TOO SOON!!
Come back mid to late February 2025 for updated events
Throughout the sailing season, we offer specialty cruises that make any day exceptional. Embark on an unforgettable tour with a carefully crafted menu of food and drink. From special Mother’s & Father’s Day cruises to lighthouse cruises, seeing the Blue Angels overhead, and many other special occasions. View a sampling of our offerings by month below, and check back in mid to late February when our full event calendar becomes available complete with the ability to purchase tickets.
Sailor’s Delight Cocktail Cruise
Sail away on one of our first sunset sails of the season. Enjoy great appetizers, cocktails, wine & beer as we enjoy the scenery of the Bay. Sail includes appetizers, three drink vouchers and a sunset sail from 5:30-7:30pm.
Appetizers:
- Black Bean Hummus
- Poblano Pimento Cheese
- Served with pita wedges and crostini
- Chicken Skewers with roasted veggies and tomato coulis
- Beef Skewers with roasted veggies and chimichurri sauce
2025 Menus, Themes, Prices & Dates may be different, check back later.
Mother’s Day
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: Bacon & Swiss Quiche Pinwheel, Spinach & Pesto Quiche Pinwheel, Mini Muffins, and Gluten-Free Pumpkin Bread, Fruit with Honey Ricotta, Grilled Shrimp with hominy, lime, cilantro and corn, Sliced Hanger Steak with balsamic grilled onions, chimichurri sauce, Mini Brioche Rolls and Butter.
2025 Menus, Themes, Prices & Dates may be different, check back later.
Lighthouse Cruise
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 11:30am, return at 3:30pm, includes bagged lunch, soft drinks and snacks.
2025 Menus, Themes, Prices & Dates may be different, check back later.
“Wine in the Wind”
Join us for a two hour sail around the Bay sampling wonderful wine. A representative from the wineries will introduce you to these special wines. This will be a relaxing sail including afternoon hors d’oeuvres, soft drinks and four samples of wine.
Wines will include:
- Pedro Xeminez (Chile)
- Chardonnay Organic (Chile)
- Bonardo (Argentina)
- Malbec (Argentina)
Special Pairings
- Argentenian Grilled Bisto Beef w/ chimichurri sauce
- Peruvian Red Lentil and Walnut Salad
- Columbian Chicken, Potato and Golden Raisin Empanada
- Chilean Sea Bass Salad w/ Moho dressing
Buffet
- Ecuadorian Cheese Filled Potato Puff w/ garlic aioli
- Brazilian Chicken Curry Skewer w/ Spicy Mango Chutney
- Argentinian Cured Meats, Cheeses, Olives, and Crusty slices of bread
2025 Menus, Themes, Prices & Dates may be different, check back later.
Father’s Day Brunch Sail
Depart Annapolis for a three-hour Brunch cruise at 10:00 am and return at 1:00 pm. Cruise comes with a free Bloody Mary or Mimosa and delicious food including homemade scones, quiche lorraine squares, baked citrus salmon with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti.
2025 Menus, Themes, Prices & Dates may be different, check back later.
Fireworks Cruise!
Depart from the Annapolis Waterfront Hotel dock at 6:30 pm, for a 2 hour sunset sail with live entertainment, then we anchor close to the
fireworks barge for the 9:15 show. We return to the dock after the show.
2025 Menus, Themes, Prices & Dates may be different, check back in January
“Everything Local” Dinner Cruise
We source everything from the Chesapeake Bay Watershed area. From Maryland Wine to Virginia spirits and all the foods that are found around this area, we create a very special dinner cruise.
Treasure the Chesapeake with this amazing dinner.
2025 Menus, Themes, Prices & Dates may be different, check back in January
Wine in the Wind: France
A three and a half-hour sail around the Bay sampling wonderful French wine. Franck Agostini represents wines from France (as he lives there for half the time, the rest of the time he lives here in Annapolis) and will introduce you to his special wines. This will be a relaxing sail including afternoon hors d’oeuvres, soft drinks, and four samples of wine. Depart Annapolis at 2:00pm, return at 5:00pm.
Wines will include
- White Bordeaux
- Bordeaux Rose
- Bordeaux and Cuvee Tradition (Cotes du Rhone Villages)
Special Pairings
- Semi-Soft Figs filled w/ chevre and chopped pistachios
- Chicken Liver Pate on Crustini
- New Smokey Salmon Flake on Brown Bread Baguette
- Tarragon Chicken and Potato Lyonnaise Skewers
Buffet
- French Cheeses (Triple Creme Brie Roquefort Blue, Boucheron) Crusty Breads, & Strawberry Coulis
- Classic Salad Nicoise with French Green Beans, Hard-Cooked Eggs,
- Albacore Tuna & Pear Tomatoes
- Open Faced Steak au Poivre on Crostini
2025 Menus, Themes, Prices & Dates may be different, check back later.
Dinner Party Cruise
Enjoy regionally themed food and drinks while cruising the Chesapeake Bay under sail! Depart Annapolis at 6:30 pm, return to the dock at 9:00pm. Includes dinner, 3 drink vouchers, soda, and water.
