Get Started with Sailing

The easy way to hit the water is to charter, or rent, a yacht. A skippered charter includes a licensed captain to do the sailing. (A bareboat charter is for those who already know how to sail.) Because commissioning a 6-ton, 35-foot boat isn’t as simple as picking up a Zipcar, here are a few guidelines:

• Relax. You’re not signing up for a Moby Dick experience. You’re hiring a licensed captain to sail the boat for you, most likely in conditions that won’t spill your drink.
• Don’t automatically pick a boat, or a destination, off the charter company’s menu; weather and other factors play into what makes sense on any given day. While you can choose from what’s available in someone’s charter fleet, talk to captains first about what sort of experience you want; they’ll usually come up with an itinerary and a vessel that match up best.

While you don’t have to help sail, if you want to try it, ask ahead of time about taking a turn steering the boat or working the winches to adjust the sails while underway.

It’s not easy to compare costs among operators. Some charge flat day rates; others go by the hour or per person. Basic rule of thumb: The total cost of a full day on the water on a 35-foot yacht (the most popular size) with a skipper should run $500 to $800; a half-day, $300 to $600. Split a half-day with friends and you might pay less than $100 for a couple of hours on the water.

Love sailing? Then take an intro course. Classroom and on-the-water instruction takes 3 to 5 full days, is offered during the week or on back-to-back weekends, and typically costs $300 to $700. You’ll be certified through U.S. Sailing or the American Sailing Association and be able to rent a boat. We asked instructors which skills to master.

Wind 101: “Every sailor has to know where the wind is in relation to the boat, and what you can do with that to make the boat go where you want it to. Once you have that down, it all flows from there.” –Michael Rice, founder, Puget Sound Sailing (pugetsoundsailing.com), Seattle and Tacoma, WA

Safety and prep: “We put students through crew-overboard drills and teach them to control the boat, under sail, in emergency situations. Mastering that stuff eliminates the fear and gives them the confidence to do everything else.” –Andrew LaPlant, Lead sailing instructor, Mission Bay Aquatic Center (mbaquaticcenter.com), San Diego

Basic boat handling: “A lot of people taking lessons have never been on a boat, much less sailed. So we show them how to handle a sailboat under power—how fast to go, how to steer, and how to stop. You need a good departure and return every time you sail.” –Anthony Sandberg, president, OCSC Sailing (ocsc.com), Berkeley

Communication: “Good sailors are good talkers—whether they’re receiving an instruction, giving one, or don’t understand something and need a quick answer. Sailing is a team sport. Everyone onboard must know what’s going on.” –Scott Pittrof, Program Director, Windworks Sailing & Powerboating (windworkssailing.com), Seattle

Fun: Not exactly a skill, but important. “Sailing can be a little scary for newcomers, but you’re not going to learn much if you’re not having fun on the water. Folks who are enjoying themselves are the ones who move up the fastest.” –Wayne Zittel, president and instructor, J/World Sailing (sailing-jworld.com), San Diego and San Francisco

Blake Island: A full-day cruise to one of the few islands on the Puget Sound that’s accessible only by boat—and so welcoming to visitors that native deer practically greet you. Sail in full view of Mt. Rainier, Mt. Baker, and the city skyline. Tie up at Tillicum Village for picnicking or kayaking.

Elliott Bay/Downtown Seattle: From Shilshole Bay Marina or another harbor in the region, you can cruise into Elliott Bay for a Seattle skyline tour from the water. Tie off at Bell Harbor Marina and walk to Pike Place Market.

Gig Harbor: A more rustic sailing getaway in a sheltered cove near the southern end of the Puget Sound, with Mt. Rainier as a backdrop. You can roam the harbor in light wind with a handful of great tie-ups, including Tides Tavern (see below) and Anthony’s at Gig Harbor.

San Francisco Waterfront: Enjoy the more spectacular view of S.F.—offshore, that is—and you begin to notice what the onshore tourists are snapping pics of: That’d be you, and your full-sailed catamaran, slipping past the piers. Start at Crissy Field, working your way east. When you get close to the Ferry Building on the eastern shore, tie up at the new public dock at Pier 11/2 and walk up for a cocktail at La Mar.

Ayala Cove at Angel Island: As close to a Caribbean sailing experience as you’ll find in the northern latitudes: Calm winds, a sandy beach, picnic benches and BBQs, and public docks and mooring balls for sailors, who can hike up to the top of the island for a three-bridge, 360° panorama of the bay.

Golden Gate Bridge to Sausalito: If sailing under the Golden Gate is on your float plan, most captains will take you out there in the morning before the afternoon winds turn a pleasure sail into a whitewater adventure. On the way back, cruise into Sausalito and Richardson Bay, and tie up for lunch at Horizons’ own dock.

Oakland/Alameda Estuary: For sailors venturing to the East Bay, there is a there there, despite what Gertrude Stein said. Sailing into the estuary from Treasure Island, float downwind (carefully) past giant container ships on the first leg of this daysail. Then turn into the estuary’s main channel with dozens of friendly marinas, starting with Jack London Square.

Anacapa Island (Santa Barbara/Oxnard): Just 12 miles offshore, Anacapa is the easiest of the Channel Islands to take in on a daysail—it’s less than three hours from Oxnard (though you’ll likely be motoring in the morning before the breeze comes up). Ask the skipper to bring kayaks so you can paddle through Anacapa’s rock caves and arches.

Santa Catalina Island (Los Angeles): If it’s more about the journey for you, skip the ferry out of Marina del Rey or San Pedro and instead sail to the island. Most people do this as an overnight sailing trip, choosing to go either to Avalon, the main harbor, with the casino built by William Wrigley Jr.; or to Two Harbors, a quieter spot.

Gray whale cruising (San Diego): Been there, done that with whale-gazing from a diesel-powered tour boat? Try coasting silently on a 40-foot catamaran. Charter out of Shelter Island or other San Diego marinas from roughly December through April.

Coronado Islands (San Diego): Plan an all-day adventure into Mexican waters: The Coronado Islands, a wildlife refuge popular as a fishing and diving destination, are about 20 miles south of San Diego Harbor and about 8 miles off the Baja Coast. Aside from the scenery—sea lions, harbor seals, blue-footed boobies, and a spectacular natural archway called the Keyhole—you’ll pass Smuggler’s Cove, an old hideout of Prohibition-era boozers and gamblers.