2024 Sailing Season is coming! See you April 13, 2024!

Sail from the US Sailboat Show – Preview Day

US Sailboat Show Dock F2 80 Compromise Street, Annapolis, MD

"Woodwind" sails up to four times daily on 90 minute cruises from temporary docks throughout the Sailboat Show October 12th - 15th from Dock "F2". Combo-Ticket Deal! Save up to a 40% discount off your ticket into the Boat Show by buying a 90 minute schooner cruise combined with your Sailboat Show Ticket.  What is ... Read more

Event Series Sail from the US Sailboat Show

Sail from the US Sailboat Show

US Sailboat Show Dock F2 80 Compromise Street, Annapolis, MD

"Woodwind" sails daily on 90 minute cruises from temporary docks throughout the Sailboat Show October 12th - 15th from Dock "F2". Combo-Ticket Deal! Save up to a 40% discount off your ticket into the Boat Show by buying a 90 minute schooner cruise combined with your Sailboat Show Ticket.  What is the Sailboat Boat Show? ... Read more

Event Series Sail from the US Sailboat Show

Sail from the US Sailboat Show

US Sailboat Show Dock F2 80 Compromise Street, Annapolis, MD

"Woodwind" sails daily on 90 minute cruises from temporary docks throughout the Sailboat Show October 12th - 15th from Dock "F2". Combo-Ticket Deal! Save up to a 40% discount off your ticket into the Boat Show by buying a 90 minute schooner cruise combined with your Sailboat Show Ticket.  What is the Sailboat Boat Show? ... Read more

Event Series Sail from the US Sailboat Show

Sail from the US Sailboat Show

US Sailboat Show Dock F2 80 Compromise Street, Annapolis, MD

"Woodwind" sails daily on 90 minute cruises from temporary docks throughout the Sailboat Show October 12th - 15th from Dock "F2". Combo-Ticket Deal! Save up to a 40% discount off your ticket into the Boat Show by buying a 90 minute schooner cruise combined with your Sailboat Show Ticket.  What is the Sailboat Boat Show? ... Read more

Acoustic Brunch with Ernie Halter

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An Intimate, Acoustic Show with, ERNIE HALTER 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 sail- we ... Read more

$129.95

Acoustic Brunch Sail with Tony Lucca

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An Intimate, Acoustic Show with, TONY LUCCA aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch.

$138.00

Sailor’s Delight Cocktail Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Sail 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

$104.65

Event Series Birds of the Chesapeake

Birds of the Chesapeake

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

The Chesapeake Bay is home to hundreds of species of birds, many living close to the shores of the Severn River. Join Jack to learn about the birds of the Chesapeake, their life histories, fun facts, and see how many different species of birds you can spot on the water! History Monday Sunset Sails occur ... Read more

Mother’s Day Brunch Sail

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Sail 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

$101.20

History of Shipping in the Chesapeake Bay

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Ever 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

Schooner Woodwind
410-263-7837