Chesapeake Bay Storytellers - Sailing Tours
Sailing is a quintessential Chesapeake experience, and there are many places and means to serve up its pleasure. Take a spirited cruise under sail and skate across the Bay with the breeze behind you and the sun kissing your face. Book a charter and anchor in a cove to swim and fish for a relaxing fun-filled day, or enjoy a tour aboard a historic workboat like a skipjack or schooner to explore the heritage of this vital and valuable waterway.
Calvert Marine Museum
Relax and enjoy a leisurely one-hour sightseeing cruise on the Patuxent River aboard the Wm. B. Tennison. You will sail the busy Solomons inner harbor, 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. Special cruises are scheduled for holidays and special occasions, including Pirate Day! Private charters are available too. 410-326-2042
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Island Chill Yacht Charters
Island Chill Yacht Charter’s Chesapeake Bay cruises build connections with family and friends. Beautiful scenery, anchoring, raft-up opportunities, and water sports are some of the ways you can enjoy the water aboard a 43’ sailboat with up to 5 of your closest friends. Half-day, full-day and sunset cruises are some favorites to relax and chill, or create a custom cruise that meets your needs and desires. 410-212-4476
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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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Annapolis Sailing Cruises: Schooner Woodwind
Sail from the heart of the Chesapeake Bay - “America’s Sailing Capital,” Annapolis - on one of two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II. Help raise the sails, steer the boat, or simply sit back and relax as you sail from the historic Annapolis waterfront, past the Naval Academy and cruise into the Chesapeake Bay. Join the Woodwind’s enthusiastic captains and crew for a 2-hour cruise, sunset sail, Wednesday Night Sailboat Race, or a special event. Private charters are also available for your group. 410-263-7837
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Chesapeake Bay Maritime Museum
Experience the unique working traditions of the Chesapeake on a 45-minute cruise aboard one of the historic boats in the Chesapeake Bay Maritime Museum’s floating fleet. Try your hand at different tools and harvest techniques while learning about different fisheries, including oysters and blue crabs. Historic Workboat Experience Cruises are available on most weekends and holiday Mondays from late May through October. 410-745-2916
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Shardana Sailing Charters
Feel the exhilaration and freedom of being under sail on the wide open Chesapeake. Come for a sailing trip, charter or cruise for up to six passengers. Half-day and full-day charters let you pick your own destination and activities. Sunset cruises are a special way to soak up the serenity of the Bay. For a live-aboard sailing experience to explore multiple ports, weekend charters and multi-day cruises are the perfect fit! Check out Shardana’s luxurious and comfortable accommodations. Trips can be as laid-back or adventurous as you want. Design a unique sailing experience that caters to your wants and needs. Skilled Captains will make your trip the best experience for you. The memories will last you a lifetime! 215-238-1635
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Historic Skipjack Wilma Lee
Experience the Chesapeake Bay on the historic skipjack Wilma Lee. The Annapolis Maritime Museum & Park offers a variety of sailing tours to fit most everyone’s tastes. Enjoy a Sunset Cruise to soak up sunshine in the golden hour on the Chesapeake Bay, or join the crew for Wednesday Night Races - a watch party of Annapolis’s weekly sailing races. You’ll have a front-row view of sailors competing in this event! Join a Heritage Cruise to explore Annapolis’s maritime history and Chesapeake Bay ecology. For student and youth groups, sail aboard the Wilma Lee for a hands-on oyster dredging experience and an immersive journey into 19th-century life on the water. Discover the diverse living things thriving in an oyster reef. The Wilma Lee also offers charters and specialty cruises to celebrate special occasions and holidays. 410-295-0104
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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. This experience reveals the cultural history of the waterman’s way of life on Deal Island and upper Tangier Sound. Stop by the Skipjack Heritage Museum to hear more stories of the island’s people from the earliest settlers to the present day. 410-251-6980
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Sultana Education Foundation
Sultana Education Foundation offers public sails on the Chester River aboard the Schooner Sultana, a replica of a 1768 vessel. Passengers are encouraged to help raise sail, steer using Sultana’s seven-foot tiller, and explore the authentically reproduced crew’s quarters below-decks. Summer camps provide three-day trips for youth who sail the Chesapeake and live on a traditionally rigged ship. 410-778-4531
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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. Campers choose from waterfront activities, including sailing on a fleet of 13 vessels. Echo Hill occasionally offers sailing excursions for adults. 410-348-5880
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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.
