Our Sailing Season Re-opens April 15, 2023

Special Events

Light House Cruise

Annapolis Waterfront Hotel 80 Compromise Street, 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 at 10:30 am and returns to Annapolis at 2:30pm. Includes bagged lunch, soft drinks and bottled ... Read more

$159.85

Acoustic Brunch Sail with Tony Lucca

Annapolis Waterfront Hotel 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

Sailor’s Delight Cocktail Cruise

Annapolis Waterfront Hotel 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. Great Assortment of Craft Beers from the Local ... Read more

$104.65

Mother’s Day Brunch

Annapolis Waterfront Hotel 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.

$101.20

Blue Angels Performance Cruise

Annapolis Waterfront Hotel 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.

$182.85

Acoustic Brunch Sail with Gareth Asher

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

An Intimate, Acoustic Show with Memorial Day favorite, GARETH ASHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch.

$117.30

Pride Bubbly Brunch Sail

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

Grab your friends and join us in celebration of Pride Month aboard our beautiful, 74-foot sailing schooners for a Bubbly Brunch on the Bay.  Enjoy a rainbow of bubbly and a delicious brunch!

$101.20

Father’s Day Brunch Sail

Annapolis Waterfront Hotel 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

Fireworks Cruise

Annapolis Waterfront Hotel 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.  We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the show.

$143.75

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.

$129.95
Schooner Woodwind
410-263-7837