Sailing at ‘Tween Waters Island Resort & Spa
Perfectly nestled between our pristine, private Gulf of Mexico beaches to the west and the natural beauty of Pine Island Sound to the east, ‘Tween Waters Island Resort & Spa uniquely combines historic charm, luxury amenities, pure relaxation, adventurous recreation, and genuine warm hospitality to bring you and your family Captiva Island’s top-rated vacation destination.
Experience miles of open water, shell-strewn beaches, award-winning sunsets and abundant wildlife and marine life that collectively make Captiva Island an ideal place for sailing. Choose from a variety of sailing courses offered right here at ‘Tween Waters through Offshore Sailing School, America’s #1 Sailing School, and get ready to set sail.
Courses and Vacation Packages Available Starting March 1, 2023
Learn to Sail
America’s #1 Sailing School® offers a learn to sail holiday in Florida requiring no prior experience. All beginner sailing courses are taught by certified sailing instructors, with a maximum of four students per course, unless you are a family of five. Offshore Sailing School also offers private sailing courses for two or more students enrolled together. Sailing vacation packages include tuition, and resort accommodations, including tax and resort fee, which may vary by season.
At the end of the course and successful completion of written and practical tests, you will receive US Sailing c Keelboat certification to skipper a boat up to 30’. This course is available as a family sailing vacation package with value pricing for two adults and two children ages 7-17, sharing two resort rooms for five nights.
Fast Track to Cruising® Vacation Package
Gain the knowledge, skills, and confidence to handle sailboats and catamarans up to 50’ without having to hire a captain or professional crew. Stay at ‘Tween Waters Island Resort & Spa Friday through Sunday nights* while learning to sail aboard a Colgate 26 for two days, then move aboard the yacht in a Live Aboard Cruising Course until Saturday, or return to the resort each night in a Bareboat Cruising Course and depart on Friday. Offshore Sailing School can take you from your couch to the Captain’s chair in a week.
Whether you have no sailing experience, sail small boats, or are returning to sailing after a hiatus, this is the perfect sailing training course from experienced and patient instructors who receive accolades from their students on course evaluations. At the end of the course and successful completion of written and practical tests, you will receive US Sailing Basic Keelboat, Basic Cruising, and Bareboat Cruising certifications to skipper a boat up to 50’.
*Course Schedule will change to Thursday to Thursday beginning September 7, 2023.
Live Aboard or Bareboat Cruising Course Vacation Package
If you already have US Sailing Basic Keelboat certification or commensurate experience and submit a Sailing Resume, you may enroll in just the cruising portion of the course, with Sunday night resort stay before the course begins on Monday. At the end of the course and successful completion of written and practical tests, you will receive US Sailing Basic Cruising and Bareboat Cruising certifications to skipper a boat up to 50’.
Performance Sailing Vacation Package
Fine tune your sail racing strategies and tactical skills. Sailboat racing classes are available through Offshore Sailing School’s Performance Sailing Course – taught on fast and fun Colgate 26 sport sailboats. Offshore Sailing School’s Learn to Sail Certification Course is a prerequisite for Performance Sailing or with commensurate experience, you may submit a Sailing Resume to enroll in a Performance Sailing Course. Through Offshore Sailing’s performance racing school, you learn how to make a sailboat perform to its highest level, improving sail trim and rigging for speed, placing you and your crew where weight does the most good, mastering the art of flying a spinnaker downwind and on reaches. If you’re an intermediate sailor, this sailing level 2 course is ideal for you.
Sailing Lessons
Learn the ropes from an experienced instructor in a 3-hour sailing lesson. These “taste of sailing” classes cost $250 per person for a 3-hour session aboard a Colgate 26 sailboat. Advanced reservations are required.
For more information, call Offshore Sailing School at 888-385-6857, or email Info@OffshoreSailing.com.