Offshore Sailing School Specials

Offshore Sailing School is dedicated to making your learning experience safe and rewarding. Learn to Sail or Learn to Bareboat Charter Cruise courses are available at ‘Tween Waters Island Resort & Spa on Captiva Island, the Downtown Hampton Inn & Suites in St. Petersburg, and at Stock Island Yacht Club & Marina in Key West, Florida; plus Scrub Island Resort, Spa & Marina in the British Virgin Islands. We also offer Fast Track® to Power Cruising certification courses from The Moorings base on Tortola, BVI. Protect your investment with Travel Insurance. View coverage options here.

Fall in Love with Sailing – Save 10% On Most Courses in Florida and the British Virgin Islands

SAILabrate the Sailing Lifestyle with 10% Savings Today

Come relax and enjoy learning to sail and bareboat charter in beautiful vacation destinations in Key West, St. Petersburg, and Captiva Island, Florida, or Scrub Island, BVI. Save 10% when you enroll in a 3-day Learn to Sail Course, or week-long Fast Track® to Cruising Course, or 6-day Live Aboard Cruising Course.

  • Learn to Sail Course 101  for those with little or no sailing experience; Monday-Wednesday, 9am-5pm (1-hour break for lunch ashore on own).
  • Fast Track to Catamaran Cruising 101/103/104/114 for those who want to quickly go from couch to captain’s chair and start chartering spacious catamarans. First two days stay ashore while learning the basics aboard a Colgate 26; then board the catamaran for a very special six day/five night live-aboard experience including most meals.
  • Fast Track to Live Aboard Cruising 101/103/104, same course as above but aboard Colgate 26 and monohull yachts.
  • Monohull or Catamaran Live Aboard Cruising Course 103/104/114 for those who know how to sail and want to jump into big catamaran yachts; Saturday 9am to Thursday 10am.
  • For new enrollments from February 14 to February 29, 2024, with courses ending by June 29, 2024.
  • Mention “SAILabrate 10” when enrolling.
  • SAILabrate savings may not be combined with any other discounts nor promotional offers.

Call 888-454-7015 or 239-454-1700; or book online for a fabulous sailing adventure today!

Family Cruising and Sailing Packages

Plan Spring Break and Summer Vacations Now!

Fast Track® to Live Aboard Cruising Course on an exciting monohull or spacious catamaran is a very special program for families, lauded by so many over the years.  Available at most of our resort locations in Florida and the British Virgin Islands, family buy-the-boat packages are wonderful bonding experiences.

Bring your kids (minimum age 12, maximum age 25) to learn sailing basics first on a 26 footer the first 2 days, then the joys of cruising on big yachts the next 6 days. This 8-day experiential sailing vacation is packed with sailing education, discovering local culture, and having just plain fun in a unique on-water environment.  You stay ashore at a neat resort the first 3 nights in accommodations with two rooms, then board a big cruising boat on the third day of this 8-day adventure, complete with 360° swimming and snorkeling options, and great places to explore ashore. You will have three cabins to share aboard the yacht.

Learn to Sail aboard a fast and fun Colgate 26 keelboat during our Family Learn to Sail course with resort stay in Key West, St. Petersburg, and on Captiva Island. We offer a value-priced family sailing vacation package with two adults and up to three children between the ages of 7 and 17. This package includes accommodations with two rooms.

Parents Savor the Joys of Being Together, Learning Together

This is absolutely the perfect to opportunity to reunite family members in a unique learning environment. Your patient and super knowledgeable instructor will guide the family through all the steps of becoming comfortable at the helm, helping each other crew the boat, and gain the experience so many seek to be able to share amazing sailing vacations together in the future. The skills you learn in this course prepare you for bareboat chartering in the Caribbean or abroad, as a team, as a family, enjoying each other’s company to the max!

The Fine Print:

  • Special Family Buy-the-Boat Option is available at a special discount off the regularly quoted price.
  • For four in your party – 2 adult parents, and 2 offspring minimum age 12, maximum age 25.
  • May add a 5th offspring for an added price, which will be quoted when you call.
  • Discount cannot be used in conjunction with other discount promotions or other courses unless otherwise noted.
  • If you have already signed up and are confirmed in this course, discounts cannot be applied retroactively.

Welcome Aboard!

Call 888-454-7015 or 239-454-1700 to book your family sailing adventure today!

‘Tweens and Teens Learn to Sail “Free”

A Value Packed Family Learn to Sail Getaway

‘Tweens and Teens family sailing course vacations are a very special way to introduce you and the kids to the joys of sailing. You can bring up to two kids ages 7-17 to take the Learn to Sail 101 Course package with you. And those 2 kids are essentially “free” as the total course package comes with a very sweet discount.

Attentive Instructors Stimulate Kids to Learn More

Offshore Sailing School instructors have lots of experience with families learning together. Everyone aboard is encouraged to get fully involved. You will take turns steering the boat and sharing  all the jobs aboard while learning how to make the boat move with sail power alone. You will all learn what to do if someone or something goes overboard. And everyone will feel the empowerment sailing provides when the boat slides effortlessly through the water because you worked together as team.

