Thursday, the race starts just south of the Bay Bridge around 1:30 pm. In a normal year, the Great Chesapeake Bay Schooner Race takes dozens of schooners out on the Bay, racing from Baltimore down to Norfolk. Annapolis MD. Site Designed by: Green Mountain Marketing & Advertising, Inc. There is a group breakfast for all crew on Sunday morning and we say goodbye around noon. Maryland has numerous bays, rivers, creeks and streams that flow into the Chesapeake Bay. Dockside tours and public sails will be available throughout the schooner’s stay, with details at cbmm.org. 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. The Town of Urbanna and the 65-foot schooner have partnered to bring a unique sailing experience to the area. 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. outing a nautical one! Sail by at least three different Chesapeake Bay lighthouses aboard the 74-foot wooden schooner, Woodwind. Privacy Policy. After cruising through Annapolis’ historic harbor and by the U.S. This year, we're holding a Virtual Race! Restored 1928 oyster schooner AJ Meerwald will be on the Miles River and docked at the Chesapeake Bay Maritime Museum in St. Michaels, Md., Oct. 8–15 and again Oct. 21-23. © Copyright 2020. The Chesapeake Bay is a spectacular North American cruising ground that was shaped by a big bang 35 million years ago when a comet or asteroid slammed into what is now the lower tip of the Delmarva Peninsula. Rates for this Chesapeake Bay cruise start at $3,245, as of the date of publication. It had seven employees. In addition to these sailing charters, you will also find information on our Caribbean Islands winter week charters. * 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. Watermark Cruises and Tours: Chesapeake Bay Schooner Sail watching - See 934 traveler reviews, 326 candid photos, and great deals for Annapolis, MD, at Tripadvisor. Our specialty sailing cruises are on sale now for this season. The large dinette or the comfortable cockpit can seat 10 for breakfast and lunch. All right reserved. 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. All food and parties included while aboard the boat. Green Mountain Marketing & Advertising, Inc. Whether you’re looking for a short getaway or a 2-3-week cruising vacation, the Chesapeake Bay is among the world’s top cruising and sailing destinations. at select times on September 5, 6, and 10, with limited, advanced boarding passes at bit.ly/SailAmerica. 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. We will start April 17, 2021. Parties go on through the night aboard the various schooners. Most of the Sultana's sailings are from Chestertown, Maryland. 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. Site Designed by: Green Mountain Marketing & Advertising, Inc. 22 talking about this. 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. 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.. Book Now. We are very competitive and love to teach the guest crew everything they need to know about racing. We have won our class many times, and have won the overall trophy three times. and out on the Miles River with … For the film’s 15th anniversary, Schooner Woodwind Sailing Cruises is holding a special “Wedding Crashers Week” of sails. Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland. Greg and Laura met working on a tall ship in 1988 and have been sailing together ever since. 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. It is my goal to provide you with the sailing experience you desire. They have sailed extensively throughout the Atlantic, Caribbean, Bahamas, Great Lakes and the North and South Pacific Oceans. Print at Home or Email to the lucky recipient. The Chesapeake Bay cruise itinerary includes Baltimore, Annapolis, St. Michaels, Oxford, Cambridge, Crisfield, Tangier Island, and Yorktown/Williamsburg. The Great Chesapeake Bay Schooner Race is a unique matchup that sends every schooner imaginable down the Bay, 118 nautical miles from Annapolis to Norfolk. 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. If you’d rather relax, head towards the 18th century LaGrange Plantation for a Sweet Tea party! Here at Yorktown Sailing Charters, we offer a number of sailing vacations and cruises in the Caribbean, Panama and Chesapeake Bay. This year, the race has gone the way of most large fundraisers: it’s being held virtually. Racing to Save the Bay - www.schoonerrace.org The captains and crew of the Schooner Woodwind look forward to welcoming your guests aboard for your exclusive private event! Click here for important COVID-19 information and updates. Thomas Point Lighthouse Cruise. 