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April 2019

Friday Night Sailor’s Delight Cocktail Cruise

April 26 @ 5:30 pm - 7:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Sunset from Schooner Woodwind II of Schooner Woodwind in lovely Annapolis

Sail away on one of our first sunset sails of the season. Enjoy 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 5:30 pm, return at 7:30 pm.  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…

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Saturday Night Sailor’s Delight Cocktail Cruise

April 27 @ 5:30 pm - 7:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Sunset from Schooner Woodwind II of Schooner Woodwind in lovely Annapolis

Sail away on one of our first sunset sails of the season. Enjoy 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 5:30 pm, return at 7:30 pm.  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…

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April Lighthouse Cruise

April 28 @ 10:30 am - 2:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United 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 10:30am, return at 2:30pm, includes soft drinks and snacks, $100 per adult, $62 per child with child’s lunch. Maximum of 35 guests.         Gourmet Bagged Lunch includes: Adult Bagged Lunches include dill potato salad, charred corn and…

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May 2019

Brunch Sail with Tony Lucca

May 5 @ 11:30 am - 2:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

Back for a 7th performance on the Schooner Woodwind! An Intimate, Acoustic Show with TONY LUCCA aboard the 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 member of…

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Mother’s Day Brunch

May 12 @ 10:00 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

Our Mother’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 (Menu TBD) $94 per person, $54 per child. Maximum 35 guests.

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Blue Angels Performance Cruise

$110.00
May 22 @ 11:30 am - 3:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Blue Angels

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 box lunch, soda, and snacks; $110 per person, $72 per child w/child's lunch. Maximum 40 guests.     Gourmet Bagged…

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Acoustic Brunch Sail with Gareth Asher

May 27 @ 10:30 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

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. Gareth Asher returns for an Acoustic Brunch Sail aboard the Schooner Woodwind promoting his new album, “Defend the Flame.” With lyricism reflecting and celebrating the inner struggles we face through life’s smiles and tears, “Defend the Flame” reminds us to accept and release the emotions that can often feel insurmountable within us. This message is…

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June 2019

June Wine in the Wind

June 9 @ 4:00 pm - 6:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Wine in the Wind

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

June 16 @ 10:00 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United 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 (Menu TBD). $94 per person, $54 per child. Maximum 35 guests.

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Father’s Day Brews in the Breeze Lunch Cruise

June 16 @ 1:30 pm - 3:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

Sail on a lunchtime cruise on the Chesapeake Bay.  Lunch will consist of all your Chesapeake favorites, including crab cakes, 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.  

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