ll likely stop for lunch or dinner at the fabled Cabbage Key and add a signed dollar bill to the collection that goes to a charity periodically. Every day on Florida’s Gulf Coast presents a new adventure, and you get to experience that adventure while learning all you need to know to skipper and charter power cats anywhere in the world.

Pink Shell Beach Resort & Marina – Ft. Myers Beach, FL Sailing School

The Fort Myers Beach Florida Offshore Sailing School on Florida’s Gulf Coast is just 30 minutes from Southwest International Airport where flights from all over the country and abroad land sailing adventurers. Sitting on miles of white sandy beach overlooking the Gulf of Mexico, the Fort Myers Beach Offshore Sailing School location is perfect for learning to sail on Colgate 26 keelboats, and Fast Track to Cruising courses on 40′-47′ sailing catamarans and big monohull sailing yachts. The marina is just minutes from Gulf of Mexico open water sailing. When you return from a day of sailing lessons or big sailboat cruising instruction that get’s you ready for charter vacations, you’ll find great activities like kayaking and paddle boarding to enjoy, followed by a delectable island meal overlooking the beach.

Downtown St. Petersburg, FL – Tampa Bay, FL Sailing School

St. Petersburg is ideal for learning new sailing skills and gaining bareboat cruising certification. We’re based at the Downtown Hampton Inn & Suites and our boats are across the street in the Municipal Marina. This convenient hotel is in the middle of this vibrant town known as a haven for sailors who love the sea and living the sailing lifestyle. Florida sailing vacations get you out on the warm waters of Tampa Bay and the Gulf of Mexico, where you can enjoy year-round sailing lessons. Whether you like laid-back beach resorts or an chic, urban cultural environment at water’s edge, our Florida sailing school in St. Petersburg, is a great location for learn to sail and sailboat cruising vacations. Learn more about our course offerings below.

‘Tween Waters Island Resort & Spa, Captiva Island, FL

Captiva Island and adjacent Sanibel Island on Florida’s Gulf Coast are known as the shelling capital of the world, with pristine shoreline, miles of sugar-sand beaches, acres of protected habitats, and wildlife on land, in the sea, and sky. There is something for everyone on captivating Captiva! We’re based at ‘Tween Waters Island Resort & Spa, situated between Pine Island Sound and the Gulf of Mexico, with a private beach, complimentary bicycle use, a spa, multiple pools, fishing dock and watersports, multiple dining options, all on property. Cruise to waterside tiki huts, restaurants, and boutiques. Escape into private anchorages and explore natural habitats on barrier islands.

Stock Island YC Beach – Key West. FL Sailing School

Offshore Sailing School in Key West Florida. This well-protected marina along the unspoiled Atlantic Ocean shoreline is the perfect location for sailing lessons on Offshore Sailing School’s Colgate 26 keelboats, and Fast Track to Cruising courses on a new Lagoon 40 catamaran. In minutes you are sailing out the Boca Chica Channel, with gorgeous maritime views. The marina has a large swimming pool if you want to take a dip after your lessons and before you head back to your hotel. There’s also a Ship Store where you can pick up some snacks and ice cream.

Set Sail in Exotic Ports Around the World!

Cruise with Offshore Sailing School on our fabulous Colgate Sailing Adventures® cruises all over the world! View our highlights video from our Caribbean sailing flotilla in the British Virgin Islands here.

Florida Sailing Lessons,Powerboat Instruction, and Advanced Sailing Adventures

In addition to sailing courses for beginners, with Offshore Sailing School you can enjoy great sailing and cruising courses on 40′-51′ sailing yachts. Take a look at this video, and sign up for sailing lessons in Florida today!

Sailing School in Florida Offering Comprehensive Sailing Courses

At Offshore Sailing School, we specialize in transforming beginners into confident sailors and helping seasoned boaters sharpen their skills. As a premier sailing school in Florida, we offer immersive on-the-water instruction, nationally recognized certifications, and exclusive Fast Track® programs. With expert instructors and exceptional locations across the state, we provide a hands-on, safety-focused learning experience that blends adventure with real-world seamanship.

Finding a reliable sailing school in Florida can be overwhelming, with crowded marinas, inconsistent instruction, and one-size-fits-all programs often leaving students frustrated and unprepared. Offshore Sailing School solves these issues with structured courses tailored to your goals, small group sizes, and proven curriculum.

We offer a wide range of sailing and powerboating courses, from Learn to Sail to Coastal Navigation and Offshore Passage Making. With over 60 years of training excellence, Offshore Sailing School is the trusted name for individuals, couples, families, and corporate groups seeking real experience and expert guidance. Connect with us now to request a quote and let our Florida-based instructors guide you toward certification, mastery, and freedom on the water.

