Chesapeake Bay Storytellers -Sightseeing Cruises
There are so many ways to absorb the sights, sounds and sensations of the authentic Chesapeake as you glide across her waters. Relax on a sunset cruise framed by an iconic screw-pile style lighthouse. Tour a bustling harbor and see historic landmarks from a maritime viewpoint like no other. Watch a skilled Osprey or graceful Great Blue Heron fish for its dinner. Whether aboard an historic paddle boat, ferry boat, skipjack, sailboat, kayak or yacht, there’s a sightseeing excursion just for you.
Choptank Riverboat Company
The Choptank Riverboat Company sails on reproduction authentic turn-of-the-century true stern paddle wheelers that operate out of Hurlock on Maryland’s Eastern Shore. You can choose from lunch cruises, crab feasts, sight-seeing cruises, dinner cruises and special themed cruises. Cruises slip through the scenic Choptank River, viewing farms, homes, waterfowl and more along the way. You may catch sight of local watermen working the river as you explore the landmarks and historic sites on your tour. Choptank Riverboats are available for both public and private cruises. 410-943-4689
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Watermark
Watermark offers a variety of themed sightseeing cruises that explore iconic landmarks around the mid-Chesapeake near Annapolis, Baltimore and St. Michaels. Marvel at the twin spans of the Chesapeake Bay Bridge that connects the eastern and western shores of Maryland. See the U.S. Naval Academy from the water, or the lights of the Baltimore Inner Harbor. The Scenic Severn River Cruise, the Chesapeake Bay Bridge Cruise and Sunset Cruises are popular tours. Or try the Spa Creek Cruise, for something more intimate that explores the historic residential areas of Eastport and Old Annapolis. There’s so much to see, you’ll want to keep coming back! 410-268-7601
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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. Sunset cruises are also available. Cruise into the golden hues of sunset for an unforgettable evening. 443-566-3386
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Chesapeake Bay Maritime Museum
Guests of all ages will delight in learning local history while experiencing breathtaking views of the Miles River aboard PATRIOT, a 65-foot, 149-passenger vessel built to resemble a traditional Chesapeake Bay steamboat. Catch a glimpse of 200-year-old historic mansions and diverse wildlife on a 70-minute narrated historical cruise, or let the music sweep you away on a Happy Hour Cruise. 410-745-3100
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Annapolis Sailing Cruises: Schooner Woodwind
Sunset is a favorite time for a sail on the Woodwinds. The sunset over the Annapolis skyline is breathtaking. The golden glow reflecting off the sails as the sun descends near the horizon is an unforgettable sight. During the day, the Woodwind sails up to four times. Each trip is unique. You may see Kent Island, the U.S. Naval Academy, the Severn River, the Chesapeake Bay Bridge and more. The Woodwinds’ captains and crew will make your trip an enjoyable and memorable experience. Their bar is stocked with beer, wine and bubbly for purchase. 410-263-7837
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Sultana Education Foundation
A two-hour trip on the reproduction 1768 schooner SULTANA is a great way to experience the scenery of the Chester River. Passengers are encouraged to help raise sail, steer using SULTANA’s seven-foot tiller, and explore the authentically reproduced crew’s quarters below-deck. The crew may even fire one of SULTANA’s swivel guns! The SULTANA Downrigging Festival in late October is a great time to sightsee from the water in Chestertown aboard the SULTANA or other tall ships. 410-778-5954
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Annapolis Maritime Museum/Skipjack Wilma Lee
Cruise on the skipjack Wilma Lee for a memorable two-hour voyage, soaking in the golden hour on the Chesapeake Bay for a relaxing journey. Is adrenaline more your style? Come to a watch party for Annapolis’s weekly Wednesday Night Races, where you’ll have a front-row view of sailors competing in this quintessential Chesapeake Bay event! Enjoy onboard color commentary about the racing as well as complimentary beverages. 410-295-0104
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Experience Smith Island
Enjoy a peaceful 90-minute cruise aboard a traditional Chesapeake Bay deadrise workboat as the sun dips below the horizon. Departing from Somers Cove Marine in Crisfield, this scenic evening tour offers stunning views, a relaxing atmosphere, and a one-of-a-kind way to experience the Chesapeake Bay. Another option is a 25-minute scenic cruise along the Crisfield waterfront. This tour features narration by a former waterman with deep roots in the region. Guests will hear stories of Crisfield’s working past, its seafood heritage, and its enduring connection to the nearby island communities of Smith Island and Tangier Island. 410-657-2705
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Island Chill Yacht Charters
