Private Sailing Charters

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Sailing on Romancing The Wind is the perfect way to relax and enjoy San Diego.  We offer Private Sailing Charters for up to 27 people that can be customized for any occasions.  Some of the most popular options include Whale and Dolphin Watching, Corporate Events and Team Buildings, Bachelor and Bachelorette parties, Family Reunions and more!  We find the perfect cruise is 3 hours long which gives plenty of time to experience San Diego’s beautiful waterfront and skyline, different kinds of marine life, and a relaxing cruise in San Diego.  Come Sail With Us Today!

Go Sailing on San Diego Bay!

Daily Sailing Charters for parties up to 27 people!Whale and Dolphin Watching, Sunset Cruise, Harbor Tours and More!Hands-on Sailing or Relaxing Cruises aboard a Stable and Spacious Big Boat!

Sunset Charters

Watch the Sunset over the Pacific Ocean on a Relaxing 3 hour charter.

Whale Watching

Get up close with the Pacific Gray Whale on it's annual migration.

Corporate Events

Perfect way to unwind after a big meeting, convention, or simply to reward your employees for a job well done!

Design Your Own Charter

We provide the Captain and the Crew and you decide where you want to sail and what you want to see!