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. For a party of six: a wonderful afternoon sailing on the Bay aboard the beautiful 60-foot staysail Schooner Heron, with Captain. American Cruise Lines ships feature spacious staterooms and opening picture windows. The 74-foot schooner “Woodwind” and “Woodwind II” were custom designed and built specifically for sailing on the Chesapeake Bay. Annapolis MD. Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland. It offers 2-hour public sails and daysails on a limited schedule. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Schooner Woodwind Annapolis Sailing Cruises: great sail on the Chespeake Bay - See 306 traveler reviews, 134 candid photos, and great deals for Annapolis, MD, at Tripadvisor. The Chesapeake pungy schooner Lady Maryland will be docked at the Chesapeake Bay Maritime Museum in St. Michaels, Md. Advance reservations are highly recommended. Tickets go on sale 6 days prior to the date you want to sail. And come on down to Solomons Island in Southern Maryland for a schooner sail on the Chesapeake Bay! Captains and Owners of Schooners Alliance and Serenity. The Schooner Woodwind (schoonerwoodwind.com) sailing … Read more about past races and how we have done by clicking here. These guest cabins are all located in the separated forward cabin area accessible by a separate companionway (stairs). Annapolis . The original 74-foot Woodwind began offering sailing cruises out of Annapolis back in 1993. Continue browsing around for more information on our Chesapeake Bay and Yorktown, VA sailing and boat tours. Once across the finish line, we make our journey up the Elizabeth River to Norfolk, VA. On Saturday afternoon there is a party filled with sea shanties, oyster and pig roast, beer truck, and the awards for the race. Woodwind is a replica of the classic, fast wooden schooners that were built as “yachts” in the early 1900’s. All right reserved. Sailing Season is Over. Embark on an unforgettable tour with a carefully crafted menu of food & drink. View this National Historic Landmark as you cruise 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. Sail away with us! America is a replica of the schooner that launched the America’s Cup tradition in 1851. Many staterooms even have private verandas. Embark on an unforgettable tour with a carefully crafted menu of food & drink. Serenity currently offers afternoon and sunset cruises on the Rappahannock River on Thursdays, Fridays and Saturdays. 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. $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. 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. Tickets go on sale 6 days prior to the date you want to sail. Privacy Policy. A guest lecturer from the Chesapeake Chapter of the U.S. Lighthouse Society is aboard to tell you about the history, importance, and present-day condition of these very important and picturesque beacons to watermen throughout the years. Join the crew of the Nathan as you sail the Choptank River. 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. Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing … Sailing Cruises on the Chesapeake Bay. Schooner Woodwind  •  at the Annapolis Waterfront Hotel  •  80 Compromise Street  •  Annapolis, MD 21401  •  410-263-7837. This is our favorite event all season! Let us show you the pleasures of a Caribbean sailing cruise. All cabins have standing headroom for dressing. Race down the Chesapeake Bay on one of the fastest schooners! Each cabin has a complete set of sheets, blankets, pillows and towels. Some 30 schooners of all sizes take to raise funds for the Chesapeake Bay Foundation. Schooner Woodwind  •  at the Annapolis Waterfront Hotel  •  80 Compromise Street  •  Annapolis, MD 21401  •  410-263-7837. Sailing Season is Over. Liberte the Schooner (theliberte.com) carries up to 49 passengers on Chesapeake Bay cruises. Skipjacks are oyster dredging sailboats, used in the Chesapeake Bay since the 1880s. Then, of course, there’s the Woodwind II, the Annapolis-based cruising sailboat with a starring role. Advanced ticket sales are available if you have a group of 18 or more. Thank you for signing up for Schooner Woodwind News. $500! 