Heart of San Francisco Celebration - Labor Day Flotilla and Skywriting Spectacle | Modern Sailing

Heart of San Francisco Celebration - Labor Day Flotilla and Skywriting Spectacle

Modern Sailing members and students with reservations to sail this Labor Day will be treated to a unique spectacle out on the water - the Heart of San Francisco Celebration! Members with a bareboat charter reservation on Labor Day also have the unique opportunity to join the flotilla.

The Heart of San Francisco is a COVID-19-safe community celebration, flotilla, and skywriting spectacle produced by Antenna Theater. Learn More

Do you have a bareboat charter reservation on Labor Day and an interest in joining this historic flotilla?  Let us know your theme and we'll connect you to the event organizers for registration. (To join in the fun, plan to decorate your charter boat and/or attire your crew in any theme of your choosing.)

Charterers are also welcome to simply sail safely in the vicinity of the flotilla and enjoy the unforgettable spectacle. Haven't reserved your boat yet? To make your charter reservation, call our office at (415) 331-8250 or email us.

Event Highlights

Vessels of all kinds will sail and motor the Bay to watch a skywriting plane draw four hearts over the Bay Area. The flotilla will be proudly headed by the tall ship, Matthew Turner. Each Heart will be a mile high and visible from yards, decks, buildings, marinas, and shorelines.* The first Heart will be drawn over the Golden Gate Bridge, then the plane will fly to Angel Island, Treasure Island and mid-Market Street.

*If you leave your property, remember to wear a mask and practice safe social distancing.

Event Schedule

2:00 PM on Labor Day, vessels will begin to gather near the Golden Gate Bridge.

2:30 PM A livestream audio and video show available via YouTube will begin. Live commentary broadcast from near the GGB will present both pre-recorded and live views of this day around the Bay. Music and performance pieces are included.

3:00 PM The sky plane will begin drawing the Heart of San Francisco above the Golden Gate, followed by subsequent hearts.

4:30 PM The fourth heart is drawn above mid-Market Street to assure that folks in the Mission, Castro and surrounding neighborhoods may join in the fun. Live stream ends.

Watch Antenna Theater's promotional video.

Watch the LiveStream beginning at 2:30 PM on Monday, September 7.

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  • John Kipping

    The meeting room was quite adequate and the location most convenient, but the course outline and instruction were outstanding. Modern Sailing is fortunate to have such a well organized instructor in Mr. Stan Lander who teaches very well from a rich professional background. Mr. Lander was generous with his time and patiently in helping students who needed more attention or time in understanding various aspects of the curriculum.

  • Salesforce (Ashley H.)

    Our team at Salesforce did the Corporate Regatta Team Buidling activity (August 2026). What a blast!! HIghly recommend for your next team activity. It's fun to be out on the water, but the skippers also did a great job of teaching us all the sailing basics. The race is set up well so that we all had a chance to try out different roles. We did it with 11 people across two boats but having more boats is also doable and would lead to even more competition.

  • John Boynton

    The class was terrific. I know you must get many compliments about your sailing instructors...But I must tell you that Robert is outstanding. Having taught SCUBA, I really appreciate the way he is so sensitive to all on board, dealing with each so well, knowing quickly their strengths and weaknesses making each feel special and cared for.

  • Lisa Butzer Wilde

    Thumbs up to (Club Skipper) Geoff (Love) and his wife Laura. I went on my first Club Sail on Sunday, January 18, 2026. They were terrific!

  • Lucas Hendren

    Got my ASA 101 here, very professional and well run class.

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