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Performance Race Week® is so popular it fills months in advance so don’t wait to sign up! In 1967 Steve Colgate launched the first ever national sailboat racing school program when he was tapped by one Design Yachtsman (now Sailing World) magazine to run Sailing Symposiums Bahamas Race Weeks. Every year since then, Steve and his Offshore Sailing School team have produced variations on that original Race Week theme in the heart of winter when most sailing back home is months away.


January 30 to February 4, 2022


In 2022, we are pleased to bring you a stellar program led by Guest Expert, Dawn Riley, Executive Director of Oakcliff Sailing Center and 2021 inductee in the National Sailing Hall of Fame. Author of Taking the Helm, a revealing first-hand account of the first U.S. Women’s Challenge for the 32,000 miles Whitbread Round-the-World race, Riley is renowned in sailboat racing circles.


Dawn Riley was the first woman ever to manage an entire America’s Cup syndicate, and the first American, man or woman, to sail in three America’s Cups and two Whitbread Round the World races. A former president of the Women’s Sports Foundation, she has served on the board of US Sailing, is a sought-after speaker, and an expert in big boat racing, match racing and building skilled sailboat racing teams.  At Oakcliff Sailing in Oyster Bay, NY, Dawn Riley leads a program for youth and adults who have progressed beyond traditional coaching methods, developing skill sets for the America’s Cup, the Olympics, and The Ocean Race (formerly the Whitbread-Round-the-World-Race). “Winning is all about building skills, knowledge, and bringing everyone aboard together as a cohesive team,” says Dawn.


2022 Performance Race Week® with Dawn Riley, the Oakcliff Team and Offshore Sailing School brings you a whole new experience, with new concepts and training techniques to jump-start your 2022 racing goals.

From Sunday evening through Thursday evening, you are immersed in a program designed to give you the confidence and skills to join the winner’s circle.

Plan to arrive Sunday evening in time for the Meet and Greet Orientation party. Monday morning you set sail, learning and racing non-stop in 2 three-hour sessions each of the first three days. Thursday morning, you head out again for another on-water coaching session. Then Thursday afternoon,  Go-For-The-Gold in an intense regatta with the entire fleet vying for line-honors in at least four races for 1st, 2nd, and 3rd place trophies.  More detailed information on the program schedule appears below.


2022 Performance Race Week® and the Fast Track® to Performance Racing Course which starts three days earlier, are held at the popular South Seas Island Resort on Captiva Island, Florida. If you have never raced before, have good sailing skills on keelboats around 22′ or more but have very little racing experience, we recommend you take the Fast Track® to Performance Racing course.

Capital of the shelling world, Captiva Island has been Offshore Sailing School’s largest winter location for 47 years. This 365-acre resort has gorgeous beaches, tennis, golf, bicycle rentals, fishing, kayaks, running paths, paddleboards, a spa and fitness center, electric cart rentals, and more for friends and family to enjoy while you learn.

Connected to Sanibel Island where you’ll find the amazing Bailey-Matthews National Shell Museum, rehabilitation center for injured wildlife called CROW, and the renowned J.N. Ding Darling National Wildlife Refuge, you probably are going to want to stay an extra day or two to absorb all these islands have to offer. While sailing, you’ll be surrounded by pelicans diving, herons and egrets wading along the shore, ospreys nesting on channel markers . . . and best of all, you might very well be accompanied by dolphins on the racecourse!


Our fleet of race-ready Colgate 26 sailboats are berthed in South Seas Yacht Harbour, surrounded by Harborside hotel rooms and Marina villas.  A short sail takes you into Pine Island Sound or the Gulf of Mexico with lots of open water and wind and wave conditions to challenge and improve your racing skills.


The Colgate 26 is a super lively, fast, comfortable, and safe keelboat that both excites and satisfies. It turns on a dime, accelerates quickly, has sophisticated adjustments not generally found on a 26-footer, and is set up for easy sail trimming and steering.  A coach station behind the helmsperson allows for plenty of room for a busy crew of four to work together as you learn. Expect tons of starts, lots of drills, and practice races to get you tuned up to win.

