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Charter Activities

Hard at work at the helm

A charter sail on the Chesapeake Bay can be almost anything you want it to be. Some people want nothing more than a leisurely sail around the Bay, while others envision a more active experience. Whichever you desire, Five O'Clock Charters can make it happen.

  • Sightseeing on the Chesapeake Bay
  • Family cruises
  • Birthday/special occasion parties
  • Office outings
  • Sunset sails
  • Swimming, paddleboarding, kayaking
  • Dockside restaurants
  • Sailboat races—watch from the water, best seat in the house!

Something else in mind? Let us know, there's plenty to do!

Charter Activities

America's sailing capital

Planing a visit to Annapolis? If you're coming to America's sailing capital, you need to to go sailing!

Office Outing

Bring your team out for a retreat, or just a unique opportunity for staff to interact in new and exciting ways.

Wedding at sea

Have your wedding on the water! What better way to start your new life together?

Romantic cruise on the Chesapeake Bay

What could be more romantic than a sunset cruise?

Annapolis Sunset

Simply put, there is something magical about sailing on the Chesapeake Bay at sunset.

Approaching the mark

Annapolis is home to a very active fleet of boats that like to race regularly, and they are fascinating events to watch.

Family sailing on the Chesapeake Bay

An opportunity to expose everyone to the great art of sailing, with a wide array of extras to make it enjoyable for the whole family.