Sunrise Schooner Race Watch Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDA rare sunrise sailing opportunity! Departs Annapolis Waterfront Hotel at 6:30am and returns at 9:30am 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 ... Read more
Wedding Crashers “Sacked” Brunch Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCan you believe its been 15 years? Enjoy a movie themed brunch and 2 adult beverages. Join Captain Jen as she tells tales about the filming of the movie and share your favorite memories of this cult classic. Food includes crab cakes (of course), meatloaf & egg sliders, scallops wrapped in bacon and other fun ... Read more
Classic Wooden Boat Regatta
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDDISCOUNTED RATE for NO LUNCH OPTION, this rate does not include the bagged lunches. We encourage you to bring a prepackaged lunch to enjoy during the sail (no buffets or displays will be allowed) Participate in the Classic Wooden Boat Regatta. The Woodwinds' have been invited to participate in the race in the "Spirit of ... Read more
October Lighthouse Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail 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, $130 per adult. Maximum of 24 ... Read more
Cocktail Cruising
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail away with great appetizers, cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, two drink vouchers and a sunset sail. Depart Annapolis at 4:00pm, return at 6:00pm. Tickets are $95 per adult with a maximum of 24 guests. Zoned Seating Pricing ~ Limited Capacity (24 person max): ... Read more
Annapolis Parade of Schooners & Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCome aboard the Woodwind for a beautiful sail that ends with a Parade of Schooners in Annapolis Harbor. Schooner Lynx, When and If, Adventurer, Sally B, both Woodwinds and the Adventure will hopefully be participating. Local craft beers, wine & bubbly available for purchase aboard. Depart Annapolis at 11:00am, return at 1:00pm. Tickets are $65 ... Read more
Schooner Rally 2020
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCome aboard the Woodwind for a beautiful sail amongst all the schooners that are currently in Annapolis for the Parade of Schooners. We will all be sailing in the company of these other schooners for a fun, 2-hour sail. Local craft beers, wine & bubbly available for purchase aboard. Depart Annapolis at 1:30pm, return at ... Read more
Halloween Brunch Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDPut on your favorite costume and join the Woodwind crew for a Spook-tacular Brunch Cruise! Cruise includes brunch (individually bagged for each guest), 2 adult beverages per person and tax. Cruise departs the Annapolis Waterfront Hotel at 11:00 am and returns at 1:00 pm. Zoned Seating Pricing ~ Limited Capacity (24 person max): 2 person ... Read more
Mother’s Day 2021 Sails
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail Mom away for two very special hours! We sail past the Naval Academy and head into the Chesapeake Bay. Fun for the whole family. Our Mother’s Day Sails departs Annapolis three times. 12:30-2:30 3:00-5:00 5:30-7:30 Sunset Sail The sailing cruise includes one free Mimosa, a glass of Bubbly, Bloody Mary, or any of our ... Read more
Blue Angels Performance Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDWatch 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