Light House Cruise
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDSail 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
Acoustic Brunch Sail with Tony Lucca
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDAn Intimate, Acoustic Show with, TONY LUCCA aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch.

Sailor’s Delight Cocktail Cruise
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDSail 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
History of oysters on the Bay and how water quality affects them
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDLearn 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, MDSail Mom away! Guests can raise the sails, steer the boat, or just sit back and relax with a cold beverage.
Blue Angels Performance Cruise
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDWatch 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.

Acoustic Brunch Sail with Gareth Asher
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDAn 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.
Pride Bubbly Brunch Sail
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDGrab 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!
Tunes & Tales of the Golden Age of Annapolis, 1750-1783
Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MDJoin 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, MDAnnapolis 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