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June 2020

June Wine in the Wind

June 14 @ 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 each wine.   Includes a…

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Father’s Day Brunch Sail

June 21 @ 10:00 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Fathers Day Sailing Cruises Annapolis MD

Please call office for information on tickets and updated pricing 410-263-7837 Sail Dad away for the morning!  Guests can raise the sails, steer the boat, or just sit back and relax with a cold beverage.  We sail past the Naval Academy and into the Chesapeake Bay. Fun for the whole family. Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody…

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July 2020

Fireworks Cruise with Stefan Heuer

July 4 @ 6:30 pm - 10:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Celebrate the 4th of July in Annapolis enjoying a sunset sail complete with fireworks from the water

Please call office for information on tickets and updated pricing 410-263-7837 Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail with live entertainment by Stefan Heuer. We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the show. Stefan Heuer is an award-winning songwriter residing in Annapolis, MD. …

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Fireworks Cruise with Don Shapelle & Don Sennett

July 4 @ 6:30 pm - 10:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Celebrate the 4th of July in Annapolis enjoying a sunset sail complete with fireworks from the water

Please call office for information on tickets and updated pricing 410-263-7837 Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail with live entertainment by Don Shappelle & Don Sennett. We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the show.   Don Shappelle is a singer/songwriter and…

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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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