"We'll Sail You Soon!"
Private sailboat charters for 2–6 guests, group sails up to 12, whale watching, sunset cruises, and themed adventures — all departing from Harbor Island. Personalized, intimate, unforgettable.
Experiences
No two charters are exactly alike. Tell us what you want — we'll make it happen. Private sails, group adventures, themed experiences — your San Diego Bay, your way.
The whole sailboat is yours. Ultimate relaxation on San Diego Bay — no strangers, just your group and the open water. Perfect for couples, families, or intimate groups.
Book Private SailGather your crew for a full group sail. Corporate team outings, friend groups, family reunions — we accommodate up to 12 for a genuinely shared experience.
Book Group TourSan Diego sunsets are legendary. Experience them from the water — sail out as the light turns gold, watch the city skyline glow, and arrive back with memories worth keeping.
Book Sunset SailPrivate whale watching on a sailboat — a quieter, more intimate experience than big charter boats. Gray whales in winter, blue and fin whales in summer.
Learn MoreBirthday? Bachelorette? Anniversary? Tell us the occasion and we'll help you customize the experience — decorations, timing, route, the works.
Plan Your EventDine on the water as San Diego lights up the shoreline. Pair with catering or bring your own spread for an evening nobody will forget.
Book Dinner SailWhy Choose Us
San Diego Sailing Tours specializes in intimate, personalized experiences. We're not a whale watching mega-boat or a party catamaran — we're a sailboat, and that's the whole point.
You're on an actual sailboat, not a motorized boat with a mast. Feel the wind, hear the sails — it's a different experience entirely.
Maximum 12 guests. You'll always have space, attention, and the ability to actually talk to each other.
Every charter is adapted to your group. Route, timing, pace — we work around what you want, not a rigid schedule.
We depart from 1450 Harbor Island Drive — central, easy to reach, with beautiful views of the bay from the moment you arrive.
Wildlife Experience
Most whale watching boats are crowded motor vessels. We offer private whale watching on a real sailboat — quieter approach, smaller group, more intimate sightings. When you're within 100 yards of a gray whale and the engine is off, you hear it breathe.
December through April — migration south to Baja and north to Alaska passes right through San Diego waters.
June through October — the largest animals on earth feed in the nutrient-rich waters off San Diego.
Common and bottlenose dolphins ride our bow wave most days of the year.
Quieter approach, smaller footprint, and no motor noise — wildlife stays calmer, sightings are better.
Private charters book fast, especially summer weekends. Tell us your date and group size.
Book Your ExperienceReviews
"We did a private sunset sail for our anniversary — just the two of us plus the captain. Absolutely magical. The personalized attention made it so special."— Karen & David L.
"Took my team of 10 out for a company outing. Way better than dinner — everyone loved it. Real sailing, not some motor yacht. Highly recommend."— Mark T., Software CEO
"Private whale watching was unreal — we turned the engine off when we spotted a gray whale and just drifted. Could hear it breathing. Unforgettable."— The Johnson Family
Get in Touch
Fill out the form and we'll get back to you to confirm availability and customize your experience. Every charter starts with a conversation.
Charter info & booking