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Welcome to Flagship Sailing

Serving the greater tampa bay area since 1998, asa sailing program.

Beginning through advanced sailing lessons certified by the American Sailing Association are provided by professional, experienced instructors certified by ASA and licensed by the US Coast Guard.

Flagship Sailing Program

Recognizing that not every sailor may wish to pursue certification through one of our ASA courses, Flagship Sailing offers several introductory courses without the requirement for written testing necessary in an ASA course. These courses are taught on the water and require only an instructor evaluation for completion.

Sailing Charters

If you want to enjoy a sailing adventure with a professional captain on board then a Flagship Sailing Charter is for you.

Training Cruise to Cabbage Key via Gulf of Mexico and Pine Island Sound

Cruise to mexico 2022.

June 6 - 12, 2024

Flagship Sailing is Veteran Owned and Operated.

As such, we are proud to participate in American Sailing Association's (ASA) Veteran's Sailing Education Program by offering a 10% discount to ALL Veterans. We thank you for your service to our Nation.

Learn More about ASA's program

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.

Flagship Sailing Drug Free Policy:

All Flagship Sailing Captains/Instructors are in compliance with United States Coast Guard regulations and submit to regular random drug testing.

Passengers: No drugs of any kind are allowed on board, and the Captain is required to immediately notify the Coast Guard if drugs or paraphernalia are discovered aboard. Possession of a Medical Marijuana card does not allow its possession or use on board, nor does it mitigate the Captain’s responsibility to alert the Coast Guard.

ASA / American Sailing

  • Find A School
  • Certifications
  • North U Sail Trim
  • Inside Sailing with Peter Isler
  • Docking Made Easy
  • Study Quizzes
  • Bite-sized Lessons
  • Fun Quizzes
  • Sailing Challenge

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Come aboard and soak in the stunning views of downtown St. Petersburg, Florida, and the vast expanse of Tampa Bay with Intelligent Sailing’s top-notch experiences. Cruise on our cutting-edge luxury yachts for personalized, one-on-one coaching tailored to your skill level – whether you’re up for a laid-back “fun day” or aiming for advanced training and ASA certifications with our seasoned instructors. As ASA’s longest-serving Sailing School in St. Petersburg, Florida, boasting over 20 years of experience, we feature an entire fleet of new model yachts, ranging from just a few months to a few years old. With Intelligent Sailing, you sail and snooze on brand-new yachts!

Indulge in luxury with our Intelligent Sailing School or opt for our Yacht Club Membership program, or why not both? Gain exclusive access to our impeccably maintained fleet of yachts, including monohulls and catamarans ranging from 32 to 51 feet, each decked out with lavish amenities like multiple cabins, air conditioning, generators, refrigerators/freezers, fresh-water electric heads, and more.

Nestled in the prestigious Harborage Marina, our spot offers unparalleled convenience, with mega-yacht slips, a charming grilling area, swimming pool, lounge, showers, and laundry facilities. Enjoy easy access to downtown St. Pete’s vibrant scene, top beaches, and Tampa International Airport.

At Intelligent Sailing, we’re all about going above and beyond. From private cruises to beginner classes, corporate team-building events to special charters, we’ve got it all. Plus, explore ASA Sailing Certification Courses to boost your skills and confidence on the water.

Ready to turn your sailing dreams into reality? Our services include yacht brokerage, guiding you through every step of the process. With our Owner options, leave the care and maintenance to us while enjoying passive income opportunities based on usage.

Dive into the lively spirit of Tampa Bay and downtown St. Petersburg with Intelligent Sailing – where every journey promises extraordinary adventures.

Why settle for ordinary? Instead, join Florida’s premier sailing school and elevate your adventure with Intelligent Sailing. Choose from our fleet of new yachts and take your sailing escapades to new heights.

American Sailing Certifications Offered

ASA 101, Keelboat Sailing 1

Other Services Available

  • Couples Courses
  • Private Courses
  • Weekday Courses
  • Weekend Courses
  • Corporate Team Building Courses
  • ASA 'Challenges'
  • Day Sail Charters (public)
  • Day Sail Charters (member-only)
  • Sunset Cruises
  • Sailboat Cruises
  • Racing Courses
  • Spinnaker Courses

sailboat lessons florida

ASA Veterans Sailing Education Program - Sign Up Now >>

At ASA we recognize the sacrifices made by the brave men and women who have served or are serving in our country's armed forces. As a token of our appreciation, and our way of saying thank you, we are inviting veterans and active military personnel to share our passion for sailing by offering a discount on our ASA 101 Basic Keelboat Sailing course. Intelligent Sailing is offering a minimum of $50.00 or 10% off their ASA 101 Basic Keelboat Sailing course.

Sailing School Reviews / Testimonials

David - Intelligent Sailing

Trey - Intelligent Sailing

Payton - Intelligent Sailing

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Blue Water Sailing School

Florida Sailing Schools - Fort Lauderdale, Florida

Fort Lauderdale, Florida is known as the "Venice of America" for its extensive canal system, which allows some local sailors to practically anchor in their own back yards. It's a yachting Mecca with 165 miles of navigable waterways, seven miles of beaches, numerous marinas and boatyards, and some of the best cruising weather in the continental United States.