2025 Menus, Themes, Prices & Dates may be different, check back later.
“Wine in the Wind” featuring wines from Down Under (Australia and New Zealand)
Join us for a three-hour sail around the Bay sampling wonderful wine. A representative from the wineries will introduce you to these special wines. This will be a relaxing sail including afternoon hors d’oeuvres, soft drinks, and four samples of wine. Depart Annapolis at 2:00pm, return at 5:00pm.
Wines will include:
- Vermentino (Australia)
- Sauvignon Blanc (New Zealand)
- Pinot Noir (New Zealand)
- Shiraz/Viogner (Australia)
Special Pairings
- Ground Lamb and Spearmint Meatball
- BBQ Shrimp with mango lime aioli
- Grilled Baby Bella Mushroom and Thin Asparagus Salad
- Chilled Cucumber Soup Shot
Buffet
- Smoked Trout and Apple on Endive w/ crème friache
- Macadamia Nut Pesto Rubbed Roasted Chicken Breast
- New Zealand Cheeses (Aged Airedale, Windsor Blue, and Livingstone Gold)
with Flatbreads and baguettes
2025 Menus, Themes, Prices & Dates may be different, check back later.
“Wine in the Wind” featuring Europe
Three-hour sail around the Bay sampling wonderful wine. A representative from the wineries will introduce you to these special wines. This will be a relaxing sail including afternoon hors d’oeuvres, soft drinks, and four samples of the wine.
Depart Annapolis at 2:00pm, return at 5:00pm.
Wines will include:
- Riesling (Germany)
- Gruner Veltliner (Austria)
- Primitivo (Italy)
- Rioja (Spain)
Special Pairings
- Roasted Pork Tenderloin w/ blueberry‐blackberry chutney
- Spicy Shrimp
- Roasted Eggplant, Sweet Peppers and Paprika Goat Cheese Skewers
- Phyllo Wrapped Asparagus Spear
Buffet
- Chicken Marabella
- Spanish Cheeses (9 Month Manchego, San Simon, Cabrales Blue),
- Chorizo Sausage,
Quince paste, Blanched Fresh Vegetables, baguettes - Mediterranean Salmon
Side w/zucchini, plum tomato, shallot relish
2025 Menus, Themes, Prices & Dates may be different, check back later.
United States Sailboat Show
Woodwind sails four times daily from “F2” Dock in the boat show.
We will be running 90 minute cruises
One of the largest in-the-water shows in the country!
You must buy a ticket for Boat Show Admission in order to sail aboard Woodwind. We do sell combo tickets which will save you some money.
Check back in early September 2025
Join the Woodwind Crew for an afternoon of beer tasting along with a delicious lunch. After we raise all sails, we’ll start with the lightest of our four beers. Lunch will be served buffet-style all while sailing on the Chesapeake Bay. Lunch will consist of all your Chesapeake favorites, including crab cakes!
Buffet
- Crab cake sandwiches
- Buttermilk fried chicken sandwiches
- Fresh corn salad
- Maryland marinated tomatoes
- Asst. cookies, brownies & bars
Departs from the Annapolis City Marina in Eastport due to Boat Show.
2025 Menus, Themes, Prices & Dates may be different, check back later.
Annual Chesapeake Bay Schooner Race
Race down the Bay from Annapolis to Portsmouth, Virginia. Over 45 schooners participate each year. Once in a lifetime experience!
Check back later.
Chesapeake Bay Schooner Race Watch
Sail with over 40 other schooners while they start the 130-mile race down the Bay. Depart Annapolis at 12:00 pm, return at 3:00 pm, includes bagged lunch, soft drinks, and snacks.
*$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.
This will sell out very quickly! Departs from the Annapolis City Marina in Eastport due to Boat Show.
2025 Menus, Prices, Times & Dates may be different, check back later.
Champagne Brunch Cruise
Join the Woodwind Crew for the classiest brunch on the Bay. Enjoy a very “bubbly” beverage selection, including sparkling wine, bellinis and other champagne cocktails. Accompanied by delicious food and always entertaining company! Depart Annapolis at 11:30 a.m., return to the dock at 2:30 p.m. Includes brunch, 3 drink vouchers, soda, and water.
Buffet
- Philadelphia Smoked Salmon- Caper Quiche
- Roasted Wild Mushroom and Goat Cheese Quiche
- Cranberry Scones, Apple Cakes, and Almond Croissants
- Dried Cherry Noodle Kugel
- Fresh Asparagus Tips w/ pink peppercorns and pink champagne vinaigrette
- Grilled Chicken Skewer with Pinenut Pesto Drizzle
Departs from the Annapolis City Marina in Eastport due to Boat Show.
2025 Menus, Themes, Prices & Dates may be different, check back later.
