Private Sailing Charter & Sailing Tours in San Diego, CA
ABOUT
San Diego Sailing Charter
San Diego Sailing Charter offers far more than a simple sail across San Diego’s iconic Big Bay and coastal waters—it’s an immersive, interactive experience showcasing the very best of America’s Finest City.
Whether you’re captivated by the historic tall ships of the Maritime Museum, drawn to the rich naval heritage surrounding our impressive fleet of military vessels and North Island Naval Air Station, or excited to drift past sea lions—and the occasional dolphin—near storied Ballast Point, your voyage will be filled with discovery, beauty, and authentic San Diego character.
Our Sail Boat
Take a closer look at the classic sailboat behind every sailing charter San Diego guests book with us. Every trip is aboard the same well-maintained vessel, not a rotating fleet, so you know exactly what you’re stepping onto.
Our Tours
From sunset sails to private group charters, explore the full range of tours available through our sailboat charter in San Diego offers, each one built around small groups and a relaxed pace on the water.
Dolphin/Seal Sailing Cruise for Two
Relax and enjoy a leisure tour up the bay and toward “The Point” of Point Loma while sailing by lazy frolicking Seals and Sea Lions amongst a plethora of sea birds including gulls, pelicans and cormorants.
Couples Sailing Cruise for Two
Private Couples Afternoon Cruise
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Sailing in San Diego is a wonderful way to experience the city’s beautiful coastline and enjoy the refreshing sea breeze....
A sailing tour in San Diego creates ultimate relaxation due to its serene waters, gentle breezes, and picturesque coastal views....
Our Sailing Tours and Pricing
From relaxed afternoon sails to private sunset cruises and hands-on lessons, there’s a trip here for every occasion. Take a look at what’s included and find the one that fits your day on the water.
Dolphin / Seal Sailing Cruise for Two Persons
Sail up the bay toward Point Loma’s “The Point” and watch seals lounge along the rocks. Keep an eye out for gulls, pelicans, and cormorants gliding overhead as you cruise.
Couples Sailing Cruise for Two Persons
A perfect afternoon out on the water for you and someone special. Pick from two scenic routes around San Diego bay and let the breeze carry you away for a couple of hours.
Private Couples Afternoon Sailing Cruise
Have the whole boat to yourselves for this relaxed afternoon sail. Between the fresh sea air and the calm rhythm of the water, it’s an easy way to slow down together.
Sunset Sailing Cruise for Two Persons
Watch the sun drop behind Point Loma as you sail across San Diego bay. The colors shift from gold to pink to purple, making for one of the prettiest views in the city.
Private Couples Sunset Sailing Cruise
Enjoy a fully private evening on the water as the sun sinks behind Point Loma. Just you, your guest, and a sky full of color, no one else on board to share it with.
Private Sailing Lesson for Two Persons
Learn the basics aboard our classic yacht “Imagination” with Captain Mike guiding you the whole way. Take the wheel, trim a sail, and get a real feel for what sailing is about.
Private Sailing Lesson for 4-6 Persons
Bring your group out on the water and learn to work together as crew. Whether it’s coworkers, family, or friends, something about sailing that gets everyone pulling in the same direction.
Private Group Charter (1-6 Persons) Sailboat
Book the boat for whatever you’re celebrating, or just for the sake of getting out on the bay. We’ll build the trip around your group, your pace, and your San Diego style.
Single Rider Add-On
Heading out on your own? Join one of our small group sails and share the deck with a few other guests. No need to book the whole boat just to get out on the water.
FAQs
1. What is included in a private sailing charter in San Diego?
Every sailing charter in San Diego guests book with us includes a USCG-licensed captain, use of the full sailboat, and a personalized route based on weather and what you’d like to see, whether that’s dolphins, the sunset, or a quiet afternoon on the bay.
2. How many people can join a sailboat charter?
Our sailboat charter in San Diego trips are designed for small, private groups. Standard charters comfortably fit up to 6 guests, and we offer separate options for larger parties.
3. Do I need sailing experience to book a charter?
No experience is needed. Every boat charter in San Diego trip is fully captained, so you can relax and enjoy the sail while we handle the sailing.
4. What makes your sailing experience different from bigger tour companies?
Unlike large commercial operators, our San Diego Sailing Tours keep things intentionally small, personal, and unique, from beginning to end.
5. How far in advance should I book a sailboat charter?
We recommend booking your sailboat charters in San Diego at least 1-2 weeks ahead, especially for weekends since our small-group model means limited availability per day. HOWEVER, don’t hesitate to book as little as a couple of hours in advance if you are looking last minute, as we may have availability or a cancellation.
Feel free to call us up to 1 hour before departure to check on status if you are able to make it to our marina within 45 minutes.
Contact Us
Not sure which tour is right for you? Call us at 619-997-7325 and we’ll help you pick the best option, whether that’s a private sailing charters San Diego trip for two or a larger group outing.