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
Cocktail Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail away on a sunset sail. Enjoy a light snack, great cocktails (Some featuring Cruzan Rum), wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes a hummus pack, two drink vouchers, a "Cruzan" shirt and a sunset sail. Limited shirt sizes and styles. Shirts will be distributed based on reservation ... Read more
The History of Annapolis – City on the Severn
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAnnapolis has a fascinating history, from its founding in 1649 as “Providence,” to the Golden Age of the 1760’s and 70’s, to the first peacetime capital of the United States, to the U.S. Naval Academy, and beyond. On this cruise, we'll hear all about the city’s past while we admire the skyline and beautiful waters ... Read more
Mother’s Day Brunch Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail Mom 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
History of Shipping in the Chesapeake Bay
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDDid you know that "ships" used to be about the size of the 74 foot Woodwind? Hard to imagine these days, join us as author and historian Dave Gendell and Mike Singer come to together to weave a path from the small ships of yesteryear to the behemoths of today. History Monday Sunset Sails occur ... Read more
Black-Side of the Bay
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDEngaging conversation sharing the history of the Bay's ties to the slave trade with the knowledge and skills that elevated the region's standing as a global powerhouse in the maritime and seafood industries, "Experiencing Black-joy as an Act of Resistance during Jim Crow," and growth of the areas Black middle class . History Monday Sunset ... 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.
Acoustic Brunch Sail with Gareth Asher
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn Intimate, Acoustic Show with Memorial Day favorite, GARETH ASHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious breakfast wrap. We will only sell 30 tickets to this really special event! We do sail rain or shine. If the musicians cannot play due to the weather, but we can ... Read more