If you love the outdoors and water, you’ll be thrilled at the endless variety of water adventures that await you in Annapolis and throughout Anne Arundel County. Whether you spend a day sailing the Chesapeake Bay, the largest estuary in North America, cruising our shores aboard a breathtaking yacht, or kayaking the many creeks feeding the Bay, you can find a water activity for everyone in the family. From performance sailing and boat shows to relaxing charter boats, the shoreline of Anne Arundel County offers great opportunities for family water excursions. Click on one of the links below to learn more.

Admiral of the Bay, LLC
Event planners for The Chesapeake Bay-Groups (2-250) people - Schooners, Custom Power Yachts - Weddings, Business meetings, lunch or dinner sunset cruises - crab feasts or formal dining.

American Classic Yachting, LLC
Enjoy cruising aboard “Windrush” a 1966 Trumpy built in Annapolis. Day cruises for up to six guests, overnight cruises and stay-a boards at our dock for up to four (May- Oct.)

Annapolis Bay Charters
Annapolis' premiere bareboat company offers a fleet of over 30 different sail and power yachts. We also specialize in customized yacht charters for social and corporate entertaining. Our reservation event department will handle every detail to ensure you occasion is memorable. Call today 410-268-2308! Or visit our website at www.annapolisbaycharters.net.

Annapolis Community Boating
Making boating accessible and fun for all. We have small boats and large boats used in various boating programs for the public. Boating industry resource for Annapolis.

Annapolis Fishing Unlimited
From single person fly fishing trips to your largest corporate groups, Annapolis Fishing Unlimited provides the most versatile, professional charter operation in town. Located right in the heart of Annapolis

Annapolis Sailing and Powerboat School
America's oldest and largest sailing school. Learn to sail the Annapolis Way from beginner to advanced. KidShip Sailing School offers age appropriate instruction for kids from 5 to 15.Sail boat rentals available. Sail all summer for one low membership fee in the Keelboat Club.

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. Departs from the downtown Annapolis Marriott Waterfront Hotel. Two 74-foot schooners offer a real Chesapeake sailing experience for public sails and private charters. Buy a ticket, or privately charter the entire boat. Fun, team match racing, corporate outings, crab feasts and catered sunset sails.

Annapolis Sailing Solutions
Experience a full or half-day sail with a licensed captain aboard a 34 foot Gemini Catamaran. Open itinerary. Limited to six passengers.

Annapolis Small Boat Rentals, Inc.
Discover beautiful historic Annapolis and our many hidden coves and creeks that make the Chesapeake Bay a place to remember. Enjoy the freedom that renting your own private boat can bring.

Catnip Charters
Chesapeake Bay Charter Fishing for rockfish, bluefish, perch and spot. Located at Happy Harbor Marina in Deale, MD. All bait, licenses and tackle included. Women and children welcomed. 46' Custom Bay Built.

Chesapeake Bay Sport Fishing, LLC
We pride ourselves on being a first-class Chesapeake Bay fishing charter. Our services are very productive for entertaining cleants as well as many private and family fishing charters.

Chesapeake Beach Resort & Spa
Enjoy luxury accommodations with balconies overlooking the Chesapeake Bay, a full-service spa, marinas, slip rentals, charter fishing, two restaurants an outdoor cafe. Create memories for a day, weekend or lifetime.

Chesapeake Boating Club
Enjoy unlimited use of quality sail and power boats from 19' to 36'. Low annual fee and online reservations make boating a breeze. Stop by for a free demo.

Chesapeake Sailing School & Charter Company
Offering learn to sail programs for adults and families. Corporate and group teambuilding event planning offered as well as private lessons. Sailing club and island vacations. Weekends and weekdays.

Classic Sail Charters
Classic Sail Charters offers Chesapeake Bay adventures on Licentia, a beautiful 2008 Catalina 42 MK II. Come out and enjoy some time sailing on the Bay.

Down Time Sportfishing Charters
World Class Chesapeake Bay Sportfishing for private groups and family fishing charters. Full Time Professional Fishing Guide services and Annapolis area Chesapeake Bay Cruising. Licensed for up to six guests. Come on aboard and have a great day on the Bay! Call 443-949-8030 or visit our website at www.DownTimecharters.com for complete details.

Felix Charter
Felix the cat is a unique 45' sailing catamaran! We can accommodate up to 12 people. This could be a birthday, corporate outing, boat and breakfast, wedding, etc. No sharing the boat with people you do not know. This will be your own event! Charter guests may choose from any number of food and drink options. Light snacks and soft drinks are included in our basic package. We cruise out of the Magothy, Severn and nearby rivers. Trips are generally 2-4 hrs. Please see website, or contact us for more specific information.

