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    July 2020

    Wedding Crashers “Sacked” Brunch Sail

    July 19 @ 11:00 am - 1:00 pm
    Annapolis Waterfront Hotel, 80 Compromise Street
    Annapolis,MD21401United States
    Christopher Walken at the helm of Schooner Woodwind II in Wedding Crashers

    Can you believe its been 15 years?  Enjoy a movie themed brunch and 2 adult beverages.  Join Captain Jen as she tells tales about the filming of the movie and share your favorite memories of this cult classic. Food includes crab cakes (of course), meatloaf & egg sliders, scallops wrapped in bacon and other fun themed items. This is one event that you want your name on the list! Cruise departs the Annapolis Waterfront Hotel at 11:00am and returns at 1:00pm.…

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    August 2020

    August Wine in the Wind Sail

    August 9 @ 4:00 pm - 6:00 pm
    Annapolis Waterfront Hotel, 80 Compromise Street
    Annapolis,MD21401United States
    Wine in the Wind Cheese and Bread Display

    Tickets sales are currently on hold for this event. We are evaluating our ability to host this event while maintaining safe physical distancing Join us for a two hour sail around the Chesapeake Bay on a 74-foot classic, schooner while sampling wonderful wines from TBD.  The representative from the winery will introduce you to four special wines while we are under sail. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along…

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    September 2020

    Classic Wooden Boat Regatta

    September 20 @ 11:00 am - 2:30 pm
    Annapolis Waterfront Hotel, 80 Compromise Street
    Annapolis,MD21401United States
    The Wooden Boat Regatta in Annapolis photo by Kate Gahs

    Tickets sales are currently on hold for this event. We are evaluating our ability to host this event while maintaining safe physical distancing 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…

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    Brunch Sail with Ernie Halter

    September 27 @ 11:30 am - 2:30 pm
    Annapolis Waterfront Hotel, 80 Compromise Street
    Annapolis,MD21401United States
    Man smiling into the camera

    Tickets sales are currently on hold for this event. We are evaluating our ability to host this event while maintaining safe physical distancing 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…

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    October 2020

    October Lighthouse Cruise

    October 3 @ 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, $130 per adult. Maximum of 24 guests. Scroll down to see menu choices. Zoned Seating Pricing ~ Limited Capacity (24 person max): 2 person zone ~ $260.00 (for 2 guests)…

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    Cocktail Cruising

    October 3 @ 4:00 pm - 6:00 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 4:00pm, return at 6:00pm.  Tickets are $95 per adult with a maximum of 24 guests. Zoned Seating Pricing ~ Limited Capacity (24 person max): 2 person zone ~ $190.00 (for 2 guests) 4 person zone ~ $380.00 (for 4 guests) 6 person zone ~ $570.00 (for 6 guests) [box…

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    Brunch Sail with Tony Lucca

    October 4 @ 11:30 am - 2:30 pm
    Annapolis City Marina, 410 Severn Ave
    Annapolis,MD21403United States
    Entertainer Tony Lucca

    Tickets sales are currently on hold for this event. We are evaluating our ability to host this event while maintaining safe physical distancing Back for an 8th performance on the Schooner Woodwind! An Intimate, Acoustic Show with TONY LUCCA aboard the 74-foot, classic schooner, Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch and a relaxing sail. Tony Lucca is a Nashville-based singer/songwriter whose catalog of music runs the gamut from…

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