Check Out This Annapolis Boat Rental Guide & Go Play On The Water

All the Annapolis boat rental, sailing boat charter, and surfing info you need to explore Chesapeake Bay

Your Insider’s Guide to A Splashing Great Time including an Annapolis boat rental

Summer in Annapolis is a water lover’s dream and an Annapolis boat rental is the perfect way to see the Chesapeake Bay. Whether you’re looking to take a scenic boat rental, embark on a sunset sailing adventure, or simply coast through this historic colonial seaport, we’ve got everything you need to plan your journey. See a list of upcoming Annapolis events happening this summer.

Known as America’s Sailing Capital, Annapolis is as famous for its crab cakes and lighthouses as it is for its 533 miles of shoreline. As one of the most historic places in the United States, Annapolis is home to more surviving 18th century architecture than any other city.

Set sail along Chesapeake Bay, paddle along the shore, or simply grab a drink and watch the stunning boats go by. There is so much to do and see in Annapolis!

Historic & Sunset Boat Tours

History buffs won’t want to miss the opportunity to learn about this unique maritime town and seaport aboard a historic boat tour. Sunset on the water is equally remarkable. Grab your favorite drink and relax as you watch the sun descend over the Annapolis skyline. With so much to see, boat tours are a great way to experience all that Annapolis has to offer.

Paddling & Kayaking

There is something unforgettable about getting acquainted with a place by paddling or rowing through its waterways. With over 533 miles of shoreline, the scenery as you paddle around Annapolis is breathtaking. There is plenty of time to take it all in and witness nature up close. Perhaps you will experience the tranquil stance of a Blue Heron before it takes flight, or admire the diversity of aquatic and wetland plants as you wind through the waterways.

Wind Or Kite Surfing

Thrill seekers looking for a bolder adventure will certainly find it. Select parks offer launch points for both wind and kite surfers. What’s even more convenient? Your bird-watching friends can also launch their canoes and kayaks from these same points. Afterwards, you can all meet up at one of the many great restaurants or bars in and around Annapolis to share your adventures.

Boat Shows in the Sailing Capital of America

There is a reason Annapolis is known as the Sailing Capital of America. With a long history of delighting boating enthusiasts across the globe, Annapolis provides plenty of opportunities to admire cutting-edge boat designs and stock up on sailing essentials. Annapolis boasts the nation’s oldest in-water boat shows, with events happening every fall and spring and catering to over 150,000 attendees from around the globe. Find all the information for Annapolis boat show dates and to purchase tickets to upcoming events.

Historic Sights

Don’t miss the Chesapeake Bay Maritime Museum, where nine exhibit buildings proudly display the history of Chesapeake Bay.  The museum’s largest permanent exhibit, At Play On The Bay, explores the bay’s history over the last 100 years as it has shifted from a place of work to a place where people come for fun. Be sure to catch the Small Boat Shed exhibit, which displays a variety of small working and recreational watercrafts, as well as skiffs used for oystering, fishing, and crabbing.

The Thomas Point Shoal Lighthouse is a National Historic Landmark, one of only ten lighthouses in the country to be bestowed this highest honor. It is accessible only by boat.  The Thomas Point Shoal lighthouse dates back to 1824 and guards the entrance to South River, where it still stands in its original location. Public tours are conducted every summer.

Wednesday Night Sailboat Races

If you’re visiting between May and August, you won’t want to miss this! Grab your favorite drink and a cool dockside seat to watch as over 150 crews compete in this fun, mid-week celebration. Participants sail around the bay before heading back for a grand finale in front of the Annapolis Yacht Club. Spectators can follow along in boats, watch from waterfront restaurants and bars, or stand along the Spa Creek Drawbridge.

Something for Everyone!

There is no shortage of unique and exciting ways to experience summertime in Annapolis and the Chesapeake Bay, the nation’s largest estuary. With so many diverse and exciting options, Annapolis is sure to delight the entire family.

Reserve your boating adventure today.

Boatsetter has fleets of private boats and sailing options ready to help you embark on your summer escape. Whether you’re looking for a guided excursion or a low-key sunset tour, Boatsetter has you covered. Reserve today, then pack your swimsuit and get ready for an unforgettable adventure!

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