Annapolis and Chesapeake Sailing Tours

Daysails, Sunset Sails… And More? Just Ask!

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Come Sailing With Captain Paul on “Non Sea Quitter” and Enjoy A Chesapeake and Annapolis Sailing Adventure….Every Trip Is A Bit Different!

  • Regularly Scheduled and Customized Private Trips 
  • Enjoy Sailing With One of The Chesapeake’s Most Experienced (And Entertaining) Captains
  • 2.5 Hour Sunset Tours (Our Most Popular)
  • 3 Hour Daysails (Or longer Upon Request  and When Available)
  • Experience The Bustling Harbor of America’s Sailing Capital
  • Cruise Up The World-Famous “Ego Alley” and Watch The Crowds…As They Watch You
  • See The Historic Skyline, State Capitol Dome and US Naval Academy
  • Sail By Yacht Races on Wednesday Evenings and Other Times
  • Sail Under The Sprawling Chesapeake Bay Bridges (On longer trips only) 
  • See the Iconic Thomas Point Light House-and other historic lighthouses (On longer trips only)
  • See the historic radio towers at Greenbury Point
  • Sail by Horn Pt, and learn about what happened there to George Washington in 1791
  • Slumber aboard soundly while “glamping” aboard a classic sailing yacht at a luxury resort marina and pool (By Special Request and When Available)
  • Relax and de-stress on your own private sailboat with professional captain
  • Get a front row seat to the boating scene in America’s Sailing Capital 
  • Escape your busy everyday life and enjoy the special kind of relaxation that comes with sailing


Interested In A Overnight Sail Or Sleeping Aboard On “Non Sea-Quitter” ?

Enjoy your stay aboard Non Sea-Quitter at the acclaimed Port Annapolis Marina and slumber peacefully. Relax by the nearby pool and cafe’. Clean restrooms, shower and plenty of parking too!

Learn more

Do you have any questions about our tours or overnight stays aboard The Non Sea-Quitter?

Call Captain Paul 443-852-2163

Book Your Trip

Annapolis/Chesapeake Sailing Tours

Instagram: #NonSeaQuitter


Chesapeake Bay Region, East Coast,  Annapolis, St. Michaels, Kent Island, Baltimore, Oxford, Galesville, Edgewater, Deale, Herring Bay, Severn River, Magothy River, West River, Rhode River, Miles River, Chester River, South River, Choptank River, Tilghman Island, Rock Hall, and many more.

Counties We Serve:

Anne Arundel, Baltimore, Kent, Queen Anne's, Talbot, Dorchester, Calvert, St. Mary's, Cecil, Hartford, and many more.