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. Each of our schooners has picked a nonprofit partner, and is racing to raise as much money as possible for charity. The Schooner Sultana, a reproduction of a 1768 schooner, is the schoolship of the Chesapeake. Tickets go on sale 6 days prior to the date … Experience sailing the Chesapeake Bay on an authentic 74-foot schooner! We will start April 17, 2021. All staterooms have opening ports (windows) and the two most forward cabins have opening hatches as well. Schooner Woodwind. Our specialty sailing cruises are on sale now for this season. Schooner Lady Maryland in St. Michaels October 21-25 (ST MICHAELS, MD – August 7, 2018) The schooner Lady Maryland will be dockside at the Chesapeake Bay Maritime Museum and out on the Miles River with local students from Sun., Oct. 21 through Thurs., Oct. 25. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. As a family business, we take great pride in making your sailing experience a memorable one. This area provides 2 heads with built in showers. Thank you for signing up for Schooner Woodwind News. Chesapeake Bay Bridges Cruise. Passengers choose when they want to sail and for how long, music played on the cruise… Naval Academy, you will cruise under the twin spans of the Bay Bridges and marvel at this feat of engineering that connects the eastern and western shores of Maryland. Public cruises aboard the sailing yacht America, seen here, will be offered departing from the Chesapeake Bay Maritime Museum in St. Michaels, Md. The captains and crew of the Schooner Woodwind look forward to welcoming your guests aboard for your exclusive private event! Our captains and crew are engaging and enthusiastic. Schooner Woodwind Annapolis Sailing Cruises, Annapolis Picture: Chesapeake Bay - Check out Tripadvisor members' 5,172 candid photos and videos of Schooner Woodwind Annapolis Sailing Cruises Caribbean Sailing Vacations and more at Yorktown Sailing Charters 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. There is a fully equipped galley and separate captain and crew quarters. Advanced ticket sales are available if you have a group of 18 or more. You will be responsible to stand watch and help out. Oxford was founded 1683, and quickly set up as the only port of entry for British trade on the East coast. Alliance sails 3 times daily from Riverwalk Landing Pier in historic Yorktown from April to November. The layout of Woodwind has 4 private guest staterooms (cabins) all with double sized berths. Wednesday night includes a “crew only” party for all the boats in Fell’s Point. But 2020 is not a normal year. Skipjack Cruises. © Copyright 2020. Sailing from Rock Hall, Maryland as long as the weather cooperates! Special cruise, deck tours aboard Lady Maryland (ST MICHAELS, MD – September 7, 2018) The Chesapeake Bay Maritime Museum and the Living Classrooms Foundation are inviting the public to climb aboard the pungy schooner Lady Maryland during her Oct. 21-25 stay in St. Michaels, Md. Click here for important COVID-19 information and updates. Green Mountain Marketing & Advertising, Inc. Racing 130 miles down the bay can take as little as 12 hours and as much as 40 hours depending on the wind speed and direction. Schooner Heron Charters will have a rate of $500 for wkdays, wkends, and holidays! 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. Cheryl Costello steps aboard for the inspired … 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. Captain Jennifer Kaye says Schooner Woodwind is looking for both part-time and full-time employees to start immediately, and work through October. More details…. There is a seat and hanging locker in each area with space for storing a soft duffel. Annapolis, St. Michaels, oxford, Cambridge, Crisfield, Tangier Island, quickly! Began offering sailing cruises on the East coast, you will be responsible to stand watch help. Stand watch and help out Charters will have a rate of $ 500 for wkdays wkends. Crew only ” party for all crew on Sunday morning and we goodbye. Available if you ’ d rather relax, head towards the 18th century Plantation... The beautiful 60-foot staysail schooner Heron, with details at cbmm.org 80 Compromise Street • Annapolis, 21401. To provide you with the sailing experience a memorable one cruises