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May 2017

Blue Angels Practice Cruise

$103.00
May 23 @ 11:00 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 11:00 am and return at 3:30 pm. Typically, we sail for a 2.5 hour cruise (while usually the 2 planes fly around and practice) and then we anchor up front in the "spectator zone" for the best view of the rehearsal of the performance, with all the planes, which usually happens around 2:00 pm. Advanced ticket purchase required, includes box lunch, soda, and snacks; $103…

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Blue Angels Performance Cruise

$103.00
May 24 @ 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; $103 per person, $66 per child w/child's lunch. Maximum 40 guests. Gourmet Bagged Lunch includes:…

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Acoustic Brunch Sail with Gareth Asher

May 29 @ 10:30 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

An Intimate, Acoustic Show with Gareth Asher & Nicki Thrailkill aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch on Memorial Day. Band's BIO: In this life, we spend our days in blissful ignorance as to what lies ahead. We work, we play, we dream, we live. In this chain of every days, there is sometimes a beginning, like any other, that is fated to hold within it a moment forever life altering, and…

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June 2017

June Wine in the Wind

$79.00
June 4 @ 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 the Pacific Northwest.  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…

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Father’s Day Brunch

June 18 @ 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: homemade scones, quiche lorraine squares, blackened salmon with cusabi sauce served with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti. $90 per person, $50 per child. Maximum 35 guests. Stay the Night? The Annapolis Waterfront Hotel (where Woodwind docks) has created a fantastic Sunday…

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July 2017

Fireworks Cruise

July 4 @ 6:30 pm - 10:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Celebrate the 4th of July in Annapolis enjoying a sunset sail complete with fireworks from the water

1 boat SOLD OUT - overflow now available  --  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 $89 per adult, $62 per child and include bottled water, soft drinks, and…

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Brunch Sail with Tony Lucca

$107
July 9 @ 10:00 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

Back for a 5th 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 captured America’s hearts in 2012 as the Team Adam finalist on NBC’s hit TV show “The Voice.” Lucca’s duet of “Yesterday” by The Beatles with coach Adam Levine (Maroon 5) landed Top 5 on iTunes Overall and Pop Singles sales charts.…

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Everything Local Dinner Cruise

July 30 @ 6:30 pm - 9:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United 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, Palate Pleasers, 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 $109 per adult and include three course dinner, 3 drink vouchers, and unlimited…

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August 2017

Brunch Sail with Ernie Halter

August 6 @ 10:00 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

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. In 2011 Justin Bieber covered…

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Dodon Vineyards Wine Dinner

August 20 @ 6:30 pm - 9:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

Established in 2007, the vineyards at Dodon are fortuitously situated on rolling hills just south of Davidsonville, Maryland. When they began their first experiments with 150 vines, the goal was clear: to practice sustainable agriculture and produce exceptional wines. As ninth generation custodians of this historic farmland, and as demanding winemakers, they are committed to using viticultural practices and winemaking techniques that permit full expression of the unique deep sandy loam ‘Dodon Series Soils’ that lend their wines distinctive aromatics and subtle…

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