Top 10 Boat Tours & Water Sports in Annapolis, Maryland (MD)

Learn to sail with America's first sailing school in beautiful Annapolis, Maryland! Our family-owned sailing school prides itself on being able to teach anyone how to sail the Annapolis Way - fun and relaxing. From introductory sailing experiences to getting your ASA certifications, we offer something for everyone. Call us today to learn more! Offerings: ASA 101, 103 and 104 Certifications, Basic Sailing Courses (2 days), 2 hour Evening Sail Cruises on Beneteau 37s, Private and Family Sailing Lessons, Rainbow 24 Sailboat Rentals, Summer Kids' Programs, And More!

Join us for an easygoing, educational and exciting guided kayak tour through one of America's oldest seaports. Annapolis harbor and the United States Naval Academy will be the backdrop for our 3-hour, "history rich" adventure. Our guided tour is designed for everyone and anyone can navigate the waters with our sit-on-top kayaks.

Enjoy your private sail charter with captain (up to 6 people) for a half day, full day, or sunset cruise in the Chesapeake Bay. Sail under the Bay Bridge, tour the light houses, or sip wine with a special someone as the sun sets over Annapolis.

Capital SUP is a clean water driven watersports company connecting people to the water by way of stand up paddleboarding and kayaking experiences. Hourly rentals, lessons, tours, fitness, racing, and adventure.

Join for a daytime or evening sunset sailing adventure on the Chesapeake Bay. Time and weather permitting we could sail out to Thomas Point Lighthouse or drop the anchor in a secluded spot and swim or just relax. There are always options for light catered food (BYOB).

The Liberte is a beautiful 74' schooner providing private, personalized sailing charters for groups of up to 49 people. U.S. Coast Guard certified. Full bar, catering available, music, short historic presentation. The perfect venue for any event and the best place to see the Annapolis area.

Kayak, Canoe, and SUP sales and rentals. Over 200 watercraft in stock. On the water right on the Annapolis Harbor! Calm protected water to the left down Spa Creek, More open water and the Chesapeake Bay itself to the right. Demos everyday we're open (weather permitting) Same folks at the same location for 28 years. Parking Annapolis Canoe and Kayak "The on the water specialty store".

The Finest Fleet on the Chesapeake Bay We offer bareboat and fully crewed sailing charters. Take a boat for a day sail or spend a few weeks exploring all the Chesapeake Bay has to offer. We provide full itinerary planning and can recommend provisioning services. We take care of the details so you don't have to. Take a half or full day cruise around the Annapolis area. The Chesapeake Bay is well-known as an outstanding waterway for sailboat cruising. Protected waters, great anchorages, gorgeous natural scenery, bountiful seafood, unique, historic towns and villages, and a forgiving bottom make the Chesapeake an excellent choice for sailors, novice and expert alike. We can coordinate sailing charters at our home base on the Chesapeake Bay and anywhere in the world. Interested in learning to sail? Our certified instructors can take you on a Learn to Sail vacation and help you obtain ASA certifications. Let Waypoints Annapolis make your dream vacation a reality.

Annapolis Electric Boat Rentals offers vessels for an environmentally friendly powerboat ride. Powered by 16 golf cart batteries, the boats travel at a top speed of 6 knots (6.9 mph) producing very little to no boat wake. Because the boats are electric, there is zero engine emissions or noise pollution to take away from the serenity of your adventure. The boats hold 10 people and is a perfect way to see both Spa and Back Creeks in Annapolis. Water is a way of life in and around Annapolis, whether you are a salty dog or a complete landlubber, Annapolis Electric Boat Rentals offers the opportunity to enjoy time at sea.

FUNtastic and relaxing SAILING trips from historic Annapolis,MD less than an hour away from Washington or Baltimore. Join me, Captain Paul Foer on my restored classic sailboat 38' sailboat, "Non Sea Quitter", as we sail on the Severn River and Chesapeake Bay where I grew up boating with my family. We offer private trips for up to six guests. While visiting, you may enjoy waterfront dining, live music and lodging at nearby restaurants and other nearby tourist, historic and outdoor attractions. Come for a few hours, a day or even an overnight adventure. Sit back and relax or help us raise sails and take the wheel as we sail across the open Bay and see globe-trotting freighters, yachts racing, the Chesapeake Bay Bridges, osprey, ducks and maybe even rays or dolphins swimming. Funtastic sailing for all ages.