Captain Jan Miles - Pride of Baltimore
Jeffrey G Katz

Chesapeake Bay Storytellers - History Tours

Captain Jan Miles - Pride of Baltimore
Jeffrey G Katz

The Chesapeake Bay teems with unique culture that has evolved from centuries of watermen and maritime heritage. Discover her fascinating stories, and experience the sights and sounds on both land and water. From Native American settlements, to colonial sites, boat-building, fish and oyster harvesting, waterfowling, U.S. Naval history and more, there is so much to explore. Some tours are aboard skipjacks, bugeyes, buy boats, paddle boats or other historic vessels, part of the Bay’s renowned fishing and transportation industry.

Chesapeake Bay Maritime Museum

Enhance your visit to the Chesapeake Bay Maritime Museum with a tour led by a knowledgeable guide. Choose from nine different hour-long tours that provide insights into the history and distinctive culture of the Chesapeake Bay. Options include: Navigating the Chesapeake, Oystering on the Chesapeake, Blue Crabs Bay to Table, Catch of the Day, Seeking Freedom, Lighthouses of the Chesapeake, Boats of the Bay: Log Bottom Boats, Boats of the Bay: Racing Boats, and Boats of the Bay: Working Boats. Narrated Historical Cruises are also available aboard the Patriot, a vessel built to resemble a traditional Chesapeake Bay steamboat. Guests discover local history while on a 70-minute cruise on the Miles River. 410-745-2916  
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Shardana Sailing Charters, Inc. 

Shardana Sailing Charters will guide you in designing a custom adventure or relaxing experience that meets your needs. Their knowledgeable and friendly captains can take you to historic sites and tell stories that reveal the hidden history of the Chesapeake’s beautiful land and waterscapes. Sailing experiences leave from Rock Hall. 215-238-1635  
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Calvert Marine Museum

The Drum Point Lighthouse is open for exploration, frequently with guided tours. The Lore Oyster House displays exhibits about seafood packing and oyster processing. Enjoy a river tour on the 1899 Wm. B. Tennison, a sailing “bugeye” boat suited for oyster dredging on the shallow waters of the Chesapeake. Hear about the adventurous history of this working vessel that was later converted into a powered buy-boat for continued oyster industry work. The Calvert Marine Museum’s calendar of events includes lectures on a variety of historical topics, including the history of watercraft and fishing in the Chesapeake, The Civil War on the Chesapeake, wooden shipbuilding and more. Check with the admissions desk for details. 410-326-2042 
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Pride of Baltimore II

Come aboard the Pride of Baltimore II, a replica of an iconic Baltimore Clipper, a privateer vessel that played a pivotal role in the War of 1812. This tall ship has sailed to more than 200 ports in 40 countries. Each season the vessel visits dozens of ports of call and welcomes over 100,000 people. Take a deck tour or day sail to discover maritime history first-hand. A lucky few can join her for overnight guest crew experiences. Check out the schedule for ports, deck tours, and public sails and follow Pride II as she sails near and far!  410-539-1151.  
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Watermark

Watermark

Step aboard the Harbor Queen to experience a narrated cruise of historic Annapolis and the banks of the U.S. Naval Academy. Hear the history of the Naval Academy, Annapolis’ role as a historic seaport, the region’s waterways and more. In Baltimore, take the National Anthem Tour by Sea from Baltimore Harbor. You will be transported to a time when Baltimore residents defended their homes, businesses and land from the British during the War of 1812. This lively cruise will leave lasting memories and is fun for the whole family. 410-268-7601 
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Annapolis Maritime Museum

Explore Annapolis’s maritime history and Chesapeake Bay ecology aboard the skipjack Wilma Lee, a member of the last commercial sailing fleet in the United States. On this Heritage Cruise you will discover Annapolis, the Naval Academy, the former working waterfront of Eastport and the Chesapeake Bay like never before. Learn about the city’s boat building industry, Chesapeake Bay watermen history, and oyster harvesting and discover local landmarks like Carr’s and Elktonia Beach along the way.  410-295-0104. 
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Experience Smith Island

The Experience Smith Island Tour offers an immersive journey into the heart of Maryland’s Eastern Shore. On this all-inclusive, six-hour tour, you’ll explore the charming island of Smith Island, known for its rich history, vibrant waterman culture, and world-famous Smith Island Cake. You’ll enjoy a Maryland crab cake lunch, participate in a blue crab demonstration, and take part in a hands-on Smith Island Cake baking demonstration. Throughout the tour, you’ll have opportunities for wildlife spotting, and you’ll learn about the unique heritage of the island from your knowledgeable guide, Captain Everett. Whether you’re a history buff, foodie, or nature lover, this tour offers something for everyone!  410-657-2705  
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Chesapeake Water Tours