The Fine Print:

  • This offer is only available for the Learn to Sail 101 course, select weeks for immediate family members.
  • You may sign up two parents and two kids (7-17), all four from the same immediate family.
  • The discount will be quoted when names and ages of kids, and names of family members are registered with your sales associate.
  • You may add a 3rd offspring (7-17) but that child will not be “free.”
  • The course package you will be quoted includes the 3-day Learn to Sail 101 course, and 5 nights accommodations at the resort where the course is offered, allowing two days following the course end to relax and enjoy cool surroundings in deal locations.
  • US Sailing Basic Keelboat Certification is included for any member of your party that takes and passes the certification test, but not required.
  • Course participation diplomas will be awarded all regardless of whether certification test is taken.
  • Resort accommodations in the package also include the applicable resort fees and taxes, but no meals are included.
  • The course does include classroom time each morning before each day’s on-water sailing lessons.

To Check Availability and Book Your ‘Tweens and Teens course, call 888-415-7015 or 239-454-1700 today!

Women Only Sailing & Boating Lessons

Women Take the Helm!

Women-only sailing lessons and powerboat lessons are a great way to learn for friends and family members who want a unique, highly rewarding, existential getaway.

On request, Offshore Sailing School will schedule women-only courses for parties of 3 or 4 women who wish to take a course together.  If you want to charter large sailing yachts, or own or plan to buy a live-aboard sailboat alone, with a spouse, or friend, we recommend the Fast Track® to Cruising 101/103/104 on monohulls or 101/103/104/114 on catamarans.

If you already own a power cruiser, have friends who have invited you aboard, or plan to start chartering powercats in the Caribbean and elsewhere, the Fast Track® to Power Cruising 109 course is the perfect segue into taking charge and boating equally with family and friends.

Learn more about Women-Only Sailing, Cruising and Powerboat Courses here!

Discounts for Retired & Active Military Servicemen & Women

Thank You For Your Service!

If you are active in the military or a retired veteran, we thank you for your service and are pleased to provide a 10% discount on your certification course package.

Here are the course packages you may apply your discount to:

Here’s how to make that discount happen:

  • Call 239-454-1700 or 888-415-7015 to enroll and state that you are active or retired military.
  • Scan and email or text a copy of proof of your military status to the sales associate you are working with, who will then get approval to verify you qualify for the military discount.

The small print:

  • If you have already signed up for a course, unfortunately the military discount may not be applied retroactively.
  • 10% military discount may not be used in conjunction with any other discount promotions or on other courses and programs offered by Offshore Sailing School unless otherwise noted.
  • 10% military discount applies only to the specific military personnel’s portion of the course package, not to others who may be taking the course with you in your party.

To learn more, please call 888-415-7015 or 239-454-1700, or send an email, and thank you again for your service!

Immerse Yourself in Armchair Sailing

When You Can’t Get Out on the Water, This is a Great Read!

There’s a whole lot of history, intrigue, and excitement in the 60 years Offshore Sailing School has been in existence. When Steve Colgate started writing his “vignettes,” Doris said, “We need to get these into a book!” And so they did, along with an amazing tale of how they built Offshore Sailing School into an iconic brand, and turned their lives into a tale of one (mostly) sailing adventure after another. Renowned author, Herb McCormick, captured the Colgate story in this intriguing biography that so may have said they couldn’t put down. Purchase OFFSHORE High on Amazon, in bookstores (list price $39.95), or order a personally autographed copy here.

Grad Discounts on Colgate Sailing Adventures® Flotilla Vacations!

Hey Offshore Sailing School Grads – These Special Sailing Vacations are for You!

And You Get Special Discounts Too!!!

Steve and Doris Colgate started flotilla cruising vacation trips for Offshore Sailing School graduates way back in 1972. These catamaran and monohull big boat cruising adventures are a whole lot of fun, taking you to fantastic cruising destinations all over the world, where cruising ships often cannot go. If you are an Offshore Sailing School graduate we truly appreciate your interest in living the sailing lifestyle and seeing the world under sail!

We Take Care of the Details, You Get to Sail with Like Minded Souls!

Colgate Sailing Adventures® Flotilla Cruises are organized and led by terrific sailors who work for Offshore Sailing School, with years of experience on the water. Sign up for a one or two-week Colgate Sailing Adventures® flotilla cruise and enjoy special discounts because you are an Offshore grad. Please check out our Flotilla Holidays for all the upcoming destination sailing trips scheduled for 2024 and 2025, including great locales in the Caribbean, the Greek Islands, the Amalfi Coast of Italy, Sicily and the Aeolian Islands, and more. Most of these cruises are on fleets of four to six monohull yachts or sailing catamarans. Don’t wait to sign up. For future dates and more information, click here.