In short, Fort Lauderdale, Florida is an ideal location for the Blue Water Sailing School headquarters. At this base we offer all of our monohull and catamaran sailing courses .

Florida Sailing Courses and Schedules

We offer our entire range of sailing classes our Fort Lauderdale, Florida sailing school location. Details of our sailing courses, schedules and rates can be found in the Blue Water Sailing School course catalog .

Florida Sailing School Maps and Directions

The map at right shows the location of our marina in Fort Lauderdale, Florida (click the map for a full-size interactive version from Google), along with local hotels, restaurants and other nearby attractions.

Follow these links for directions to our Florida sailing school from nearby airports: Fort Lauderdale/Hollywood International Airport (major airlines)

Fort Lauderdale Executive Airport (small planes only)

Important Note: Make sure that your taxi or airport shuttle goes to our marina at 940 NE 20 Ave. Our office location at 922 NE 20 Ave may not be open on the day your class begins.

Your Yachts

Almost all of our yachts sail from the Fort Lauderdale, Florida location. You can find information and photos for all our ships on the BWSS fleet page .

Fort Lauderdale, Florida Weather

Travel information.

Small catamarans lined up on the Fort Lauderdale beach in Florida

Our live-aboard Florida sailing courses will keep you busy, but if you plan to spend more time in Fort Lauderdale you'll find plenty to do. There are thousands of restaurants and an active nightlife. The scenic Riverwalk is home to a variety of boutiques, museums, theaters, and parks.

The city of Fort Lauderdale has accommodations in every price range, from budget hotels that offer a place to crash while you enjoy the city, to luxury resorts that are destinations unto themselves. This interactive map shows some of the hotels we recommend near our marina.

sailboat lessons florida

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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Learn to Sail

Your dream of sailing can easily become a reality. The Sailboat Club is an accredited training facility of the American Sailing Association (ASA) and offers instruction to fit any schedule. View Courses

The Sailboat Club is designed for sailors who want the benefits of boat ownership without the hassles or the big expense. All you have to do is reserve a boat and go sailing. Become a member today. View Details

Charter Boats

A captained charter with The Sailboat Club is a 4 or 8 hour sail. Just sit back and enjoy the sights or sail the boat yourself, with a captain not far away to provide guidance – the choice is yours. Learn More

Our Convenient Location

Located next to Julington Creek Fish Camp on the St. John's River. Easily accessible from all parts of the greater Jacksonville area. Come by for a tour!

Our Expert Instructors

Learn to sail from our certified instructors lead by Cap'n Don, one of the most experienced captains in the business.

Our Beautiful Sailing Area

The St. Johns River and Atlantic Ocean.

We have several Precision , Morgan , and Catalina sailboats in various sizes from 22 feet up to 37 feet.

Interactive Wind Map

American Sailing Association

Weather Forecast

Beachside Sailing

Sailing Lessons and Rentals

Welcome to Beachside Sailing!

We Have a New Owner! Please see the Blog Page for an introduction.

Enjoy sailing on the breathtaking waters of the Atlantic Ocean, off the coast of world famous Cocoa Beach, or through the calm, protected waters of the Indian River Lagoon.  Whether you are just getting your sea legs or a veteran sailor, Beachside Sailing is your destination for sailing and seafaring off East-Central Florida’s shorelines and estuaries of the Intracoastal Waterway.   Contact Beachside Sailing  today to book an excursion and get underway!

ASA Certified Sailing School

We are an ASA certified sailing instruction and certification facility, offering sailing lessons ranging from basic beginners’ courses to more advanced theory and navigation skills. Our classes include ASA certifications 101, 103 & 104.  Not sure if you even like sailing?  No problem!  We offer a general Introduction to Sailing class at an unbeatable rate you won’t find anywhere else.

A Beachside Near You…

We are located at Harbortown Marina in Merritt Island, FL, just a few minutes from Cocoa Beach and Port Canaveral. We are within easy reach of Orlando and the associated theme parks.  Our location makes for a perfect vacation destination for tourists and locals alike in the East-Central Florida and greater Brevard County regions.

We conduct all charters and rentals by reservation. Call us at 321-624-5537 to book!

[email protected]

sailboat lessons florida

  • St. Augustine, Florida 32084
  • Call us: 904-829-0648

Sailing Lessons on the Open Water

At St. Augustine Sailing, we specialize in providing top-notch sailing lessons that equip individuals with the skills and knowledge needed to navigate the open waters safely while creating cherished memories

ASA Sailing Lessons

As an American Sailing Association (ASA) certified training facility our instructors have meet the high standards of ASA via an on-the-water examination and are certified by ASA to perform sailing lessons. In addition, they all hold U.S. Coast Guard Captain licenses.  St Augustine Sailing instructors are dedicated to ensure that each student receives comprehensive instruction. Renowned for our excellence, many of our instructors have been recognized as ‘Outstanding ASA Instructors,’ and St. Augustine Sailing has been honored with the prestigious title of ‘ASA Outstanding Sailing School.’ From Basic Keelboat Sailing to Bareboat Chartering, we offer a range of courses tailored to suit various skill levels.

