First Reef Sailing
Smith Bay, St. Thomas, US Virgin Islands
| (617) 466-3317 |

Welcome to First Reef Sailing, the premier sailing school in the heart of St. Thomas, USVI, offering a truly exceptional experience for sailing enthusiasts of all levels. With a legacy of excellence spanning 11 consecutive years, our passionate staff has been teaching students sailing in the tropics, creating unforgettable experiences on the turquoise waters. Our staff’s expertise and dedication have been honored with the prestigious ASA’s Outstanding Instructor of the Year award over five times!

At First Reef Sailing, we believe in offering a diverse range of ASA certification courses, specializing in both monohull and multihull cruising, as well as bareboat charter certification. We understand that every student’s learning journey is unique, and that’s why we offer flexible options, including single certifications in a week or combinations like ASA 101/103, ASA 103/104, ASA 104/114, and ASA 105/106 courses over seven days.

Our philosophy is simple – we don’t rush the learning process. Unlike other programs, we ensure our students fully comprehend key concepts, acquire practical skills, and feel confident as skippers aboard a bareboat charter. Our experienced instructors take the time to reinforce knowledge, and our students benefit from the in-depth exploration of critical sailing techniques.

Rest assured, at First Reef Sailing, you’ll be training on the newest, most modern, and most comfortable training yachts in the VI thanks to our partner company, SailTime. This experience perfectly prepares you for future charters on your own, providing you with the confidence and expertise to navigate the waters independently.

The beauty of St. Thomas and its surrounding islands provides the perfect backdrop for an unforgettable sailing vacation. Our knowledgeable team, with decades of experience living, teaching, and sailing in the region, will guide you through the most popular mooring fields, picturesque beaches, snorkeling and diving sites, and hidden coves far from the crowds.

We believe in offering the best possible experience for our students. Whether you choose to pursue one ASA certification with a relaxed schedule or embark on a more intensive journey earning two certifications within a week, we ensure that each course builds upon the other, reinforcing your skills and knowledge.

Our pricing includes everything you need for a stress-free sailing experience. From ASA certification courses, testing, and certification fees to delicious breakfasts, lunches, dinners aboard, snacks, and non-alcoholic beverages – it’s all taken care of. Additionally, we cover charter fees, customs and immigration fees (for BVIs check-ins/outs from St. Thomas), and all operating costs, including fuel, water, trash, and moorings.

At First Reef Sailing, we’re excited to welcome you to the islands and embark on an unforgettable journey of learning, exploration, and adventure. Let our dedicated team, celebrated for their outstanding teaching, show you the ins and outs of the Virgin Islands, ensuring you leave with the confidence and skills to sail with pride. We can’t wait to share the magic of the Caribbean waters with you!

American Sailing Certifications Offered

ASA 101, Keelboat 1
ASA 101, Keelboat 1
Learn to skipper a 20' - 27' sloop-rigged keelboat by day, in light to moderate winds and sea conditions. Learn basic sailing terminology, parts and functions, helm commands, basic sail trim, points of sail, buoyage, seamanship and safety including basic navigation rules to avoid collisions and hazards.
ASA 103, Basic Coastal Cruising
ASA 103, Basic Coastal Cruising
Learn to skipper a sloop-rigged auxiliary powered 25'-35' keelboat by day in moderate winds and sea conditions. Learn cruising sailboat terminology, basic boat systems, auxiliary engine operation, docking procedures, intermediate sail trim, navigation rules, basic coastal navigation, anchoring, weather, safety and seamanship.
ASA 104, Bareboat Cruising
ASA 104, Bareboat Cruising
Learn how to sail a sloop-rigged, auxiliary powered 30'-45' sailboat during a multi-day cruise upon inland/coastal waters in moderate/heavy winds and sea conditions. Learn about provisioning, boat systems, auxiliary engines, advanced sail trim, coastal navigation, anchoring / mooring, docking, emergency operations, weather, and more.
ASA 106, Advanced Coastal Cruising
ASA 106, Advanced Coastal Cruising
Learn to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions.
ASA 114, Cruising Catamaran
ASA 114, Cruising Catamaran
Learn to skipper an auxiliary-powered sailing cruising catamaran of approximately 30-45' feet in length during a multi-day liveaboard cruise upon inland or coastal waters in moderate to heavy winds (up to 30 knots) and sea conditions.

Other Services Available

  • Women Only Courses
  • Private Courses
  • Corporate Team Building Courses
  • ASA 'Challenges'
  • Day Sail Charters (public)
  • Day Sail Charters (member-only)
  • Vacation Charters
  • Sunset Cruises
  • Sailboat Cruises
  • Sail Trim Courses
  • Spinnaker Courses


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. First Reef Sailing is offering a minimum of $50.00 or 10% off their ASA 101 Basic Keelboat Sailing course.

Sailing School Reviews / Testimonials

  • Excellent experiences. Sailed with Paul in the USVI/BVI to get my ASA. Could not have asked for a better instructor! A week on a 50' Beneteau, performing all the necessary drills to feel completely comfortable to skipper a bareboat.

    Rob Frimmel - First Reef Sailing

  • Forrest has a very impressive amount of experience and skill, and I completely agree that he is always 3 steps ahead of the vessel. These guys are highly recommended and I look forward to sailing with First Reef again.

    Chris Petersen - First Reef Sailing

  • We have taken classes with both Paul & Forrest, and cannot recommend them highly enough. Extraordinarily patient and willing to review the material as many times as is necessary, they focused on teaching good sailing lessons vs passing certifications

    Chris Cancian - First Reef Sailing

  • I was fortunate enough to further my education by sailing with Forrest from RI to Bermuda, an experience and high that I continue to chase. I look forward to continuing my sailing education with Forrest and Paul!

    Jeffrey Capobianco - First Reef Sailing

  • Couldn’t ask for a better sailing experience with First Reef Sailing. If you’re looking for a great winter sailing charter or to get down to the Florida Keys and sail with them this winter… you won’t regret it!!

    Phillip Skrabut - First Reef Sailing

  • I can honestly say that learning to sail with Paul changed our lives. Many (many) people have helped us make this dream a reality, but none with the attitude, impact, and confidence of Paul and his fellow captains.

    Jeremie Mailloux - First Reef Sailing

Contact Information

First Reef Sailing

Address IGY American Yacht Harbor84GX+34C, Smith Bay RdSmith Bay, St. ThomasU.S. Virgin Islands00802United States
Phone (617) 466-3317
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