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Learn to handle a 44’ monohull and a 40’ catamaran in a one-week Fast Track® experience that’ll knock your cruising socks off!

Novice to Big Boat Skipper in One Week

This amazing Bareboat Cruising Certification adventure starts with two days learning the basics on a highly responsive Colgate 26 open-cockpit keelboat. On days 3 through 5 you spend 2.5 days each on Offshore Sailing School’s brand new 40’ catamaran and 44’ monohull – learning how to handle the sails, steer, anchor, dock, and maneuver under power on these two gorgeous cruising yachts.

Comprehensive Learn to Cruise Training at Its Best

Over nearly 60 years of training would be sailors to become confident skippers and mates, Offshore Sailing School has seen the evolution of small boat sailing to big boat cruising – big time! The original Offshore Sailing School Fast Track® to Cruising course – learning to sail from scratch first on a 26’ footer and then gaining the skills to cruise on a 40’ or larger yacht, provides a choice of a monohull or a catamaran, not both. In this Ultimate Cruising Course you are trained on both!

Catamaran and Monohull Cruising in the Ultimate Cruising Course Experience

Many Offshore Sailing School participants have expressed the desire to learn the differences between monohull and catamaran sailing. Yes, there are differences, and in this very special ULTIMATE CRUISING COURSE OSS 110 you get to experience the nuances that come with handling a single-hull and a two-hull cruising yacht in one first-hand course.

Choose Your Dates Now, Space is Very Limited!

This course is scheduled for just two start dates – September 28 and November 30 – with maximum of eight 8 spots available per week.

  • Ultimate Cruising Course 1: Arrive Sept. 27-Depart Oct. 5
  • Ultimate Cruising Course 2: Arrive Nov. 29-Depart Dec. 7

Sail the Beautiful Cruising Grounds Surrounding Captiva Island, Florida

During this course you stay in private air-conditioned accommodations at ‘Tween Waters Resort & Spa, gateway to Pine Island Sound and the Gulf of Mexico. Each day you spend 6 hours learning to sail and cruise, returning to the resort by 5 p.m. for a relaxing swim in its beautiful pool, perhaps a spa session, then dinner and fun conversations with your classmates before heading to bed. Lunches are provided while learning on the monohull and catamaran as you sail up the sound or out into the Gulf.

Ultimate Cruising Course OSS 110 Course Package

  • Double Per Person/Sharing Room Ashore – $6535 per person
  • Buy the Boat/Up to Four Together Sharing Two Rooms – $5995 per person


  • Two days learning first on a Colgate 26 keelboat
  • 2.5 days learning on a Jeanneau 440
  • 2.5 days learning on the Lagoon 40
  • Lunch aboard each of the 5 days on the cruising yachts
  • Testing for 3 US Sailing Certifications – Basic Keelboat, Basic Cruising and Bareboat Cruising
  • Three course textbooks
  • 8 nights accommodations at ‘Tween Waters Resort & Spa, including applicable taxes
  • Diploma and Logbook

 Course Schedule

  • Arrive Wednesday, check in at hotel is 4 p.m.
  • Only four participants are taught on each boat each session, with instructor aboard at all times
  • Course sessions start for all 8 participants at the same time each day
  • Thursday-Friday – 4 each on two Colgate 26s with a lunch break on own ashore
  • Saturday-Sunday-Monday morning – 4 on the Lagoon 40 catamaran and 4 on the Jeanneau 440 monohull learning at the same time
  • Monday afternoon – Each group of 4 switches from catamaran to monohull or vice versa
  • Tuesday-Wednesday – Cruising course continues with 4 each on monohull and 4 each on catamaran
  • All sessions start at 9 a.m. Thursday-Friday and Tuesday-Wednesday
  • Monday sessions start at 8 a.m. to accommodate time to switch boats
  • Thursday at end of week-long course – depart by 11 a.m.
  • Complete schedule will be sent when you enroll indicating whether you start your cruising training first on the monohull or catamaran


239-454-1700 | 888-454-7015