Annapolis Water Activities

Annapolis’s lifeblood stems from the regional waterways that descend on the productive and beautiful waters of Chesapeake Bay. The city was founded to take advantage of the unique convergence of the Severn River and hundreds of smaller streams and rivers, and the focal point of the city today is still its historic downtown waterfront and harbor. This charming district, with over 300 years of history, is home to the City Docks and the U.S. Naval Academy and countless marinas, yacht clubs, and sailing-themed establishments. Boating enthusiasts flock to Annapolis year-round to enjoy the inviting shallow waters of the bay, especially during the Annapolis Yacht Club’s sailboat races during the month of May and the annual yacht show in October. When you are planning your next trip to this playground on the water, be sure to browse our selection of luxury vacation rentals with their own waterfront and dock access and check out all the amazing things to do on the water in Annapolis.

Exploring the Bay

With an average depth of only 21 feet, the Chesapeake and its countless inlets and tributaries is perfect for exploring. Many vendors in the Annapolis area offer canoe, kayak, and stand-up paddleboard rentals, as well as more extreme modes of transportation like kite surfing and wind surfing. Two of the more convenient ones, located in the heart of the city on Spa Creek, are Capital SUP and Annapolis Canoe and Kayak. Capital SUP even offers nighttime SUP excursions which make use of LED’s on the underside of the boards for a truly glow in the dark experience. The narrated guided tour of the city’s waterways has a party atmosphere thanks to mobile waterproof speakers, and is a unique way to try this fun, fast-growing water sport. If you have your own gear or are renting long-term, there are numerous parks and launch sites scattered around the city for you to use when planning your own Annapolis water activities.

Sunset Sails, Yo Ho!

Dozens of tour operators offer cruises on the glistening waters of the bay, and sunset cruises are perhaps the most popular. Rent your own schooner for a private pirate or family dinner, or climb aboard the 74-foot Schooner Woodwind for a 2-hour cruise. They even offer “Boat and Breakfast” overnight packages. If you are a kid at heart or have kids in tow, you’ll love the pirate ship Sea Gypsy. These scenic tours feature treasure hunts in the bay, spectacular views, dress-up for the kids, and water cannon battles with other pirates. It’s a blast!


 All this activity is bound to make you feel more than a little hungry, but that doesn’t mean you have to leave the water to enjoy a fabulous meal! In addition to the dinner or breakfast cruises mentioned above, many of the waterfront restaurants found in the area are designed to feed your soul as much as the meals fill your stomach.

Sam’s on the Waterfront, located at 2020 Chesapeake Harbour Drive E, is a local tradition serving up all your seafood favorites with views that are a bigger treat than the sweetest of desserts. Try their Jumbo Stuffed Shrimp, served with lump crabmeat, sweet peppers, and a creamy sweet pea risotto, or test their claim that their crab cakes are the best in Annapolis! Titled Annapolis’s Best Crab Cakes and served with a lemon caper remoulade, Israeli cous cous and fresh vegetables, we have to admit we can’t state for certain whether they are the best, but we do love every single bite we take!

The Boatyard Bar & Grill at 400 E Fourth Street is another local favorite, designed for a casual meal that complements your day on the bay. This is where the fishermen chow down, and of course, they advertise that their crab cakes are the best as well; maybe your Annapolis adventures won’t be complete until you sample every crab cake in town!

Finally, when seeking an elegant night out on the town (with more of our crab cakes, of course!), a visit to Carrol’s Creek Café at 410 Severn Avenue is bound to become a highlight of your getaway. Offering a carefully thought out surf and turf menu, you can’t ask us to suggest a favorite dish because we love them all!

Your Private Pool Offers Fun as Well

Even though the bay is the primary source of watery fun for residents and visitors alike, when you choose At Home Annapolis for your vacation abode, you may discover your own watery oasis in the private backyard; some of our properties contain private pools for your entertainment delights! Lounge in the chairs on the deck, working on your tan and reading that summer blockbuster you’ve been looking forward to, practice cannon balls into the deep end, or float around in that kitschy flamingo float you found at the local department store and couldn’t resist purchasing! Your day of fun in the sun will be enhanced by the warmth and welcoming of your At Home Annapolis rental with a pool.

Enjoy Annapolis Water Activities During Your Stay

The Chesapeake and its tributaries are the heart and soul of our city, both in geography and spirit. There are countless ways to explore and enjoy Annapolis water activities, from the comfort of your own waterfront vacation rental from At Home Annapolis to watching the weekly sailboat races (or you can even learn to sail) to exploring the history of the U.S. Naval Academy. No matter which of our properties you choose, be sure to enjoy the many things to do on the water in Annapolis!

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