Father’s Day Brunch Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail Dad away! Guests can raise the sails, steer the boat, or just sit back and relax with a cold beverage. We sail past the Naval Academy and into the Chesapeake Bay. Fun for the whole family. Departing Annapolis Waterfront Hotel Dock at 11:00am and returning at 1:00pm. Maximum 30 guests on each sail. Includes ... 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 $149.50 per person ... Read more
Black Ankle Vineyards Dinner Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCaptain Jen fell in love with this winery's location, wine and people that work at Black Ankle Winery. Black Ankle Vineyards is the culmination of a long-time dream of founders Ed Boyce and Sarah O'Herron. They believe that the central Maryland Piedmont, sitting at the foothills of the Appalachian Mountains, has the right mix of ... Read more
Full Moonshine Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail with us on the Chesapeake Bay while the full moon rises on the horizon plus we have added a moonshine tasting from Pathfinder Farm and Distillery. Sample three, 2-oz cocktails made with their moonshine while sailing on a classic, 74-foot schooner. When finished with the sampling you may purchase your favorite cocktails (or beer ... Read more
Acoustic Brunch Sail with Ernie Halter
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn Intimate, Acoustic Show with, ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat. Ernie Halter will play acoustically while at anchor in a secluded cove. He will play for over an hour and after the performance we will set sail on the 74-foot, classic wooden schooner, Woodwind. Raise the sails, steer the ... Read more
The Last Days of the Schooner America Book Release Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDDavid Gendell's latest non-fiction book, "The Last Days of the Schooner America: A Lost Icon at the Annapolis Warship Factory" will be released in August 2024. The book reveals the extraordinary history of the iconic schooner and its unlikely but inextricable relation to the fast, focused rise of the Annapolis Yacht Yard as that facility ... Read more
Full Moonshine Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail with us on the Chesapeake Bay while the full moon rises on the horizon plus we have added a moonshine tasting from Pathfinder Farm and Distillery. Sample three, 2-oz cocktails made with their moonshine while sailing on a classic, 74-foot schooner. When finished with the sampling you may purchase your favorite cocktails (or beer ... Read more
Schooner Race Watch
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDThe Annual Great Chesapeake Bay Schooner Race Start Watch aboard the 74-foot, Schooner Woodwind II. Join in the excitement and watch the start of the 130-mile race from Annapolis to Norfolk. There could be as many as 25 schooners at the starting line (maybe more!). Some of them are 100+ feet. This is going to ... Read more
Thomas Point Shoal Lighthouse Cruise
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDSail to Thomas Point Shoal Lighthouse and learn about its history, importance, and present day condition by guest lecturer David Gendell, author of “Thomas Point Shoal Lighthouse: A Chesapeake Bay Icon” & "The Last Days of the Schooner America: A Lost Icon at the Annapolis Warship Factory" Departs Annapolis at 10:00 am and returns to ... Read more
Sail with 59 North from the US Sailboat Show
US Sailboat Show Dock F2 80 Compromise Street, Annapolis, MDJoin the 59º North Sailing team on the WOODWIND! Andy Schell, Mia Karlsson, August Sandbergand friends will be onboard for the afternoon sail to share stories of past adventures and talk about FALKEN's upcoming season in the South Pacific! Andy got his sailing start working as a deckhand on the Woodwind back in 2006, and ... Read more