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

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

Sailing Cruise from Annapolis City Marina

Annapolis City Marina 410 Severn Ave, Annapolis, MD

Enjoy this rare opportunity to join us for the only public sail this weekend aboard the Woodwind II!  This 74 foot schooner was custom designed and built specifically for sailing on the Chesapeake Bay. Our bar is stocked with wine and beer, including a nice selection of local craft brews. Each trip is unique. All cruises ... Read more

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

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