Schooner Woodwind

2025 Sailing Season starts April 12th!

Fireworks Cruise

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

Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30pm for a sunset sail with live entertainment by "Ship's Company". We will then anchor close to the fireworks barge for the 9:15pm fireworks display and return to the dock after the show. Tickets ... Read more

$84.00

Classic Wooden Boat Regatta

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

Participate in the National Sailing Hall of Fame Classic Wooden Boat Regatta. They have invited the Woodwinds' to participate in the race in the "Spirit of Tradition Class". The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with pursuit style race. Each boat has a ... 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. Tickets* are $83 per adult and $45 per child and include bagged lunch bottled water, soft drinks, and snacks. Beer and wine are available for purchase. *$10 of each ... Read more

$83.00

Friday Night 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 appetizers, 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.  Tickets are $74 per adult with a maximum of ... Read more

$74.00

Saturday Night 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 appetizers, 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.  Tickets are $74 per adult with a maximum of ... Read more

$74.00

Blue Angels Practice Cruise

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

Watch the Blue Angels perform their aero-acrobatics during this special cruise. Depart from Annapolis at 11:00 am and return at 3:30 pm. Typically, we sail for a 2.5 hour cruise (while usually the 2 planes fly around and practice) and then we anchor up front in the "spectator zone" for the best view of the ... Read more

$103.00

Blue Angels Performance Cruise

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

Watch 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. Advanced ticket ... Read more

$103.00

Fireworks Cruise

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

Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail with live entertainment by "Ship's Company". We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the ... Read more

$89.00

Solar Eclipse Cruise

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

Due to popular demand the first boat has sold out and we have opened a second boat for this event. Both boats are now sold out Sail away and watch the event being called the "Great American Eclipse".   While we are not in the area that will see the total eclipse, Annapolis is in the ... Read more

$54.00

Classic Wooden Boat Regatta

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, 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. Participate in the National Sailing Hall of Fame Classic Wooden Boat ... Read more

410-263-7837