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

Brunch Sail with Ernie Halter

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

An Intimate, All Ages Acoustic Show with ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Ernie Halter will play acoustically while at anchor in a secluded cove. He will play for over an hour and after the performance we will set sail on the 74-foot, ... Read more

$93.00

Wedding Crashers “Sacked” Brunch Sail

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

Can you believe its been 15 years?  Enjoy a movie themed brunch and 2 adult beverages.  Join Captain Jen as she tells tales about the filming of the movie and share your favorite memories of this cult classic. Food includes crab cakes (of course), meatloaf & egg sliders, scallops wrapped in bacon and other fun ... Read more

Halloween Brunch Cruise

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

Put on your favorite costume and join the Woodwind crew for a Spook-tacular Brunch Cruise!  Cruise includes brunch (individually bagged for each guest), 2 adult beverages per person and tax. Cruise departs the Annapolis Waterfront Hotel at 11:00 am and returns at 1:00 pm. Zoned Seating Pricing ~ Limited Capacity (24 person max): 2 person ... Read more

$95.00

Mother’s Day Brunch Sail

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

Sail Mom away for the morning (or afternoon)!  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.  Maximum 30 guests on each sail. Two Sailing times to choose from: 10:00 ... Read more

$100.05

Father’s Day Brunch Sail

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

Sail Dad 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.  Maximum 30 guests on each sail.  Departing Annapolis Waterfront Hotel Dock at 11:00am and returning at 1:00pm. Includes: ... Read more

$100.05

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

Mother’s Day Brunch

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

Father’s Day Brunch Sail

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

Sail Dad 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

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
Schooner Woodwind
410-263-7837