Embark on a Sightseeing Canal Cruise in historic Chesapeake City. Cruise west on the Chesapeake & Delaware Canal, and explore the Elk River and Upper Chesapeake Bay. This lightly narrated tour offers insights into the history of the canal and its surroundings. Panoramic views reveal the waterway’s beauty from the comfort of a shaded canopy. There’s a chance you’ll spot oceangoing ships too. This is a perfect family-friendly experience. 443-566-3386 
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Rent-A-Tour

Rent-A-Tour is your one-stop shop tour guide and receptive services in the Chesapeake Bay region. We'll work with you and your group to plan a custom experience that highlights what makes Maryland so special. In Baltimore, explore history and heritage in America’s City of Firsts! From walking tours through historic neighborhoods, to chartered cruises on Baltimore's Inner Harbor, to motorcoach excursions to wine country, Rent-A-Tour can make your unique vision a reality. Our guides love sharing unforgettable stories and our tour planners are here to help work out the details. Whether you're visiting for a couple of hours or staying for a couple of days, Rent-A-Tour looks forward to welcoming you!  410-464-7994 
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Greenspring Tours

Whether you need transportation, a tour package, a guide, or destination management services, Greenspring Tours has your group covered. Serving Baltimore and beyond, Greenspring Tours provides student field trip and group travel packages. Their dedicated tour managers create itineraries and tour packages that include transportation, guide service, attractions, meals and more at an affordable price, showcasing the history, culture and cuisine of each destination. 410-561-1119  
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Havre de Grace Decoy Museum

Havre de Grace Decoy Museum

Located on the banks of the Susquehanna Flats, the Havre de Grace Decoy Museum houses one of the finest collections of working and decorative Chesapeake Bay decoys. Now valued for their artistic character, decoys have been an integral part of waterfowl hunting and a central element of Chesapeake culture for centuries. Group tours of the museum’s galleries are available by reservation. Many of the guides are carvers, hunters, museum founders, and life-long residents of Havre de Grace. They treat visitors to colorful stories about the history of decoys and waterfowl hunting in the Upper Chesapeake Region. 410-939-3739 
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Island Chill Yacht Charters

Explore the treasured Chesapeake Bay, a special place where over 10,000 years of Native American history plus over 400 years of key events in our nation’s history have transpired. Discover historic colonial Londontowne, a former bustling seaport, the South River and the Thomas Point Shoal Lighthouse from the water on a scenic cruise. Find out for yourself why Captain John Smith in 1608 described the Bay as “the most pleasant place ever knowne…” 410-212-4476 
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Annapolis Sailing Cruises: Schooner Woodwind

Mondays are extra special on Schooner Woodwind’s sunset sailing cruises. During History Mondays, a different guest speaker presents on a special topic each week. These guided tours explore the history of the Chesapeake area and the sights you see while on a sail. The bar includes a selection of craft beer or wine for your enjoyment. Check out their exciting schedule of tours and topics provided by notable experts in the field. 410-263-7837  
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Thomas Point Shoal Lighthouse Tours

Come see the Thomas Point Shoal Lighthouse, a National Historic Landmark and icon of the Chesapeake Bay. Tour the interior of one of the most photographed lighthouses in the United States, accessible only by boat. You will be guided by an experienced lighthouse docent and learn the history of the light, the life of a keeper in the early days and the role of our modern-day Coast Guard. Built in 1875, Thomas Point Shoal Lighthouse is the last intact lighthouse of its kind on the Bay left in its original location. 301-440-8763 
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Solomons Island Heritage Tours

Join Solomons Island Heritage Tours to discover stories of the largest naval engagement in the history of Maryland that took place during the War of 1812. Leaving the Solomons Island Harbor, your cruise will make a 5 mile trip up the Patuxent River to St. Leonard Creek while “recreating” the battle that occurred here when British Commodore Joshua Barney sailed his flotilla up the Patuxent to attack the new American nation. Reflect on how the area has changed since that time on this scenic journey.  301-672-3509. 
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Echo Hill Outdoor School

Echo Hill Outdoor School provides educational experiences for school groups and summer camp opportunities for youth. Students explore folklore and traditions on the water, discovering that history is about real people, ideas, events, and cultures. Students sail on the Skipjack Elsworth, learning basic sailing and navigational skills. Echo Hill occasionally offers tours or programs aboard sailing vessels for adults. 410-348-5880 
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Echo Hill Outdoor School

Maryland's Great Chesapeake Bay Loop Getaway Guide

Find a treasure trove of ways to explore the Bay, and meet our skilled Chesapeake Bay Storytellers.

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