Ask Away

A getaway for a sailor and a landlubber

Offshore Sailing School will teach one of your party how to sail, while the other one lounges at the beach.

Offshore Sailing School will teach one of your party how to sail, while the other one lounges at the beach.

Diane Bair for the Boston Globe

Q. My husband likes to sail and would like to go on a one-week vacation to learn to sail better. I don’t want to sail and would like a place with a hotel and beach, etc. Any ideas?

Elana Markovitz, Lexington


A. Offshore Sailing School ( offers classes from three to seven days on Captiva Island, Fort Myers Beach, and St. Petersburg, Fla., among other locales. If you’re all about relaxing on a shell-strewn beach, consider Captiva, where the sailing school will put you up at the South Seas Island Resort. If you like more action, you’ll probably prefer the school’s Fort Myers Beach location (based at the Pink Shell Resort & Marina). Your husband could sign on for the one-week “Fast Track to Sailing” course, or take a five-day class that runs half-days. Five-day courses (including accommodations) start at $2,275. They also offer a course in Tortola, the British Virgin Islands, one of the most spectacular sailing grounds in the world.

Would you consider living aboard a sailboat for a week in the Florida Keys? Captain Bruce of the Florida Keys Sailing School ( on Marathon Key gives sailing courses on the water by day; by night, you sleep aboard a sailboat (it’s included in the fee). Rates start at $475 per day. If you’re a true landlubber, book one of the local hotels. Sombrero and Coco Plum beaches are handy, plus you can do day trips by car to Key West.



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