All food and parties included while aboard the boat. This is your opportunity to explore the Chesapeake Bay tidewaters for a sightseeing cruise, or for the more adventurous soul, explore the emerald waters of the Caribbean on a 7 day cruise. $1000 plus tax per person Race down the Chesapeake Bay on one of the fastest schooners! Blue Crab Chesapeake Charters is home to Rock Hall's Original Sunset Cruise and will surely top off any visit to Maryland's Eastern Shore. Continue browsing around for more information on our Chesapeake Bay and Yorktown, VA sailing and boat tours. * Specialty Cruises * Schooner Racing * Wednesday Night Racing – Public Sails * Great Chesapeake Bay Schooner Race * Team Building * Past Great Chesapeake Bay Schooner Races * __ Close * Ship’s Store * Schooner Woodwind Merchandise * Schooner Woodwind Gift Certificates * __ Close * __410-263-7837 * Buy Tickets * PUBLIC SAILING. For the film’s 15th anniversary, Schooner Woodwind Sailing Cruises is holding a special “Wedding Crashers Week” of sails. Captain Jennifer Kaye says Schooner Woodwind is looking for both part-time and full-time employees to start immediately, and work through October. Chesapeake Bay Bridges Cruise. After training we participate in a breathtaking Parade of Sail with all the other participating schooners- there were 54 last year with sails up and cannons firing. Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland. This year, the race has gone the way of most large fundraisers: it’s being held virtually. Tickets go on sale 6 days prior to the date … Let us show you the pleasures of a Caribbean sailing cruise. The Chesapeake pungy schooner Lady Maryland will be docked at the Chesapeake Bay Maritime Museum in St. Michaels, Md. The hosts at Yorktown Sailing Charter have over 30 years of sailing experience so you will feel comfortable sailing with them each and every time. Sailing Season is Over. They’re some of the most recognizable sailboats on the Bay, thanks to a little movie called Wedding Crashers.And this year, the Schooner Woodwind family celebrates its 25th birthday.. Maryland has numerous bays, rivers, creeks and streams that flow into the Chesapeake Bay. Thank you for signing up for Schooner Woodwind News. That impact left a crater 55 miles wide that became a convenient depression for rivers to flow into as the glaciers of the last Ice Age melted some 10,000 years ago. We set sail on Wednesday, October 10 to train all “guest” crew how to sail Woodwind on our way from Annapolis to meet up with the other schooners in Baltimore’s Inner Harbor. Our specialty sailing cruises are on sale now for this season. Greg and Laura met working on a tall ship in 1988 and have been sailing together ever since. at select times on September 5, 6, and 10, with limited, advanced boarding passes at bit.ly/SailAmerica. Sailing Season is Over. Groups can purchase tickets more than six days in advance so you can start planning your event now and know you have that date reserved. This year, we're holding a Virtual Race! Schooner Woodwind Annapolis Sailing Cruises: fun sail on the chesapeake bay - See 306 traveler reviews, 134 candid photos, and great deals for Annapolis, MD, at Tripadvisor. Whether you are interested in a sunset on the beautiful Chesapeake Bay or cruising down the Florida coast with dolphins playing in our wake, you're in the right place. The captains and crew of the Schooner Woodwind look forward to welcoming your guests aboard for your exclusive private event! Racing to Save the Bay - www.schoonerrace.org American Cruise Lines ships feature spacious staterooms and opening picture windows. Schooner Woodwind Annapolis Sailing Cruises: The Best Chesapeake Bay Experience - See 306 traveler reviews, 134 candid photos, and great deals for Annapolis, MD, at Tripadvisor. We are very competitive and love to teach the guest crew everything they need to know about racing. Advanced ticket sales are available if you have a group of 18 or more. View this National Historic Landmark as you cruise the Chesapeake Bay … Most of the Sultana's sailings are from Chestertown, Maryland. It had seven employees. outing a nautical one! In addition to these sailing charters, you will also find information on our Caribbean Islands winter week charters. More details…. It offers 2-hour public sails and daysails on a limited schedule. Sailing from Rock Hall, Maryland as long as the weather cooperates! Private cruises aboard the Schooner Woodwind offer your group exclusive use of one or both schooners and can accommodate up to 48 guests aboard each vessel. 22 talking about this. As a family business, we take great pride in making your sailing experience a memorable one. Alliance sails 3 times daily from Riverwalk Landing Pier in historic Yorktown from April to November. and out on the Miles River with … The Schooner Woodwind (schoonerwoodwind.com) sailing … We break into crew watches and sail the boat day and night until we reach the finish line at Thimble Shoal Light at the mouth of the Chesapeake Bay. These guest cabins are all located in the separated forward cabin area accessible by a separate companionway (stairs). Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. If you’re interested in booking a charter for the upcoming spring season, our Charter Specialists will be happy to help you develop a customized itinerary for your trip. You will be responsible to stand watch and help out. Your hosts are full-time residents of Rock Hall and are ready to sail 7 days a week up to fives times daily, from April through October. Dockside tours and public sails will be available throughout the schooner’s stay, with details at cbmm.org. Schooner Woodwind Sailing Cruises, based at Annapolis City Dock, is hiring crew to work aboard its boats, customer service reps to sell tickets, and dock hands to tie up boats at Pusser’s Grille. Sailing Cruises on the Chesapeake Bay. Green Mountain Marketing & Advertising, Inc. Experience sailing the Chesapeake Bay on an authentic 74-foot schooner! Privacy Policy. The Chesapeake Bay cruise itinerary includes Baltimore, Annapolis, St. Michaels, Oxford, Cambridge, Crisfield, Tangier Island, and Yorktown/Williamsburg. The layout of Woodwind has 4 private guest staterooms (cabins) all with double sized berths. 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