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May 2020

Mother’s Day Brunch Sail

May 10 @ 11:30 am - 2:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Mothers Day Brunch Sail

Sail Mom 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 Mother’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 11:30 am and returns at 2:30 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food $94 per person, $54 per child. Maximum 35…

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Blue Angels Performance Cruise

$115.00
May 20 @ 11:30 am - 3:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Blue Angels flying in formation

Watch the Blue Angels perform their aero-acrobatics during this special cruise. Depart from Annapolis at 11:30 am and return at 3:30 pm. Typically, we sail for a 2 hour cruise and then we anchor up front in the "spectator zone" for the best view of the performance which usually happens around 2:00 pm. Advanced ticket purchase required, includes bagged lunch, soda, and snacks; $115 per person, $75 per child w/child's lunch. Maximum 40 guests.     Gourmet Bagged…

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Acoustic Brunch Sail with Gareth Asher

May 25 @ 10:30 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Entertainer Gareth Asher

An Intimate, Acoustic Show with Memorial Day favorite, GARETH ASHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Music has the power to transport us to another time and place. Gareth Asher loves to harness that power one song at a time and deliver a piece of it directly to you with every performance. His voice will captivate you immediately, and his messages of hope and healing will send your senses soaring to…

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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

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 take-home, boat friendly, wine glass by Go Vino with the Woodwind's logo on it.…

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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

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 Mary or Mimosa and delicious food $94 per person, $54 per child. Maximum 35…

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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

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.  Heuer blends elements of Motown, Soul, and RnB in his original and cover music.…

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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

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 guitarist who grew up on the banks of the mighty Susquehanna River and sings…

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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

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 take-home, boat friendly, wine glass by Go Vino with the Woodwind's…

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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

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. Tickets are $113 per adult and include three-course dinner, 3 drink vouchers, and unlimited…

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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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