888-454-7015 ♦ 239-454-1700


Sunday arrival night kicks off with the casual Meet and Greet Orientation Get-Together with drinks and light hors d’oeuvres served.  After brief introductions, and an overview of how the next four days will unfold from Steve Colgate and Guest Expert Dawn Riley, coaches and teams gather to get to know one-another. And then it all begins . .


Monday, Tuesday and Wednesday coached drills, practice starts, and racing are held 9 am to noon and 2-5 pm with Dawn Riley and the 7 coaches alternating between boats each session.

Thursday morning, 9 am to noon, drills, practice starts, and races continue followed by a box lunch seminar back in the harbor. Thursday afternoon, 2-5 pm you are back on the water for an intense series of races in the Go-For-The-Gold Regatta.


Monday-Thursday box lunch seminars take place ashore between each sailing session. During these informative seminar sessions, Dawn Riley will inspire you to learn more with discussions about teamwork and crew dynamics, regatta preparation, and specific subjects related to the day’s drills.

Monday and Wednesday evening, Dawn will hold après sail seminars and recaps of the day’s events with wine, beer, and soft drinks provided. Videos shown during the Wednesday evening seminar and the Thursday night Awards Dinner reveal how you and your teammates progressed through the week.

Tuesday evening enjoy a fabulous buffet on Sunset Beach as the sun sets over the Gulf, and maybe even see the Green Flash! And Thursday evening celebrate all you learned with teammates, coaches, family and friends as you gather for cocktails and the gala Awards Dinner where trophies are awarded.

“Performance Race Week was fantastic. What you learn in one week is more valuable than anything you’ll learn in years of sailing.”

Winter Hawley – Manitowoc, WI
Read more testimonials here


Here’s what’s included in your 2022 Race Week package:

  • 5 nights accommodations at South Seas Island Resort
  • 21 hours of on-the-water coached race training
  • Four midday seminars
  • Box lunches provided each day
  • Two evening seminar recaps; wine, beer, non-alcoholic drinks provided
  • Video recaps Wednesday and Thursday evenings
  • Buffet on the beach Tuesday
  • Gala awards dinner Thursday
  • UV protective Performance Race Week® shirt
  • Commemorative Performance Race Week® hat
  • Reusable water bottle
  • Colgate Logbook
  • Course diploma
  • Textbooks
  • Go-For-The-Gold Trophies for 1st, 2nd, 3rd place teams

Package rates are available for singles and parties of two, three and four planning to participate together. Book a crew of four to sail and learn together in the same boat and deduct $200 per person. If a spouse or friend joins you who will not be in Performance Race Week, they are welcome to attend all three social events/dinners for a charge of $270, plus $27 daily resort amenity fee for guest in room. Call 888-454-7015 or 239-454-1700 for more details and reservations. Harborside Rooms and Marina Villas are in the North part of the resort around the yacht harbor where the Colgate 26 fleet and classrooms are located. Bayside and Beach Villas are at the South end where there is a Doc Ford’s and many other restaurants within walking distance. Free trolley service is available.

“I’ve attended many courses in 37 years as a Navy pilot and airline pilot. The course and particularly the Offshore instructor were outstanding.”

Tom Corboy – Annapolis, MD
Read more testimonials here 

Required Race Week Resume

The Greatest Classroom In The World!®

888-454-7015 ♦ 239-454-1700

Depending on weather conditions and the learning pace of all those aboard your boat, Performance Race Week® will cover the following:

  • Starting tactics
  • Sail shape
  • Stalling and accelerating
  • Upwind and downwind tactics
  • Racing strategy
  • Covering and breaking cover
  • Racing rules
  • Proper sail trim on all points of sail
  • Boat speed and tuning
  • Spinnaker techniques
  • Finishing tactics
  • Weather and wind shifts
  • Rounding marks
  • Teamwork and crew preparation

Prerequisite: Colgate Performance Sailing Certifications or sailing skills and knowledge equivalent to the Offshore Sailing School Performance Sailing Course. All Race Week participants will be required to submit a completed Sailing Resume before you are fully confirmed.

