Family Sailing · San Diego Bay
Family Sailing San Diego Bay
Private charters for all ages — calm water, real wildlife up close, and the kind of memory your kids retell for twenty years.
Your kids are going to tell this story. You know exactly the kind — the memory that resurfaces at Thanksgiving twenty years from now. “Remember when we sailed in San Diego and saw the sea lions right next to the boat?” That one.
Sterling Sails offers private family sailing charters on San Diego Bay aboard Mojave, a 42-foot Catalina sailing yacht. The bay is calm. The wildlife is real and close. There’s something about being on a sailboat together that pulls a family into the same moment in a way that very few experiences actually do.
Explore the Bay
Tap around — see what your kids will spot.
Why San Diego Bay Is Perfect for Families
San Diego Bay is protected from the open-ocean swell, which means the water stays calm and comfortable even for guests who’ve never been on a boat before. You get everything that makes sailing feel alive, and the boat is spacious, safe, and comfortable. The bay also happens to be extraordinarily rich with things to see. From the water, your family gets:
- Sea lions laying out on the rocks near Point Loma — close enough to hear them and understand why everyone loves them
- Active U.S. Navy aircraft carriers and submarines docked in the bay — a genuine sense of scale that photos don’t capture
- The USS Midway Museum from the water, sitting exactly where it’s sat since 1992
- The Coronado Bridge from directly beneath it — completely different from any view you get on land
- Great blue herons, cormorants, pelicans, and an unpredictable variety of seabirds
- Dolphins, when they visit the bay — sightings vary but they’re more common than most people expect
- The San Diego skyline from a perspective most residents have never actually seen
Your Sterling Sails captain narrates all of it naturally as you sail — not a scripted tour, just genuine local knowledge about the bay, the wildlife, the ships, and the history of what you’re looking at. Kids always have questions, and we love answering them. It is educational, relaxing, and fun.
Family Charter Options
Pick your adventure.
2-Hour Family Cruise
$600Bay highlights, wildlife spotting, Navy ships or Point Loma — choose your direction. All ages.
Book now3-Hour Gilligan's Tour
$800Full bay experience — downtown, Point Loma Lighthouse, sea lions, open-ocean air. Best for the complete picture.
Book now3-Hr Sail & Swim
$950Sail to Point Loma, anchor in calm water, swim and paddleboard. Paddleboards included.
Book now4-Hr Sail & Swim
$1,200Everything above plus a grill on board. The full family day on the water.
Book nowWhat to Know Before You Sail with Kids
Age: There is no minimum age at Sterling Sails. Mojave is a stable, spacious 42-foot yacht and everyone finds a comfortable spot. We’ve hosted three-generation family groups — grandparents, parents, and grandchildren.
What to bring: Layers are smart since it can feel breezier on the water than on shore. For Sail & Swim charters, bring swimsuits, towels, and any food you want to grill on the 4-hour version. BYOB beyond the included drinks is always welcome.
Every Charter Includes
- Complimentary drinks, snacks, and champagne for adults
- Soft drinks and water for all guests
- JBL Party Box speaker with karaoke on board
- A restroom and refrigerator below deck
- USCG licensed captain
- Up to 6 guests — fully private charter
- Life jackets in all sizes including children’s
- All safety equipment and required permits
- Paddleboards on Sail & Swim charters
Parents Ask
Good to know.
Yes. San Diego Bay is a protected, calm body of water with minimal wave action. Sterling Sails operates a USCG-compliant 42-foot yacht with a licensed captain and all required safety equipment, including life jackets in children’s sizes.
The sea lions are out there. The bay is waiting.
Keep Exploring
Other ways to sail San Diego Bay.
- Sail & SwimAnchor off Point Loma, jump in, and paddleboard — the full active day on the water, drinks already cold before you get in.View this charter
- Burial at SeaA private, dignified maritime ceremony beyond San Diego Bay — every permit and detail handled with care, so your family can simply be present.View this charter
- Whale Watching & WildlifeA private nature charter on a quiet sailboat — sea lions up close, dolphins, seabirds, and gray whales in winter season.View this charter
Not sure which sail suits your group? Compare every option on all charters & prices, see the boat and the bay in the Sterling Sails photo gallery, read what past guests said in our guest reviews, or get to know Captain Liz, our USCG-certified captain.
For seasons, timing and local tips before you book, browse the Sterling Sails sailing journal, or read the press coverage of Sterling Sails.