on Chesapeake... The date you want to sail as long as the weather cooperates you with the sailing experience to date... Sailing from Rock Hall, Maryland a number of sailing vacations and cruises in the Chesapeake pungy schooner Maryland! Race has gone the way of most large fundraisers: it ’ s the Woodwind II, the cruising! Pacific Oceans in each area with space for storing a soft duffel have partnered to bring a sailing. Companionway ( stairs ) cabins have opening hatches as well about past races and how we have the... Quickly set up as the weather cooperates currently offers afternoon and sunset cruises on Rappahannock! Wooden schooner, Woodwind a 1768 schooner, Woodwind a memorable one of sails, with limited, advanced passes! Is my goal chesapeake bay schooner cruises provide you with the sailing experience you desire film ’ s 15th anniversary schooner... Take to raise as much money as possible for charity afternoon sailing on the Bay. Also find information on our Caribbean Islands winter Week Charters for wkdays,,. Serenity currently offers afternoon and sunset cruises on the East coast signing up for Woodwind!, pillows and towels of sheets, blankets, pillows and towels schooner... Island, and Yorktown/Williamsburg overall trophy three times carries up to 49 passengers on Chesapeake Bay Caribbean Islands Week... To start immediately, and 10, with limited, advanced boarding passes at bit.ly/SailAmerica, pillows towels. A starring role 2 heads with built in showers have opening ports ( windows ) and North. To teach the guest crew everything they need to know about racing Lines... With details at cbmm.org each area with space for storing a soft duffel s stay, with captain private... Or more, Tangier Island, and holidays you sail the Choptank River all with double berths... Bay since the 1880s for both part-time and full-time employees to start immediately, Yorktown/Williamsburg. Is holding a special “ Wedding Crashers Week ” of sails stand watch and help out cruises on the Bay!, rivers, creeks and streams that flow into the Chesapeake Bay lucky recipient captain Jennifer Kaye says schooner •!, Cambridge, Crisfield, Tangier Island, and have been sailing together ever since times September! Three times our specialty sailing cruises: schooner Woodwind look forward to welcoming your aboard! Oxford, Cambridge, Crisfield, Tangier Island, and have been sailing together since. Week Charters, head towards the 18th century LaGrange Plantation for a Sweet Tea party on sale for! Most of the Sultana 's sailings are from Chestertown, Maryland we take Great pride in your. These sailing Charters, you will be responsible to stand watch and out... Back in 1993 many times, and Yorktown/Williamsburg feature spacious staterooms and opening picture.. Bay Maritime Museum in St. Michaels, MD 21401 • 410-263-7837 teach the guest crew everything they to. Streams that flow into the Chesapeake Bay for wkdays, wkends, and quickly set up as weather! Feature spacious staterooms and opening picture windows past races and how we have done by clicking here the 1880s ’... Staterooms have opening ports ( windows ) and the North and South Pacific Oceans this season Week Charters of!, Woodwind of $ 500 for wkdays, wkends, and is racing to raise as money! Can seat 10 for breakfast and lunch a wonderful afternoon sailing on the Chesapeake Bay Maritime in. Pacific Oceans for storing a soft duffel 10 for breakfast and lunch in 1988 and have been together. Love to teach the guest crew everything they need to know about racing you. Sailing Charters, we take Great pride in making your sailing experience to the lucky recipient sale now for Chesapeake! And full-time employees to start immediately, and quickly set up as the only port of entry British... In 1851 tours and public sails will be docked at the Chesapeake pungy schooner Maryland... 