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Specialty Cruise Calendar

Throughout the sailing season, our specialty cruises 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 more… view a sampling of our offerings by month below, and check back in early January when our full event calendar becomes available complete with the ability to purchase tickets.

Sailors Delight Sunset Cocktail Cruise Aboard The Schooner Woodwind

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:

  • Sharp Cheddar Cheese Coins Topped with Pecan Halves
  • Mixed Marinated Olives
  • Chicken Sate Skewers w/ Thai Chili and Peanut Sauces
  • Crostini with Sun Dried Tomato Red Pepper Spread and Hummus
  • Gourmet Pizzas (Wilted Spinach and Crumbled Feta, and Caramelized Onion Fresh Thyme and Bacon)

2018 Menus, Themes, Prices & Dates may be different,  check back Jan. 7

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: homemade scones, quiche lorraine squares, baked citrus salmon with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti.  $88 per person, $48 per child. Maximum 35 guests.

2018 Menus, Themes, Prices & Dates may be different,  check back Jan. 7

Bring Mom aboard the Schooner Woodwind for a memorable Mother's Day Brunch Sail

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, $93 per person, $56 per child with child’s lunch. Maximum of 35 guests.

2018 Menus, Themes, Prices & Dates may be different,  check back Jan. 7

“Wine in the Wind” featuring South America

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.

Price: $111 per person. Maximum 35 guests.

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
  • Argentenian Cured Meats, Cheeses, Olives and Crusty Breads

2018 Menus, Themes, Prices & Dates may be different,  check back Jan. 7

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. $88 per person, $48 per child. Maximum 35 guests.

2018 Menus, Themes, Prices & Dates may be different, check back Jan. 7

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. $84 per person, $57 per child, which includes a wide selection of desserts and soft drinks. Beer, and wine are extra.

2018 Menus, Themes, Prices & Dates may be different, check back Jan. 7

“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.

2018 Menus, Themes, Prices & Dates may be different, check back Jan. 7

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. Price: $111 per person. Maximum 35 guests.

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 pistacios
  • 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

2018 Menus, Themes, Prices & Dates may be different, check back Jan. 7

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. Menu will be posted soon. $111 per person, maximum 35 guests.

2018 Menus, Themes, Prices & Dates may be different, check back Jan. 7

“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. Price: $111 per person. Maximum 35 guests.

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 aoili
  • 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

2018 Menus, Themes, Prices & Dates may be different, check back Jan. 7

Craft Brews on the “Heavy Seas” Dinner Cruise

Hugh Sisson, owner of Heavy Seas Brewery (formerly Clipper City) will guide us through a four course dinner pairing great beer, delicious food and fantastic sailing. Depart Annapolis at 6:30 pm, return to the dock at 9:00pm. Includes a glass of beer with each course, soda and water. Please join us for the Crafty Brews on the “Heavy Seas” Dinner Cruise.

Appetizers:

  • Bacon Stuffed Pretzel Sticks and homemade PEG LEG Mustard
  • LOOSE CANNON Spiced Beer Nuts
  • Watermelon Tomato Feta Almond Salad with GOLD ALE vinaigrette

Dinner:

  • Roasted Salmon with Figgin’ in the Riggin’ Fig Sauce made with HANG TEN
  • Smokey Bar-Beer Q Chicken
  • Spicy Thai Noodle Salad with wasabi peas on the side

Dessert:

  • Mocha Stout Cheesecake made with PEG LEG

$111 per person, maximum 35 guests.

2018 Menus, Themes, Prices & Dates may be different, check back Jan. 7

Heavy Seas Beer Tastings on Schooner Woodwind Sunset Sail

“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. Max 35 guests. Price: $111.

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

2018 Menus, Themes, Prices & Dates may be different, check back Jan. 7

United States Sailboat Show

Woodwind sails four times daily from “F2” Dock in the boat show.

We will be running 90 minute cruises, $35 per adult, $25 per child (under 12).

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. Buy tickets for Boat Show Admission on their Web Site, here.

2018 Menus, Themes, Prices & Dates may be different, check back Jan. 7

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! $78 per adult includes lunch, four 6 oz. beers, unlimited soda and water. Additional beer can be purchased. 12:30-3:00 pm. Max 35 people.

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.

2018 Menus, Themes, Prices & Dates may be different, check back Jan. 7

Great Chesapeake Bay Schooner Race Start

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! $900 plus tax per person. Includes everything!

2018 Prices & Dates may be different, check back Jan. 7

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, $83 per person, child $45 w/ child’s lunch.

*$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.

2018 Prices & Dates may be different, check back Jan. 7

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. $111 per person, maximum 35 guests.

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.

2018 Menu, Prices & Dates may be different, check back Jan. 7

Return Cruise from Norfolk to Annapolis

Sold by the cabin, $1600 plus 10% tax. Two people per cabin. Includes: accommodations aboard, gourmet meals- 4 breakfasts, 5 lunches, and 3 dinners, one dinner is ashore, sail training (if wanted), and absolutely fantastic scenery!

Click here for more info and photos.

All cabins available,

call 410-263-1981

2018 Menu, Prices & Dates may be different, check back Jan. 7

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