History of Shipping in the Chesapeake Bay
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDEver since the colonists arrived here IN SHIPS, there has been shipping. Come discuss with us, the fascinating history and differences of early local maritime shipments and how drastically different things look today. History Monday Sunset Sails occur every Monday, May-September 22. Different topics and speakers vary throughout the season. Our bar includes a selection ... Read more
Greenbury Point – Towers to the Past
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDFor over the course of two world wars and well beyond, the people of Annapolis played golf next to and boated past America’s most top-secret military communication facility and didn’t have a clue they were living near our nation’s first line of defense. On our sunset sail, we will unravel the guarded government secrets that ... 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
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