Our Sailing Season Re-opens April 15, 2023

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

History of oysters on the Bay and how water quality affects them

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

Learn more about oysters, from growing habitats to different types of oysters and how water quality affect them. Learn about the Severn River Association’s water quality monitoring, its history, and how it impacts the health of our water in general. Learn how this monitoring gives us the scientific facts to know where to ‘plant’ new ... Read more

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

Tunes & Tales of the Golden Age of Annapolis, 1750-1783

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

Join us on the Woodwind for a lively set of tunes & tales about life during the heyday of Annapolis (1750-1783), the social life and events that created the American Revolution. History Monday Sunset Sails occur every Monday, May-September 24. Different topics and speakers vary throughout the season. Our bar includes a selection of Craft ... Read more

Legends and Lore of the Annapolis Waterfront

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

Annapolis sailor and author David Gendell brings aboard stories of Annapolis, the Naval Academy, sailing, and the people who make the Chesapeake Bay one of the world's most vibrant sailing grounds. History Monday Sunset Sails occur every Monday, May-September 24. Different topics and speakers vary throughout the season. Our bar includes a selection of Craft ... Read more

Schooner Woodwind
410-263-7837