Sunset (or Sunrise!) Cruises, Full Moon Rising charters, Night Owl Parties, Half-Day Sails, Full-Day Sails and Custom Cruises are all possibilities with Island Chill Yacht Charters. Choose from a sailboat or two powerboats to design your own trip and experience the beauty of the Chesapeake and its rivers. Cruise the gorgeous South River, Rhode River or anchor in Harness Creek to chill and swim. Longer cruises can explore the shoreline of Quiet Waters Park, or see the Thomas Point Shoal Lighthouse and Chesapeake Bay Bridge. You may spot dolphins or ocean-going ships along the way! 410-212-4476
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Shardana Sailing Charters
Charter the Shardana for a half day, full day or sunset cruise to explore the Chesapeake Bay from Rock Hall. Trips can be as laid-back or adventurous as you wish. Swim, visit a historic site, anchor out to star gaze or enjoy dinner ashore at a restaurant. Shardana is a 43-foot semi-custom built sailboat that can accommodate up to six passengers. Overnight, weekend and multi-day sailing trips are also available. Your captain can help plan a trip personalized to your needs. Bring your family or friends for an experience to remember! 215-238-1635
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Calvert Marine Museum
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. Relax and enjoy a leisurely one-hour sightseeing cruise on the Patuxent River. See Solomons Island and the Chesapeake Biological Laboratory, pass underneath the Governor Thomas Johnson Bridge, and turn back at Pt. Patience and the Naval Recreation Center. Hear about the adventurous history of this working vessel that was later converted into a powered buy-boat for continued oyster industry work. 410-326-2042
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Tuna the Tide
Design your own sightseeing cruise with Tuna the Tide and Captain Mark Galasso, a former oceanographer with the National Marine Fisheries Service. Cruise on a charter fishing boat from Kent Island in the mid-Chesapeake to some wonderful destinations, such as the Wye River, with its many historical sites, or explore St. Michaels and its waterfront restaurants. Cruise up the Chester River to the colonial port of Chestertown, try out a crab house in Rock Hall, or set out for the Eastern Bay to see a remarkable sunset across the water. 410-310-1200
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Fish the Bay Charters
Fish the Bay Charters’ Chesapeake Bay Sunset Cruise is a great way to unwind or kick-off the weekend! Sit-N-Sip (BYOB) aboard a vintage Chesapeake Bay charter boat and see sights like the Point No Point Lighthouse and wildlife as you soak in the serene beauty of the southern Chesapeake Bay. 301-904-0935
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VanAlstine Seafood & Farm
John VanAlstine is a commercial fisherman, oysterman, crabber and farmer who can take you fishing, crabbing or sight-seeing. He owns 35-acres of oyster beds on the Rhode and West rivers near Dunkirk. Explore these storied waters and hear tales from an experienced waterman. Live high quality crabs, hard and soft, seasonal oysters and fish are also available for purchase. 443-223-3433
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Solomons Island Heritage Tours
Cruise the Patuxent River for a relaxing sunset (or sunrise!) tour. Some highlights along the way include Mill Creek, St. John’s Creek, Back Creek, The Narrows, Drum Point, Governor Thomas Johnson Bridge, the Patuxent River Naval Air Station, Point Patience, and the Solomons Naval Recreation base. Solomons Island Heritage Tours can customize the trip if you have another destination in mind. 301-672-3509
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Megalodon Adventures
Join Captain Dan for a custom cruise to enjoy the sunset on the lower Chesapeake Bay from Port Republic. Or take a kayak trip and paddle a few miles inland on Parker’s Creek to enjoy one of the most pristine and picturesque watersheds remaining on the Western Shore of the Chesapeake. 410-474-0396
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Deal Island Skipjack Sailing Tours Aboard Skipjack Kathryn
Sail on the Skipjack Kathryn and discover the heritage of the people who built, owned, captained or worked on majestic skipjack vessels - the oldest working sailing vessel - dredging oysters under the power of the wind. While you soak in the beauty of the lower Eastern Shore, you’ll get a flavor of the cultural history of the waterman’s way of life on Deal Island and upper Tangier Sound. 410-251-6980
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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 explore the Chesapeake’s waters and sites first-hand. 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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Echo Hill Outdoor School
Echo Hill Outdoor School occasionally offers sailing and sightseeing excursions for adults on one of their vessels, such as the Skipjack Elsworth. Explore folklore and traditions on the water, while taking in the sights. Sultana Downrigging Weekend in Chestertown in late October/early November is a great event where you can join them on a sail on the Chester River. 410-348-5880
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Bunky’s Charters
Bring your family and friends for a two hour cruise on a charter fishing boat out of Solomons on the Patuxent River. Snacks, water and sodas are available on board. 410-326-3241
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Maryland's Great Chesapeake Bay Loop Getaway Guide
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.
