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
Father’s Day 2021 Sails
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail Dad away for two very special hours! We sail past the Naval Academy and head into the Chesapeake Bay. Fun for the whole family. Our Father's Day Sails depart Annapolis four times. 11:00-1:00 1:30-3:30 4:00-6:00 6:30-8:30 Sunset Sail The sailing cruise includes one free Mimosa, a glass of Bubbly, Bloody Mary, or any of ... Read more
Fourth of July Weekend 2021 Sails
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDMake Woodwind part of your Fourth of July holiday weekend! Sail away for two very special hours! We sail past the Naval Academy and head into the Chesapeake Bay. Fun for the whole family. Our Sails on Saturday July 3rd depart Annapolis four times. 11:00-1:00 1:30-3:30 4:00-6:00 6:30-8:30 Sunset Sail On Sunday, July 4th our ... Read more
Fireworks Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin 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. 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 $140 per person ... 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
Schooner Race Watch Cruise
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDThe 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! ... Read more
Sailing Cruise from Annapolis City Marina
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDThe 74-foot schooner Woodwind and Woodwind II were custom designed and built specifically for sailing on the Chesapeake Bay. Our bar is stocked with wine and beer, including a nice selection of local craft brews. Go sailing during the US Powerboat Show, departing from Annapolis City Marina. Each trip is unique. Sail by the United States Naval Academy and then into ... Read more