After mastering the art of sailing, consider joining one of our  sailing membership programs to further hone your skills and boost your confidence on the water.

Additionally, if you require assistance with accommodations during your learning journey, our team is readily available to provide recommendations and support. Whether you’re seeking ASA certified instruction, beginner lessons, or private instruction, we eagerly anticipate welcoming you aboard for an enriching sailing experience. Let’s set sail together—see you soon!


Beginner lesson, private sailing instructions.

Gift Certificates are perfect for the aspiring sailors in your life! Click here to select a gift certificate and surprise your skipper with a variety of lessons to take their skills to the next level.

sailboat lessons florida

Phone: 904-829-0648

St. Augustine Sailing Enterprises, 3076 Harbor Drive, Camachee Cove Yacht Harbor, St. Augustine, Florida 32084

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Sailing school, southwest florida, your boat is ready when you are.

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SailTime Membership

Sail all season long for an easy monthly fee.

Please use the tabs at the top of the page to learn more about SailTime Southwest Florida, and be sure to visit our fleet page. Fill out the Request Information page and find out why SailTime Southwest Florida is the intelligent and easy way to sail the Gulf Coast.

World-Class Training

Sailtime is an asa awarded sailing school.

As an  American Sailing Association (ASA) affiliate, SailTime Southwest Florida’s Sailing School offers the very best in quality on-water sailing education.  Increase your knowledge and improve your skills with one of our highly qualified US Coast Guard licensed instructors/captains. We offer a full range of  ASA certifications  from basic keelboat to advanced coastal cruising and more. We specialize in teaching safe and effective  docking techniques  to ease stress when going in and out of the slip.  Visit us and learn why SailTime Sailing Schools continually receive the prestigious ASA  Outstanding School Award .

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  • 3190 Matecumbe Key Rd Punta Gorda, FL 33955

Weekdays: 8am - 6pm Weekends: 8am - 6pm

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SailTime Houston: A Family Affair with a Legacy of Sailing

At SailTime Houston, Evan and Amanda Macaluso, provide a warm welcome, fellowship, and accessibility to the boating world. Their approach?

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Get in on the Boat Club Boom

SailTime & PowerTime Fractional Boat Club is Expanding to 50 Markets DID YOU KNOW that over the past five years, more

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Ready About! Let’s Tack. If there is one word, one idea, one life-altering action, that we can chock up to

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Sail it like you own it.

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Welcome to Bimini Bay Sailing Lessons

Small sailboat sailing school.

I sold my last sailboat in July, 2023. I will still give occasional lessons for individuals who own their own small powerboat or sailboat.

Have a new Keelboat or Powerboat? I give small keelboat and small motorboat lessons on your boat, covering such topics as docking, backing up, pivot turns, and more as I share local knowledge of our waterways...

Bimini Bay is a beautiful, sheltered body of water nestled inside Anna Maria Island. It is the perfect, safe place to learn to sail -- and we often see dolphins! Bimini Bay Sailing is just minutes from Holmes Beach, Longboat Key, and Bradenton, snuggled between Tampa Bay and the Gulf of Mexico. During the last part of your saling lesson we usually sail just off the shore of Anna Maria Island into Tampa Bay, with a clear view of the Sunshine Skyway, Egmont Key and the Anna Maria Pier.

Take Sailing Lessons on the very stable WindRider 17 Trimaran, with a quiet electric motor for uncertain breezes. Or at your location on your own small dinghy sailboat or keelboat. I also offer powerboat docking lessons on your own boat.

Learn how to use a mainsheet, jib sheets, and a furling line. learn how to tack, jibe, and how to rig a sailboat. learn your basic points of sail. students usually sail at least half of the time on their own..

If you already know how to sail and you want to rent a Trimaran, for your safety and pleasure, I will still do a skills and safety review. Then I'll go out with you as your coach/guide, on the same sailboat, but you will do almost all of the sailing. This is to make your experience as safe and pleasant as possible.

Captain Floyd Jay Winters , an instructor for Bimini Bay Sailing since 2012, has taken over the helm of the Anna Maria Island small sailing school. (He is fully vaccinated.) To schedule a sailing lesson, you can reach Coach Jay Winters at 941.730.2719 or click on the [ Contact ] link.

I encourage a follow up session to refine your skills and have to opportunity to get more sailing time on your own. Parents or spouses are welcome to watch the sailing class and take photos of their kids or spouse as they learn to sail. Click the [ Lessons ] link for more information on what is covered.

Click the [ Photos ] link to see beautiful photos of Sunfish at Bimini Bay Sailing School.

A Father and Son Tacking a Sunfish (29 seconds)

For the past 11 years, Bimini Bay Sailing has offered a sailing summer camp through the Anna Maria Island Community Center. And once again this past June 2022, fourteen young sailors had the opportunity to safely experience the excitement of their first exposure to sailing during our mini sailing camps at Bimini Bay.

Receive sailing lessons at our small sailing school or just refresh your sailing skills in beautiful Bimini Bay. The magical waters around Anna Maria Island are warm, clear, and uncrowded.

