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Team Building Cruises

Team Building on San Diego Bay

Bring your team together for an unforgettable experience aboard the Pacifica Sailing Charters Team Challenge Regatta. Designed for collaboration, leadership, and friendly competition, this 3-hour sailing adventure turns teamwork into an exhilarating race across San Diego Bay. Each yacht is crewed by a licensed USCG captain who guides your team through real sailing maneuvers — hoisting sails, trimming lines, and navigating the course.

Perfect for:
Corporate retreats, sales teams, and leadership groups, this event blends excitement and cooperation while enjoying the sun, sea breeze, and iconic skyline views.

The Experience

Your group will be divided into small teams of 4–6 per yacht to compete in a hands-on sailing regatta. No sailing experience is required — participants learn the basics, rotate through crew positions, and work together to maneuver and race their boat.

Each event emphasizes:

Communication

Teams must coordinate and adapt quickly under changing wind and course conditions.

Leadership

Participants rotate roles, encouraging collaboration and problem-solving.

Camaraderie

Shared success builds trust and lasting connections within the group.

Booking Details

Choose the perfect Team Challenge experience to match your group’s size and goals. Each option includes a licensed USCG captain, professional crew, and catered lunch, with add-ons like photography, trophies, and branded team shirts available upon request. Whether your team wants a relaxed sail or a full regatta competition, every event is customized for collaboration, fun, and memorable results on the San Diego Bay.

Packages & Pricing

  • Ranger 37 Team Challenge – 4–6 guests · Includes captain, crew, and catered lunch
    3-hour private charter · $1,800
  • Big Boat Dual Challenge – Two boats · 8–12 guests · Includes captain, crew, and catered lunch 3-hour event · $3,800
  • Ancient Mariners Challenge – 55’ twin-masted ketch · Up to 27 guests
    Includes captain, crew, facilitator, and lunch · $3,800
  • America’s Cup Challenge – Compete aboard Stars & Stripes and Il Moro (78′ race yachts)
    Up to 36 guests · Includes captain, crew, catered lunch, photographer, and team shirts · $4,800

Team Masquerade Sailing Shirts

Team Masquerade "Naughty Mermaid" Team Shirt

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Team Masquerade "Mardi Gras"

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Team Masquerade "Ranger 37 Mechanical" Team Shirt

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Team Masquerade "Black Sails" Team Shirt

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Team Masquerade "Vintage Mermaid" Team Shirt

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Team Masquerade "Ladies Tank" Team Shirt

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