Quick connect

Bookmark and Share

Weekend Learn to Cruise Adventure

An introduction to big boat sailing and a refresher for "rusty" sailors

Take the helm, feel the power, learn what it's really like to steer a big boat with wind alone. Imagine yourself at the helm of a $300,000+ cruising yacht – with an expert Offshore Sailing School instructor at your side. This two-day introduction to cruising sailing is taught aboard a beautiful 43' to 45' cruising sailboat. This is a weekend escape that will really knock your socks off!

Learn and cruise in two glorious locations — north or south

  • Captiva Island, Florida on the Gulf of Mexico
  • St. Michaels, Maryland on the Eastern Shore of the Chesapeake Bay

The Gulf of Mexico

Beautiful South Seas Island Resort on the tip of Captiva Island is only an hour from Ft. Myers and light years away from the hustle of normal every day life. You'll sail in the Gulf of Mexico and Pine Island Sound, where the sun shines nearly all the time, the water is warm and dolphins and manatees play.

Chesapeake Bay

The Inn at Perry Cabin – a classic Orient Express Resort – is adjacent to the fabled Maritime Museum in St. Michaels, Maryland, where sailors go to play in each summer. Imagine sitting on a grassy lawn, sipping afternoon tea or a cocktail, as boats of all vintage and type sail by.  You will be out there too, on one of our beautiful cruising yachts.

Plan to arrive Friday evening. Saturday you sail and learn from 8:30 a.m. to 5:30 p.m., with a stop on the hook (at anchor) for lunch. Sunday you'll go out at 8:30 a.m. again and return by 1:30 p.m. giving you time to head home or just relax at the resort. As you take the helm of this impressive cruising yacht and fill its sails with wind, you'll experience the awesome sensation of big boat sailing at its best.

Who may take this course?

Anyone with a yen to find out more about the sailing lifestyle! You don't have to have any sailing experience. Though not a course that gives you Certification, this Weekend Learn to Cruise getaway teaches you enough basics to decide for yourself if you want to continue on the learning path some day. If you have no experience, you'll start from scratch. If you already sail and are thinking about moving up to bigger boats or need a refresher, this is a great way to gain more skills.Our instructors will tailor your lessons to your level of sailing knowledge and skill.

All inclusive package

Your Weekend Learn to Cruise package starts at $870 per person, double occupancy ($1045 single) and includes everything below. Please bear in mind these are the lowest season rates and are higher November through April. We need a minimum of two to open a course date. Minimum age is 10. If you are traveling alone, you may opt for a totally private Weekend Learn to Cruise experience at $2435; or give us a few date options and we'll see if we can pair you with someone else who wants the same date.  

  • Fourteen hours of hands-on learning aboard a 43'-45' cruising yacht
  • All instruction aboard, with an expert Offshore Sailing School instructor
  • Steve Colgate on Cruising textbook
  • Two nights accommodations ashore at the beautiful South Seas Island Resort in a Harbourside Room
  • Course certificate and celebration

Big boat sailing techniques you'll learn

  • How to get away from and return to a dock safely
  • How to anchor
  • How to trim your sails to move the boat efficiently without any engine power
  • Safety procedures aboard
  • How to maneuver a cruising boat under power
  • Introduction to Rules of the Road and navigation aides
  • How to tie the most important knots

Call 888-454-7015 to book your weekend now. Click here to tell us when you want to go.