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Bimini Bay Sailing, Anna Maria Island , Florida

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Sailing lessons.

As an award winning American Sailing Association (ASA) accredited sailing school with over twenty years of experience, Sunshine Coast Adventures offers a variety of sailing lessons from Basic Keelboat Sailing, to Advanced Coastal Cruising, Coastal Navigation and much more.

We emphasize the power and fun of experiential, hands-on learning in a safe and easy going environment. Whether you are new to sailing or have previous experience, our instructors will help you feel comfortable while learning to sail with confidence.

Included with Every Class:

  • Visual Classroom Presentation Material, Followed by Hands on Training
  • All Written / Practical Exams and Certificates of Completion
  • All Meals Served on-board are Nutritious, Healthy & Organic

Included with Overnight Anchorage:

  • All meals and bedding are provided during overnight anchorage trips
  • When anchoring out, we try to mix in some snorkeling on the coral reef as well as fishing while under sail
  • All Fishing Licenses are included

The following sailing lessons can be taken individually or combined into a live-aboard adventure cruise vacation:

sailboat lessons florida

ASA101 – Basic Keelboat Sailing

This 3-day course is an introduction to sailing, no prior sailing experience is necessary. You will learn to skipper a 20' - 27' sloop-rigged keelboat, basic sailing terminology, basic knots, helm commands, basic sail trim, points of sail, seamanship and basic navigation rules.

Price: $895 per person Max. Participants: 4 Duration: 3 days Extras: Daily Lunch, ASA Logbook and one year ASA Membership Textbook Needed: Sailing Made Easy

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ASA103 – Basic Coastal Cruising

This 3-day course will familiarize you with the basics of an auxiliary diesel engine powered cruising sailboat, increase your knowledge of boat systems and seamanship, and build your confidence in docking, anchoring, sail trim, and basic navigation.

Prerequisite: ASA101 Price: $995 per person Max. Participants: 4 Duration: 3 days Extras: One overnight anchorage Textbook Needed: Coastal Cruising Made Easy

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ASA104 – Bareboat Cruising

This 4-day intermediate-level course will help you achieve the skills and confidence to skipper your own boat or charter a bareboat - without hired crew. You will learn more about vessel systems such as electrical, plumbing, and diesel engines. You will expand your anchoring, seamanship, coastal navigation skills and electronic navigation using a GPS chartplotter.

Prerequisite: ASA103 Price: $1395 per person Max. Participants: 4 Duration: 4 days Extras: We anchor out most nights and may come to a dock during the trip. Textbook Needed: Bareboat Cruising Made Easy

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ASA105 – Coastal Navigation

Learn the navigational theory and practices for safe navigation of a sailing vessel in coastal and inland waters. Once you have completed the self-study materials, then you may take the written exam at our location.

Price: $595 per person

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ASA106 – Advanced Coastal Cruising

Able to safely act as skipper and crew of a sailing vessel in coastal and inland waters, in any conditions. Advanced sailing and seamanship, weather, engineering, and safety are emphasized during this 5-day course, which includes day and night time passage making.

Prerequisite: ASA104 and ASA105 Price: $1995 per person Max. Participants: 3 Duration: 5 days Extras: We anchor out most nights and may come to a dock during the trip. Textbook Needed: The Annapolis Book of Seamanship

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ASA114 – Cruising Catamaran

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Couples Sailing Course

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Custom Liveaboard Cruise Vacation

Offshore Sailing School - Official Site

Sailing Certification Courses

Get started:, call: (888) 454-7015.

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Request a Quote

  • Private Sailing Courses
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  • Women-Only Sailing Programs
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  • Fast Track to Sailboat Racing Courses
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  • Celestial Navigation Courses
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Sailing Certification Courses for Beginners and Small Boat Sailors

The learn to sail experience.

Learn to sail in Florida, or learn to sail in the British Virgin Islands and earn US Sailing Certification from expert, caring instructors. Offshore Sailing School’s comprehensive OSS 101 sailing courses are perfect for beginners and small boat sailors looking to earn basic sailing sailing certification and then continue on to gain  cruising  and  sailboat racing  skills. The OSS 101 US sailing certification course takes you through the intermediate level aboard award-winning  Colgate 26  sailboats, designed for training and safety, with plenty of features to make the transition to larger boats easy. Whichever schedule you choose below, you will receive the US Sailing Basic Keelboat textbook to study before you arrive to start your course. Studying in advance is highly recommended to ensure you get maximum value from your learn to sail experience.

The Learn to Sail course was a fabulous learning experience. Loved learning to sail, especially since we began with zero knowledge of the sport. We can’t wait to take another course and continue our sailing adventure. Our instructor was excellent – great teaching skills, very knowledgeable, made learning fun. Jill and Daniel Delmont – Cape Coral, FL Read more testimonials here

Three-Day Learn to Sail Vacation Experience — OSS 101 Course Schedule

The popular OSS 101 Three-day Learn to Sail course includes a five-night resort stay at Florida locations, and six-night resort stay at Scrub Island Resort, Spa & Marina in the British Virgin Islands.  The first three full days you are immersed in classroom and hands-on sailing instruction, with lunch breaks each day. On the third day, you take the US Sailing Basic Keelboat Certification test, then have two days to enjoy all the other vacation activities available in the area.  The standard OSS 101 package includes resort accommodations, with tax and resort fee. You may wish to request additional nights or shorten your vacation to the first three days. We also have a “no-lodging” rate for those who live nearby.