We know your sailing goals are more than just skills; they’re about confidence, independence, and unforgettable memories on the open sea. At Offshore Sailing School, we understand what this journey means to you. If you’re searching for a sailing school in Florida that truly cares about your progress and safety, you’ve found the right crew. Contact us today and let’s make your dream of sailing a reality.

Why Choose Offshore Sailing School in Florida

• Decades of Proven Instruction: As the most trusted sailing school in Florida, Offshore Sailing School brings over 60 years of experience to every course. Founded by an Olympian and run by sailing pioneers, we’ve helped thousands of students develop lifelong sailing skills through expertly crafted sailing instruction. From basic sailing to advanced certification courses, our curriculum is built on real-world application and a deep passion for sailing. Whether you’re seeking your first sailing lesson or a full sailing adventure, our track record speaks for itself.
• US Sailing Certified Instructors: Our team of experienced instructors includes professionals with worldwide experience and credentials from the highly respected US Sailing Association. Every one of our sailing instructors is trained to deliver safe, effective, and engaging sailing education to students across all experience levels. You’ll learn from an acclaimed instructor who knows how to tailor each lesson to your skill level, ensuring you fully grasp the essential aspects of sailing in a way that’s fun, challenging, and rewarding.
• Multiple Convenient Florida Locations: With locations in Captiva Island, Fort Myers Beach, and St. Petersburg, Offshore Sailing School offers easy access to some of the best sailing destinations in the state. Each location is surrounded by beautiful waters and provides the perfect backdrop for immersive sailing classes, active sailing vacations, and in-depth training.
• Real Boats, Real Experience — Not Simulators: At Offshore Sailing School, you don’t sit in a classroom pretending to sail. You get on the water immediately. All sailing lessons take place on high-performance monohulls or cruising catamarans like the Leopard 40, Leopard 45, and Lagoon 40. We believe sailing experience is built by doing, not simulating.

Explore Our Florida Sailing Courses

Florida’s scenic coastal waters and beautiful waters offer the perfect training ground for all types of sailors. Whether you’re just beginning your sailing journey or seeking higher-level courses to refine your sailing abilities, Offshore Sailing School delivers expert sailing school services tailored to a wide variety of classes based on experience, interest, and ambition.

• Learn to Sail – For Beginners of All Ages: Start with basic sailing skills in an engaging, hands-on format designed for passionate sailors of all ages. Our proper training introduces the science of sailing, basic boat handling, and sailing exercises to help you feel confident on the water. Learn to sail in familiar waters with compassionate instructors and a curriculum that meets the highest standards for sailing education.
• Fast Track® to Cruising – From Novice to Cruising in 8 Days: This immersive training program takes you from beginner to qualified sailor in just over a week. Learn docking, anchoring, and practical application of navigation and seamanship skills. It’s the ideal course for those ready to embrace the sailing lifestyle and prepare for a future chartering experience in diverse sailing waters.
• Live Aboard Cruising Courses: Dive into the real sailing lifestyle with liveaboard sail training courses that combine intensive learning with true adventure. Train during the day and spend nights anchored near beautiful locations, charming villages, or even a historic village, gaining real-world experience in provisioning, voyage planning, and sailing with confidence.
• Catamaran Training on Leopard 40, Leopard 45, and Lagoon 40: Discover the dynamics of multihull sailing with hands-on sail training courses aboard modern catamarans. Perfect for those transitioning into multihulls or preparing for ocean sailing experiences, this course provides sailing demonstrations, maneuvering practice, and insights into typical sailing conditions in Florida’s prime sailing waters.
• Powerboat Cruising Courses: Prefer a powered experience? These leisure lessons are ideal for those who enjoy cruising at speed or want to master another form of boating. Learn how to safely operate and dock motor yachts while navigating through coastal waters, spotting marine life, and enjoying the awesome experience of sailing with friends or motoring in style.

At Offshore Sailing School, every course is designed to turn beginners into accomplished sailors and advanced sailors into exceptional sailors. Our coaching techniques, personalized instruction, and commitment to excellence ensure you leave with not just sailing knowledge but lifelong memories.

Start Your Sailing Journey with the Premier Florida Sailing School

Ready to turn your sailing goals into reality? Offshore Sailing School offers expert-led sailing lessons in Florida for all experience levels. With hands-on training, US Sailing Certified Instructors, and stunning locations, our Florida sailing school is your gateway to confidence on the water. Contact us now to speak with a sailing advisor and enroll in your first course!