And we’re sailing! Our season started in April.

Black Ankle Vineyards Dinner Cruise

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

Captain 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 rolling ... Read more

$148.35

Schooner Race Watch

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! ... Read more

$125.35

Sail from the US Sailboat Show – Thursday

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

Annapolis Waterfront Hotel 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
Schooner Woodwind
410-263-7837