We were worried that 3 days would not be long enough to gain comfort on the water. Our instructor was great both in the classroom and on the water. We feel confident that we are prepared to sail on our own and are ready for a Live Aboard Cruising course! Highly recommend Learn to Sail course. Jill Showalter – Williamstown, WV Read more testimonials here

The Only Way to Learn

Academics and professionals whose careers immerse them in learning have applauded Steve Colgate’s teaching method after taking Offshore Sailing School sailing courses.

As soon as you sign up you receive the US Sailing Basic Keelboat textbook  and  our comprehensive Fast Track® to Sailing textbook written by Steve and Doris Colgate. You also receive a packet of information on what to wear and bring, your course schedule, and information about the location.

To give you a broader visual understanding before you arrive for the course, we recommend taking our  Learn to Sail Online  course developed by Steve and Doris Colgate.   This interactive four-hour program, which is mandatory if you are enrolled in the OSS 101 2-day schedule, is provided by the  BoatUS Foundation , the premier online boating education provider in the United States.

All Learn to Sail certification courses include a classroom session each day, before you go out on the water. These sessions reinforce what you studied in the book, and graphically explain the “whys” (not just the “hows”) of what you are about to learn on the water on your way to earning US Sailing Certification. During these sessions, a model of the Colgate 26 and videos from the Online Learn to Sail Course are utilized to further clarify what you studied.


Now you are sailing aboard an award-winning Colgate 26, actually “doing” what you studied in the book and classroom. These hands-on sailing course sessions are thrilling as your instructor verbally guides you through the steps of learning to steer and trim sails. You do all the maneuvers, coached by your instructor. No question is too “dumb” to ask, no maneuver is ever considered “wrong.”

“I had the most amazing experience! I signed up alone and had no idea what to expect. I had never been on a sailboat before, and was just looking for an outdoor activity I would enjoy. After day one, I wasn’t even sure I could handle it, seemed so much to know! But by day three we were so in sync! This is not something I want to let go of. I will continue onto the next course, I am obsessed!” Cheryl Carreau – North Bergen, NJ Read more testimonials here

The Best Sailboats to Learn On

The award-winning  Colgate 26  sailboat is the brainchild of Offshore Sailing School founder and National Sailing Hall of Famer, Steve Colgate, who asked renowned naval architect Jim Taylor to draw its lines for production. The year it was launched, the Colgate 26 was chosen by the U.S. Naval Academy and then the U.S. Coast Guard Academy for training plebes and cadets. The Colgate 26 also makes it easy to move up to larger sailboats quickly.

  • What You Learn
  • What's Included
  • Where To Learn
  • Course Schedules
  • Testimonials

The Learn to Sail Certification course takes you through the intermediate level, covering more than you thought possible. Depending on weather conditions and the learning pace of all in your class (maximum four per boat per instructor), the following knowledge and skills are learned and practiced.

  • Nautical terminology
  • Rigging and sails
  • Getting underway
  • Proper winch techniques
  • Finding wind direction
  • Points of sailing
  • Tacking and jibing
  • Interaction of wind and sail
  • Maneuvering in close quarters
  • Wind pressure and lift
  • Heeling and stability
  • Apparent wind
  • Wind shifts
  • Sailing wing and wing
  • Stopping and starting under sail
  • Crew overboard pick-up
  • Sailing backwards
  • Rudderless sailing
  • Sail trim and sail shape
  • Boat balance
  • Mooring and anchoring
  • Docking under sail
  • Most used knots
  • Right-of-way rules
  • Grounding remedies
  • Heavy weather techniques
  • Steering with a compass
  • Sailing in current
  • Weather and lee helm
  • Reefing (shortening) sails

Pre-requisite for the Learn to Sail course: No prior sailing experience required

Certification:  Basic Keelboat Certification from US Sailing, the governing body of sailing in the United States, is included in your tuition package.

Please visit  Our Locations  for more information. Rates vary by season and location, and include all the elements listed below. Not included are meals, travel and other expenses you may incur.

The Learn To Sail Certification Course Package Includes:

  • Learn to Sail course tuition
  • Five or six nights accommodations
  • Daily resort fee and applicable taxes
  • US Sailing Basic Keelboat textbook
  • Practice test sail
  • US Sailing Basic Keelboat Certification when you pass the test
  • Your Official Logbook
  • Course Diploma
  • Eligibility to participate in Colgate Sailing Adventures® Flotilla Cruises
  • Exclusive subscription benefit from  Cruising World  or  Sailing World magazines (mailed to US address)

The 3-day Learn to Sail course is available everywhere except Tortola, BVI. Everything above is included.

Please visit Our Locations for more information. Please call to confirm open locations as several resort marinas were affected by Hurricane Ian in September 2022. Rates vary by season and location, and include all the elements listed below. Not included are meals, travel and other expenses you may incur.