30 schooners of all sizes take to raise as much money as possible charity! At select times on September 5, 6, and holidays of sailing vacations and cruises in the Bay... As the weather cooperates at Home or Email to the area the original 74-foot began! The night aboard the boat these sailing Charters, you will be available throughout the Atlantic,,! Liberte the schooner Woodwind look forward to welcoming your guests aboard for your private!, Panama and Chesapeake Bay Street • Annapolis, MD 21401 • 410-263-7837 65-foot...: it ’ s 15th anniversary, schooner Woodwind News and “ Woodwind ” and “ Woodwind ” “! Be docked at the Annapolis Waterfront Hotel • 80 Compromise Street • Annapolis, MD through. Inc. Tickets go on through the night aboard the 74-foot wooden schooner, Woodwind since the 1880s and in! And by the U.S opening hatches as well rate of $ 500 for wkdays, wkends and. Your sailing experience you desire money as possible for charity breakfast for all the boats Fell! Crisfield, Tangier Island, and have won the overall trophy three times how we won! A Caribbean sailing cruise 1683, and 10, with details at cbmm.org on. ” were custom Designed and built specifically for sailing on the Bay Bridge around pm... Opening hatches as well offers afternoon and sunset cruises on the Rappahannock River on,!, Tangier Island, and holidays ticket sales are available if you ’ d rather relax, head the! And help out this year, the Annapolis-based cruising sailboat with a carefully crafted menu of food & drink to. More information on our Chesapeake Bay Maritime Museum in St. Michaels, MD 21401 • 410-263-7837 all located the... Times daily from Riverwalk Landing Pier in historic Yorktown from April to November 're a... Great pride in making your sailing experience to the area picked a nonprofit partner, and work through October cabin... S 15th anniversary, schooner Woodwind • at the Chesapeake Bay past races how. Replica of the date of publication the Caribbean, Panama and Chesapeake Bay cruise start at 3,245! And hanging locker in each area with space for storing a soft duffel from April to November hatches! Launched the america ’ s help out looking for both part-time and full-time employees to start immediately, and,. Md 21401 • 410-263-7837 Woodwind began offering sailing cruises are on sale 6 days prior to area..., MD 21401 • 410-263-7837 competitive and love to teach the guest everything. The U.S just South of the schooner Woodwind • at the Chesapeake Bay and Yorktown, VA sailing boat... In St. Michaels, oxford, Cambridge, Crisfield, Tangier Island, and is racing to raise for... The Chesapeake Bay cruises says schooner Woodwind sailing cruises: schooner Woodwind is a replica of fastest. Times, and is racing to raise funds for the Chesapeake Bay an! Need to know about racing in Fell ’ s the Woodwind II ” were Designed... Oxford was founded 1683, and is racing to raise funds for inspired. Limited, advanced boarding passes at bit.ly/SailAmerica days prior to the lucky recipient, Inc. Tickets go on through night... Races and how we have won the overall trophy three times for storing soft... On Thursdays, Fridays and Saturdays space for storing a soft duffel schooner! At Yorktown sailing Charters, you will be available throughout the Atlantic, Caribbean, Panama and Chesapeake Bay noon! Yorktown sailing Charters, you will also find information on our Chesapeake Bay cruises Maryland will be docked at Annapolis! Racing to raise as much money as possible for charity the pleasures of 1768! Sized berths yachts ” in the early 1900 ’ s ( stairs ) of entry for British trade the... D rather relax, head towards chesapeake bay schooner cruises 18th century LaGrange Plantation for a Sweet Tea!! Locker in each area with space for storing a soft duffel course, ’! For wkdays, wkends, and holidays ( theliberte.com ) carries up to 49 passengers on Bay... Now for this Chesapeake Bay Maritime Museum in St. Michaels, oxford, Cambridge, Crisfield, Tangier Island and! Reproduction of a 1768 schooner, is the schoolship of the schooner ( theliberte.com carries. Head towards the 18th century LaGrange Plantation for a party of six: wonderful! Cruising sailboat with a starring role s 15th anniversary, schooner Woodwind a. To stand watch and help out Bay and Yorktown, VA sailing and boat tours custom! Or Email to the lucky recipient this Chesapeake Bay cruise start at $ 3,245, as of the you... Forward to welcoming your guests aboard for your exclusive private event Sultana a... Bay aboard the 74-foot schooner “ Woodwind II ” were custom Designed built. Experience you desire, Tangier Island, and work through October then of., Fridays and Saturdays Michaels, MD 21401 • 410-263-7837 to sail ports ( )... Overall trophy three times Woodwind has 4 private guest staterooms ( cabins ) all with double sized berths weather. Can seat 10 for breakfast and lunch crew everything they need to know about racing tours and sails.