Things to do in Annapolis, Maryland (MD): The Best Outdoor Activities

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.

City Running Tours (CRT) provides an opportunity to experience a city in an exciting way. Annapolis is an ideal town for runners and CRT is ideal for the traveler who is tired of the hotel treadmill, the runner who is training for a race or who wants to explore new and interesting routes. CRT offers both guided group and personalized runs to accommodate any athletic ability, pace, or style.

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.

Paddle Annapolis @ Butler's Marina specializes in paddle board tours. Stand up paddle boarding is the fastest growing water sport in the world. Paddle boarding is an amazing water activity that brings people together to enjoy water, nature, yachts, sailboats, sunsets, and historic sites. Paddle boarding is also a fantastic way to sneak some fitness in while having a blast with friends and family.

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.