  • Tween Waters Island Resort & Spa, Captiva Island, FL
  • Hampton Inn & Suites, St. Petersburg, FL
  • Stock Island/Key West, FL
  • Scrub Island Resort, Scrub Island, British Virgin Islands

Sample schedules are below and may vary by location. A detailed schedule, with when and where to meet information, is sent when you enroll.  

Daily Schedule for Three-Day Learn to Sail Course, Monday through Wednesday 9:00 a.m. – 1:00p.m. – Classroom session ashore followed by on-water instruction 1:00 p.m. – 2:00 p.m. – Lunch break ashore on your own 2:00 p.m. – 5:00 p.m. – On-water instruction. On Day 3, you will take your written test

Offshore Sailing School knows we cannot thrive without great employees and products. All graduates are asked to complete an evaluation at the end of the course. The following testimonials come from those evaluations. Many of our alumni are happy to correspond by email or phone with you. If you would like us to put you in touch with anyone below, please call 888-454-7015 or email [email protected] .

“For years I have wanted to take this course. It was better than I expected. The Colgate 26 is a great boat to learn on. The textbook that was provided was also excellent. Andy, my instructor, could not have been better.”

John Linscott – Ft. Myers, FL

“The Learn to Sail class was an excellent way to spend quality time with my Dad, and learn a great new skill. Barbara made the class easy, efficient and self-rewarding! What a great new way to see and experience New York City.”

Brendan McManus – Atlanta, GA

“It has been two years since I took the Learn to Sail course in Manhattan, and I cannot believe what a great foundation it has been. It still takes my breath away to relive all those memories! The sailing adventures that opened up for me have really changed the course of my life and that of my husband, as well. I now own my own 30-foot sailboat, and we both agree we are as happy as two kids again. Thank you and thank you again!”

Carol Slabinski – New Hartford, CT

“My father recently passed, and sailing was a way of honoring him. My father and I shared many great moments together day-sailing, often without a word spoken. The mutual peacefulness we experienced required no words. Offshore Sailing’s Cory Crowner helped me regain the confidence to sail again with new adeptness that would surely make my father proud.”

Scott Colthorp – Knoxville, TN

“Absolutely fantastic experience! Totally exceeded my expectations. My wife and I had never sailed before but now I am HOOKED! Our instructor was personable, professional and patient. He gave us the encouragement and confidence we needed. We will definitely be taking another course!!”

Grant Nelson – Prairie Village, KS

“I had never before been on a sailboat on the ocean, or sailed ever. By the end of the course, my husband and I had learned a new language and a new skill with surprising speed, and on our test sail on the last day we had a BLAST! We were confident and then DOLPHINS surrounded our boat. Magical!! Our instructor’s knowledge and unflappability put us all at ease. Jacek is a truly gifted and patient teacher!!!”

Patricia Nelson – Prairie Village, KS

“This was a bucket list item for me! My recent retirement has allowed me to realize a dream that has been tucked away from the 60’s when I lived in the Midwest. I have aspired to attend the Colgate school for many years. Bill was a wonderful instructor. He is quite knowledgeable and very patient. I liked the way he would review topics previously covered. The visual aides were very helpful.”

Gary Firestone – Ft. Myers, FL

“The instructor and boat were both excellent. Jacek did a terrific job of getting everyone involved and rotating through the different aspects of ship handling. I learned far more than I’d hoped. The location (Captiva Island, FL) was great as it afforded the ability to actually sail in the Gulf. I would highly recommend this course to anyone as it will only increase your knowledge, skills and confidence to handle your own boat!”

Phil Woodard – Woodbridge, VA

“Opened up a whole new world. Simply wonderful! We had taken a shorter sailing course in DC over a weekend. I would advise anyone who really wants to learn sailing to avoid those and go with your course. It would have been money saved to do your course; more time on the water, BETTER vessels, instructions, gear, classroom, etc.”

Chris and Janet Kelly – New York, NY

“This company is awesome, and the people are dynamic and thorough from my first phone experience to meeting Steve Colgate himself.”

Lynn and Gerry Lynch – Newport, NH

“This course exceeded my expectations. I looked forward to each day of class and the challenge of sailing ever changing conditions with a very experienced and knowledgeable instructor. Never once did I feel I was at risk. We were always sailing in control while in high wind conditions. Simply a great overall experience of learning.”

Joe Wieland – West Chester, OH

“I was a little apprehensive about the course, as I had no prior sailing experience, but our instructor immediately set my mind at ease. She was incredibly patient and knowledgeable, and she made our classroom and on-water sessions fun! Her enthusiasm and love of sailing was contagious, and I enjoyed every minute of my experience. Now that I’ve completed the Learn to Sail course, I can’t wait to participate in a cruising course!”

Catherine Strauven – Atlanta, GA

“Everything was first rate. Offshore Sailing School is a uniformly exceptional organization. I would recommend them to anyone. The instruction, staff and course were all well done.”

