Two Private Hours Under a Peace-Sign Sail, San Diego Bay
A two-hour private sail on San Diego Bay aboard a 42-foot Catalina, with the deck, the route and the playlist yours.
The Mojave carries a peace sign on her mainsail, which is how you pick her out from the Harbor Island docks. She is a 42-foot Catalina, and for two hours she carries one group and no one else. One price covers the whole boat, up to six guests.
Captain Liz sails her. Nobody aboard needs sailing experience, and the wheel is offered to anyone curious enough to take it.
Two hours is the shortest of the charters this operator lists, and it leaves an evening intact for dinner afterwards. Marina Cortez sits on Harbor Island with the airport across the water.
Departure time is set when you book. Each route is built around what the group asks for, so the sail can lean toward the skyline, the Navy piers or a quiet stretch of water.
2-Hour Private Sailing Experience in San Diego BayPrivate charter on San Diego Bay for up to six guests, champagne included.www.viator.comWhat Two Hours on the Bay Reaches
From Harbor Island the water opens toward downtown, and the skyline stands close enough to pick out single towers. Navy grey fills the far shore. Coronado sits across the channel.
The operator lists its harbor-history route, the one that passes the USS Midway, the Star of India and the Coronado Bridge, at two to three hours. Its Point Loma wildlife run is a three-hour charter, so a two-hour booking stays inside the bay. Say what you want to see before the lines come off.
Sea lions still turn up on bay sails. A traveller who came aboard with young children in July 2025 wrote that the captain "made sure we were super comfortable and safe, especially our young kids who had never sailed before", and counted the sea lions among the sights.
What Is Already on Board
A chilled bottle of champagne comes with every charter, and extra bottles are available on board. Drinks, water and light snacks are included, and the refrigerator holds whatever you bring.
There is a restroom below deck. The operator says it is one of the questions asked most.
A Bluetooth speaker takes your playlist and runs karaoke. Cushions, blankets and shade are already out. Commentary on the bay comes from the captain, in English or in Spanish.
Who Is Sailing the Boat
Sterling Sails is Elizabeth Hinton's company, and she sails the charters herself as Captain Liz. By the company's own account it has run since 2021, it is woman owned, and she holds a U.S. Coast Guard licence.
On the company's press page she puts the idea plainly: "I wanted to build something that let people slow down and feel the water the way I do."
Guests are welcome at the helm. Nobody is required to touch a line.
Before You Book
- A full refund needs a cancellation at least 24 hours before departure.
- Six guests is the ceiling on this boat.
- The charter is listed as suitable for all fitness levels.
- Bring a layer for the breeze, sunglasses and sunscreen. Your own food, or a bottle for a celebration, is welcome.
- The captain's gratuity sits outside the fare. The operator's own journal puts U.S. charter tipping at 10 to 20 percent of the base fare, with 15 percent as its default.
Captain Liz meets the group 15 minutes before departure at the picnic tables beside the 30-minute parking in front of Marina Cortez. There is parking at the marina, and more of it free across the street.
📍 1880 Harbor Island Dr, San Diego
Sunset is the charter this operator is asked for most, and the skyline turns gold well before the boat points back at the dock.