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Corporate Events


Corporate Sailing Events in Annapolis

Team-building, leadership development, and unforgettable experiences on the Chesapeake Bay

65+ Years of Sailing Excellence, American Sailing Accredited, 5-Star Reviews, Trusted by Leading Companies


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Take your team off the conference room floor and onto the water. Sailing builds communication, leadership, and trust—naturally.

Why Choose Corporate Sailing?

Leadership Development

Chinook Sailboat on open water.

Team Collaboration

Chinook Sailboat being manned by crew.

Memorable Experiences

Rainbow Sailboat on open water.
  • Participants rotate roles, make real-time decisions, and learn to lead under changing conditions.
  • Staff gains insight in both teaching and learning new tasks
  • Success on a sailboat requires clear communication and teamwork—skills that transfer directly to the workplace.
  • The ability to give clear and concise directions is rewarded on the water
  • A day on the Chesapeake Bay leaves a lasting impression on employees and clients alike.
  • Our sailors regularly spot Blue Herons, Osprey and sometimes Dolphins

Corporate Event Options


Team-Building Sailing Experiences

  • Hands-on sailing with professional instructors
  • Ideal for teams of 6–50+
  • Half-day or full-day options
  • On the water Scavenger Hunt (either competitive or cooperative)

Corporate Regattas

  • Friendly competition between teams
  • Strategy, coordination, and fun
  • Awards ceremony optional

Client & Executive Entertainment

  • Private sailing charters
  • Catered experiences available
  • Perfect for relationship building

Leadership Retreats & Workshops

  • Custom curriculum combining sailing and leadership principles
  • On-water and shoreside sessions

Sample Event Schedule

Half-Day Corporate Sailing Event

  1. Welcome & Safety Briefing
  2. Sailing Instruction & Crew Assignments
  3. On-the-Water Sailing Experience
  4. Regatta-Style Challenge
  5. Debrief & Wrap-Up

Full-Day Corporate Sailing Event

  1. Welcome & Safety Briefing
  2. Sailing Instruction & Crew Assignments
  3. On-the-Water Sailing Experience
  4. Lunch
  5. Regatta-Style Challenges
  6. Debrief & Wrap-Up

(Schedules are fully customizable)

What’s Included

  • ASA Certified Instructors
  • Well-maintained sailboats
  • Safety equipment and insurance
  • Event coordination and logistics
  • Optional catering and photography

Location Advantage

Sail from the Heart of Annapolis

  • Located on the Chesapeake Bay
  • Easy access from Washington, DC & Baltimore
  • America’s Sailing Capital

Testimonials

Group Testimonies

  • “We Loved It!!!!!!!!!!!!!!!” – Everyone LLC
  • “Best corporate event ever, my team had a great time out on the water. School had better boats than us.” – AYC
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