Sailtime San Diego, San Diego

Parks, restaurants, and eye-catching vistas stretch for 34 miles across San Diego's waterfront. SailTime San Diego's proprietors, Ian and Gill Bossenger, find that the water itself is the best way to take in the sights. With a fleet of three sailboats docked at the bustling Harbor Island Marina, the husband-and-wife team help open up a coastal world of breezy adventuring along with the bay's dolphins, whales, and thriving submarine populations.

In sailing classes, U.S. Coast Guard–licensed captains and ASA-certified instructors guide prospective sailors through the operation of basic keelboats and large cruising boats alike. The already-certified can hop aboard a late-model Hunter 38 to captain their own charters along the coast or to Catalina Island about 70 miles away or join as members to enjoy sailing without the hassle and expense of being a full-time boat owner or the neck aches of being a full-time stowaway.