Loading Events

Upcoming Events

Events List Navigation

April 2017

Friday Night Sailor’s Delight Cocktail Cruise

April 28 @ 5:30 pm - 7:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Sunset from Schooner Woodwind II of Schooner Woodwind in lovely Annapolis

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 35 guests.         Cocktail Cruise Menu: Assortment of Savory Dips served with Crostini and Crackers Pimento Cheese Olivada (Black Olive Spread) Hummus…

Find out more »

Saturday Night Sailor’s Delight Cocktail Cruise

April 29 @ 5:30 pm - 7:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Sunset from Schooner Woodwind II of Schooner Woodwind in lovely Annapolis

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 35 guests.         Cocktail Cruise Menu: Assortment of Savory Dips served with Crostini and Crackers Pimento Cheese Olivada (Black Olive Spread) Hummus…

Find out more »
May 2017

May Lighthouse Cruise

May 7 @ 10:30 am - 2:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Schooner Woodwind Chesapeake Bay Lighthouse Sailing Tours in Annapolis, Maryland

Sail to as many as three different lighthouses on the Chesapeake Bay and learn about their history, importance, and present day condition by a guest lecturer from the Chesapeake Chapter of the U.S. Lighthouse Society. Depart Annapolis at 10:30am, return at 2:30pm, includes bagged lunch, soft drinks and snacks, $93 per adult, $56 per child with child’s lunch. Maximum of 35 guests. Scroll down to see menu choices. Gourmet Bagged Lunch includes: Gourmet Sandwich (choose one) Grilled…

Find out more »

Mother’s Day Brunch

May 14 @ 10:00 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Bring Mom aboard the Schooner Woodwind for a memorable Mother's Day Brunch Sail

Our Mother’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food. $90 per person, $50 per child. Maximum 35 guests. Brunch Menu: Homemade Scones & Biscotti Bacon and Swiss Quiche Squares Baked Smokey Salmon with Hearty Bread Grilled Flank Steak Fresh Fruit Salad Orange Juice

Find out more »

May Wine in the Wind

May 21 @ 4:00 pm - 6:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Wine in the Wind

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines.  The representative from the winery will introduce you to these special wines. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine is a delicious, perfectly paired bite (we call them magnificent morsels) to go with each wine.   Includes a take-home, boat friendly, wine glass by Go Vino with the Woodwind's logo on it. Raise the sails, steer the boat…

Find out more »
$103.00

Blue Angels Practice Cruise

May 23 @ 11:00 am - 3:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Blue Angels

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 rehearsal of the performance, with all the planes, which usually happens around 2:00 pm. Advanced ticket purchase required, includes box lunch, soda, and snacks; $103…

Find out more »
$103.00

Blue Angels Performance Cruise

May 24 @ 11:30 am - 3:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Blue Angels

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 purchase required, includes box lunch, soda, and snacks; $103 per person, $66 per child w/child's lunch. Maximum 40 guests. Gourmet Bagged Lunch includes:…

Find out more »
June 2017

June Wine in the Wind

June 4 @ 4:00 pm - 6:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Wine in the Wind

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines.  The representative from the winery will introduce you to these special wines. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine is a delicious, perfectly paired bite (we call them magnificent morsels) to go with each wine.   Includes a take-home, boat friendly, wine glass by Go Vino with the Woodwind's logo on it. Raise the sails, steer the boat…

Find out more »

Father’s Day Brunch

June 18 @ 10:00 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Fathers Day Sailing Cruises Annapolis MD

Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food.  $90 per person, $50 per child. Maximum 35 guests. Brunch Menu: Homemade Scones & Biscotti Bacon and Swiss Quiche Squares Baked Smokey Salmon with Hearty Bread Grilled Flank Steak Fresh Fruit Salad & Orange Juice

Find out more »
July 2017

Fireworks Cruise

July 4 @ 6:30 pm - 10:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Celebrate the 4th of July in Annapolis enjoying a sunset sail complete with fireworks from the water

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 show. Tickets are $89 per adult, $62 per child and include bottled water, soft drinks, and a wide selection of desserts including fresh fruit. Beer…

Find out more »
+ Export Listed Events

© Copyright 2017. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

Site Designed by: Green Mountain Marketing & Advertising, Inc.