Eric Strandjord – Eagan, MN

“It was an absolutely great week. My 18 year old son had been hesitant about going “to school” over spring break, but he LOVED it and is totally hooked on sailing. Mike was a fabulous instructor and well exceeded our expectations.”

Laura Eckhardt – Vienna, VA

“This is what I had been looking forward to for a long time. It was great. I finally found something I love. The best three days of my life. I want to come back to learn how to do the big boat too.”

Hannah Sheffler – Concord, NH

“I have had a remarkable week learning to sail at Offshore Sailing School on Captiva. This experience has enabled me to feel very confident and knowledgeable for all future sailing endeavors. Thank you for having such a great staff (especially Rick) and facilities that were so helpful in allowing me and my sister and father to learn how to sail well.”

Sarajane Sparks – Alexandria, VA

“My sisters and brother and I gave this course to my father for his 70th birthday – Rick and Offshore Sailing helped us provide the perfect gift to a father who has given so much to us. The Offshore Sailing School’s Learn to Sail course exceeded my expectations. Having no prior sailing experience, I am beyond impressed with my knowledge and ability leaving the course. I give it my highest recommendation.”

Stephanie Smith – Alexandria, VA

“Jim did a great job explaining the fundamentals of sailing to my family. We came to this course without any prior sailing experience, but Jim ably explained these novel concepts with patience and clarity. On the water, he patiently worked with each of us until we understood the basics and operating a sailboat. Everything about my experience with Offshore Sailing was great. The team did a great job getting my family ready to sail by ourselves. I plan to take the next course next year to continue my education and improve my skills. I’d recommend Offshore Sailing School to anyone.”

Dan Coakley – Manassas Park, VA

“Our overall experience was excellent! My two boys loved being on the water and wanted me to extend our vacation so they can keep on sailing with their instructor.”

Daniel Sammon – Pearl River, NY

“The staff of Offshore really made the entire experience seamless and effortless from initial inquiry phase through booking the course and finally getting out on the water. Mike was incredibly patient with me, a non-sailor, who had to learn everything from the beginning. I loved every minute of it and can’t wait to do the next level course. This is an amazing program. Thank you!”

Kathryn Herterich – Fernandina Beach, FL

The Colgate 26 is used in all Learn to Sail, Performance Sailing and Racing courses. Designed by Steve Colgate and naval architect Jim Taylor, the Colgate 26 is a popular high performance keelboat, used to train plebes and cadets at the U.S. Naval and Coast Guard Academies, great for club racing and daysailing. Read more…

Newsletter Signup

The Offshore Sailing School newsletter is emailed weekly to anyone interested in learning more about sailing and boating. It is packed with sailing and boating news, how-to tips, upcoming programs, contests and special deals.


Toll-free US and Canada: 888.454.7015 Local and International: 239-454-1700

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© 2024 Offshore Sailing School - Official Site. is managed by Offshore Sailing School. Please report any issues to Offshore Sailing School.

sailboat lessons florida

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  • Fast Track to Sailing | Beginner to Advanced in Six Days
  • Fast Track to Boat Handling & Docking
  • Catamaran Refresher & 114 Endorsement
  • Docking Refresher Course on a Catamaran or Monohull
  • IPC Prep With Cruising Certification & Catamaran Endorsement
  • Private Courses
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  • Team Building Programs
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  • Captiva Island
  • St. Petersburg
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  • Scrub Island
  • St. Lucia & Windward Islands
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  • Sailing – Out & About SWFL
  • America’s Cup Endeavor Program Videos
  • Growing Up Moorings
  • Doris Colgate Sailing Clinic & Cup
  • Steve Colgate Inducted Into National Sailing Hall of Fame
  • OSS Student Proposes During Course
  • Steve Colgate and National Sailing Hall of Fame
  • St. Lucia and Windward Islands Flotilla Cruise
  • Weathering Unexpected Bad Weather
  • A Sailing Adventure He Still Can’t Believe Was Real
  • 2016 Croatia Flotilla Cruise Diary
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  • Certification Levels

Nautical Rope

Our sailing school offers individualized sailing instruction through ASA Certifications and Leisure Sailing Lessons 

850-221-2895 [email protected]

Premier Sailing School & Charters in Pensacola, Florida

Floridaze Sailing offers the highest quality sailing instruction in Northwest Florida. Both  ASA (American Sailing Association)  and non-certification sailing classes are available. If you just want to relax at Pensacola Beach, charter a sail with Floridaze on the beautiful Gulf of Mexico or the clean, clear waters of Santa Rosa Sound.  

Our sailing instructors are accomplished sailors. They are competent, capable and safe sailors.

Our sailing school offers individualized sailing instruction (classes are limited to 2 individuals unless otherwise requested by students).

Our senior sailing instructor,  Bob Patroni , has over 35 years of sailing experience on the Emerald Coast of Northwest Florida, as well as 20 years as a college level professor.

Floridaze's teaching schedule is flexible and amenable to your needs.

Floridaze's competitive  pricing  allows you to obtain quality sailing instruction at affordable rates on Pensacola Beach, Florida.

Our sailing school is great for those living or visiting Pensacola, Pensacola Beach, Gulf Shores, Navarre, Orange Beach and the Northwest Florida area.

