business directory

Annapolis Sailing Cruises: Schooner Woodwind

Sail the Chesapeake on a 74-foot schooner! Raise the sails, steer the boat, or sit back and relax on a two-hour sail. Special, longer event cruises, too. The Woodwind and Woodwind II offer a real Che...

Cruises on the Bay by Watermark

Cruises on the Bay by Watermark has been offering sightseeing cruises to visitors and residents of Annapolis for over 40 years! Cruises run daily through early Spring until early Fall with Special Eve...

Liberte, The Schooner

Private, personalized charters for up to 49 guests. Sail aboard Annapolis’ most spacious schooner—corporate and team-building outings, weddings and events. Call Captain Chris and entertain the pos...

Yacht Charters on the Bay by Watermark

Chartering a beautiful yacht for a corporate or social event is easy at Yacht Charters on the Bay by Watermark. With a fleet of 13 yachts from 24' to 99’, our boats are elegant, luxurious and unique...

Annapolis Sailing School

America's oldest sailing school and Annapolis' largest sailing school. Learn to sail the "Annapolis Way" from beginner to advanced. KidShip Sailing is a weekly sailing camp that offers age appropriate...

Cruise Annapolis

We offer luxury bareboat & crewed yacht charters on the Bay, onboard one of our world class Jeanneau monohulls or Fountaine-Pajot catamarans. Most of our fleet consists of new yachts. All are well...

Sail the Pintita

The sailing ketch Pintita is licensed for groups up to 20 and is one of the most economic vessels available.  She can heat or air condition underway and has an all weather enclosable cockpit.  Overn...

Sailing Lessons with Cruise Annapolis

Learn to sail on the boat you ultimately want to own. Catamaran sailing schools are our specialty. Go out at any time, for any length of time, to learn with a certified instructional captain. Your cap...

Snag-A-Slip

Snag-A-Slip is a brand-new online boat slip rental system that allows boaters to explore marinas by region and search for boat slip availability based on length, beam, depth and power requirements. On...

Annapolis Community Boating

Annapolis Community Boating is a 501©3 organization dedicated to creating safe, fun and educational on-the-water opportunities for the entire community. Annapolis Community Boating is constantly putt...

Annapolis Electric Boat Rentals, LLC

Enjoy the serenity and beauty of Annapolis' waterways on a Duffy electric boat, all year round! As easy to drive as a golf cart, so anyone can be their own captain.  Seats up to 10 passengers. Bring...

LoosenUp Charter Fishing

Maryland Chesapeake Bay Fishing ChartersLicensed for up to 44 passengers Departs out of Deale, Maryland, only a short distance out of Annapolis and Chesapeake Beach, Maryland. Fishing for Maryland St...