Certification: No certification



888-454-7015 ♦ 239-454-1700

Please call one of the numbers above or email for more information on package rates. There is an extra charge for non-sailors traveling with you who wish to attend the social event dinners (Sunday Welcome Party, Tuesday Beach Buffet, and Thursday Awards Dinner). The cost for guests attending just the social events is $270 per person. The 2022 Performance Race Week® package includes:

  • 5 nights accommodations at South Seas Island Resort
  • Nightly per accommodation resort amenity fee and taxes
  • 21 hours of on-the-water coached race training  with Dawn Riley and her coaching team
  • Four midday seminars
  • Box lunches provided each day
  • Two evening seminar recaps; wine, beer, non-alcoholic drinks provided
  • Video reviews Wednesday and Thursday evenings
  • Buffet on the beach Tuesday
  • Gala awards dinner Thursday
  • Steve Colgate’s Performance Sailing and Racing, published by McGraw-Hill – sent in advance to study
  • UV protective long/sleeve 2022 Performance Race Week® shirt
  • Commemorative Performance Race Week® hat
  • Reusable water bottle
  • Colgate logbook
  • Course diploma
  • Go-For-The-Gold Trophies for 1st, 2nd, 3rd place team

Non-Sailing Guest Costs and Sharing Room Rates: If a non-sailor stays in your room, we must collect a daily resort amenity fee for that guest. The Offshore Sailing School sales associate you made your reservation with will confirm any additional costs for guests.

Sunday – Arrival day
Welcome Meet and Greet Happy Hour 6-7 p.m.
Monday – Day 1
9:00-noon – Sailing/racing instruction with coaches aboard
12:30-1:30 – Seminar ashore with box lunches provided
2:00-5:00 – Sailing/racing instruction with coaches aboard
5:30-6:30 – Recap and seminar ashore

Tuesday, Wednesday – Days 2 and 3
9:00-noon – Sailing/racing instruction with coaches aboard
12:30-1:30 – Seminar ashore with box lunches provided
2:00-5:00 – Sailing/racing instruction and practice with coaches aboard
5:30-6:30 – Aprés sail video review (Wednesday)
6:00-9:00 – Buffet on Sunset Beach (Tuesday)

Thursday – Day 4
9:00-noon – Sailing/racing instruction and practice with coaches aboard
12:30-1:30 – Seminar ashore with box lunches provided
2:00-5:00 – Go-For-The-Gold Regatta
6:00-9:30 – Cocktails and Gala Awards Dinner

Daily schedules are subject to change.

Here’s what our Performance Race Week® participants have to say:

This has been a great learning experience and it delivers. With the same skipper (back home) we never finished better than 4th. Yesterday we got a second and 2 firsts!

John Breyfogle – Countersville, AL

I’ve attended many courses in 37 years as a Navy pilot and airline pilot. This course and particularly the Offshore instructor were outstanding.

Tom Corboy – Annapolis, MD

If you love to go fast and strive to be better, you can’t bet the combination of owning your own Colgate 26 and taking the Performance and Racing classes. They are top notch instructors.

Phil Weintraub – Hopewell Junction, NY

I was not comfortable taking the helm during a race until I attended this camp. I have since become quite confident in my driving skills and feel very competitive with the rest of the fleet – hence 3rd place finish in the Marblehead NOODS!

Shawna Gauthier – Marblehead, MA

The printed curriculum looked great but it was even more power-packed than I expected. I have waked away with more knowledge and experience than I ever expected. This was a total success.

Diana Augsburger – Kenmore, NY

Race Week was absolutely the BEST!!! Many thanks for a wonderful and really educational week. I can’t believe how much I learned, and I loved meeting all the other participants and, of course, our coach.

Kim Frisbie – Ft. Washington, PA