Things to Do Boating

Annapolis Sailing Cruises: Schooner Woodwind

80 Compromise St., Annapolis, MD 21401
(410) 263-7837
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About Annapolis Sailing Cruises: Schooner Woodwind

Sail the Chesapeake on a 74-foot schooner! Raise the sails, steer the boat, or sit back and relax on a two-hour sail. Special, longer event cruises, too. The Woodwind and Woodwind II offer a real Chesapeake sailing experience for public sails and private events. Buy a ticket, or privately rent the entire boat. Fun, team match racing, corporate outings, crab feasts and catered sunset sails. Sailing is a great way to celebrate birthdays, reunions, and a wedding weekend. Departs from the downtown, Annapolis Waterfront Hotel.

Attraction

General

- Family Friendly

- Maximum Group:

96.00

- Minimum Group:

- Reservation Recommended

Onsite

- Alcohol Served

- Box Lunch Available

- Group Tours Available

- Private Tours Available

- Restrooms Onsite


General

Pricing

- Payment Methods Accepted

American Express, Discover, Master Card, Visa,

October Lighthouse Cruise
Annapolis City Marina

October Lighthouse Cruise

October 14, 2018

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 10:30 am, return at 2:30 pm, includes bagged lunch, soft drinks, and snacks, $96 per adult, $58 per child with child’s lunch. Maximum of 35 guests. Scroll down to see menu choices. Cruise Departs from Annapolis City Marina (Boat Shows are in town)

Schooner Race Watch
Annapolis City Marina

Schooner Race Watch

October 11, 2018

The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! They will be racing to the Norfolk area, we will cheer them on till it’s time to go in. We will be under sail with the schooners (and yes you’ll be sailing on one too). We will not cross the starting line, but we will be sailing around them all as they come down from Baltimore. Includes Lunch. Tickets* are $89 per adult and $50 per child and include bagged lunch bottled water, soft drinks, and snacks. Beer and wine are available for purchase. *$10 of each ticket purchased will be donated to the Great Chesapeake Bay Schooner Race, a non-profit organization that races to save the Bay in conjunction with the Chesapeake Bay Foundation. Due to US Power Boat Show this event departs from Annapolis City Marina

Brews In The Breeze Lunch Cruise
Annapolis Sailing Cruises: Schooner Woodwind

Brews In The Breeze Lunch Cruise

October 7, 2018

Sail on a lunchtime cruise of beer tasting on the Chesapeake Bay. After we raise all our sails, we will start the tasting with the lightest of the four beers. Lunch will consist of all your Chesapeake favorites, including crab cakes, served buffet style while sailing on the beautiful Bay! Tickets are $86 per adult and include lunch, four 6 oz. beers, and unlimited soda and water. Additional beer will be available for purchase.  Departs  Annapolis at 11:00 am and returns at 1:30 pm. Maximum 35 guests.

September ~ Wine in the Wind
Annapolis Sailing Cruises: Schooner Woodwind

September ~ Wine in the Wind

September 23, 2018

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. You will be able to raise the sails, steer the boat or just sit back and relax with your wine and food. Depart Annapolis at 4:00 pm, return at 6:00 pm. Maximum 40 Guests

August ~ Wine in the Wind
Annapolis Sailing Cruises: Schooner Woodwind

August ~ Wine in the Wind

August 12, 2018

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. You will be able to raise the sails, steer the boat or just sit back and relax with your wine and food. Depart Annapolis at 4:00 pm, return at 6:00 pm. Maximum 40 Guests

Local Everything Dinner Cruise
Annapolis Sailing Cruises: Schooner Woodwind

Local Everything Dinner Cruise

July 29, 2018

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. Menu to be determined Tickets are $111 per adult and include three-course dinner, 3 drink vouchers, and unlimited soda & water. Maximum 35 guests.

July ~ Wine in the Wind
Annapolis Sailing Cruises: Schooner Woodwind

July ~ Wine in the Wind

July 15, 2018

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. You will be able to raise the sails, steer the boat or just sit back and relax with your wine and food. Depart Annapolis at 4:00 pm, return at 6:00 pm. Maximum 40 Guests

4th of July Fireworks Cruise
Annapolis Sailing Cruises: Schooner Woodwind

4th of July Fireworks Cruise

July 4, 2018

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 $91 per adult, $64 per child and include bottled water, soft drinks, and a wide selection of desserts including fresh fruit. Beer and wine will be available for purchase. Maximum 40 guests. 

Father's Day Brunch Sail
Annapolis Sailing Cruises: Schooner Woodwind

Father's Day Brunch Sail

June 17, 2018

Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. The sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, bacon & swiss quiche squares, blackened salmon with cusabi sauce served with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti. $92 per person, $52 per child. Maximum 35 guests.

