Schooner Woodwind

Thank you for a great sailing season. See you in April 2025!

Thomas Point Shoal Lighthouse Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

Sail 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

$126.50

Schooner Race Watch

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

The 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

$142.60

Sailing Cruise from Annapolis City Marina

Schooner Woodwind at the Annapolis City Marina Dock 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

Schooner Race Watch Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, 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

October Lighthouse Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

Sail to as many as three different lighthouses on the Chesapeake Bay and learn about their history, importance, and present day condition by guest lecturer David Gendell, author of "Thomas Point Shoal Lighthouse: A Chesapeake Bay Icon". Departs Annapolis City Marina at 11:30 am and returns to Annapolis City Marina at 3:30pm. Ticket Price includes soft ... Read more

$105.00

Sailing Cruise from Annapolis City Marina

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

The 74-foot schooner Woodwind and Woodwind II were 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. Go sailing during the US Powerboat Show, departing from Annapolis City Marina. Each trip is unique. Sail by the United States Naval Academy and then into ... Read more

$75.00

Schooner Race Watch Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, 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

$120.00

Brews in the Breeze Lunch Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

Reduced Ticket Price - not including Lunch (the order has already been placed with our caterer).  Be sure to bring your own lunch to enjoy aboard.  Lunch must be self contained (boxed or bagged) - no buffets or displays will be allowed aboard. Sail on a lunchtime cruise on the Chesapeake Bay.  Tickets are $69 ... Read more

Acoustic Evening Sail with Tyrone Wells

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

Schooner Woodwind is pleased to announce the return of TYRONE WELLS to perform aboard the boat for an Intimate, Acoustic Show.  We will cruise to a secluded cove for the performance and then enjoy a sunset sail back to the dock.   This will be Tyrone's fourth time singing and sailing on the Woodwind. It all ... Read more

$120.00

October Lighthouse Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

Reduced Ticket Price - not including Bagged Lunch (the order has already been placed with our caterer).  Be sure to bring your own lunch to enjoy aboard.  Lunch must be self contained (boxed or bagged) - no buffets or displays will be allowed aboard. Sail to as many as three different lighthouses on the Chesapeake ... Read more

410-263-7837