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Offshore Sailing School News, Specials and Events

15% OFF LEAP YEAR SPECIAL

Leap Year and Love go together!  Now’s the time to Fall in Love with Sailing with a 15% discount and a lifetime of fun on the water. Make a new reservation for our signature 5-day Learn to Sail Course with a friend at South Seas Island Resort in sunny Florida this winter – save 15% on your course package, get a $250 value resort coupon book, and a copy of the beautiful Sail America book with stunning photos of all kinds of yachts sailing in America’s waters! 

To take advantage of this very special deal, sign up with a friend or loved one between 8 a.m. Monday, February 10 and 3 p.m. Saturday, February 29. Pick any available Sunday arrival date, starting March 1 through April 26, with course ending by May 1, 2020. The course runs half-days from Monday morning through Friday afternoon. Depart Friday or book another day or two to “chill out” before heading back to colder climes. Sanibel and Captiva Islands are known for shelling, beautiful beaches, biking and hiking. Enjoy boutique shopping, touring Ding Darling National Wildlife Refuge or the Edison-Ford Winter Estates, visit art galleries, and experience casual to fine-dining restaurants. Revel in the most glorious sunsets in the world!

This Leap Year Special is only for two enrolling together.  One Sail America book will be sent per reservation for two. Previously booked Learn to Sail courses are not eligible for this Fall in Love with Sailing Leap Year deal; and other discounts (Military, ‘Tweens & Teens family sailing package to name two) may not be combined with this offer.

CALL TODAY!

888-454-7015 or 239-454-1700
Sail@OffshoreSailing.com


A BRAND NEW COURSE — FAST TRACK TO SAILING™ — DEBUTS AT SOUTH SEAS ISLAND RESORT ON CAPTIVA ISLAND, FLORIDA

Offshore Sailing School has done it again. We listened to our graduates, and we deliver! This brand new 6-day course provides total immersion in learning the nuances of sailing and navigation. Offered June 7-13, 2020, with just 16 spots available, this very special program is sure to be a sell-out.

Earn Two Certifications and a Small Boat Cruising Certificate

The links below take you to the courses that are combined to bring you the Fast Track™ to Sailing program. Whether you are just getting into sailing or returning to refresh your skills, this complete program is offered only in its entirety.

Learn more here . . .


SAVE UP TO 60% WITH OUR ‘TWEENS AND TEENS LEARN FREE PROGRAM

One of our most important special activities is our ‘Tweens and Teens Learn Free program where up to three 7-17 year old kids learn to sail with two adults for free. That’s a savings of nearly 60% when three kids learn for free. This is an absolutely amazing experience, one that many parents say is the best way for the family to bond. To take advantage of this very special offer, pick a date when your kids are out of school and sign up for a 5-day Learn to Sail course at South Seas Island Resort on Captiva Island or Pink Shell Beach Resort on Ft. Myers Beach. Both of these young-people-friendly resorts of tons to do when you are not out on the water. All we need is two adult tuitions, and you can bring up to three 7-17 year olds FREE to learn with you!

Learn More!

Call 888-454-7015 or 239-454-1700
Sail@OffshoreSailing.com


GIVE YOUR TEAM THE CORPORATE ADVANTAGE WITH A SAIL-RACE CHALLENGE®

Offshore Sailing School continues to host an annual group from Suffolk University’s Executive MBA program at Pink Shell Beach Resort & Marina on Ft. Myers Beach in Florida each December. With temperatures in the 70’s, participants, their course leader and professors, who would normally be shoveling snow that time of year, love the sunny weather, beach BBQs, and sailing in the Gulf of Mexico during their week of team building and leadership training.

Sailing is the by far the best way to bring teams together and develop leaders who will deftly guide those teams. Mistakes on the race course are turned into project sessions. Wins are examined to provide a basis for achieving goals. Offshore Sailing School can accommodate teams of 8 to 50 easily. In addition to the Pink Shell Beach Resort on Ft. Myers Beach, Offshore Sailing School hosts team building and group sailing excursions at South Seas Island Resort on Captiva Island, and The Westin Cape Coral Resort in Cape Coral, Florida. groups of up to 10 may also be accommodated at Scrub Island Resort in the British Virgin Islands. Contact Beth Oliver today to learn how you can make your team the best ever: BOliver@OffshoreSailing.com, 239-985-7516.

Start Learning Now!

888-454-7015 or 239-454-1700
Sail@OffshoreSailing.com


EXCLUSIVE CRUISING VACATIONS FOR SAILORS WHO LOVE TO SAIL

We have a full spectrum of sailing vacations available through our Colgate Sailing Adventures Flotilla Cruises – for Offshore Sailing School grads and sailors who love to sail. The group in this photo are at the Meet and Greet dinner for the St. Martins flotilla cruise that started February 9, 2020. These fabulous adventures take you all over the world. They are the most delightful, hassle free sailing vacations you’ll find. We book the boats, research and provide the itinerary, put the crews together based on friendships and sailing experience, and best of all – we provide expert tour leaders who love to sail and want you to have the time of your life! If the trip you desire is sold out, request a spot on the wait list. Here’s what’s coming up in 2020. The 2021 schedule is in the works now. Check out this video from our 2019 Colgate Sailing Adventures flotilla sailing vacation aboard 6 Moorings cruising yachts in the British Virgin Islands.

Book a Cruise!

888-454-7015 or 239-454-1700
Sail@OffshoreSailing.com


THE GREATEST CLASSROOM IN THE WORLD® IS IN THE BRITISH VIRGIN ISLANDS

Offshore Sailing School is in great company! The Summer 2019 issue of Elite Traveler Magazine included a super spread about the gorgeous British Virgin Islands and our two BVI partners. Take a look and come on down to paradise where summer is always in season. Did you know that Scrub Island Resort is Offshore Sailing School’s Caribbean cruising sailboat school Caribbean base? It’s an incredible Marriott Autograph Collection Resort with gorgeous accommodations looking out to the most beautiful sailing grounds you’ll ever find. Courses here fill up fast, especially Fast Track to Cruising Courses on monohulls and catamarans. Don’t wait, call today to book your experiential island getaway and find out why Offshore Sailing School is indeed “The Greatest Classroom in the World®.”

Book Now

888-454-7015 or 239-454-1700

Sail@OffshoreSailing.com


OUR 56TH YEAR AND STILL CELEBRATING!

Not too many companies surpass 55 years with their original leaders still at the helm. Living in southwest Florida, those leaders have become somewhat of a legend. Case in point: Doris was featured in the October 2019 Gulfshore Life Magazine as one of five impressive “Game Changers” in Southwest Florida.  

And every day the Colgates wake up with a smile, do their morning walk, then head to the office to work closely with a dedicated team that works tirelessly to introduce more people to the sailing lifestyle. And at the end of very busy days, the Colgates often say, “Where did the years go?”

Steve Colgate started Offshore Sailing School on the back of a cocktail napkin in November 1964. Doris met Steve in January 1968 when she took a racing course he ran in the Bahamas. Read more about the evolution of Offshore Sailing School in our About Us section on this website: Steve’s bio here and Doris’ bio here.


SIGN UP FOR OUR NEWSLETTER AND LEARN MORE

Our bi-monthly newsletter is full of interesting stories, creative specials, sailing deals, upcoming flotilla cruises, contests, and other opportunities to keep you sailing and boating. If you haven’t already, visit our Sailing Newsletter Sign-Up page. Beth Oliver, Offshore Sailing School Director of Marketing, gathers information to keep you informed, shares sailing news, develops contests, and posts photographs and experiences that come from you. Got an idea? Send it to Beth at Boliver@OffshoreSailing.com.