June ~ Wine in the Wind
Annapolis Sailing Cruises: Schooner Woodwind

June ~ Wine in the Wind

June 10, 2018

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. You will be able to raise the sails, steer the boat or just sit back and relax with your wine and food. Depart Annapolis at 4:00 pm, return at 6:00 pm. Maximum 40 Guests

Blue Angels Show Cruise - SOLD OUT
Annapolis Sailing Cruises: Schooner Woodwind

Blue Angels Show Cruise - SOLD OUT

May 23, 2018

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; $106 per person, $68 per child w/child’s lunch. Maximum 40 guests.  SOLD OUT

Local Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Local Music Sunset Sail

May 17, 2018

Sit back and relax as different local musicians entertain you while sailing on the Chesapeake Bay. The Singer/Songwriter genre will be well represented as they play acoustically aboard the Woodwind.

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Wednesday Night Races

May 16, 2018

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will start on the AYC starting line at 6:45pm, and then race out to a slightly different race course, probably a little longer. During the race, passengers (“guest crew”) will be able to participate in helping to sail the boat and steer the boat, when appropriate of course.

History Monday Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

History Monday Sunset Sail

May 14, 2018

Sunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind. The Woodwinds features a History-slanted sunset sail every Monday night. When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries.  We sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town.  Topics change weekly.

May ~ Wine in the Wind
Annapolis Sailing Cruises: Schooner Woodwind

May ~ Wine in the Wind

May 13, 2018

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. You will be able to raise the sails, steer the boat or just sit back and relax with your wine and food. Depart Annapolis at 4:00 pm, return at 6:00 pm. Maximum 40 Guests

Mother's Day Brunch Sail
Annapolis Sailing Cruises: Schooner Woodwind

Mother's Day Brunch Sail

May 13, 2018

Our Mother’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. The sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, bacon & swiss quiche squares, blackened salmon with cusabi sauce served with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti. $92 per person, $52 per child. Maximum 35 guests.

Local Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Local Music Sunset Sail

May 3, 2018

Sit back and relax as different local musicians entertain you while sailing on the Chesapeake Bay. The Singer/Songwriter genre will be well represented as they play acoustically aboard the Woodwind.

Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Beer Tasting Sunset Sail

May 1, 2018

Sunset Sails & Beer Tasting, aboard a 74-foot, classic wooden schooner, Woodwind. We feel that everyone should be able to enjoy great, craft beer while sailing on the Chesapeake Bay. And on every Tuesday’s sunset sail, we feature 3 beers from a regional micro-brewery. A brewery representative comes aboard and educates in a very casual manner about beer. Sample three, 4 oz samples of this month’s feature brewery while sailing from Annapolis on a 2-hour cruise.  When finished with the sampling, you may purchase your favorite beers for the rest of the sail.

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Wednesday Night Races

April 25, 2018

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will start on the AYC starting line at 6:45pm, and then race out to a slightly different race course, probably a little longer. During the race, passengers (“guest crew”) will be able to participate in helping to sail the boat and steer the boat, when appropriate of course.

Sailor's Delight Cocktail Cruise
Annapolis Sailing Cruises: Schooner Woodwind

Sailor's Delight Cocktail Cruise

April 21, 2018

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. The cruise includes appetizers, two drink vouchers, and a sunset sail.  Depart Annapolis at 5:30 pm, return at 7:30 pm.  Tickets are $76 per adult with a maximum of 35 guests. Cocktail Cruise Menu: Assortment of Savory Dips served with Crostini and Crackers Pimento Cheese Olivada (Black Olive Spread) Hummus Sun Dried Tomato Dip Grilled Vegetable Crostini Chicken and Sundried Tomato Crostini Grilled Asian Shrimp & Pineapple skewers with Snow Peas Great Assortment of Craft Beers from the Local Area, Wine and a couple of fun cocktails to choose from.

Sailor's Delight Cocktail Cruise
Annapolis Sailing Cruises: Schooner Woodwind

Sailor's Delight Cocktail Cruise

April 20, 2018

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. The cruise includes appetizers, two drink vouchers, and a sunset sail.  Depart Annapolis at 5:30 pm, return at 7:30 pm.  Tickets are $76 per adult with a maximum of 35 guests. Cocktail Cruise Menu: Assortment of Savory Dips served with Crostini and Crackers Pimento Cheese Olivada (Black Olive Spread) Hummus Sun Dried Tomato Dip Grilled Vegetable Crostini Chicken and Sundried Tomato Crostini Grilled Asian Shrimp & Pineapple skewers with Snow Peas Great Assortment of Craft Beers from the Local Area, Wine and a couple of fun cocktails to choose from.

First Day of 2018 Sailing Season
Annapolis Sailing Cruises: Schooner Woodwind

First Day of 2018 Sailing Season

April 14, 2018

Sailing season begins today on the Schooner Woodwind. Come enjoy sailing on the Bay. We will have two sails: 12:30 pm - 2:30 pm & 3:00 pm - 5:00 pm