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June 2019

Father’s Day Brunch

$94.00
June 16 @ 10:00 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Fathers Day Sailing Cruises Annapolis MD

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 guests.         Father's Day Brunch Menu: Bacon, Ham, Caramelized Onion and Swiss Cheese Quiche Square Spinach and Tomato Quiche Square Mini Muffins and Gluten Free Pumpkin Bread Fruit with Honey Ricotta Grilled Shrimp with hominy,…

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Father’s Day Brews in the Breeze Lunch Cruise

$88.00
June 16 @ 1:30 pm - 3:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United 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.  Children under 12 are $51 per person including lunch and soft drinks.  Departs  Annapolis at 1:30pm and returns at 3:30 pm. Maximum 35 guests. Father's Day Lunch  Cruise Menu: Herb Grilled Chicken with tomato coulis…

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Take Dad Sailing on Father’s Day

June 16
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States

Take Dad sailing this year on Father's Day. We have opened our 2 hour public sails up early so you can book yourself and your "Dad" on a sail on Father's Day Now! Sailing times: 11:00-1:00 1:30-3:30 4:00-6:00 6:30-8:30 Ticket Pricing: $48/Adult $46/Senior $31/Child/Infant  

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July 2019

Fireworks Cruise

$93.00
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 "Ship's Company". We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the show. Tickets are $93 per adult, $66 per child and include bottled water, soft drinks, and a wide selection of desserts. Beer and wine will…

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Brunch Sail with Jesse Ruben

July 7 @ 10:00 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States

An Intimate, Acoustic Show with JESSE RUBEN aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch and a relaxing sail. Jesse Ruben is a Philly born singer/songwriter currently living in Brooklyn. His songs have been heard on TV shows such as One Tree Hill, Degrassi, Switched at Birth, and Teen Mom. His most recent single, "This Is Why I Need You", reached the top 10 in 12 different countries, and has been…

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July Wine in the Wind

July 14 @ 4:00 pm - 6:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Wine in the Wind

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from France.  Celebrate Bastille Day as the representative from the winery introduces 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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Everything Local Dinner Cruise

July 28 @ 6:30 pm - 9:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Local Everything Dinner Cruise aboard Schooner Woodwind

Enjoy our “Everything Local” 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 2019

August Wine in the Wind

August 11 @ 4:00 pm - 6:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Wine in the Wind

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from South America.  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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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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October 2019

Acoustic Evening Sail with Tyrone Wells

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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