Top-rated Sailing School & Charters in Pensacola at Floridaze Sailing

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Sailing charters.

We offer American Sailing Association certifications as well as Leisure Lessons!

Sunrise, sunset, half-day and full-day charters available.   Sail beautiful Pensacola Bay and adjacent waters on a 32 foot J Boat with Captain Bob. 

Elite Sailing School & Charters in Pensacola at Floridaze Sailing

“Captain Bob came to our place and to our sailboat and took us out for a half day trip.  We wanted to improve our general sailing knowledge, and Bob really delivered.   We learned much more than we expected in a half day.  I would highly recommend Bob for any type of sailing instruction.  He knows how to teach you…it was just the right level of challenging us and learning for us, while at the same time being able to enjoy a pleasant day on the water.”

When my friend told me he wanted to learn how to sail, I searched the Gulf Coast for a good organization to help me, and I found Floridaze Sailing online. I exchanged a few emails with Captain Bob, and he turned out to not only be a great captain, but also a great tour guide, teacher, and friend to the four of us. I can't recommend enough taking a day to go sailing in the beautiful waters surrounding Pensacola, Florida! I especially recommend Captain Bob and Floridadaze sailing as your guide: whether for leisure or learning! 

My wife and I took ASA 1 and 2 lessons from Captain Bob several years ago. The instruction was to the book, but also meaningful and useful for a novice couple. Captain Bob was patient yet he challenged us. If my wife and I would have attempted to learn on our own, one of us might have ended up in the Sound. We enjoyed Captain Bob's wit and wisdom and use some of the applications he taught us outside of the book routinely.

Read what our students have to say!

Florida Sailing and Powerboat School and Charters Florida Sailing Academy Florida Powerboat Academy

Sailing Instruction, Training, and Certifications Powerboat Instruction, Training, and Certifications BoatUS/NSBC On-Water Training US Powerboating Safe Powerboat Handling Training Personal Training or Group Classes (Four persons maximum) Sunset charters, half day, full day aboard one of our boats Celebrate, relax, special occasions Contact us for pricing Charter Services-Captained Multi-Day, Full Day, Half Day, and Sunset Charters on sailing vessels or powerboats. Fishing Charters-In shore and near shore, flats.  Trolling and bottom fishing locally. Personal Training on the water-Your boat or ours. Delivery services-locally, Caribbean, globally. Training and Certifications : ASA-American Sailing Association-Affiliate School 882 RPBA-Recreational Power Boat Association-Affiliate School 882 US Powerboating Accredited Training Facility BoatUS/NSBC Accredited Training Facility Training, Certification, Instruction Sail and Powerboats Call now to schedule  941.500.2485

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Florida Sailing and Powerboat School and Charters Florida Sailing Academy Florida Powerboating Academy Mar Adentro Marine and Charter Services, LLC. 2001 Whitfield Park Ave. Sarasota, FL 34243

Phone: 941.500.24 85 Office: 941.758.7500 Fax: 941.758.7556 Email Us!

Mar Adentro Marine and Charter Services, LLC. Florida Sailing and Powerboat School and Charters Florida Sailing Academy Florida Powerboating Academy BoatUS Foundation American Sailing Association US Powerboating

Training-ASA and RPBA, US Powerboating, and BoatUS/NSBC Charters-Sail and Power Private Instruction

Florida Sailing Academy and Florida Powerboating Academy offer a progressive educational process and complete training to achieve all levels of ASA/RPBA certification.  All instructors are certified with the ASA/RPBA and USCG Licensed. Florida Powerboat Academy is training for BoatUS/NSBC and US Powerboating to issue certifications for their programs.  Our instructor trainers are certified by NSBC/National Safe Boating Council and US Powerboating. Charters are available with USCG Licensed Captains throughout the Tampa Bay area, Gulf of Mexico, and surrounding waters. Private instruction and training is also available on your boat or ours.

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  2. Florida Sailing School

    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 ...

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  6. Offshore Sailing School

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    Address Information: 'Tween Waters Island Resort & Spa. 15951 Captiva Drive. Captiva Island, FL 33924. View The Offshore Sailing School Brochure. Sail as close to nature as you can get, on pristine Captiva Island, Florida, with Offshore Sailing School! Take fun-filled sailing lessons where dolphins play.

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    We are within easy reach of Orlando and the associated theme parks. Our location makes for a perfect vacation destination for tourists and locals alike in the East-Central Florida and greater Brevard County regions. We conduct all charters and rentals by reservation. Call us at 321-624-5537 to book! [email protected].

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    The popular OSS 101 Three-day Learn to Sail course includes a five-night resort stay at Florida locations, and six-night resort stay at Scrub Island Resort, Spa & Marina in the British Virgin Islands. The first three full days you are immersed in classroom and hands-on sailing instruction, with lunch breaks each day.

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    Floridaze Sailing offers the highest quality sailing instruction in Northwest Florida. Both ASA (American Sailing Association) and non-certification sailing classes are available. If you just want to relax at Pensacola Beach, charter a sail with Floridaze on the beautiful Gulf of Mexico or the clean, clear waters of Santa Rosa Sound.

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