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    July 2020

    July Wine in the Wind Sail

    July 12 @ 4:00 pm - 6:00 pm
    Annapolis Waterfront Hotel, 80 Compromise Street
    Annapolis,MD21401United States
    Wine in the Wind Cheese and Bread Display

    Please call office for information on tickets and updated pricing 410-263-7837 Join us for a two hour sail around the Chesapeake Bay 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 with each wine is a delicious, perfectly paired bite (we call them magnificent morsels) to go with…

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    Local Everything Dinner Cruise

    July 26 @ 6:30 pm - 9:00 pm
    Annapolis Waterfront Hotel, 80 Compromise Street
    Annapolis,MD21401United States
    Local Everything Dinner Cruise aboard Schooner Woodwind

    Please call office for information on tickets and updated pricing 410-263-7837 Enjoy our “Local Everything” themed dinner and drinks while under full sail on the Chesapeake Bay. This cruise will focus on food that you can grow yourself or purchase locally.  Our caterer, Light House Bistro, prides themselves on getting produce, meats, and many other ingredients from the local area.  For our wonderful selection of alcoholic beverages, we choose independent breweries and distilleries within a 70-mile radius.…

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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

    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 with each wine is a delicious, perfectly paired bite (we call them magnificent morsels) to go with each wine.   Includes a take-home, boat friendly, wine glass by Go…

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    Brunch Sail with Michael Tolcher

    August 30 @ 11:30 am - 2:30 pm
    Annapolis Waterfront Hotel, 80 Compromise Street
    Annapolis,MD21401United States
    Michael Tolcher crouching in front of a wall

    An Intimate, All Ages Acoustic Show with MICHAEL TOLCHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Michael Tolcher 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. Michael Tolcher is an American singer/songwriter that blends southern, soul, improv, sincerity and comedy all together to form his art.…

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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

    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

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

    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. What’s a typical day in…

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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, $100 per adult, $62 per child with child’s lunch. Maximum of 35 guests. Scroll down to see menu choices. Adult Bagged Lunch includes: Dill potato salad, charred corn…

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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 $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…

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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

    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 soul-infused pop to tear-jerker folk balladry. His music has been featured in shows like “Parenthood,” “Friday Night Lights,” “Felicity,” and “Brothers and Sisters.” He was a frequent…

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    Schooner Race Watch Cruise

    October 15 @ 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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