Learn to Sail—And Set Off For The World's Top Sailing Spots

I'm thrilled to introduce "Sail Away," our latest TPG monthly series providing you with everything you need to know to make the sailing lifestyle a reality. Today, TPG Contributor Shayne Benowitz takes us inside San Francisco Bay's OCSC Sailing School with its founder Anthony Sandberg. A sailor herself with countless hours on the water in New York Harbor, Key West and along the California coast, Shayne spoke with Sandberg about what it takes to become a confident sailor and some of his favorite destinations worldwide.

For Anthony Sandberg, there was never a distinct moment of learning how to sail. Growing up in Hawaii, sailing, skiing, swimming and surfing came as second nature to him as learning how to walk.

Born into a large Norwegian family of sailors with eleven bothers and two sisters, an active lifestyle and a passion for the outdoors was engrained in him from the beginning. Before founding OCSC Sailing School in San Francisco Harbor in 1979, he attended Dartmouth College where he was a member of the sailing, skiing and rowing teams. From there, he went onto skipper yachts throughout Europe and race sailboats around the world.

Today, his six-acre campus, with 50 yachts and a direct wind line to the Golden Gate Bridge, is a place to learn to sail and connect with a community of sailors. They offer a rigorous, structured curriculum with 45 courses of hands-on experience combined with classroom instruction. "We're not right for everyone, but if you want to be good, this is the place to learn," says Sandberg.

US Sailing Certified Courses

For most people, the starting place is Basic Keelboat, a US Sailing Certification class that is designed to be completed in two weekends and enables you to confidently skipper 18- to 27-foot monohulls in protected waters with light to moderate conditions, or crew a similar-sized vessel in open water and more challenging conditions. To simply get a taste for sailing, two-hour introduction courses are also available.

San Francisco Harbor is a notoriously challenging proving ground for sailors with strong currents and storms rolling in every afternoon kicking up winds to 18 knots. It's necessary to also hold a Basic Cruising certificate in order to confidently take family and friends out sailing on your own here. The Basic Cruising course provides the instruction needed to skipper a boat in more challenging conditions.

The next level is Bareboat Cruising, which means you'll be able to confidently charter a sailboat without a hired skipper on vessels as large as 40'. This is the ability level needed to make those dreams of an autonomous sailing vacation a reality.

Advanced courses in navigation and passagemaking are also on offer at OCSC and will further your expertise on the water.

Daily Newsletter

Reward your inbox with the TPG Daily newsletter

Join over 700,000 readers for breaking news, in-depth guides and exclusive deals from TPG’s experts

Email address

Sign up

By signing up, you will receive newsletters and promotional content and agree to our Terms of Use and acknowledge the data practices in our Privacy Policy. You may unsubscribe at any time.

All three of these US Sailing Certification courses can be completed in two weekend sessions at OCSC, ranging in price from $1,195 to $1,595. Once you've completed Basic Keelboat, you may choose to become a member of OCSC for discounts on additional coursework and access to their fleet of yachts for charters. After all, the only true way to become a better sailor is through practice and good instruction, notes Sandberg.

Sailing Vacations with OCSC

OCSC also arranges group travel adventures by land and sea. Join a flotilla as crew or skipper and sail through exotic locales in a supportive atmosphere on a fleet of chartered vessels. Upcoming flotillas are being planned in Greece for September 2015 and in Belize for February 2016.

Sandberg is also committed to culture and social good. He and his sailing school regularly reserve blocks of tickets to the San Francisco opera and ballet for its members. He also plans "bucket list-worthy" land adventures with a mission of leaving the destination better than how they found it. In the past, they've bought 100 girls out of sex slavery in Nepal and raised $25,000 to create a birthing clinic in Copper Canyon, Mexico, home to the last of the Aztec Indians, where women's mortality rate in childbirth is perilously high at 20 percent. Next up, is a cultural journey and hike around Machu Picchu, Peru in October 2015.

Sandberg acknowledges that sailors have an inherent interest in travel. "With sailing, the world opens up in a way that traveling by car, bus or plane can't," he says. Here are some of his favorite sailing spots around the world to stoke your wanderlust and desire to sail.

Sandberg led with the state of Maine. "It's such an authentic place to sail," says Sandberg.

In the Pacific Northwest, he's particularly drawn to the raw beauty of Washington State's San Juan Islands.

An hour and a half north of Los Angeles, the Channel Islands in Southern California make for an exciting and beautiful offshore adventure from the nearby town of Ventura.

With his family hailing from Norway, this is a natural favorite of Sandberg's. "It's like Switzerland got flooded," he says of the mystical waterways.

The Mediterranean is the site of his annual flotillas in September, rotating between Turkey, Greece and Croatia. Of the three, Turkey is his favorite. "Every stop leads to more amazing people, food and culture."

"I'm a little jaded when it comes to the Caribbean," Sandberg says, remembering a time when it was less crowded and undiscovered. Still, he concedes it's a prime place to get started with bareboat crusing. "It's easy, fun and the islands are close to one another," he says.

Belize is a new favorite destination of Sandberg's for coastal sailing on catamarans with fascinating archeology everywhere.

Phuket, Thailand is a favorite destination for Sandberg's flotilla vacations.

Hanoi, Vietnam offers surprising sailing delights and unparalleled scenery.

Sandberg describes the sailing terrain of New Zealand similar to that of the dramatic Pacific Northwest.

Australia is a draw not just for sailing, but also incredible diving and snorkeling at the Great Barrier Reef.

In the South Pacific, Sandberg feels that Tahiti is no longer the paradise it once was, but he still loves Tonga and its innumerable pocket islands.

Are you a sailor? Do you want to learn how? Where are some of your favorite sailing destinations?