Fly & Light Tackle Fishing Charters
Enjoy fly or light tackle fishing for striped bass and other species on the Chesapeake Bay. ORVIS Endorsed Fly Fishing Guide Capt. Tom Hughes provides everything and boarding is just 15 minutes from Annapolis.

J World Performance Sailing School
Specializing in personalized hands-on instruction, our courses are taught by top level sailors aboard late model performance sailboats. Limited class sizes, courses for beginners to advanced sailors and racers in both weekend and wee-long formats.

Kayak Annapolis, LLC
Enjoy an educational and exciting guided tour on sit-on-top kayaks through one of America's oldest seaports. The harbor and the Naval Academy will be the backdrop for our 3 hour tour that is history rich and designed for everyone- corporate groups, families, and leisure vacationers.

Let's Go Cruising
LetsGoCruising is located on the Annapolis harbor, and offers a variety of brand new and immaculately maintained monohulls and cruising catamarans.

Liberte, The Schooner
Private, personalized charters for up to 49 guests. Sail aboard Annapolis’ most spacious schooner – corporate and teambuilding outings, weddings and events. Call Captain Chris and entertain the possibilities.

Old Bay Charters
Enjoy a day on the bay aboard the Old Bay a 50' trawler USCG certified for 50 passengers. Fish, sightsee custom cruises. Reserve your adventure today.

Pintail Yacht Charters & Nautical Destinations
Pintail Point Charters features a fleet of beautifully appointed luxury yachts and is sure to make waves with your next event. Weddings, corporate parties & meetings, fishing…We've got it all.

Pirate Adventures on the Chesapeake
Come aboard for a Pirate Cruise. Let your child enjoy life a s a pirate while you relax and enjoy the ride. Kids get their faces painted, dress up in pirate garb, fire water cannons and more!

Sail the Pintita
The sailing ketch Pintita is licensed for groups up to 20, and is one of the most economic vessels availbale. She can heat or air condition underway and has an all weather enclosable cockpit. Overnight cruises available for up to 6 passengers.

Sandy Point State Park
Offering sandy beaches with swimming, playgrounds, hiking, crabbing, fishing, and an excellent view of the Bay Bridge. Marina offers 22 ramps, seasonal marina with small boat rentals.

Sarles Boatyard and Marina
Sarles Boatyard and Marina offers transient slip rentals, small boat rentals, kayak rentals, dingy and kayak storage and boat maintenance.

SJ Koch Duffy Electric Boat Rental/Sales LLC
Enjoy the serenity and beauty of Annapolis waterways in a luxurious 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.

South River Boat Rentals
Powerboat and sailboat rentals and charters on the Chesapeake Bay. We offer bareboat or captained charters by the half day, full day and weekly. Team building and corporate charters.

Springriver Annapolis Canoe and Kayak
Canoe and Kayak sales and rentals. Expert staff and large inventory on hand. Try before you buy from our floating dock in Eastport directly across from Ruth's Chris Steak House.

SunTime Rentals, Inc.
New nineteen foot Inboard powerboats and new Yamaha waverunners available for hourly, half-day and full day rental on the South River in Annapolis. Also, wake boarding, tubing and water skiing

Watermark Tours, Charters, Cruises
Getting out on a boat in Annapolis is fun for adults and kids-and dog-friendly too. Enjoy a Watermark 40 minute Annapolis Harbor Cruise, a 90 minute Chesapeake Bay Cruise, a 2 ½ hour Lighthouse Cruise, Pirates of the Chesapeake, or a full Day on the Bay to St. Michaels. Charter Watermark’s luxury yachts on the Chesapeake Bay for weddings, corporate outings, team building and special occasions. For more information call 410-268-7601 or on-line at www.watermarkjourney.com

West River Cruises
Cruise the beautiful West and Rhodes Rivers on the historic Chesapeake Bay built Richard Lee. The Richard Lee, a classic 65 foot, 110 passenger, Coast Guard certified, double decked tour boat offers sunset cruises and custom charter events.

Womanship, Inc.
The renowned sailing school for women, taught by women - USCG licensed instructors. We guide novices to advanced sailors to joyful, confident competence onboard. "Nobody Yells!"

Yacht Basin Co., Inc.
Our marina is conveniently located between the Annapolis Marriott and the Annapolis Yacht Club. Slips for rent by day, week, month or year. Facilities include gas and diesel, ice, laundry, showers and parking.