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Private Charters/Tours

Pacific Sail’s Skippered Charter options offer a fun and carefree sailing experience with one of our U.S. Coast Guard Licensed captains at the helm. Perfect for any celebration, special occasion, or simply treating yourself and friends to an unforgettable outing. Enjoy the natural beauty of Monterey Bay’s scenery and abundant sea life, including sightings of sooty shearwaters, whales, and occasionally juvenile great white sharks.

Skippered Charters stay within Santa Cruz coastal waters, providing protection from ocean chop and stronger winds.

Interested in learning to sail on your own? Explore our ASA Sailing Courses.

  • Skippered Charter

Private Charters/Tours

  • Capacity: Up to 6 passengers per boat
  • Duration: Minimum 2-hour cruise
  • Food & Drinks: Guests are welcome to bring food and beverages (hard alcohol is not permitted).
  • Availability: 9:30 AM – Sunset (choose your ideal 2-hour window)
    • Mornings: Calm conditions, light winds
    • Afternoons: Steady wind for an enjoyable sailing experience
    • Sunsets: Typically calm with stunning views
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  • Skippered Charter

Team Building Challenge

  • Our Team Building Challenge is a three-hour sailing regatta designed to strengthen communication and leadership, all while having a blast on the beautiful Monterey Bay.
    • Multiple boats available for large groups
    • Learn basic sailing terminology and teamwork skills
    • Race as a fleet toward a shared goal
    • Hands-on roles for each team member—helmsperson, trimmers, lookout, and more
    • No strenuous activity required
    • Fun, safe, and guided by expert skippers
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