Sterling Sails

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Sterling Sails Sailing tours in San Diego Bay
Private Charters
6 person max
Beverages, Champagne, & Snacks

10/24/2026

Spooky season is upon us 👻 book your Halloween sailing trip on the water w/ Sterling Sails. Treat or treat! 🍭

10/19/2026

Congratulations to the happy couple! Wishing you all the happiness in the world ❤️

Check out our most romantic package at www.sterlingsails.com 💍 That Someone Special

10/15/2026

Behind the scenes look 👀I’m not perfect. Boat life. Thank you John Kirkendall 🫡Thank you.

🚨 Here’s a peek inside my head: I can’t stand when I mess up. It bothers me so much. I have nobody to blame but myself which is the worst. I don’t even care when other people fully destroy the boat. I expect that. But when I do mess up with something so small like having a dock line in the water when going into reverse🙄 When I know better..idk. Maybe I’ll forgive myself tomorrow. Not likely. Lesson learned for sure now. Btw when I see people do this I think “smh. Stupid.” And here I am 😂🫣 I may not be perfect but I’m more humble that’s for sure.

10/14/2026

Yes, there is an “inside” to the boat 💙 Check out Mojave down below, it’s so much fun! 🙌

10/05/2026

Sometimes we sail to Mexico 🇲🇽 Sometimes Mexico sails to us 🇺🇸

I am so honored to see the Mexican Navy Sailing Ship the ARM Cuauhtémoc BE 01 for a second time in San Diego, CA. I saw people stand in a line wrapped around Harbor Drive for hours all weekend in 100 degrees just to go on board this amazing vessel. I was so happy to see it again as it continues it’s mission to spread peace across the globe 🌍

América Yamilet Sánchez & Adal Jair Maldonado Marcos, nosotros recordamos tu vida.

10/02/2026

Beat the heat in the splash zone on Mojave 😎 Wind, Waves, Water, Ice, Sunshine, Boats, Sunsets🥂 Grab your besties and let’s go sailing ⛵️in San Diego Bay!

09/27/2026

It’s goin down in San Diego this weekend 😎 So many events and it’s absolutely beautiful outside. I love it. If there’s a “sailing season” it’s definitely now.

Don’t forget about Night Sailing! Stunning.

09/27/2026

Boat life is the best life ⛵️

09/18/2026

Such an honor to have Captain Chris at the helm of Mojave 🫡 Thank you Christopher Smith for always having my back in times of need over the last 7 years. I feel so blessed.

Teamwork makes the dream work! Sterling Sails would be nothing without friends and family. I am so grateful ❤️

***Want more Captain Chris? Everyone does. Cruise w/ him at 💕 Pink Private Boat Cruise in San Diego Bay where the fun never stops 💕

09/15/2026

Experience San Diego from the water with the people you love most 🥂 Enjoy a peaceful sunset cruise on a 42’ private sailing yacht

Address

1880 Harbor Island Drive
San Diego, CA
92101

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