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Blue Angels flying in formation

Blue Angels Practice Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

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 ... Read more

$103.00
Blue Angels flying in formation

Blue Angels Performance Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

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 ... Read more

$103.00
Entertainers Gareth Asher and Nicki Smaller

Acoustic Brunch Sail with Gareth Asher

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

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 ... Read more

$84.00

Wine in the Wind Cheese and Bread Display

June Wine in the Wind

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

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 ... Read more

$79.00
Fathers Day Sailing Cruises Annapolis MD

Father’s Day Brunch

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, 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 ... Read more

$90.00

Celebrate the 4th of July in Annapolis enjoying a sunset sail complete with fireworks from the water

Fireworks Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

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 ... Read more

$89.00
Tony Lucca

Brunch Sail with Tony Lucca

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

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 ... Read more

$107
Heavy Seas vs. Flying Dog Breweries both schooners racing

Maryland’s Brewer’s Cup Race

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Join Heavy Seas and Union Craft Breweries aboard the Seventh Annual “Maryland’s Brewer’s Cup”. Buy a ticket aboard your favorite brewery’s boat!  Union Craft vs. Heavy Seas! Battle of the Baltimore Brews. During the race, passengers (guest crew) will be able to participate in helping to sail the boat, where appropriate, of course. This will be ... Read more

$46.00
Local Everything Dinner Cruise aboard Schooner Woodwind

Everything Local Dinner Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

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 ... Read more

$109.00

Entertainer Ernie Halter

Brunch Sail with Ernie Halter

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

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, ... Read more

$89.00