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Family Learn to Sail Programs

Buy the Boat Option for Families and Friends

Get the most out of your vacation with our fun sailing for kids and family programs. Special pricing is available for families who want to learn together, allowing up to four students to learn to sail or cruise all on one boat for one package price. Buy the Boat reservations are designed for families and close relatives who want to learn together. The reservation must be made and paid for by one person for the entire party, with all students participating in the course named on the contract. For a quote on our sailing with family options, call 888-454-7015 and ask for “Buy the Boat” options which includes two resort rooms in the package.

‘Tweens and Teens Learn Free in the OSS 101 – Learn to Sail Course

Treat your family to a memorable family sailing vacation at one of our family-friendly seaside resort locations on the Gulf of Mexico. A 3-day Learn to Sail Course package includes 2-room resort accommodations and the cost of just two tuitions for a family of up to four (one or two adults and up to two youth ages 7-17). Anyone age 18 or above is considered adult. Up to five family members may take the course together and share the two-bedroom accommodations at the resort, but the fifth person will be charged an additional $750 for tuition, and resort amenity fee if applicable.

Sail, Play and Explore

The sailing lessons for kids package has a half-day learning schedule that allows plenty of quality time to enjoy other activities to round out your vacation. Rent bicycles, jet skis, fishing skiffs. Enjoy paddle boarding on the Gulf of Mexico, go swimming and collect amazing seashells. Explore nearby wildlife preserves, fish off the pier.

Sailing with Kids At Beautiful Beach Resorts

Check out these two great resort locations and call 888-454-7015 for rates on terrific family sailing vacations.

‘Tweens and Teens Learn Free and Family Sailing packages include:

  • Instruction for everyone aboard in the 3-day Learn to Sail Course
  • Two copies of Steve and Doris Colgate’s Fast Track to Sailing book, published by McGraw-Hill for Learn to Sail
  • US Sailing Basic Keelboat Certification for two paid students (additional certification for ages 7 and above is $75 per person)
  • Diplomas and log books to take home
  • 2-room accommodations, room tax and resort amenity fee (for up to four people; fifth person may need to add daily resort fee)

“Jacek was a great instructor. I attended this course with 3.2B_Ft.MyersBeach_Slide_13_Family_Learning_700x465my wife and three of our children. He was very patient and made sure everyone understood the material. We all loved the course.”

Jeff Breymaier – Maumee, OH

Book Early for First Choice Dates at Resort Locations

Courses for sailing family vacations start on Monday morning. Plan to arrive Sunday night and leave the following Friday afternoon, or stay an extra day to make getting home less of a rush. Don’t forget to purchase trip insurance to give you peace of mind when you book family sailing lessons.


  • Buy the Boat options are available only for groups of three or more. Private* courses for two are also available
  • All parties participating in a Buy the Boat or Private* Couples option must be booked at the same time on the initial contract and paid for by the individual booking the course on that contract; additional students may not be added at a later date
  • Tweens and Teens Sail Free is only available if you purchase the full accommodation packages
  • Offer available only on the 3-day Learn to Sail course; Buy the Boat discounts available on all courses except Performance Sailing, Racing and Passage Making courses
  • Reservations for resort-based courses are taken on a space available basis, minimum three weeks in advance of course start date
  • Black-out dates may apply
  • Tuition and package rates subject to change and vary by season
  • Terms and Conditions Agreement sent when course is booked, must be signed and returned before course is confirmed
  • ‘Tweens and Teens must be between the ages of 7 and 17
  • No age limit on Buy the Boat discount
  • At least one adult (preferably a parent) is required to participate with ‘Tweens and Teens
  • These deals may not be combined with any other discounts or offers
  • *Private refers to time on boat only. Classroom sessions may include other students in same course but on different boat

“This was a family course for us and my two children (9 6.12_Couture_Kyle_2012and 11), who were a little apprehensive at times. Despite that, on our sail Friday without an instructor, we all put what we learned to work and had an excellent day at sea! It is obvious that Offshore Sailing School puts a lot of effort in their selection of instructors. We thoroughly enjoyed the class and look forward to getting back out on the water with our newly gained sailing confidence.”

Kyle Couture – Birmingham, AL