Sailor’s Delight Cocktail Cruise
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDSail away on one of our first sunset sails of the season. Enjoy great 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 5:30 pm, return at 7:30 pm. Great Assortment of Craft Beers from the Local Area, ... Read more
Captain Boomies Sailing with MJ Sailing + Ryan & Sophie Sailing
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDCaptain Boomies presents Sailing with the YouTubers: MJ Sailing plus Ryan & Sophie Sailing Enjoy a fun question and answer session about cruising and boats- all while sailing on a beautiful, 74-foot schooner, Woodwind, on the Chesapeake Bay for 2 hours. Aboard the boat, you can help raise the sails, steer the boat, or just ... Read more
History of oysters on the Bay and how water quality affects them
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDLearn more about oysters, from growing habitats to different types of oysters and how water quality affect them. Learn about the Severn River Association’s water quality monitoring, its history, and how it impacts the health of our water in general. Learn how this monitoring gives us the scientific facts to know where to ‘plant’ new ... Read more
The Birds of Annapolis and the Chesapeake Bay
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDDan Haas will be discussing the birds, bird habitats and movements for our region. He will highlight and point out any birds within view, and also discuss landmarks, habitats, and local hotspots within our view as we sail on the Bay. He will discuss migration, bird movements, historic rare bird sightings from our area, feeding ... Read more
Mother’s Day Brunch
Annapolis Waterfront Hotel 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

Birds of the Chesapeake Bay
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDHave you ever wondered what all the birds are doing out in the Chesapeake Bay? Look no further! Jack 'Wildlife' Turner has spent years documenting the birds of the Chesapeake Bay and beyond and is ready to fill your evening with interesting facts, bird stories, and ways that you can participate in the wonders of ... Read more
Socializing on the Severn: After Hour Entertainment Off the Water
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDWhile the Bay is well known for its significance to maritime history and the oyster industry, not all was work and no play. The tour focuses on fun after hours in the 19th/20th century, such as the Severn Rowing Club, Bay Ridge Resort, Eastport private clubs, Carr-Sparrow beaches, and the tradition of sock burning. History ... Read more
Blue Angels Performance Cruise
Annapolis Waterfront Hotel 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
Annapolis Waterfront Hotel 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 brunch. 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 still ... Read more
Tunes & Tales of the Golden Age of Annapolis, 1750-1783
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDJoin us on the Woodwind for a lively set of tunes & tales about life during the heyday of Annapolis (1750-1783), the social life and events that created the American Revolution. History Monday Sunset Sails occur every Monday, May-September 24. Different topics and speakers vary throughout the season. Our bar includes a selection of Craft ... Read more