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    September 2019

    Classic Wooden Boat Regatta

    September 22 @ 11:00 am - 2:30 pm
    Annapolis Waterfront Hotel, 80 Compromise Street
    Annapolis,MD21401United States

    Participate in the Classic Wooden Boat Regatta. The Woodwinds' have been invited to participate in the race in the "Spirit of Tradition Class". The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with pursuit style race. Each boat has a rating, and by the rating they will get a start time. The pursuit style race challenges the competitors to sail through the other race boats to win the regatta. This…

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    Brunch Sail with Ernie Halter

    $93.00
    September 29 @ 11:30 am - 2:30 pm
    Annapolis Waterfront Hotel, 80 Compromise Street
    Annapolis,MD21401United States

    An Intimate, All Ages Acoustic Show with ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Ernie Halter will play acoustically while at anchor in a secluded cove. He will play for over an hour and after the performance we will set sail on the 74-foot, classic wooden schooner, Woodwind. Raise the sails, steer the boat, sit back, relax and meet Ernie while sailing the Bay. "Influenced by some of the…

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    October 2019

    Cocktail Cruising

    October 5 @ 4:30 pm - 6:30 pm
    Annapolis City Marina, 410 Severn Ave
    Annapolis,MD21403United States
    Sunset from Schooner Woodwind II of Schooner Woodwind in lovely Annapolis

    Sail away with great appetizers, cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, two drink vouchers and a sunset sail.  Depart Annapolis at 4:30pm, return at 6:30pm.  Tickets are $78 per adult with a maximum of 35 guests. Cocktail Cruise Menu: Black Bean Hummus Poblano Pimento Cheese Served with pita wedges and crostini Chicken Skewers with roasted veggies and tomato coulis Beef Skewers with roasted veggies and chimichuri sauce Great Assortment of…

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    October Lighthouse Cruise

    October 6 @ 11:30 am - 3:30 pm
    Annapolis City Marina, 410 Severn Ave
    Annapolis,MD21403United States
    Schooner Woodwind Chesapeake Bay Lighthouse Sailing Tours in Annapolis, Maryland

    Sail to as many as three different lighthouses on the Chesapeake Bay and learn about their history, importance, and present day condition by a guest lecturer from the Chesapeake Chapter of the U.S. Lighthouse Society. Depart Annapolis at 11:30am, return at 3:30pm, includes bagged lunch, soft drinks and snacks, $100 per adult, $62 per child with child’s lunch. Maximum of 35 guests. Scroll down to see menu choices. Cruise Departs from Annapolis City Marina (Boat Shows are in town)  …

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    Acoustic Evening Sail with Tyrone Wells

    $120.00
    October 6 @ 4:00 pm - 7:00 pm
    Annapolis City Marina, 410 Severn Ave
    Annapolis,MD21403United States

    Schooner Woodwind is pleased to announce the return of TYRONE WELLS to perform aboard the boat for an Intimate, Acoustic Show.  We will cruise to a secluded cove for the performance and then enjoy a sunset sail back to the dock.   This will be Tyrone's fourth time singing and sailing on the Woodwind. It all started in 2007 when Captain Jen fell in love with his music and asked if they wanted to go sailing when they were in town.…

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    Brews in the Breeze Lunch Cruise

    October 13 @ 11:00 am - 1:30 pm
    Annapolis City Marina, 410 Severn Ave
    Annapolis,MD21403United States

    Sail on a lunchtime cruise on the Chesapeake Bay.  Lunch will be served buffet style while sailing on the beautiful Bay! Tickets are $88 per adult and include lunch, two beers, and unlimited soda and water. Additional beer will be available for purchase.  Departs  Annapolis at 11:00 am and returns at 1:30 pm. Maximum 35 guests. Brews in the Breeze Lunch  Cruise Menu: Herb Grilled Chicken with tomato coulis Grilled Shrimp with hominy, lime, cilantro and…

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    Schooner Race Watch Cruise

    October 17 @ 10:30 am - 1:30 pm
    Annapolis Waterfront Hotel, 80 Compromise Street
    Annapolis,MD21401United States
    Great Chesapeake Bay Schooner Race Start

    The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! They will be racing to the Norfolk area, we will cheer them on till it's time to go in.   We will be under sail…

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